How to Take (some of) the Stress Out of Negotiating

One of the biggest challenges I’ve seen many sales reps work through is negotiating a deal.

It’s completely understandable in a way. You’re judged on performance, on results, and if you don’t deliver deals then you’re out. In many sales roles it’s rare that you simply put a contract in front of a prospect, they look it over, and then they sign it. The back and forth of negotiating is 100% expected.

If this is so normal, something we all expect to happen, why is it stressing sales reps out?

By negotiating a rep feels like the whole deal is at risk. They don’t know whether or not it gets signed at the end of the negotiation.

How do you typically feel when you’re not sure what’s going to happen next?

Uncertainty is difficult to handle mentally and emotionally, and that’s what a negotiation feels like.

It becomes even more of a nightmare when your job is measured on how well you’re able to come out on the other side of a back and forth with a signed contract and a check.

On top of that you’re negotiating a number of terms. Dollar value, length of deal, terms to cancel, services provided, payment schedule, and the legal jargon that holds everyone accountable can all be brought up in a negotiation. It can be downright maddening to try and navigate these waters.

Pick the wrong area to push back on and the deal could be dead.

The worst part, and you may be doing this yourself, is when a rep is running back and forth between the Manager, finance, and the prospect to get a deal done. Why are reps rarely taught how to negotiate for themselves?

After all, shouldn’t it be the sales rep who confidently brings a deal that’s essentially done to get the official approval?

Learning negotiating fundamentals, as well as what’s an acceptable deal and what’s not, should be part of any sales team’s training.

Let me give you an example of a move I learned in my first sales job. Before I presented any counteroffer to my boss I had to confirm that if we agreed to these terms we had a deal.

My first question would be, “Other than X, is there anything else holding you back from moving forward?”

Ask yourself, does it matter if the prospect wants a discount, a shorter contract, or extra services if she’s not willing to sign?

What if there are other concerns that aren’t on the table?

Time to get them squared away.

Then I’d ask my second question. “If I can’t get X done, will that hold you back from moving forward?”

Let’s be realistic here. A lot of prospects will ask for something while negotiating simply to ask. They’re not serious, they’ve already made a decision, they just want to see if they can get a better deal out of you.

There’s no point in negotiating if you don’t have to.

Of course, you will have to negotiate a lot of the time. Deals get more complex than one or two asks. Contracts can go back and forth multiple times with a number of different terms discussed.

How can you simplify what is an acceptable deal and what isn’t?

Smart sales teams use a tradeoff system to help the reps negotiate.

This could be a point system or a prioritized list that shows what both sides should ask for. It needs to be a simple document to reference any time a negotiation is going on.

Prospect asks for a 10% discount – what do we have to get in return to say “yes” to her ask?

Look at the document, make the offer, and move on.

Treating deals this way becomes even more important in complicated negotiations. Sometimes a prospect will ask for too much, or for things you can’t offer. You shouldn’t be wasting anyone’s time to approve a deal unless it’s one you know your team is likely to say “yes” to.

Early on in my sales career my boss gave me a set of price and billing negotiating rules to go with. As long as I stayed within those parameters I knew he was going to give me the thumbs up on a deal, even if he didn’t feel like it was the deal I should be pushing for. Yes, something might come up outside of those rules. Those were the deals we needed to talk about and hash out.

Having a fundamental set of rules helped me know quickly if the opportunity I was working on was a good fit or not without needing to ping my boss every step of the way.

It made both our lives a lot easier. He didn’t get badgered with basic pricing and terms every week until I was ready to put a formal proposal in front of a prospect, and I learned how to hash out a deal on my own much faster.

That guide put both myself and my boss at ease when I’d talk initial terms with a prospect because we knew I was playing by a set of rules everyone was on board with.

I didn’t have to worry about how to negotiate. My focus was on showing the prospect a better reality if they bought from me and ironing out the core terms to get a deal done.

Until I left that company I had no idea how important that guide was for me. In my next role we had no such guidelines and very little oversight for approval.

There were a couple times I heard how bad one of my deals was months after we started working with the client. Other deals would get rejected even though we stuck by the loose guidelines we had because of the strange final approval process we had in place. I wasted a lot of time on minor details on one deal, then I’d have to completely backtrack on my next because the big boss said “nope” to terms I thought were great.

It definitely messed with my head, and I think it’s a big reason why few sales reps lasted longer than six months. No one knew when a deal was a good one!

Set your reps up with the most common negotiation terms and some basic idea as to how to negotiate and everyone will feel a lot more at ease talking terms with prospects.

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Are Sales Reps Losing the Art of Storytelling?

I feel like so many sales reps are failing to learn how to present to a prospect.

I’ve sat on demos as both a Manager and as a prospect. If there’s one thing I’ve seen that surprises me to no end it’s that so many reps have little ability to tell an interesting, informative, and compelling story while presenting their product.

Honestly, many of these presentations have barely gone beyond something I could have gotten from a pre-recorded demo, and I have to commit twice as much time to have that conversation.

The future of sales will be reps doing the things computers can’t, and the number one things computers can’t do is weave an interesting story as you steadily understand a prospect better while walking through what your company does and how that can solve important problems.

Early in my sales career I never had the pleasure of selling truly amazing products. Long before I had my first tech sales role I had the opportunity to sell some of the least sexy products imaginable.

My first real sales role was one I took while in college. You may have heard of people selling this, you may have done it yourself. I worked for Vector Marketing selling Cutco knives.

Talk about a brutal game.

Here I was, calling on the middle class families I knew in my small town, setting up demos to present a set of knives that cost ten times what most people would spend on something to simply chop up vegetable and prepare a chicken. When we all submitted our initial prospecting lists, mine had less than half the names my peers’ had written down. You couldn’t script a better way to fail as a sales rep.

A couple weeks later I was one of the top reps on the team.

Selling knives was more art than science. Sure, we had a presentation that everyone learned. Anyone could deliver the presentation. Anyone. The top performers were precisely that: performers.

Too many reps take the amazing and turn it into merely “better than the status quo.”

I had the opposite challenge. I had knives that cut better and were more durable, but for ten times the money. They were merely better than the status quo. My job wasn’t to sell you on the fact that they were better knives, because that was obvious.

My job was to turn the person using the knives into the star of their own kitchen.

What does the star of the kitchen use? That’s right, knives meant for a chef, not a mere mortal.

Any time you simply run through the demo of your product you are missing a golden opportunity to help your prospect see how their world could be different. How they could make an even bigger impact.

Products should never be the star of the show, they should focus on how the product makes the prospect the star of the show.

After graduating from college I sold something even sexier than high-end knives: industrial cleaning chemicals. For many businesses I was selling a product they literally did not want to have to think about, ever.

Knowing this, it actually made it easier for me to sell what we did instead of our products.

One of our biggest pitches was the fact that we did everything for you up until the point you went to use the product. We supplied you with the containers, equipment, setup, and maintenance so you didn’t have to think about it. All you did was use it when you needed to.

The catch? Well, I had to make cleaning chemicals interesting enough to get the prospect to consider changing vendors!

My boss was a master of this. His presentations were a mixture of information, competitive advantages, and humor, all held together by a compelling narrative.

I’ve seen too many demos where the rep seems to think the product will do the talking. If that’s all you can do, how long will it take your company to find software that can do the same?

Great reps tie their key points together with an interesting and informative a story, while the rest will lose their jobs to AI and webinars.

My customers were the ones who realized that our story – a business where you don’t have to think about the cleaning chemicals you buy, one with a simpler, safer, well maintained, and better managed system in place – fit their vision of the best version of their business.

I wasn’t in the business of selling cleaning chemicals. I was in the business of telling a story and finding prospects who believed that yes, they could make their business better by changing vendors for a product everyone took for granted yet was absolutely essential to getting the job done.

To understand what story you should be telling, ask yourself….

How do my prospects view their world, and how is that different from the way my customers view their world because of our products?

Here’s the key. Your story isn’t your story. It’s the story about how your prospects change.

The whole point of tying your presentation to the story instead of your product is because people resonate with stories. We learn from stories. And along the way we laugh, cry, things go bad, things get better, and we hopefully wind up in a better place.

Your demos should be more like a rollercoaster ride. Take your prospects for a ride. Hey, some might not like it, sure. I guarantee you more people will remember it, talk about it, buy from you, and refer other prospects to you if you spend your time with them helping them to see the way things could be instead of walking them through your product.

Dust off the costumes. Act like you’re a floor scrubber. Crack a well-timed joke. Put on a show.

Whatever you do, please don’t walk your prospects through a simple product demo. That’s what the robots are going to be for.


When an AE becomes an SDR: Here’s the Biggest Lesson I Learned

Nine years ago I managed a direct marketing team for a small agency. We were a hybrid agency in a sense. What we delivered to our clients was a mixture of appointment setting and deep research into the specific accounts we targeted. If you just wanted one or the other there were tons of other agencies to hire. If you wanted to really understand your market and get a head start in the lead department, there was no one better than us.

I took this role after being an outside sales rep for over three years. After all the glory of closing deals I was thrust into a cold calling seat for the next 18 months. For that year and a half, running the team meant running with the team.

Early on I learned a crucial lesson, one I wish I had truly understood while I were responsible for finding and closing new business. That lesson?

It’s more important to understand your prospects and your market than it is to close a deal.

If you’re wondering… JV, do you really mean you’d be willing to trade a meeting, a next step, or even a deal, just for new information?

Yes, absolutely.

One of the biggest areas I see SDRs (and AEs who prospect) struggle with is playing the long game. Focusing on something other than getting the next step.

I get it, you have a quota for RIGHT NOW. This month. This quarter. There’s no guarantee you’ll be in your seat tomorrow if you can’t deliver something today. Sales is all about answering the question, “What have you done for me lately?”

Here’s my issue with that mentality. Getting new, important information is actually going to help you more, right now, than getting one more meeting.

Your best leads aren’t going to suddenly go cold on you because you took a little time to get to know them and understand their needs.

Put yourself in the prospect’s shoes for a moment. Who would you rather do business with, the rep who’s always asking for the sale or the rep who’s always trying to help you out?

Who are you going to give time to, the rep who’s had a little back and forth with you and can show you something genuinely interesting to you, or the rep who closes every email with “Can I have 15 minutes?”

“But JV, I can help the prospect! I just need… well, 15 minutes to do so!”

Yeah, but how are you going to PROVE it if you can’t spend a little up front effort understanding the prospect?

We’ve become more interested in the transaction than the relationship.

This was a cardinal sin as an outside sales rep. I didn’t get new accounts shuffled into my name if I wanted them, I owned my territory and the actions I took inside of it.

If I ticked someone off? Well, I have to hope that (a) no one else in the company found out and (b) that person would change jobs before I’d get another shot. I couldn’t simply give that account back to Marketing and get a new one.

I see so much “I want mine” in SaaS sales that I really question if it’s harder to sell software, or if companies just stopped teaching basic sales skills like building a relationship within an account.

By trading information for taking a shot, you’re taking that shot at least partially blindfolded.

Here’s the other bone I have to pick: who’s better off when you go for the close instead of trying to learn a little bit up front?

The prospects who say yes to the “15 minutes” request are already warmed up in a way. They’re looking at vendors. Or they’re bored and want to take a look at your demo so they can regurgitate your pitch and look smarter internally. You’re not selling anyone, you’re just tripping over good leads.

I’ve sat on both sides of the table and I hate to say it, but it’s hard to buy software. Everything looks so cool yet rarely works half as well after you sign on the dotted line.

Reps have fallen out of my personal buying process because they focused on their product instead of my needs.

Even if it means passing on the best damn product out there, I’m a stickler for working with a company that’s going to put their best foot forward to understand my world.

More information leads to being able to do a far better job targeting prospects, developing a relationship, and ultimately close deals you would have lost.

Odds are your prospects are all similar, or fall into specific categories.

Would it be easier to sell to them if you took the time to listen and understand what’s going on across each segment so that you could go into your next call already knowing what to expect?

Yet the problem is that you’re not going to gain that level of understanding if you’re always trying to get one more prospect to close. It takes a number of conversations and some diligent note taking to start to make connections that will win you more deals. There are nuances you won’t pick up on without having those conversations.

The rep who can head into a call with that level of insight and be able to call some of the key shots is going to look far better at each step of the process.

Here’s a good example: what’s your go-to line when a prospect hesitates?

If you’ve had these conversations then you know exactly why the prospect hesitates, the real motivation behind it. You’re not depending on objection handling techniques. You can call it for what it is and have a more open dialogue about what’s causing it.

The rep who’s using a script will have to depend on the script and not their own personal experience.

Which also means that rep can be replaced with someone else who can use the same script.

You have to bring something to the table other than your ability to talk and overcome objections to be successful in sales over the long haul.

If you understand your prospects and your market, if you have ideas as to how to sell them better than you were trained, then you’ve gained an upper hand that no one can take from you.

The sales professional of the future will be the one who has the rolodex, who knows the prospects and companies inside and out, who has had hundreds of meaningful conversations and can tell you all the subtle things that will lead to a deal.

It won’t be the rep who can send customized emails. It won’t be the person who does demos. Both will be replaced by software.

It will be the rep who has real conversations and understands the market in a way that no piece of software could replace.

Yes, Most of Sales is Hearing “No”

Today I heard back from someone I had been in touch with about next steps. In less than five words I already knew the answer was “no”, I simply had to wait out the other few dozen words to make it final. The highlight of the call was getting a bit of honest feedback, which confirmed my hunches. Always good to confirm a hunch, whether it’s a “yes” or a “no”.

Before I hung up I thanked the person. After all, this is what sales is.

The majority of what we do as sales professionals ends without a deal.

Most cold calls end with no meeting.

Half of those first meetings won’t get close to being a deal.

Most of your proposals will get shot down.

I think this is the biggest reason why most early career sales people won’t be in sales in 5 years. Everyone tells you just how great sales is. Except they don’t tell you, really tell you, that you’re doing to get knocked down every single day.

It’s so easy to focus on the reps making the big paychecks when you’re on the outside looking in.

It’s just as easy to focus on the last person who said “no” to you when the person at the other end of the phone hangs up on you.

When you take a good, honest look at what sales is all about, it’s about getting back up after “no” and moving on to the next thing.

This is why every sales manager out there is so concerned with pipeline.

I remember in my first sales role that my boss laid it out very clearly to me. Every month I needed to make 4 sales. To make a sale I needed 2 on site demos with clients. To get 2 on site demos I needed 4 discovery meetings. Every week those were my targets.

It’s so easy to think, “I’m getting better, I can sell a deal with only 3 discovery meetings, I don’t need to face as much rejection as before!”

The first time I did that I missed my quota. Whoops.

Looks like I needed 4 discovery calls each week to land my deals.

Picking myself back up after each “no” wasn’t easy in the beginning. I knew rejection was part of sales. It’s one thing to know that you’re going to get shot down and it’s another to realize your job, your paycheck, and your immediate career hang on your ability to get enough people to say “yes”.

That’s the scary part of sales. There is no “I’ll stay later than everyone else to get more done” if you can’t get someone to say “yes”.

The quickest way to get over hearing “no” is to categorize each one and take the appropriate next step.

Let’s start with the easiest ones: prospects who shut you down no matter what you do. Hang ups, including the people who say “not interested” after you’re 6 seconds into a pitch.

Once the phone line is dead, cross them off your active list and put them in a rotation to be called back in 6-12 months. Done.

The next easiest category are prospects who throw you an objection, a real objection, and no matter what you do they still say no. There’s a little you might be able to learn, but for the most part you have to move on like you did with the hang ups. Most of these you have to chalk up to timing.

That leaves everyone else in one final bucket: the group you can learn from.

This sounds exciting on a high-level until you realize that yes, after every single rejection you need to sit down, take some time, and figure out what happened.

If at all possible see if the prospect will give you their insights. You may not take them at face value, but at least you’ll hear how they thought out their decision.

You won’t always learn something you’re hoping to learn, mind you. All you may learn is that your competition is crushing you and boy will you wish you worked for them.

Still, what can you learn from that scenario?

You might realize that in those competitive situations you’re likely to lose. Or that your products aren’t competitive any more and you should be looking for a new thing to sell. Either way, it’s helpful as long as you take a next step.

Learning from rejection turned getting a “no” from being solely a disappointment into an expected and useful event for me.

First off, being able to accept that getting shot down is simply part of the job made it a lot easier for me to swallow.

In the beginning you may want to find that “magic bullet” to handle your worst objection. It doesn’t exist. Once you realize that and focus on being as effective as possible then you understand that you’re dividing your prospects into the “now” and “not right now” buckets.

If there’s one thing that wastes an incredible amount of sales people’s time, it’s chasing after prospects who aren’t going to do anything new.

Focusing on the real prospects, the ones who might buy, is the biggest win you could ask for. Spend most of your time on the prospects who are most likely to buy and you’re going to close a lot more deals.

If there’s a secret to sales, it’s to celebrate your wins and forget your losses.

There is no way to eliminate getting another “no”. Heck, there are very few ways to even win half the time (unless you’re selling a magical product that kills the competition, in which case you’re in for a rude awakening at your next job).

The next “no” will come. So will the next “yes”, if you do your job well.

If you can smile at the end of every week, month, and quarter, knowing that you helped enough prospects become new customers that you, your company, and your clients are all better off, then you did all you need to do as a sales person.

The 3 Questions That Turn “No” Into A “Yes”

Over a number of years I’ve developed a three question system that I use to land better meetings, move deals along quicker, and sweep the objection mine field clear to close more deals.

I wish I could say that this came to me easily, quickly, and naturally in my sales career, but that’s not the case. In all honesty I discovered this technique because I had to.

Ten years ago I put myself in the ultimate ‘no looking back now’ scenario: I joined a startup as a cofounder and the first full-time salesperson.

In other words, if I failed then we all failed, even if everyone else involved succeeded.

I had never felt pressure like this before.

Within a few days I had already set up my first meetings with prospects. It was go time.

Yet I realized it wasn’t my company’s name on the line this time, it was mine. Wow. I bet you can think of a time you had the same feeling I had that day. It wasn’t about selling something, it was about making a mark.

Before my first meeting I asked myself, “If these were going to be my customers forever and ever, how would I treat them?”

That question changed the course of my sales career in an instant.

Three months later we all huddled to talk about how 2007 was going to be a big year for us.

After all, I was forecasting an absolutely massive month. Not only was I projecting a good number of new orders, I had promised a boatload of new customers. Not in Q1. Nope. I promised they were all coming in right now, in January.

Have you ever committed to a big number? I had before, except this time I was sweating bullets. It was one thing to pull off a big quarter. It was another to promise the biggest month yet after coming off a slow holiday season.

The other three cofounders all wondered if this kid they had bet the company on would pull it off.

If I missed this month – not this quarter, this one month – the gig was up. Either we’d fold or I’d get fired.

And what happened? I delivered. Oh, did I deliver. The pipeline I had built was so good that I was closing at least one deal every single day. New customers were lining up for their first order and existing customers were placing even bigger second orders. One of the cofounders nicknamed me Cal Ripken because I landed an order every single business day like clockwork.

(I finally missed on 2 days the final week of the month, but the nickname stuck)

I wish I could say that was the beginning of an amazing run but alas, startups succeed for the same few reasons yet can die a million different ways. Before the year was out, before we landed the funding we needed to stay afloat, the other cofounders split and we ran out of cash.

Thankfully I walked away with the closing system that had changed my life.

You too can learn this system. I know, that’s a corny as hell line. It’s true, though.

I’ve taught this approach to dozens of sales reps over the past five years in different industries. Could it work for you? I’ll let you be the judge.

Closing – whether you’re closing a meeting, a next step, or finalizing a deal – comes down to doing one thing and one thing only.

Guiding the prospect through the buying process.

Notice I didn’t say SELLING them. Notice I didn’t mention features, benefits, value propositions, or showing them ROI. None of that matters if you don’t understand the most fundamental rule up front.

Prospects BUY, and your only job is to guide them down that process, whether it means you personally close a sale at the end of the process or not.

This is all about showing the prospect HOW to buy something. If you take only one thing away from this post, you should literally write down what a “How to buy my product the best way possible” process looks like.

After all, if you can’t help a prospect figure out how to buy something, how do you expect they’ll figure out how to buy from you?

The best part is that it doesn’t matter if we’re talking software or services, automobiles or analytics, plane tickets or Lear jets. A sale doesn’t happen unless the prospect goes through a process to buy something.

Here’s the fun part: when first you meet a prospect you have absolutely no idea where they are in the buying process. Even worse, your prospect probably doesn’t know where they are in the buying process.

And you were wondering why they paid sales people the big bucks!

You get to be the one who figures out where the prospect is in the buying process. Your goal is to help them along the rest of the way without getting lost or distracted, but if that’s going to happen anyway I’d recommend letting them wander off sooner than later.

Back when I had that conversation with myself about how I’d treat my new customers, the ones I thought I’d have forever and ever, I started acting differently. Specifically, I stopped using all the silly tactics I had picked up trying to push, pull, prod, and pummel prospects into signing on the dotted line.

These were going to be my customers for life and I realized I needed them to want to buy from me.

I knew that the only way to guide someone in a buying decision was to ask them questions. I needed to act more like an advisor than a quota carrying sales person. Specifically, my forever customers’ advisor.

The first question I knew to ask was one I had used for years. It was my best friend at every step of the buying process, from cold call to close.


“If we’re in agreement here, will you take the next step?”

The classic A/B close. Strong enough for a personality Type A, soft enough for a Type B.

Now before you start going out asking this exact question, let’s take a step back to understand what’s going on here and how to ask this question. This one can be used at every step of the buying process, so pay close attention to how it transforms based on the situation you’re in.

Say you’re calling to schedule a first meeting. The prospect has given you just enough information that you’re ready to book it.

Your close would be, “It seems like X and Y are your big priorities, and that’s an area we’ve helped dozens of companies get even better results. If you’d like to have a deeper discussion on how we might be able to do that for you, when could we set up a 30 minute meeting next week?”

At the end of that call (great call, btw!), you know the next step in the buying process is to give the prospect a test drive. You might call it a trial, you might call it a proof of concept. Whatever it is, you know the best way for them to experience your product is to actually get them to use it.

Your close would be, “It seems like this could be a great fit for you. The next logical step for you to take would be to set up a 14 day trial so you can really understand how much easier X and Y will be for you and your team. If that sounds like something you’d like to see, when can we set that up?”

The test drive goes great and then you’re ready to move forward. This is where things get sticky. This is where you’ll run into objections – budget, timing, pricing – and you’ll realize your prospect has suddenly wandered away from the buying process and straight into the Tire Kicking cul-de-sac.

You’re going to need to keep the A/B question by your side. You’re also going to need some reinforcement to get the buyer back on track.


“What would prevent you from moving forward?”

Wait, did I just invite the prospect to throw objections at me?

You’re absolutely right I did. This was my first golden discovery when I was building the startup.

When you ask your guiding questions, the ones designed to get a “yes”, what you’re doing is painting a picture of what things could be like. These feel safe to you because you feel in control. You’re avoiding a “no”. You’re avoiding everything that could derail the deal. Right?

Nothing could be further from the truth.

Whether you choose to surface those objections or not, they’re still there.

A sales professional understands that objections are likely lurking in the shadows. What you gain by inviting the prospect to point out the important land mines that are right next to both of your on the buying process is that you’re asking them to guide both of you through the tough spots.

The prospect feels safe because they’ve said “no” to you. They get to keep status quo for another moment.

Except that’s not entirely the truth.

You’ve empowered your buyer to be the leader on their buying journey by letting them tell you “no” and giving them the illusion of control.

Now that their objections are in PLAIN SIGHT!

Ah ha, they’ve shown you all the rough terrain before you’ve gotten there!

The best part is that the prospect suddenly feels more relaxed. Calmer. All those fearful emotions that you’re used to battling through disappear.

Your prospect is relaxed, focused, feeling in control, and ready to talk to you to see if they should buy.

What should you do? You show the prospect how both of you can overcome them. After all, the only way the prospect can complete their journey through the buying process, the only way they can get all the amazing benefits you’ve been discussing, is by joining forces with you to overcome them.

They’re more than open to having this conversation now that they’re calm, cool, collected, and feeling in control.

How do you handle these objections? By asking a variation of Question #1, of course.

Before I show you how, let me give you the why. The inexperienced sales rep hears an objection, panics, and spits out a canned rebuttal, praying it works.

You? You’re a professional. You’re better than that. You ask them your A/B close BEFORE addressing their objection to make sure nothing else is holding them back at this point.

Let me give you three different ways you can ask this.

“If that’s something we can do, will you be ready to move to the next step?”

“Other than this objection, is there anything else holding you back from moving forward?”

“Before we dig into this I need to ask you, if we can iron this out will you be ready to move forward?”

Some of you might have noticed that there are two things you’re asking with this question.

First off, are we discussing everything that could end the buying journey? Because there’s no point in turning land mines into guideposts if there is another one still buried in the ground, waiting for you to step on it.

You won’t be able to move forward without getting all the objections out in plain sight as soon as possible. Once they’re all clearly defined, yes, go about handling them (and get the prospect to help).

Second, the prospect is committing to moving along the buying process with you.

This one is so simple and super important. Do you really want to waste your time with a prospect who needs something you can’t offer? Of course not! They’re not going to buy from you. You’re a sales professional, and you focus your time with prospects who can buy from you.

There’s no point in continuing along if the prospect flat out says, “You know, I need Z,” and Z is something you absolutely cannot do for them.

However, what if the prospect is confusing must haves with nice to haves? What do I do then?

You still have one more question in your arsenal.


“Have you given up on this?”

This one is so amazingly powerful in all its variations.

The last thing most people want to do is give up on someone else. When you ask this question you’re communicating that the prospect is letting you down.

That’s right. The prospect has failed you, not the other way around.

You’ve spent all this time trying to guide the prospect through the frightening buying process and now you’ve fallen short. Except it’s the prospect’s journey, not your’s. You’ve been their guide. And now the prospect isn’t going to finish the journey you’ve been helping them along.

What kind of person gets all this help only to stop short?

Oh, and it eats at the prospect! They have a moment, thinking, “What can I do to help this person who I’ve clearly failed?”

There’s only one way to make things right, and that’s for the prospect to see if they can save you.

Now, this doesn’t always work. This is your last ditch effort when it’s clear the prospect is stuck on their buying journey with you. The interesting thing is that it will work more often than you’d expect, and far more often than anything else you could do.

By asking the question, by letting the prospect choose to re-engage with you (not the other way around), they’ve committed to you that they will deliver one more strong effort to complete their buying process.

Their mindset is much like when you asked them to put their objections on the table. Your prospect is calm and relaxed and ready to see what you can do together.

The prospect is your partner again.

There are different ways of phrasing this, depending on your situation.

If you’re talking with them in person, you might want to say:

“It seems like there’s nothing we can do to move forward today.”

Pause and see how they respond. Give them a good ten seconds if need be.

If you’re sending an email to try and get back in front of them, all your subject needs to say is:

“Did I lose you?”

Especially if you’re forwarding along all the past conversations and outreach you’ve had. That subject line has worked like magic for me.

It’s always worth trying to get the prospect back even when it looks like you’ve lost. You’ve gone on a long journey through the buying process with your prospect, and you might be on the verge of closing the deal. All they need is someone to help them take those final steps.


Now that we’ve helped the prospect through the buying process and gotten to the very end, you have to ask for the sale. It’s time to close them.

We just need to say the magic words.

“Prospect, if this is all agreeable to you, when can we start?”

You might be wondering if this is all a dream. Or a hoax.

Can you really schedule more meetings, develop more deals, and close more sales all by asking 3 questions?

I assure you, yes, you can.

You can spend your days trying to trap prospects, or waiting until you trip over the people who are so far long the buying process that they’re ready to buy…

Or you can learn how to help your prospects buy from YOU.

The best part is this: not only will they buy, they will buy quicker and pay more because it’s clear you know how to help them make a great decision.

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Are you an SDR today? Odds are you won’t be in sales in 5 years

Most SDRs won’t be selling in 5 years.

By selling I mean spending your days focused on closing new business. If you’re an SDR today, right now, then odds are you will not be a closer in 5 years.

I know, you just read someone’s post on how being an SDR is the hardest role in sales. Is that true? Absolutely. It is the hardest role in sales.

What you might have missed is why it’s the hardest role in sales. Spending 100% of your time calling, emailing, and cold prospecting is a brutal way to spend all day, every day. You have to deal with the fact that most people don’t pick up the phone and that most people who do pick up say “no.” Almost all of your emails will not be replied to. Most of your replies will be a “no” as well.

Being an SDR is the hardest job in sales because you’re doing the dirty work for someone else.

It’s not the hardest job in sales because closing deals is easier than setting appointments. Taking a prospect from initial curiosity through the buying journey all the way up to the point where he signs on the dotted line and pays for the thing? That’s much harder to accomplish than to book a meeting.

Booking a meeting requires getting someone who looks right to give up a few minutes of their day.

Closing a deal involves convincing your prospect, and a handful of their peers, that exchanging thousands (or tens or hundreds of thousands) of dollars for your product is the best thing they could do right now.

It’s much, much easier to get half an hour from someone than to get thousands of dollars from them.

I looked back at everyone I’ve hired over the past 5+ years to see how many of them became sales reps, people responsible for closing new business.

The answer: less than half of them did.

Not just as a whole, mind you. If I look at each individual year and included all the reps I hired for an entry-level sales role, less than half are a closer today.

I can only imagine what’s going through your head right now. It’s probably a mixture of fear, confidence, and wondering, “What will it take for ME to become a closer?”

I can’t guarantee you that you’ll make it and become a closer. Nope. I wish it were that simple.

What I can do is tell you how to stack the odds in your favor.

First, commit to becoming a closer, no matter how long it takes.

The key to that statement is the second half: no matter how long it takes.

Nearly 5 years ago we unveiled a defined career path at Brafton. You spent your first 9 months as solely an SDR (we called them Lead Gen Reps, same thing). If you had been consistently hitting your numbers you were eligible to get a pay bump and get put on a track to sales. You stayed on the SDR team but in addition to booking meetings you took demos, built a pipeline, and worked to close deals. All you had to do to move into a closing seat fully supported by the SDR team was close a certain amount of business.

When we rolled this out I expected that sooner than later we’d have a pipeline of future closers fighting over the next opening.

It never happened.

Most of the reps who made it into the program would spend months learning the ropes, taking demos, building a pipeline… and then quit for another job.

What surprised me was that most reps left for a job that wasn’t a closing role. Heck, a lot of them left and took another SDR role. Some moved to client services or account management. A few completely left business to pursue another career path entirely.

So many of our best reps never became closers.

What’s just as interesting is that a number of our middle of the road performers, or the reps who barely made it to the sales track, did become closers. It was always the ones who took the job, realized they wanted sales but didn’t see it happening with us for one reason or another, and never gave up on landing a closing role.

You might be wondering, JV, seriously, how long is “no matter what it takes?”

One of the reps who worked for me years ago earned his way into the sales training track at Brafton. Eventually he felt he wasn’t going to earn a spot as a closer, so he left for a different SDR role. His new employer hit a much rockier spot than he expected and he jumped for another SDR role. When he realized he wasn’t getting a promotion there after a year? He took a break to search for his next job, and picked a different kind of sales process, hoping this would be his breakthrough.

He told me this week he’s getting his shot at closing deals.

Does this mean anyone can become a closer if you’re willing to stick it out for as long as it takes?

Honestly, no. Sales is a profession and certain talents make it far easier for some people. If you don’t have those talents then developing the skills you’ll need to be successful will be much, much harder.

If you have those talents though, yes, you can get there if you commit to it.

Odds are if you’re reading this the question isn’t, can you?

The question is, will you commit to playing the long game?

Are you simply focused on booking that meeting, or are you learning your craft?

Are you more concerned with getting promoted to an AE seat, or by making sure you’re successful if you get that shot?

Think about what that career transition is like. As I said before, it’s much harder to get someone to part with money than it is for them to give up half an hour.

Because it’s not about making the leap, it’s about landing and making yourself at home once you’re on the other side.

Stop trying to close prospects with every email

Yesterday I received yet another prospecting email following a familiar pattern.

Over and over I see this exact same pattern. The biggest mistake I see SDRs make is to constantly try to close for a phone call over email. Here’s what a 5 touch email campaign looks like:

1) Do a little research, name drop clients and results that border on impossible. Ask for a phone call.

2) Tell me all about this client that kinda sorta might be similar to me (not really) who got some absurd 447% ROI in a month and that if I talk to you for 15 minutes I might do the same.

3) Reply all to the first 2 emails with something you think is witty and I think is dumb like, “Did you get my previous email?”

4) Send me a case study, which you’re clearly tracking with your email software, and ask for another meeting.

5) The bus doors are closing, are you on the bus or are only the cool kids getting on?

In my entire career I have never supported my team to take every kitchy spam email tactic, slap them together across a handful of touches, and pray prospects raise their hand to talk to me. Why not?

Sales professionals focus on getting inside the mind of the prospect and figuring out how to help them out.

I feel that reps who use this strategy. have no idea that their prospects have a job to do. A hard job to do. One they clearly don’t understand, don’t care about, and won’t bother learning a thing about, because connecting the dots like that is hard and might not lead to booking another mediocre sales meeting. It feels good in the moment to notch the leaderboard, but who’s going to respond to these kinds of emails?

Prospects who are either looking for a vendor right now and probably want to use you to help them negotiate harder with their preferred choice… and bored people looking for a way to kill time, learn something, and look smart at the right moment because they can regurgitate some value prop from their vague recollection of your demo.

You know where the best prospects are? Researching options like you right now. And when you email them if you send them that crap there’s a reasonable chance they’ll gag over your pitch and move along to someone, anyone, other than you.

The fatal mistake reps make is thinking they’ve done just enough research, found a gold nugget, and truly personalized that first touch.

Unfortunately, most reps read a LinkedIn profile and don’t go beyond there. If you can’t research the company, stay up on some industry news, or pick up the phone to talk to some of the prospect’s colleagues, then why would you think the most public of all information is going to be the gold?

Then you launch the classic trigger, value prop, short client list, and close. That gold nugget isn’t a gold nugget, it’s not your way in, and it’s not going to get you very many meetings.

Let’s think about this from the prospect’s perspective for a moment.

If you’re in a store and someone walks up to you in a store and says, “We’re the biggest and best in our industry! Here are some random names of happy customers! Do you want to talk to me?”

How do you respond?

I know what’s going through my head: get away from me!

That’s your email strategy in a nutshell, except your emails are a little more polished and easier to swallow. If you’re doing this here’s the honest truth: you’re one misstep away from being the world’s most annoying retail salesperson.

Pitching them every time you reach out shows that you really don’t understand them. You don’t understand their needs, values, and priorities. You only understand how to ask them for their time and money.

Top reps have a formula: give value first, then ask, and focus on being the top of mind vendor when the time is right.

You might be wondering what I mean by give value if I’m literally saying don’t give your value prop.

Your value prop isn’t valuable to the prospect, it’s a short and sweet way of telling someone about you. You’re not asking what’s valuable to the prospect. That’s what I mean by give value first.

So how do you give value?

One of my favorite opening emails is to show the prospect that I’ve done research on them, their industry, and understand their likely challenges. Then I tell them I have a few ideas on those specific challenges and ask them if they’d like them.

This email requires considerably more research than looking up a LinkedIn profile. It requires a lot of time spent understanding a day in the life of that prospect.

The key to it, though, isn’t the research. The research merely gives me an opening. What makes this email work so well is that I’m merely asking if they want some ideas or not. It’s asking if they want to opt-in to a deeper conversation.

Those ideas I send? Often they’re spot on. They nail things the prospect would love to do, to solve, to fix, to create. And if the prospect is a good fit, those are things they are having a really hard time doing.

With two emails you not only establish yourself as someone who’s helpful, you’ve discovered whether or not you’re reaching out to a good prospect.

Another way I’ve used email to provide value is to literally take the prospect on a product tour from the perspective of similar customers. Establish the most likely challenges they’re facing and show them a different world. Showcase how things could be, and not only in a perfect scenario.

This is massively different from a value prop or customer testimonials, mind you. Your emails are short, have visuals, and put the spotlight on how your customers are able to overcome their challenges now. Odds are you’re sprinkling in ideas on how your prospects could do the same even if they don’t buy your product.

I know it’s hard to do this, because it means giving up control.

This is where reps have a really hard time. How on earth are you supposed to sell anything if you’re not focused on your value prop and your product?

Think about that for a second.

Do customers buy your product for its value prop… or do they buy a solution to their problem?

And if they’re buying it to solve one of their problems, then what’s the worst way to demonstrate what you have to offer? Offer ideas to help them solve their problems, showcase how customers have solved the problem, or state your value prop?

You ask for the meeting once you’ve established that you’re worth talking to and not a moment sooner.

Here’s the kicker. If timing is bad there’s a reasonable chance there’s nothing you, or any other sales rep, can do to change that. The important question to ask is, if things change down the road, who’s going to be in place to earn that business?

That’s right: the rep who provided value up front, time and time again.


What Kind of Sales Role is Best for Me?

If you’ve ever found yourself asking this question, don’t worry, you’re not alone.

Personally I’ve asked myself this a number of time. For most of my career I’ve been part of and managed Inside Sales teams. It’s been a good fit for me compared to my time in outside sales. Every time I think about returning to outside sales I remember all the perks and get dreamy about it before all the reasons I left outside sales start to creep up in my mind.

A lot of reps are curious about how the other half lives. It’s smart to be a bit curious about what else is out there.

Here are the most important things you should consider as you figure out what your next, or even first, ideal sales role would be.

First and foremost ask yourself, where are you in your sales career? This is crucial in understanding what options are open to you at this exact stage in your career.

Early Career

If this is your first Sales role you’re going to have to take a job where you do a ton of prospecting. It doesn’t matter if you get hired as someone who closes business or set appointments for the Sales team who closes business, you’re going to do tons of prospecting.

In my first Sales role I was responsible for developing and managing a geographic territory. What that meant was on day one I had exactly zero customers and zero leads. I had no professional network, either. The only was I was going to find new business was to research my territory for companies in our target industries and prospect into them.

The roles I interviewed for early in my career all had the same theme, whether the role was selling insurance, advertising, professional services, or borderline commodity products. Everyone told me to be ready to prospect a lot.

For most of the past nine years I’ve been hiring entry-level Inside Sales reps. The role? Prospecting. Appointment setting. I’ve overseen reps who made over 100 calls every single day to mainly cold leads. Two of my teams did highly strategic enterprise account development, which involves a lot of figuring out who you need to talk to and what they’d potentially be interested in. All of them spent most of their day prospecting into accounts.

I can tell you firsthand that it’s not glamorous work at all.

Why do companies start reps out making tons of prospecting activities? A few key reasons.

First off, companies want to weed out the people who want to succeed from the reps who want it to be easy. Sales isn’t easy, no matter how long you do it. If you’re not willing to prospect early on in your career then how are you going to be successful later on?

Because reason number two is that yes, odds are you will have to prospect into accounts for the rest of your sales career. No matter how good you get, no matter how cushy the company is, there are very few sales roles that involve zero prospecting.

Inside vs Outside Sales

Trying to describe the difference between inside and outside sales is difficult because there is no hard and fast set of rules. There are a few general advantages to each.

Outside sales reps typically have a home office and are constantly on the road driving. Your employer may provide you with everything you need to do the job, and they may not provide you with anything other than a territory and a quota.

Some reps have huge geographic territories and are constantly flying to meet with clients and prospects.

Most of your day you’re out meeting or trying to meet with people. There is a lot of flexibility in this type of role. If you need structure or struggle with planning, odds are you will fail in an outside sales role because your employer is going to expect you to be completely self sufficient and organized.

The role can also be lonely because most of your conversations are over the phone. If you live close enough to the office you’ll likely have a weekly or monthly meeting with the whole team there. It’s not all lonely, though. Your focus is meeting with prospects and clients, so you will have a lot of interaction with them.

When you’re an inside sales rep you go to work in an office. The company provides you with everything you need to do your job, just like anyone else in the office.

It’s a far more structured environment because your boss sits near you and everyone is working similar hours with similar territories. The sales team sits all around you as well. Have a question? Walk up to someone’s desk. It’s a far simpler set up.

This also means it’s hard to find a quiet place to make calls. You’re going to have most of your sales conversations in the middle of the sales floor, where everyone else sits and has their sales conversations. The sales floor can get very loud.

Working successfully in an inside sales environment requires a different kind of discipline to being an outside sales rep. Unlike an outside sales rep you wake up, get ready for work, then commute to work before starting your day. It’s easy to get distracted in side conversations. There’s always something going on in the office, whether it’s sales related or not.


If there’s one thing I can’t stress enough, it’s to make sure you sell something you think is interesting, useful, and that you’d sell to your own family if they were your prospect.

Keep that in mind as you consider what industries you’d like to sell in and sell to.

Most industries are fairly vague. Here’s a short list of industries: technology, industrial supplies, professional services, logistics, manufacturing, marketing and advertising, financial services, food and beverage, insurance, and transportation.

Can you name at least one company in each industry? I bet you can.

Now, can you name one more company in each industry that doesn’t compete with the first company you named?

How about a company that sells to each of the companies you named from all of the other industries?

Picking an industry is more complicated than merely picking what you sell, it’s also picking how you sell and who you sell to. All of those factors are going to affect your job. Let’s talk about each one a little more.

When you think about the industry you want to work in, you have to consider both what you sell and who you sell to. Let’s take healthcare for example. What do you want to sell in healthcare? Do you want to sell hospital supplies, medical devices, or the software the facility depends on to track their patients? All three are drastically different in sales process, who you sell to, and what your work is going to look like.

Sales process is extremely important to consider. There are tons of short sales cycle companies in almost every industry, and many of those same industries have products and services that an experienced enterprise sales professional navigates over a twelve month buying process.

Early on in your career you will be selling in shorter sales cycles, so don’t worry about which is right for you yet. You will have a chance to figure out what suits you best long-term once you’re proven you can sell.

Who you sell to is crucial. If you ever want to change industries, knowing the prospect you sell to is an easy way to make a case to a new employer that you’re going to be able to do well selling for them.

Trust me, it easier to go from selling professional services to marketers one day to offering marketing software the next than it is to go from selling software to marketers one day and then selling software to IT professionals the next. There’s a huge difference between marketers and IT professionals. You’ll have an easier time learning a new product than learning a new customer.

Focus on who you sell to. It’s just as important as selling something you like and would sell to your friends and family if they were the prospect. You can figure everything else out down the road.

Figuring out the kind of company you should sell for

One of the biggest challenges is figuring out the size company you should work for. I’ve worked for big national companies, in 100+ employee startups, in an established small company, and as a startup cofounder. They’re all dramatically different in their own ways.

What I recommend doing is to think about what kind of experience you want in your next role and work backwards from there. Key questions to ask yourself:

How much training, coaching, and mentoring are you looking for? What are the odds you’ll be successful without these resources?

How much structure and guidance do you want? Are you comfortable with ambiguity?

How fast do you want to advance your career? Are you more focused on short-term advancement or long-term career stability?

How much risk are you willing to take? What it mean to you if you don’t succeed in the job?

How much money do you want to make and how quickly do you want to hit that number?

Prioritize each of these. Why? Because there’s no sales role that has extensive training and coaching, tons of structure and support, a super fast career path, has a huge paycheck, and is extremely stable and secure. None. You’re going to have to pick what’s most important to you based on where you personally are in your career, what you want to achieve, how quickly you want to get there, and how much risk you’re willing to take on to make that happen.

Your priorities are going to change over time, which is perfectly normal.

Early in my career I was looking for fast career advancement and I was willing to take on risk. I had some amazing experiences, but I also found out firsthand what happens when you bet your immediate future on a startup and that company goes under. Personally, I’m glad I did that when it made sense for my career.

After the startup went under I focused heavily on skills development to set myself up for the next phase of my career. More recently I’ve been more focused on roles where I can see myself in them for at least 2-3 years. I’m sure someday that will change again and I might move back into a bigger risk/reward situation.

It’s all relative to what you want to achieve.

Hunting, Farming, Inbound, Outbound, Upsell, New Logo – What’s the Right Fit?

One crucial area reps don’t always consider early on is the kind of sales work they’ll be doing and how that will impact their future.

What do I mean by that?

Sales roles are not all the same. In fact, there are many reps with the exact same title with similar responsibilities, yet the actual roles themselves are significantly different in specific ways. These differences matter, both for you now and for you down the line.

The most important question to ask is, who are you selling to?

True sales roles will focus on selling to new customers. Sometimes it will include selling new products into existing customers, or selling into other business units in existing customers. You may be responsible for keeping your customers happy and get paid commissions if they continue to do business with you.

All other things equal, the biggest paychecks go to the sales reps who solely source new business. It’s the hardest sales role, hands down. You spend your days either trying to earn business by displacing a current vendor, or, if you really want a challenge, you do so by trying to earn business by showing your prospect they need to buy something they’ve never bought before.

Reps who close new business are faced with the task of changing someone’s mind completely. It’s a massive challenge, one that most new reps don’t appreciate until they’re trying to wrap up their first deal.

If you’re selling to existing customers – and only existing customers – you’re working on the client side of the house. Odds are you won’t be able to move to the new business sales team, because your job is nothing like their’s. Be cautious moving to a client facing role for too long if your goal is to close new business.

Now, the second most important question to ask is, where are your leads coming from?

Some sales reps do not source any of their leads as their focus is 100% on taking meetings from an inside sales (SDR/BDR/LG/etc) team and turning them into opportunities whenever possible. These are great organizations to get into as an SDR as they’ll often have a career path into a closing role. Plus once you’ve been promoted you’ll spend your days developing deals instead of chasing prospects for a first meeting.

For the reps who have to set up meetings, there are three kinds of leads: cold, warm, and BOFU (bottom of the funnel).

Cold leads are exactly what you think they are, prospects who have shown little or no clear signs of interest up to this point. It’s your job to generate enough initial curiosity and value that they’ll take an introductory meeting.

Warm leads are typically people who’ve requested some information from your company but have not requested a demo specifically. This could mean they downloaded content from your website, replied to a direct mail or direct response piece, or even emailed your company looking for some info. You have their contact information, yes. You do not usually have a perfect idea of their intentions and if they’re a good prospect or not.

BOFU leads are prospects who have raised their hands and requested a demo. These are the easiest leads to follow up on, by far.

Much like above, the most valuable and hardest skill set is developing cold leads.

There’s a shift happening now that’s segmenting reps who source cold leads from reps who source warm/BOFU leads as the difference between sales and client services. Companies are already making that a clear line in terms of your career potential.

My two cents on this: I’m all for this separation. The skills you develop chasing cold leads is lightyears beyond the skills you develop with warm leads. Why? Because you have to learn how to get the prospect to speak with you without a guaranteed conversation starter. I’ve seen a number of reps do great with warm leads and struggle with cold leads for this very reason.

One thing to consider for your career. If you realize you’re not a cold leads, new business, hunt and close deals kind of rep, then good for you. There are a number of career options still open to you that have sales aspects to them. On the flip side if you realize that hunting is for you make sure you take a hunting role. It’s much easier to go from closing new business to working with existing clients and warm leads than to go from client facing to hunting. Many companies will not take that risk because they know you lack certain base level skills that are essential to hunting and closing new business.

Sales Cycle: Transactional, Short, or Enterprise

I put this last because in a certain way it’s the easiest aspect of a sales job to figure out.

Start out by asking yourself what parts of the sales process you like the most. Are you someone who’s always looking for a way to build relationships, consensus, and get more people involved in a deal that seems to take forever to finally close? Do you prefer to be able to close prospects in one call and notch another deal on the board?

You may not feel strongly about one or the other. That’s okay. There is a wide spectrum of sales roles and you fit somewhere on it.

The key here is to always ask yourself what excites you about sales. What do you wake up and look forward to when you’re trying to advance and close a deal?

Your ideal role won’t necessarily stay the same. Over time you might find yourself leaning one way or another. You might start to want to spend more time developing deals. You may realize you need to constantly be closing deals so you can move onto the next one.

Reps who love closing deal after deal should look for sales roles with shorter sales cycles. This can be as short as one call. If you’ve never done that, think about the rollercoaster of getting a prospect to buy-in strong enough to say “yes” at the end of your first call. It’s quite a thrill!

Enterprise reps spend their days working on major accounts, meeting new people, finding their champion or mobilizer, building consensus, and steadily working towards a deal that often takes 6, 9, 12, or even 18 months. Some teams work on deals that take years before a decision is made. These deals are often hundreds of thousands of dollars, if not millions. Think about the huge sense of achievement you’d feel after working on a single deal for nearly a year to finally close it!

If neither of those sounds perfect, there are a lot of in-between sales roles. Many products need a little more time and effort to close than a transactional deal, yet don’t involve the complex development and buy-in that an enterprise deal would take.

Whatever path you go down, stay true to yourself and put yourself in the best position to succeed!

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The Best SDRs Don’t Book Meetings

Every time I hear the words, “I’m only paid to book meetings,” a small part of me dies.

Have you ever heard an SDR mutter that phrase? Drives me nuts. Especially since I know that same rep is going to pester me about getting promoted into an AE seat.

That AE seat is going to require a lot more skill than being able to just book meetings, along with a better attitude.

I know those words are often said partially in jest. I know where that feeling is coming from. The SDR team gets kicked around when the pipeline is low, then rarely gets a whiff of praise when sales crushes their numbers because of the SDR pipeline.

When I hear those words I simply wonder if the SDR understands that succeeding in sales means playing the long game.

Succeeding in sales means you have to be a helluva lot better than someone who just books meetings.

Nearly a decade ago I ran a direct marketing team for a tiny 12-person agency outside of Boston. When I say direct marketing, I mean we were almost all cold callers. We typically had a writer or a creative marketer for the team, but typically that person took the job because they’d learn about sales by cold calling.

We were unlike 99% of other agencies out there because we did two things together: appointment setting and company profiling.

When we’d kick off a new campaign we’d always tell the client, “Yes, we’re going to get you some great leads, and your sales team will close more deals. We typically find that at the end of our campaigns the information we provide our clients on everyone who said ‘no’ to us is more valuable than the leads we found for them during the campaign.”

I loved having those feedback meetings after the end of our campaign. We were often hired to develop a new industry or for a new product launch, which meant no one could teach us the nuances of how to target prospects. Nope. We had to write our own scripts and learn as fast as possible.

At the end of the 2-3 month campaign we’d review everything we learned and make a series of recommendations for them to carry out.

Client after client would say, “Wait, so if we do this and target them and say these things, we’ll do a ton more business?”

Guess who’d earn a much bigger campaign after that call.

Great SDRs focus on learning and understanding as much as they can about their prospects.

This is one of the keys to being successful in sales, too. If you can have deeper conversations, connect ideas, and understand your prospects with depth and breadth that’s well beyond a casual sales conversation then you’re going to win a lot more business.

Learning how to uncover what’s really going on inside a target account is more than simply a stepping stone into that AE seat, though.

The reps I hired at that agency worked for us came on board weren’t looking to earn an AE seat with us. There we no AE seats, and odds are you’d never earn a promotion. We were too small to offer that kind of career path. Our reps joined because they needed a steady paycheck for a while and could crush the phones, then they’d move on to something bigger.

We had a motto at that agency: make sure when you leave that this company is better than when you started, whether you’re here 6 weeks, 6 months, or 6 years.

Look at the opportunity that’s in front of you today if you want to figure out where you can develop new skills to make it more likely you’ll get promoted or land a job that’s a step up next time.

The smart reps know that if they take an AE seat that life will be harder. Getting a meeting is easy, when you think about it. Your goal is to get a prospect to take a half an hour sales call. Half an hour. That’s it.

An AE is trying to turn that half an hour sales call into the stepping stone to sell something that’s often tens of thousands of dollars, if not hundreds of thousands or even millions of dollars.

How can you make that first call even better for the AE?

That’s the question you should be asking yourself.

The top reps are always looking for ways to have a better call at every step of the sales process, both in terms of what is said and who they’re talking to.

I personally feel I got lucky working at that tiny agency simply because of who I worked for and what they taught me.

The founder of the agency got this idea because of two experiences he had. In the late 80’s he built a cold calling machine at IBM when he was responsible for launching their new AS/400 servers. What really happened is he took the half of the budget for advertising and sunk 100% of it into outsourcing a cold calling center, which was wildly successful. After that he joined Forrester Research when it was under 20 employees, helping the company land its first international clients.

He loved the idea of combining prospecting with deep research and felt it filled an obvious hole in the market, so he left Forrester to launch his own agency.

The company’s operations were run by a retired high school teacher who had taught sociology. She understood more about how to work with people than most business leaders because she spent more than three decades trying to open up the eyes and minds of teenagers to the world around them.

The pay wasn’t great, the deadlines could be brutal, and getting ready for big kickoffs or launches often meant a late night in the office to make sure we tied up every loose end.

It was like a bootcamp for developing leads and companies, and it was a blast.

Take a look at who you’re working with and ask yourself, when is the last time you set up a meeting that the AE came over and thanked you for it? How did it feel when that happened?

Focusing on little wins and incremental changes is the best way to develop your skills.

Think about the next role you want. What skills do people in that role have that you could spend some time working on in your current role?

Pick one and figure out how you can get a little bit better at it every day for the next few weeks. Ask your coworkers who are really good at it what they do.

Try things out, see how they work on the phone. Get feedback. Repeat.

If the only thing do is book meetings, how are you going to prove you’re ready to do bigger things?

One of the differences I’ve seen between people who progress in their career and people who get stuck is very simple.

People who progress in their career are focused on becoming the person they need to be in that next role. Those who get stuck are often focused on doing the things they need to do in their current role.

Let me tell you how I became the manager of the direct marketing team at that agency.

When I started there I wasn’t hired to run the direct marketing team, I was hired to manage the analysis of one client’s campaigns in somewhat of a consulting capacity. It sounded like an interesting career move, to still work in sales but not be the person selling all day.

On my first day the manager for the direct marketing team gave his notice.

Even though I was brand new I walked up to my bosses and said, “If you show me how to run these campaigns I’ll do it for the next few months while I’m trained for the job I was hired to do, and by then you can figure out a long term plan.”

I had NO intentions of running a cold calling team. That was the last thing on my mind. I didn’t want to cold call all day and be surrounded by cold callers, I wanted to do this interesting analytical work. It was bad enough I’d have to cold call with the team for my first few months!

Four months later the client changed the contract to a part-time analyst role and I was running the direct marketing team.

Here’s the interesting thing to think about: what would have happened to my job – and my career – if I had said, “Not my problem, for the next few months I’m only here to learn the ropes and book meetings”?

I hope you ask yourself the same question about your situation.

I’d love to know – what skills would you love to learn in the next 3 months on the job?


The Easiest Way To Tell If Someone Is A Top Prospector

Six months into my first sales job I was being grilled by my boss. He wanted to know everything.

Specifically, he wanted to know everything about every prospect and customer in my territory.

At this point all I had were some lists. I knew most of the prospects in my territory. I had called on them at least once. Some weren’t qualified yet, just suspects I kept hoping would pick up the phone, tell me how horrible their current vendor is, and beg me to save them from overpaying for a lousy product with no support.

This wasn’t going very well, though. I had hoped my visions of territory domination would be enough, along with my stunning rookie track record.

My boss didn’t want to know how well I had been doing, he wanted to know who else we could sell to and how we were going to sell to every single one of them.

He wanted to know what percentage I already had sold to and where I’d be in three months, six months, and in a year. Oh, and he wanted me to tell him what my plan was to hit those numbers.

I had no clue. About any of it. This was when I realized why my boss was so successful at what he did.

The mark of a top notch prospector is how well he knows his territory.

It was frightening how well he knew his territory. He could run through his prospect list with details on every meeting and conversation. He knew exactly where new businesses were opening that would be potential new business. As I listened to him I realized I had a long way to go as a sales professional.

I didn’t own my territory because I should have known my territory better.

Over time I put together a framework for me to follow while developing my sales territory. My framework covers the key things you need to know if you want to know, and own, your territory.

What does the top notch prospector know?

A top prospector knows who every single company in his territory that fits his customer criteria, whether they’re a client or a prospect.

This sounds so simple and yet it’s hard to do right.

A top prospector knows more than the name of every single company he could sell to. He knows the key contacts at each company. He knows who they’re currently using. He knows when they’re likely to reevaluate their current solution, why they bought it, and what he’d need to do to have a great shot at earning their business.

Because he knows all these things, a top prospector also has a plan of action to win the business. He has a realistic understanding of how likely it is he can win that business next time, too.

Knowing this, a top prospector understands which prospects are his best ones and which ones are going to be tough to win.

He also knows which customers of his are the least likely to stay with him, and why each one might change vendors.

Getting to this point involves a considerable amount of legwork. It’s crucial if you want to have a better chance of closing business than simply being in the right place at the right time.

A top prospector knows who is likely to be ready to talk in the upcoming months and what his plan of action is to earn that business when the time comes.

Think back to a time when you called up a company who told you they were wrong buying your competitor all those months ago and now that the contract was up it was yours.

Yeah, that’s never happened to me either.

However, there have been many times when I knew when I was reaching out and what I’d need to learn to figure out if – and how – I could earn a piece of business I didn’t win before. Often times I was the only vendor who stayed in touch after hearing “no,” giving me a huge upper hand if they wanted to change vendors.

Staying on top of companies in my territory earned me business when everyone else had moved on and forgotten about prospects.

Now, you can’t always do that. Not every prospect will talk to you when you reach out and keep you in the loop. What do you do when you haven’t been able to talk to a prospect in a while?

A top prospector knows who he hasn’t reached out to recently, when he’s going to reach back out, and why that’s the right time to reach out.

This is more than listening to the prospect when they tell you to reach back out in 6 months or a year. A top prospector will try and keep the relationship warm during that period, like I said before, and won’t wait that long to reengage with a prospect.

He has a system for following up on prospects who say “no”.

He has a system for following up when the prospect doesn’t pick up the phone or reply to an email.

The key to these systems is making sure you don’t prospect into an account too heavily when you don’t get traction. You should know how long you have to lay off an account when you’re shot down. You should know how long to stop calling after you’ve tried your hardest to get in.

Most importantly, you should have enough accounts to be able to call on enough businesses that you don’t feel the need to keep prospecting into the same account every single week.

How long should you wait? Long enough that it won’t feel like you’re bombarding the prospect with your calls and emails, and short enough that you won’t miss an opportunity if something changes. My rule of thumb is often 3 months when no one responds and 6 months if I’m told “no”. Your mileage may vary.

It’s important to keep reaching out because you’ll always need more pipeline, no matter how well things are going at the moment.

A top prospector understands he needs more than his current pipeline. He can explain how he’s going to develop pipeline this quarter and when that pipeline is likely to close.

He knows when his pipeline is going to dry up and how far in advance he needs to find some new opportunities so he’s always working active deals.

It’s tough to close 3 deals to hit quota when you only have 2 proposals. I should know, I’ve been in that spot. Those are tough months.

A top prospector understands that things will go wrong. Yes, sometimes most of your deals will come in and you’ll look like a superhero. Sometimes you get a surprise “no”, and your champion gets fired in that big one you were working, and then your 50/50 shots push to the next month.

That’s why you always need to know how much pipeline you need to generate before you wish you had it, and you do what you need to do to find it.

Spending a day frantically cold calling won’t fill the void, either.

You need a system like the one I described above to make sure you always have a list of prospects to call. One with notes from past conversations and a relatively good idea as to who is most likely to raise their hand now, so you don’t have to chase everyone to find a good opportunity.

The one thing that saved me when I had a bad month was the fact that I always had a list I was digging into to make sure my next month was better. Thankfully I had a great manager to learn from, who made sure that even though I had a bad month, even though I didn’t know my territory, I had a solid system to be able to prospect and make up the gap for future months.

And I had a top prospector to learn from.

What else helps you stay on top of prospecting and keeping the pipeline full? Leave a comment, I’d love to hear what you have to say!