The Ultimate Guide on Handling “Send me an email”

The words every sales rep has heard a thousand times now: “Send me an email.”

In many sales roles this is the most common objection. Thankfully I’ve also found it’s the easiest objection to handle, as long as you understand 3 things.

First, you have to understand why you’re getting this objection. In some instances I’ve found that people genuinely want an email with more information as part of the buying process. Those prospects are becoming rarer, though.

Most prospects say it to get a sales rep off the phone (because it works, too). Why would a prospect say, “Send me an email,” if they had zero interest?

Reps often battle every other objection… because there’s at least a little bit of information in that objection. Asking for an email is the nice way of saying “no.”

If you’re calling someone who has little to do with what you’re selling, often times it’s their way of avoiding the dreaded “oh, can you tell me who handles that?” question because you’ll name drop them to their colleague and get called out for sending a sales hound on their trail.

No matter what the typical reason is, figure it out and understand what’s likely going through a prospect’s head before working on a reply.

Second, you had better be ready to hold your ground. One of the most powerful sales skills to learn is to value your own time. Too often I see sales reps willing to give the prospect anything and everything he wants without knowing they will get something valuable in return. Negotiating starts long before you talk numbers, and how you handle simple objections sets the tone.

If you’re going to be successful in your sales career, learn how to hold you ground better now.

Third, why would someone benefit from taking a meeting with you? The answer to this better not be “I don’t know, I just want to hit my opp creation goal,” or even worse, “It’s sales, it’s a numbers game, I gotta sell someone!” What’s the value in that first sales meeting? Do you offer some kind of demonstration or take away that you can’t easily package in an email?

Make sure you have something to offer the prospect, because no one wants to take a sales call unless they have a reason to be actively looking to buy a solution.

Let’s say you have a pretty good idea why your prospects ask for an email. Here’s how I’d handle each of those scenarios.

Scenario 1: A 30 second pitch lacks a big enough hook to get me into a meeting.

If you read this, realized your prospects simply need to take the time to get to know you and your company a little better before taking that next step, this is still a tough one. Hang onto your enthusiasm for a moment.

Let me give you my personal experience with this specific objection.

Nine years ago I took a job managing a direct marketing team and was immediately thrown into fire.

The agency’s newest client, a SaaS startup, had us test-calling into a major market for their initial product launch. We were targeting huge food production companies and distributors, and right before I started the agency had promised 5 meetings by the time our CEO had his first in-person progress meeting.

And the only rep who was getting any success was a part-timer. He didn’t know how he got the meetings, he just knew he scheduled them.

Then one day a week before that big client check-in, I booked a meeting. That afternoon I did the same thing and got another. Breakthrough!

I was conquering the email objection.

These prospects were at least somewhat interested in learning more. My issue was that I was talking about a technology no one had ever heard of or even fathomed. It sounded like one of those things that was too good to be true, if you get what I mean.

I couldn’t get anyone interested in taking a demo or a trial until I started using this exact script:

Me: 30 second pitch, then, “Are you interested in learning more?”

Prospect: “Yeah, could you send me an email?”

Me: “Yes I can, however I can do one better – I could set up a time where you actually get to see the product in action with your team in the room. That way everyone will get a really good idea whether or not this is something you want to look deeper into, and there’s no way I can send an email that tops a product demo that takes less than half an hour. If you’re interested in checking that out, could we set that up for next week?”

Why did this reply work so well?

The key to this reply is having a valuable hook in taking that next step, something you can’t offer in an email.

Let’s walk through another scenario. Maybe you can’t do a full product demonstration on the next call, but you have another hook prospects are interested in.

One team I managed had such a hook: specific industry examples. Prospects wanted to see the work we were doing for our clients, but because everyone does their own marketing on top of what they hired an agency to do there was no way of telling the difference. On top of that every client is different, so sending over examples was a huge time-waster for everyone since no one understood why we did specific things.

Many of my reps used a variation of the same email reply that worked extremely well:

Prospect: “Can you send me an email with client examples?”

Rep: “I’m happy to send over an email, and what I’ll do is have my colleague pull together some relevant client examples for a follow up conversation. That way she can walk you through not only the work we did for similar clients, she will also walk you through the strategy behind it, show you the kinds of results we delivered, and briefly talk about how this could work for your company. After that conversation she’ll send over the presentation so you have it on file. When could we set up that follow up conversation to walk you through the examples?”

This worked because we did customized projects for every client, which is hard to showcase in an email. We’d offer our more generic case studies and testimonials if a client asked for specific examples via email, because we know if they didn’t take a half hour call they weren’t a good fit.

Scenario 2: prospect wants to get you off the phone

This is the most likely reason someone is saying they want an email. Here’s the sad part: reps fall for this line every single day. Here’s what the conversation looks like:

Prospect: “Can you send me an email?”

Rep: “Sure, can I just confirm your email first? I have it down as topcontact(@), is that correct?”

Prospect: “Yes it is.”

Rep: “Great, I’ll send something over and follow up with you in a few days.”

Prospect: “OK, yup, bye.”

What are the odds the prospect responds to your email or picks up your call to talk about next steps? ZERO.

(Except for random acts of kindness, generosity, and pure luck)

Here’s what happened: the prospect set up the trap and you fell into it headfirst.

Remember, asking for an email is the nice way to say “no.”

My personal favorite way of handling this objection is to understand whether or not the prospect is or could be even remotely interested in what I have to offer. Before I go over how to do it, I want you to know there are two challenges using this reply.

First off, you need to adopt the mindset that your time is valuable and you don’t want to wast your time chasing bad prospects. I’m reiterating this point now because it’s that important. This is a crucial skill to learn as a sales professional. The more time you spend on good opportunities, the more successful you will be.

Second, you should frame this approach as “I’m only trying to help you, prospect.” The more you try to help the prospect and the less you try to combat the objection, the more likely it is you’ll get what you’re looking for. Don’t fight for what you want, help the prospect out.

Here’s the approach I use. I’m going to run through this approach multiple times so you can see how I handle each specific scenario, since the prospect can respond in different ways at each juncture.

Prospect: “Can you send me an email?”

Me: “Yes I can, happy to send something over. I’m wondering though, if you like what you see will you be willing to set up an initial meeting?”

Prospect: “Sure.”

Me: “Great. So I make the best use of your time, what would be the 1-2 key things you’d want to know about this to decide whether or not you take a meeting?”

Prospect: “I’d want to know about specifics X and Y.”

If you get an answer, often these are things you can explain on the spot. Do so and close for the meeting.

Me: “Great, I can give you some more details right now instead of you sorting through a long email reply to figure it out…. <explain>…. If I’ve given you enough insights and that suits your needs, I’d recommend the next step which would be a first meeting to discuss those things in depth as well as A, B, and C <and close>.”

Sometimes the prospect will respond with things you’d address in a first meeting. My reply would be:

Me: “Thanks for letting me know. To be honest, if I sent you over an email digging into these topics it would be so long you’d never read it. We’ve had a number of customers like you ask these same questions and the best way to address them would be a follow up meeting. I’d hate to waste your time with anything other than the best next step. If you’d like to learn more, <close for the meeting>”

If you read both of those replies carefully you’ll realize I’m focusing on being helpful and practical. I’m giving the prospect what she wants. It’s not in an email and that’s fine.

What I’ve done is made a simple trade in a negotiation. The prospect wants more information and I want to schedule a (good) meeting. As long as I deliver the details and she agrees they fit what she’s thinking, then it’s win-win if she schedules a meeting.

Things don’t always go that smoothly, of course. How do you handle those scenarios?

Let’s go back to the top. Sometimes you’ll ask that first question – “Would you take a demo if you liked what you saw?” – and you will get “no” or “maybe” or something other than a firm “yes.” How do you handle that?

I personally like to be direct without being pushy.

Me: “So you asked for an email and then you told me you won’t take a deeper look at this no matter what I send you. I have two guesses – either I’m barking up the wrong tree, or you picked up the phone hoping it was someone other than a vendor cold calling you. Am I right with either guess?”

Some prospects will hang up, some will admit they’re not the right person, and some might laugh a little or give you a few more seconds. If you get those seconds ask for a call back later:

Me: “I get it, I caught you out of the blue. The reason I’m calling you is because we’ve helped companies like yours solve X and Y, and I’d hate for you to say ‘no’ only because I called you at a bad time. I’ll let you go in a few seconds, I have one ask before I go. Can I get 5 minutes later today when things aren’t as busy?”

Often times you will get a yes with a time. If they give it to you thank them and send them a calendar invite for 5 minutes at that time. Typically they will pick up more than 50% of the time.

Then there are the prospects you get to battle.

These are my favorite. A lot of people hate using this technique because it’s an arm twister. I like a bit of banter. These are the prospects who say “yes” to the meeting and then ask for the most generic info possible.

Here are a few different ways you will hear this:

Me: “So I make the best use of your time, what would be the 1-2 key things you’d want to know about this to decide whether or not you take a meeting?”

Prospect: “Just a general overview will work, thanks.”

Me: “I could do that, it would simply cover the information I’ve already told you though and I’d hate to waste your time with it. Can you help me out a little? What’s the one thing you’d like to know before taking a meeting?”

Prospect: “Nothing in particular, I’m just looking for a high-level overview first.”

Me: “I understand, the thing is that I’ve already gone over what would be in a high-level overview email. So I can be as helpful as possible, can you tell me what’s missing at this point?”

There are dozens of ways of saying the exact same thing (and some prospects will do this a handful of times before finally giving you a real reply). Find one that suits you and typically you’ll only have to say it once to make it clear that you have no new info to give them unless they tell you a little bit more about what they are looking for.

It’s challenging to do this for a lot of reps, though. Focus on being helpful, respecting both your and the prospect’s time, and standing your ground, and you will have a tremendous amount of success with this objection.

There’s one thing I want to add real quick.

The hardest part about handling objections is that there’s no magic answer. Not a single reply will work every time. The name of the game is to get the best results possible from your calls, not to get everyone to say “yes.” If you keep that in mind and work on getting better it will be 100 times easier get shot down.

What’s your experience handling “Send me an email?”

What Hunter S. Thompson Taught Me About Sales

Reading Hunter S. Thompson’s “Fear and Loathing in Las Vegas” changed my life.

Not because he was a literary genius, or because the book was so funny I couldn’t read three pages without laughing hard.

I realized long before I got to the end that I wanted to know how much of this story was true and what was made up. How far did he really go before he started typing? Where did reality end before Hunter’s imagination began?

The book itself was a page turner, and the story behind it had me obsessed.

Around the same time I began to apply the same concept to my sales calls. What if I could create enough curiosity in a prospect that they’d take an initial demo? What could I do on a demo that would make them truly want me to keep going?

Most sales reps are focused on developing other things. Rapport, interest, buy-in. Are these things important? Absolutely.

However, there each one of those is missing something crucial. They’re all missing a human element. Something that compels a prospect to want you to keep going because they want to know what’s going to happen next.

That human element was something I had found in Thompson’s writing, which was finding it’s way into my sales conversations.

What do I mean by a human element? Let me give you some examples as to questions sales reps often ask that lack the human element:

“How do I give the best pitch?”

“What do I say when the prospect says they’re not interested?”

“How can I make a one call close?”

“What email trigger is going to get the prospect to say yes to a half hour meeting?”

None of these questions address one key thing:

What would the prospect love to know more about?

They’re all about how the sales rep makes the call and gets the result. Me me me me me!

Good question to ask: Who ends up making the buying decision, you or the customer?

Notice I said buying decision, not selling decision. Customers are the ones who buy things.

So why are we so damn focused on how do we make the people we want to buy from us do the things we want them to do? Why not focus on enabling them to make a smart decision around what we have to offer?

Yes, it’s frightening to think this way at first. Once you realize that’s the way it already is, the concept becomes a bit easier to swallow.

That first step down the process is driven by one of two things. Either the prospect is actively seeking to make a change, or the prospect is open to learning more about alternative ways of doing things.

Think about it for a moment if you don’t agree (skip this paragraph if you get it). When someone tells you about a solution that can help you out, unless you have a fully developed need, like a burning need where you need it fixed right this second, are you going to go buy it? No, you aren’t.

However, you might be curious about what it is, and you will be curious about something long before you buy it.

Therefore if you’re doing outbound prospecting of any kind, you’re going to encounter a lot of people who are open to learning more but aren’t actively seeking to make a change yet.

With that in mind, let’s take a step back and talk about what the purpose of a prospecting call is.

The goal of a prospecting call is to
1) Start to understand the prospect to see if your product or service can help them.
2) If it can, create enough interest so the prospect chooses to learn more.

Most training is focused on the first part, getting to know someone. In fact, a lot of sales advice is around rapport building, developing a relationship, and digging deeper into a prospect’s needs, wants, and desires.

So little sales training focuses on creating a conversation that the prospect actually enjoys being lured, even seduced, into having.

What’s missing is the soft skills that help you get the prospect curious enough to take the first step in the process.

It’s skipping over how to create enough curiosity that your prospect is actually engaged on your demo.

Too little is focused on the setting up and unveiling your proposal so the prospect is captivated, intrigued, and pleased.

Instead everyone wants to talk about the methodology on how to pitch a prospect on your first call. How to ask questions, likely after regurgitating 20 minutes of memorized product knowledge. Then how to negotiate price because the prospect doesn’t see the value in what you have to offer.

It’s not a coincidence that performance means both entertainment and results.

“Buy the ticket, take the ride.”
-Hunter S. Thompson

Prospects don’t want to be sold to, they want to go for a ride. No matter what happens they want to walk away with a story to tell, because that’s what everyone else will want to hear.

The first step is getting them curious.

You might be asking yourself, how do you define curiosity on a sales call?


Here’s how I think about it as a question a prospect would feel: “How are they going to do what they said they can do?”

That question has a bit of suspense and desire to it. Enough for the prospect to want to see what happens next.

If your goal is to set up an initial sales call to truly introduce your product, how can you create a sense of curiosity?

Biggest mistake I see is when a rep tries to dig into the product a lot in that first call. Why is that? Because if you give the prospect just enough information, often times they think they understand everything about your product and can easily say, “nah I’m good, thanks, I get it though!”

Seriously, how often does anyone fully understand a product in 5 minutes or less?

An engaged and informed prospect is much deeper into the buying process, whereas a curious prospect is ready to take a first look.

You’re curious if the restaurant your friend recommended to you is really good. You’re interested in dinner. That’s the difference between the two. People buy dinner but are curious about restaurants.

And you’ll go to the new restaurant if you want to tell the story of what it was like going there. Buy the ticket, take the ride.

Going to the restaurant for the first time is like getting someone to agree to and show up to a first demo. Becoming a regular is like turning them into a customer.

How do you translate this into getting someone to agree to a demo?

You need to create a gap between what they’re likely interested in and what you have to offer.

It’s how you tell a story. The hero wants glory, and he sees where it is, but he doesn’t know exactly what will happen on the journey between where he stands and where he’s headed. That’s why we read the story, to see what happens on the way there and once the hero reaches the other side of the gap.

If you’re wondering, how do I apply this to a SaaS offering? – great question.

Most SaaS products are things people already do, have, or spend effort on. They’re interested in sales analytics. They’re interested in having a central record for each patient that’s updated in real time. They’re interested in having an email platform that can send drip campaigns and track what the recipients do. They’re curious about what you do and how that might be better than what they’re already doing.

And they’re curious because of the gap between what they’re currently doing and what you’re talking about.

You need to find people who are curious about what’s out there. You need to target people who are interested in what you have to offer because they already value it. Interest leads to buying, and long before that curiosity leads to people taking a look. The whole purpose of prospecting is to get people to take a look at what you have to offer.

Think about what that gap is between where your typical customer is when she first talks to you and where she will be after she buys.

How can you articulate that? What story can you tell around it?

How can you frame the ride (demo) so your prospect wants to buy a ticket?

Once you can perform well enough to get ready to ask the prospect to buy that ticket and take that demo you have to ask them to buy the damn ticket.

How to close a demo is another post in itself, but let me leave you with one idea on what you can say. Yes, I’ve said this before – and if you’ve done everything right up until this point, if you’ve created a gap, if you’ve put on a bit of a performance, it can work.

Ask, “Are you curious enough to want to learn more?”

Because if you’ve done your job, it’s hard for the prospect to say no when she really wants to buy that ticket.

Ace the Interview Question “Where do you see yourself in 2-3 years?”

One of the most common interview questions you’ll come across in your job search seems pretty harmless. The question?

“Where do you see yourself in 2-3 years in your career?”

On the surface it seems like a question designed to help the interviewer get to know the candidate better. It’s like asking “what are your hobbies?” but in an interview setting, right?

Nope. This question is a trap, because there are very few great answers and dozens of bad ones.

Let’s walk through some of the most common bad answers.

1) “I’d expect to be in Management by then.”

This answer is only appropriate if you’re interviewing for a management trainee position or you’re already a few years into your career and see management as a logical option. For any other position you’re sending the wrong signals by saying this.

Wait, hold on! Doesn’t this answer scream I’m motivated and want to be promoted? Isn’t that the kind of person a top-notch company wants?

Think about it a moment. If you’re interviewing for an entry-level job and you want to be promoted to Manager  2-3 years into your career, who is going to be working for you?

That’s right: the people who take the entry-level job you’re applying for.

Next question: who’s currently responsible for that? The hiring manager you’re interviewing with. Which means you’re after her job.

Do you think a hiring manager wants to hire you tell them “I want YOUR job and I’m coming to take it!” while they’re personally interviewing you? Even if she is motivated to get to the next level, that’s how it comes across. It’s a targeted threat, and no one wants to risk their job by hiring a hotshot.

Now let’s go back to why you’d answer this way. Say you truly do want to get into management so of course you’re going to push to move into a managerial role as quickly as you can.

Have you considered what it would be like being responsible for managing entry-level employees?

How are you going to advance your career if the only thing you’ve ever done is an entry-level job or managed people doing an entry-level job?

Next question: have you realized that you’re going to be competing against your peers for what’s likely one opening, if (and it’s a huge if) that role opens up?

This is what the most sensible candidate is thinking.

Many candidates aren’t sensible, though, and the hiring manager knows this. She’s managed entitled reps who try to bend every rule to get ahead and whine when they have to stick to the program. She’s dealt with reps who think they’re amazing at their jobs for hitting 105% of quota every month, which is like thinking you’re an amazing student for getting a 3.1 GPA.

Passing on someone who’s likely to be a constant headache is 100% worth it every time to both the hiring manager and the team.

Especially for an entry-level sales role, where a bit of competition and bragging rights are the norm.

Worst of all it could be a signal that you’re not interested in the role you’re applying for. Great sales reps want to be selling bigger deals. Saying all you want is a management job makes the hiring manager wonder if you even want the job you’re interviewing for in the first place.

2) “Hopefully I’m running my own company by then.”

This one sounds ambitious as well, doesn’t it? On the surface it might, but it raises a massive red flag.

If you wanted to declare that you’ve already got one foot out the door before you even landed the job, this is the answer to give.

Trust me, as someone who majored in Entrepreneurial Studies I know exactly the feeling you’re describing. When you want to build your own company it’s something you can’t shake. It’s part of your soul.

But don’t bring up how badly you want to do something other than the role you’re discussing in the interview.

There’s nothing wrong with being ambitious and thinking you might jump ship in under 3 years. I personally co-founded a startup when I had been out of college for a little over 2 years. I’m thankful I started my career in sales and focused on that as much as I could for those first 2+ years until the right opportunity came along.

My first manager figured it out, too. He realized in my first year that I was not a career salesperson and some day I’d move on to do my own thing. Let your manager figure it out for themselves.

3) “I don’t know, I haven’t thought that far ahead.”

No one knows where they will be in 2-3 years. However, to have no thoughts about where you’ll be in 2-3 years would be shocking.

If you answer this way because you don’t want to admit the truth, whatever that is, then you should reconsider even applying to the job in the first place. Figure out how to get there and do something which gets you closer.

Let’s say for a moment you’re really not sure what you want to do in 2-3 years. How does this role fit in what you want to do in the next 12 months?

Look, we understand when it’s an entry-level job that you’re half guessing where you want to be in the next 12 months. Ask yourself, who do you want to become if things work out? What do you want to be doing? How does this role get you closer?

If this role requires experience and you’re not sure? That’s even worse. Good luck finding a hiring manager who’s dying to add a sales rep to their team who can’t say they see themselves in sales just 2 years down the line.

How should you answer “Where do you see yourself in 2-3 years?”

The obvious answer is to think one step above where this role is and give that as an answer.

It’s not necessarily the best answer, though. One way of thinking about this is to ask, what’s the question behind the question? In this case the question behind the question is, who are you right now and who do you want to become?

Having a level of self-awareness is the core of career development.

If you don’t know where you are and what you’re able to do right now it’s impossible to figure out where you could be in a month, a year, or a decade. You’re starting a journey without knowing where you started from. Even if someone gives you a map to where you want to go, how are you going to get there without knowing where you are in the first place?

So the smart answer is to start by figuring out where you are in you career and who you want to become in the next few years. Then explain how this job is a stepping stone to getting there.

Wondering what that hiring manager is really looking for? I’m giving away my guide to Ace the Interview right here!

Ace the Interview Question “What are you looking to do in your next job?”

Hiring someone for an entry-level sales role is a challenging task. Just ask any hiring manager and they’ll tell you the same thing: we all wish it were easier.

Why is it so hard?

Part of it is the fact that hiring decisions are made on candidates with very little experience for the job. The other part is the inexperience candidates have interviewing for a sales role. It makes our job tough to figure out who has the right mix of talent, personality, and drive, and who won’t survive their first year in sales.

What makes is worse is that every year I hear the same bad answers to common questions, especially from recent college graduates. These answers are cringe-worthy enough to prevent a candidate from ever getting a shot at an entry-level sales job.

The most common question I get a bad answer to is, ”Tell me about your job search. What are you looking to do right now?”

There are two answers that make me cringe every time.

Bad Answer #1: “The biggest thing for me is I’m looking to grow and learn.”

If that’s your answer, please, STOP.

There are two major issues with this answer coming from a recent college grad:

  1. Right now you have very few developed skills. College graduates have very little work experience to draw on, and sales is very different when it’s your full-time job. Even if you’ve been in a sales role you’re applying for an entry-level one for a reason, and that’s likely because you’re not ready for a more challenging sales role yet.
  2. Taking a job means you have to be able to produce something, not simply learn. That’s why you pay to go to college, whereas you’re paid to do a job.

Here’s the twist: I do want to hire reps who are looking to grow and learn. However, I don’t want to hire reps who give me the impression they’re going to spend their days learning and growing instead of making calls. Sorry, it doesn’t work that way. You go through training and you get on the phones within two weeks, tops. There will be coaching, call shadowing, mentoring, and even continued training, but the reality is you signed up for a job with a quota. You need to start hitting that quota, and fast.

So if stating you’re looking to grow and learn is important, but not a great answer in itself, how should you reframe this answer?

Start by answering why you applied for the specific position. Not the company, or your friends working there, or the free lunch. Why do you want to take on this role?

I’ll give you my personal answer from many years ago. I was highly focused on starting a company one day and I knew the two best skill sets I could learn were sales and management. Sales was my top choice and most of the jobs I interviewed for were sales roles. My answer was framed around my long-term goal and how that aligned with the roles I was interested in.

“As someone about to graduate with a major in Entrepreneurship, my ultimate goal is to start my own company some day. Right now my focus is taking on a role that fits my skills while setting me up so I’m more likely to succeed when I start my own company, because I don’t have a company to launch today. I believe Sales is the best way for me to achieve both of those things. I will have to be able to find and sell new customers. If I want funding or a business loan I will have to sell someone on the idea that putting money in my hands is a smart decision. I’ve also enjoyed being in a customer facing situation in some of my roles and internships throughout college, which makes me believe that I will be successful in a sales role.”

Notice I never said the words “I want to grow and learn,” yet I conveyed that was exactly what I was looking to do. Come up with an answer that tells a story as to why you want sales. Think about what you’ve done and what you’d like to do 5-10 years down the road.

Bad Answer #2: “I’d like to keep my options open right now and explore different things. I’m looking at Sales, Marketing, Finance, etc”

This answer is less common… and even worse than the first one.

Yes, it might be honest and yes, you might be looking at a number of career options. The problem is that it shows you’re at best uncommitted… and at worst you’re completely lost and will quit within 6 months.

Do you still not agree? Alright, let’s consider this answer from the hiring manager’s side of the table.

I have an opening to fill: entry-level Sales rep. The role will be challenging and not everyone I hire will make it past 6 months. In fact, if I do an amazing job 80% of my hires will ramp successfully and stay with me past those 6 months. On top of that if I hire you as someone who sets appointments for the sales team, which is the most common first job college graduates take in tech sales, your only career path is to become one of those sales reps closing deals. Only my best ever make it to that seat.

I also have a pool of candidates. Dozens of soon to be college graduates have been applying, in addition to people who have been out of college a year or two.

If you were the hiring manager, who would you be more likely to hire, the person who is “exploring options” or the candidate who is dead set on landing a SALES role?

I can hear a few people in the back saying, “but what about the candidates who have the most potential? Hiring top talent has to matter the most!”

It’s easy to fall into this line of thinking. Hire the best person, regardless of their career ambitions, train them right, manage them well, and they will do an amazing job.

I wish this were true.

There’s one common theme among the best Sales reps I’ve worked with in my career: they work hard. Really hard. They make more calls, send more emails, and work as large a pool of prospects they can without being stretched thin.

Talent doesn’t matter when the person sitting next to you wants it more and will do everything they can to succeed. Odds are they’re about as talented as you. Whoever pushes harder will have more conversations, learn quicker, and become the better rep. When your job involves getting rejected far more than you hear a “yes” then you have to be committed to succeed over the long haul.

Now, what if you’re considering two different career paths? Should you mention that you’re only considering two?

It depends on the answer to one key question: can you link the two together?

If you can’t link the two then don’t do it. Seriously, don’t do it. It might feel like lying or cheating but in reality if you’re considering two fairly distinct career paths then you’re better off interviewing for each role as part of a process to figure out which one you want to do. Then when you figure it out, only pursue that job.

Let’s go back to how to link two different jobs together. My personal choices were sales or a management training program. I’m going to reword my answer so you can see how I’d tie it together and still make it sound good for a sales role.

“My long term goal is to start my own successful business, but right now I don’t have a business to launch. I decided to search for roles where I’d develop the skills I’ll need to grow my own company. The two roles that make the most sense for me are sales or a management trainee position. Both require some similar skills as well: solving the customer’s problems, getting people to buy in to my ideas, and learning how to be a leader. I also know a lot of people who start their careers in sales eventually move into management, and a lot of people who start their careers in management training move into sales. My background really suits both paths because of their similarities as well, and I want to take on a job where I’ll be able to do well and be a valuable employee.”

Depending on which role I was interviewing for, I’d add one sentence about why that path was interesting to me.

As a hiring manager I’m going to want to know which path you’re more committed to. If this role is the way you’re leaning, say that you’d really want this kind of job over the other.

Will I never find a job if I keep my answer?

The truth is you will find a job eventually, as long as you’re willing to take an entry-level job.

That job will not be one of the best opportunities out there for college graduates, though. The hiring managers with the best jobs available get to be the pickiest, and there’s no way they will take a chance on someone who’s clearly not committed and focused. They will have great candidates fighting for those spots.

Take the time to write out a thoughtful answer to this question. You will hear it in nearly every interview because it’s one of the most useful and informative questions an interviewer can ask to determine if this person is worth getting to know or not. Practice it until you can say it in your sleep. Then you’ll be ready.

Should I ask “how are you today?”

There are a million bits of advice on whether or not you should open up a call asking how someone is. Almost every article I’ve read recently has heavily sided with one word: “never.”

I disagree with that.

However, there is one and only one way I’ve seen asking “How are you today?” effectively every single time. This technique is hard to do well. I’ve taught people how to do it, but even I prefer to not use it because it doesn’t suit my style.

Right now you might be wondering, if it’s hard to do well, why bother?

Because I’ve never seen anything break the ice as quickly and consistently as this technique. If nothing else learning it will help you understand how to conduct a better sales call even if you never use it once in your entire life.

Let’s start with how sales reps get asking “How are you?” wrong.

Most calls go like this:

“Hi Prospect, this is Jonathan with ACME Corp, how are you?”

“I’m fine.”

“Great! I’m calling because…”

Re-read that exchange one more time before moving on.

Now tell me, if you ran into a friend and asked them “how are you?” and they said, “I’m fine,” what would you answer with? My guess is answering with “Great!” isn’t even on the list, unless you and your friend live and breathe sarcasm.

It’s completely inappropriate to say that to your friend.

Yet this is what sales reps do, even veteran reps.

Here’s the worst part: most prospectors will have a low connect rate. Nowadays 15% is a strong connect rate. I’ve seen a lot of connect rates around 10-12%, and some are as low as 5%. The person at the other end of the line rarely picks up and instead of getting a real live human being they get a half-hearted “how are you?” followed by the sound of a canned pitch getting opened.

This is one major reason prospects are more than willing to tell you they’re too busy, to send an email, or that they’re they’re all set.

It’s why they’ll say they’re “not interested” after not listening to your pitch.

Prospects have no idea what they’re turning down and they don’t care. The name of the game is to get the pesky salesperson off the phone and get back to REAL work. It’s not their job to listen to you, it’s your job to earn a moment to speak with them.

If you’re going to ask “how are you today?” you better be ready to react to their response.

There are two key things you will have to do to make this work well.

First, your immediate response is crucial. You need to convey that you heard them. Not just their words but their tone of voice. Your response needs to be the same reaction you’d have for a friend.

Say the prospect picks up and says “I’m fine.” She sounds busy, rushed, and probably waiting to drop a killer “not interested” right as you wrap up your pitch so she can go back to anything other than talking to you. What should you say?

Start by acknowledging what you’re picking up on. “It sounds like you’re busy so I’ll be brief.” It’s a simple sentence, yet it let’s the prospect know that you’ve heard them, both their words and their tone.

Let’s walk through the exact opposite scenario to see what I mean by this.

If she picks up and says, “I’m doing great, how are you today?!?” Acknowledge how rare a treat it is to get a prospect who sounds delighted to get your phone call today.

“I’m doing well! You’re the happiest person I’ve spoken with today, I’m curious, what’s your secret?”

Have a little fun with it. Nothing over the top, just one good sentence.

The second thing you need is a pitch that fits both of these scenarios.

That might sound crazy to you, but it’s not. I know, these scenarios sound completely different. One prospect is busy and ready to run you off the phone, while the other one sounds ready to spend an hour chatting with you. Most of the time you don’t have to change anything.

The key is that what you say next needs to be short enough for the busy prospect in mind with a close that fits the scenario.

This is where so many people go wrong. This doesn’t mean you should have a one size fits all canned sales pitch, this means that where you take the call from here should basically be the same.

Let me give you two simplified examples I’ve used before.

“Prospect, the reason to my call is we help companies like yours get more leads and conversions organically through their website. Do you have just 30 seconds so I can give you a thumbnail sketch of that?”

Take a moment to walk through both scenarios in your head. Do you feel either prospect would be turned off by asking for 30 seconds? I know they won’t – if the prospect is going listen they will let you talk, and if they’re to hang up on you they’re going to end the call.

The second example to consider.

“Prospect, the reason for my call is we help companies like yours get better insights across their sales team. Our clients are able to manage their pipeline better to win more deals, quickly see areas to help individually coach their reps, and have the peace of mind that they will forecast accurately to the CEO and board members. I’m only looking for 5 minutes to see if this could be a good fit, so if now works could I ask you a few questions to better understand….”

Read the second pitch out loud and you’ll realize it’s short and to the point. If you’re busy you’ll feel like I gave you a quick pitch out of respect. If you were talkative I gave you enough value before asking for a longer conversation.

In both instances the pitch is short and to the point.

Fun question: are there any added benefits to asking “how are you today?”

Yes, there’s one. It takes someone an average of 18 seconds to disconnect from what they were doing when they pick up the phone before fully engaging in a new conversation. Asking “how are you today?” Gets the clock ticking in your favor.

In a world where no one picks up the phone, you need every advantage you can get.

Should I Steal My Colleague’s Pitch?

“Good artists borrow, great artists steal.”
– Pablo Picasso (supposedly, popularized by Steve Jobs)

A few years ago I started a new job managing a cold calling team. We agreed my first few days would be the same training program for new reps and I’d spend a couple days making calls so I could see what it was like firsthand.

When they handed me the pitch I didn’t see a mere pitch. I saw a short story. If this were an elevator pitch you would have needed to pitch in the Empire State Building, and the only way you’d finish in time is if your prospect was getting off on the 102nd floor and the door opened on every single floor.

All I could think was, “There is no way I can say this over the phone to a prospect and expect them to listen to the whole thing without cutting me off. Absolutely not.”

(I was wrong about that – on my second call someone not only listened, they bought almost immediately. That’s the only reason someone will listen to a lousy pitch, when they absolutely need what you’re selling.)

I took at look at the team to see how they were doing. A few reps were hitting their numbers, a few were around 80% of quota, and the lowest performers weren’t cut out for a high-volume cold calling role.

I couldn’t really help the reps in the wrong job, but it took me a few weeks to realize there was one clear difference between the top reps and those who were hitting 80%.

Why did it take weeks instead of a few days? It wasn’t anything easy to pin down. I realized the best weren’t necessarily the brighter reps. Nor did they work harder, or smarter. They didn’t do anything different from their peers except for one thing.

The top reps didn’t use the pitch they were given in training.

There was no consistent pitch between the top reps – it’s not like someone rewrote it, handed it to a few of their colleagues, and said “hey say this instead, it’s better.” Each one of them had streamlined the pitch into a few core points and added their personal style. They all sounded compelling, too.

It seemed so obvious to me that the reps hitting 80% should just steal from their colleagues… except it wasn’t obvious to them.

Within a few months everyone on the team was using a consolidated version I came up with. Which I basically stole from the top reps.

Right here is where you might think I’m going to say, yes, you should steal the top rep’s pitch. It’s not that simple. Here’s why.

About a year later we formalized the pitch again. This time my boss and I collaborated on a borderline masterpiece. We pulled out our best tactics, tweaked the weak spots, and fine-tuned the pitch until the structure of it was as good as I’d ever seen for a training pitch. Until my boss suggested everyone say it word for word.

It worked like training wheels, which is to say no one used the pitch word for word once they were two months into the job. They simply stole changes from one of their colleagues and made it their own.

You see, the perfect pitch isn’t one that someone else writes for you. The perfect pitch is the one you steal nearly everything and make a few changes that work better for you.

I had a rep who had her own version of the pitch that was shorter and worked great for her. She’d pull reps aside and teach them her pitch. It didn’t always work. However, it did show them what was possible, and they’d steal the parts they thought were the best.

By then I had learned that the best reps didn’t need to be given a magic pitch, they just needed to know what to keep and what they could change.

Unfortunately, using someone else’s pitch word for word comes with one caveat: odds are you won’t do as well as the person you’re stealing it from.

You see, that pitch has been perfected for the person using it. Specifically for her.

It likely needs some tweaking to suit you as perfectly. Not making tweaks to the pitch to suit you would be mistake #1.

However, mistake #2 would be changing the pitch without using it word for word, or at least trying to use it word for word. Most great pitches need subtle changes by each person using it. Too many reps overhaul the pitch in the beginning because it’s not comfortable.

The reason it’s not comfortable? Because you’ve never gotten used to it. That’s what comfort really is, getting used to saying something.

Back to the pitch they gave me when I was training. One day I heard the other Manager give his team feedback and suddenly he was saying the pitch word for word. It was perfect. I don’t think he should have taken out anything. That’s when I realized the pitch was exactly what he had said while he was a rep, and because it worked for him he figured it should work for his team.

Months later, when we were actively working on a revised training pitch we had a meeting with the CEO. He pulled out an old pitch he wanted us to reference. I read it over and asked him why he was giving me an altered version of the Manager’s old pitch. After all, we had already come up with a better pitch the whole team was having more success with, why would we go back?

The CEO said, “That’s the pitch I wrote years ago. The other Manager took most of it and made it his own when he was a rep, and when we promoted him that’s the pitch he used to train the team.”

I was not surprised one bit.

Which brings me to another point: if you have no one else to steal from, steal from the CEO. Odds are the CEO doesn’t have a pitch so steal the words he uses talking about the company.


Learning how to properly change a pitch well is an art form that takes a lot of time. What I can give you right now is the shortcut version:

Do your best to say the pitch word for word every single time you use it. Write it down and try to say it perfectly. I don’t mean read it or memorize it – try to say it word for word the best you can. This might sound easy, but it’s not.

That begs the question: how hard can it be to say a pitch word for word?

From personal experience, both my own and my team’s, the answer is: it’s almost impossible. It’s very simple as to why. You don’t talk exactly like that person! Yes, even when you’re the one writing the pitch down.

I wrote scripts for years at a direct marketing agency and on my best day I’d struggle to say every single word I wrote, even when I wrote what I considered to be a masterpiece. It’s really hard to nail the words so perfectly.

Even if you think you wrote it perfectly you will face this dilemma. You will have specific word preferences. There will be a twist you add. Maybe you hit the key points a little faster or you like to slide an extra phrase in that makes you feel right at home. You might change it based on how the prospect sounds when she picks up. Whatever the change is, it suits you better. It’s like wearing the same outfit as your style icon but with a specific accessory that you love and feel completes the look.

That’s what you’ll figure out if you steal the pitch and try to say it word for word. You will figure out how to change it just by using it.

When you say the pitch, write down the changes you’re making. Ask yourself, does this change work? Am I communicating the same message? It’s crucial you do this because it’s too easy to rework the whole thing and lose the essence of what made that pitch so good in the first place.

After all, that essence is precisely why you set out to steal the pitch in the first place.

Keep the essence and add a dose of your personality.

One favor: if you write a great pitch and see someone struggling with their pitch, or if they ask about your’s, please, trust me, let them use your pitch.