An Honest Way to Develop Empathy

Go buy something.

Go buy something. Today. Go visit your favorite clothing retailer, or your favorite electronics shop, or your favorite widget emporium. It doesn’t matter what you’re buying as long as you’re genuinely interested in the product. Put on your shoes—or at least pick up the phone—and go buy something.

While you’re buying, here’s what you shouldn’t do: judge how good or bad you think the sales rep is.

Here’s what you should do: focus intensely, deeply, wholeheartedly, on what it feels like to be a buyer.

Do you feel excited? Nervous? Bored?

Do you feel rushed to make a purchase? Do you feel like your sales rep is acting in your best interests? Do you feel like a purchase will make you better off?

Capture these feelings, and remember them, because these are the exact feelings your buyers have when they buy from you.


You hear a lot about empathy being important in sales. You need a high EQ, they say. You need to step into the buyer’s shoes, they say. And yet, too often, you hear this from sales gurus who do little but talk about themselves.

Most salespeople have heard it’s important to think in terms of the buyer’s interests. Those who act on this understanding are few.

In defense of sales gurus everywhere (and let’s be honest, in our own defense, too), thinking in terms of your own wants and needs is entirely natural. It’s no easy task to put your needs second.

“I just wanted to…”

“I’d like to…”

“I know that…”

“I was just saying…”

“I would love…”

“Personally, I…”

New sales reps, take note.

There is zero room in the sale—zero—for you.

Your sale is exclusively about your buyer.

These sales legends say it best.

“The word ‘I’ has no place in a sales presentation.” –Jerry Vass, Soft Selling in a Hard World

“The only way on earth to influence other people is to talk about what they want and show them how to get it.” – Dale Carnegie, How to Win Friends and Influence People

“Selling is no place to get your needs met.” – David Sandler, Best of Sandler

Be relentless in thinking in terms of your buyers’ needs. Be unforgiving in your use of “I”.

Here are a few rules you can use to stay focused on your buyer’s perspective.

  1. Never, ever, ever, start an email with “I”.
  2. Before sending an email, challenge yourself to see how many “I”s you can replace with “you”s.
  3. Never show your buyer a benefit that she didn’t ask to see. Just because you think it’s cool doesn’t mean your buyer does.

But these rules are only rules. They don’t mean a thing unless you genuinely understand how your buyer feels.

So go buy something. Soak in what it feels like to be a buyer. And the next time you propose next steps to your buyer, ask yourself, “If I were the buyer, would I say yes?”

Empathy will give you the answer.

Yours on the grind,


The Gatekeeper Is the Decision Maker

Let’s take the gatekeeper’s point of view.

Your job is to greet visitors and answer the phones. Your job requires some emailing, and you might be in charge of the internal company newsletter. When callers want to do business with your company, you direct them to the information that best addresses their inquiries.

Beyond answering the phones, though, as the gatekeeper, you serve a vital function: you are responsible for directing the flow of information throughout the company as efficiently as possible. You are the company’s ear to the outside world, and you are the voice of the company to those who call.

When a salesperson calls, as the gatekeeper, every time you must make a prediction: will the requested contact be happy to speak with this salesperson?

In other words, you ask yourself:

“If I call my boss and say John Smith with ABC Company is on the line, how will my boss react?”

The gatekeeper’s decision to put you through might look something like this:

  • “My boss will be happy you called.” ➡ Put the caller through.
  • “My boss will be unhappy you called.” ➡ Get rid of the caller as politely as possible.
  • “I’m unsure how my boss will feel about your call.” ➡ Ask the caller to send an email (the safe bet).

Of course, variations to this logic exist. For example, sometimes the “polite” way for the gatekeeper to get rid of you is to ask you to send an email that she knows your prospect will never read.

Now, with this understanding of the gatekeeper in mind, would you agree with the following rule?

When you’re speaking with the gatekeeper, at that very moment,
she is the decision maker.

Never fight the gatekeeper, because when it comes to putting you through to the eventual decision maker, she will have her way every time.

Sure, when you’re speaking with the gatekeeper, feel free to use an authoritative tone. Sure, impress that you have an important reason for calling. Respecting the gatekeeper’s authority doesn’t mean that you have to degrade your own.

But when the gatekeeper pushes back on you, don’t expect to “authority” your way through the gate.

Instead, consider a different approach.

How effective could you be if you treated your conversation with the gatekeeper like any other sales conversation? This would involve asking questions to understand the gatekeeper’s interests and the company’s interests. You would then position your ask—a conversation with the decision maker—as a clear boon to both.

What if you asked your gatekeeper how she decides whether to put a caller through? Or whether her company has a “don’t put salespeople through” policy? Or what topics she thinks might catch the decision maker’s attention?

At the very least, these questions would set you apart from the billion other salespeople who are calling.

If the gatekeeper pushes you to email or asks you to leave a message, she’s probably not ready to go to bat for you. That’s okay. Help her go to bat for you by understanding the decision maker’s business well enough that you can prove your call will be relevant. It might take 5 or 6 calls with the gatekeeper to get to this place.

To prove your call’s relevance, make it a goal to develop your understanding of the prospect’s business on every single call.

That’s right. No more, “Is Mary Sue there? No? Okay, thanks. Well please tell her I called.”

One more note for you.

Your relationship with the gatekeeper is unique. Unlike everyone else who you sell to, the gatekeeper’s job requires her to pick up the phone without fail.

When you dial your prospect directly, you might only reach your prospect 1 out of every 10 times. But when you dial the gatekeeper, you reach her every time.

Can you see an opportunity here?

How might being able to consistently reach the gatekeeper help you build a relationship? Knowing the gatekeeper’s name, any weekend plans, and having an inside joke at the ready will make your 5th and 6th touches far more likely to make it through to the decision maker. At the very least, the gatekeeper will pass your message along, and she might even add in, “Seems like a nice guy.”

“Seems like a nice guy,” sets you apart.

“Seems like a nice guy,” gets you noticed.

“Seems like a nice guy,” gets you a conversation with the decision maker.

Here’s a parting thought for you.

We often speak in sales about getting past the gatekeeper, or getting around the gatekeeper, as if the gatekeeper is an obstacle, a nuisance.

The gatekeeper isn’t a nuisance. She’s an important part of your sales call.

Let’s change our tune. Let’s talk about getting through the gatekeeper, where engaging the gatekeeper receives the respect and attention it deserves.

Offer the gatekeeper respect, understand her needs, and earn her friendship. You might find that the decision maker hops on the phone more often than you thought possible.

Yours on the grind,


A quick note on gender: the use of “she” in this article is consistent with its use throughout as a modern substitute for “he or she” or “one”. There’s no intention here to label the gatekeeper as a feminine role. Given the (too) colorful history of women in the secretarial role, I feel this clarification is important.

Respect Yourself

If you’ve been at the cold call grind for any amount of time, you’ve probably felt at one time or another that the grind can take a toll.

Tell me if you agree with this: one of the places that cold calling can hit hardest is your sense of self-worth.

Have you ever gotten off a call and felt like you were unimportant?

Can you think of a call that made you toss your phone down and go for walk?

Wait—take it a step further.

Have you ever gotten off a call and felt like your life was going in the wrong direction?

Cold calling is tough. After a few hard calls, it’s easy to get down on yourself. Remember, though, that when you get down on yourself, you, your prospect and your calls all suffer.

Your calls will dramatically improve if you implement strategies to keep your ego in tact day in and day out. “Ego”, in this context, doesn’t mean you hop on the phones like, “Look at me! I’m a phone god.” Rather, it means you should establish rules for what respect you will give yourself and what respect you will require from your prospects.

Your prospects will only respect you as much as you respect yourself.

Respect protects your self-worth, and from a practical perspective, it’s also vital to your credibility on the phones.

To make sure that you treat yourself with the respect you deserve, here are 3 principles to keep in mind every single time you pick up the phone.

Every. Single. Time.

Principle One:

You are in control.

Every second your prospect speaks with you is a second that you made possible. You placed the call. You introduced yourself. You asked your prospect about her business. When your prospect picked up the phone, you made yourself a part of her day. In a dramatic (but literal) sense, you changed her life.

Treat your control responsibly.

Did you know that prospects almost always ask for permission to end a call? No one likes hanging up on somebody. It breaks the conversational norms that we learned from our parents and teachers.

Sometimes prospects will signal with their tone that they’d like to hang up—listen for shorter, choppier sentences and lower, authoritative tones. Sometimes prospects will ask you outright to end a call. When a prospect asks you for permission to end your call, if ending your call will make you less likely to do business together, and if your service might genuinely help, don’t give permission. Let your prospect know that you both have more work to do, then ask her a question.

Not granting your prospect permission to end the call, in practice, might look like this.

Prospect: “Yea, I really don’t think we’re interested, but I appreciate you calling.”

You: “You know, Ms. Prospect, that means I probably failed to interest you. It means you have a business priority that I didn’t ask about, so I wasn’t able to draw a connection between your priority and our service. If we talk this out for a second, we might be able to find a connection, so let’s give this a shot: what would you say is your top priority right now when it comes to ___?”

Principle Two:

Your prospects are always looking to improve business—ALWAYS—and you might
be able to help.

Even status quo objections—“we’re good”—have layers to them. Who’s “we”? Every single person in your prospect’s company? If your prospect could have the results you’re promising for free, would she want them? If no, why not? Has your prospect ever championed a product or service like yours before? Would she even be capable of doing so?

A “no” means that your prospect perceives the cost of doing business with you to be higher than the value you’re offering. If you’re to truly understand your prospect’s “no”, you need to understand how she perceives both your costs and your value. Locate the roadblock. Is what you’re offering too expensive, time-consuming, or risky, or is the service you’re describing not helpful enough?

Principle Two reminds you that your call matters. You’re not a nuisance. You’re doing legitimate business.

Principle Three:

Your prospect can say “no”, but so can you.

If your prospect says, “Let me call you back tomorrow,” you don’t have to say, “Gee, sure!” Tell your prospect that it sounds like she’s busy and that most often, people forget to call back when they’re busy. Explain that you have 3 questions that you could ask right now to see if speaking later makes sense, and then ask one of your questions as an example.

Here’s what this strategy could look like in practice.

Prospect: “Hey, I’m swamped. Could I call you back tomorrow?”

You: “We can definitely set time to talk tomorrow. To be honest, though, it might not even make sense for us to talk depending on a few bits of information. There are 3 questions that if we tackle now, we’ll know whether talking tomorrow might be worthwhile. For example, do you currently use VoIP phones for your business, or do you use landlines?”

And with that, you can move right into your qualification questions.

Let’s conclude by refocusing on the why of this article.

Why should you use the 3 principles? What good will they do you?

The 3 principles are guideposts for a big picture rule of cold calling. The big picture rule is a little spin on the Golden Rule.

Treat yourself as you want to be treated.

Prospects will follow your lead.

When you receive respect on the phones—from yourself and from others—both your attitude and your performance will soar.


Yours on the grind,


Big Words

Have you noticed that the bigization of words is a growing problem in sales?

Here’s a theory for you.

The average sales development rep is younger than ever. More 20-somethings are selling to 40-somethings. If you’re a fresh-out-of-college sales development rep, the contrast in experience, achievement, and power between you and your buyer can be terrifying. As a result, reps use big words and dry, businessy language to try to gain legitimacy with their buyers.

Of course, however, big words won’t make you sound more professional. Instead, they add layers of confusion between you and your buyer—layers that make your conversation difficult to understand, layers that make your conversation less relatable, layers that can ruin your call.

How do you know if you might be going overboard with big words? Try this test.

If you’ve used the word “utilize” in the past week, you might be a youngin’.

If you’ve used the word “streamline” in the past week, you might be a youngin’.

If you’ve used the word “algorithm” in the past week, you might be a youngin’.


Sales expert David Sandler said it best.

Explain your solution like you’re selling to a 6-year-old.

As you explain your product’s value, push yourself to use words that no one could misunderstand. Your buyer should be able to understand what you’re saying so easily that she’s often a step ahead of you.

Your buyer should be able to finish your sentences.

In your sales conversations, when your buyer doesn’t understand what you’re communicating, there are only two possible outcomes. The better outcome is that she stops you and asks you to clarify. The worse outcome – and the far more common one – is that she pretends to understand and becomes less engaged with each passing second.

Avoid both scenarios with clear, simple, natural language.

To clarify, the point isn’t that you shouldn’t use smart vocabulary. If you’re looking for a word to describe the full set of the people who might be affected by a particular business decision, then “stakeholders” might be just right. But if that’s not the case, take a moment think about what you’re really trying to communicate. Most often, instead of “stakeholders”, the words “co-workers” or “people on your buying team” will do you just fine.

Consider a final example. Would you rather buy an innovative disruption engine or a phone that allows you to use the Internet wherever you go?

David Sandler got it right. Steve Jobs got it right. Simplicity sells.

Yours on the grind,


P.S. This article is coming to you from a tried and true youngin’. It took me too long to realize that talking about streamlined algorithms was hurting my calls. Hopefully, this article spares you some trouble.

Don’t Ask Stupid Questions

We’re all adults here. So let’s take a second to make sure we’re on the same page.

It makes perfect sense to teach our kids that there’s no such thing as a stupid question. It probably makes them more likely to engage in the classroom and ask for help when they need it. But since we’re all grown-ups, we can drop that old adage, square up our shoulders, and get real for a minute.930-1

Stupid questions exist.

We’ve heard them. We’ve asked them. And when they rear their tiny little heads on the phone, stupid questions kill calls.

As you practice asking insightful, targeted questions, see if you catch yourself asking any of these counterproductive questions instead.

The Child’s Why

“Why” questions are all the rage on the sales-osphere these days. And I wouldn’t dare hate on a good “why”. But then, there’s the Child’s Why.

Think of the “why” questions that kindergarteners sometimes ask – the ones that annoy the hell out of their parents. The ones that parents don’t know how to answer, because the question lacks fundamental understanding of how the world works. The ones for which there is no good answer.

That’s the Child’s Why.

Let me give you an example. Have you ever heard a cold call that goes something like this?

Prospect: “You know, there’s a lot of pressure right now to improve our top line.”

Salesperson: “I totally understand. Why is boosting your top line important to you?”

Prospect: *Uncomfortable laughter* “Because then we’ll make more money. What do you mean?”

Salesperson: “Yea, of course. Like how would that help your business?”

Prospect: “Are you asking me how making more money would help our business?”

If you use your “whys” strategically, they’ll help you uncover depth in your prospect’s pains. If you don’t, your prospect will perceive that you don’t understand her business. As a result, Child’s Whys can obliterate your credibility.

The Gotcha Question

Here’s a good rule of thumb: never ask any question to which you don’t genuinely want to know the answer.

Like the Child’s Why, The Gotcha Question comes from a good place.

Salespeople realized that when it comes to the buying process, prospects weigh their own words more heavily than the salesperson’s, even if they’re saying the same thing.

There’s a salesperson’s axiom that sums this up perfectly.

“Your prospect will believe 10% of what comes out of your mouth,
and 100% of what comes out of her own.”

Great axiom.

Now here’s where many salespeople go wrong. Your goal is to put guide lanes on the conversation, so your prospect’s speech is generally in line with the value you’re selling. Your goal is not to puppeteer your prospect into giving you the exact sentences you’d like to hear. The more attention you dedicate to subtle manipulation, the less attention you can dedicate to discovering real value that will solve your prospect’s pains.

Your conversation is not about what you want to hear. It’s about what the prospect wants to say. So take a genuine interest in what your prospect says, think about how it might relate to your value, and ask away.

The Backfire

The Backfire. This is a question where there are a number of answers that could hurt your case rather than help it.

Consider an example I noticed just this past week. A sales rep was presenting on his company, which had strategically decided to limit the analytics its software would offer customers. The analytics, the company determined, were more likely to distract from the company’s value proposition than bolster it. And yet, what did the rep ask his buyer?

“What analytics would you find most useful here?”

As you might expect, the buyer began asking about analytics, and down a rabbit hole they went. The rep spent more time backtracking than selling.

To avoid Backfires, make sure every question you ask passes the following test.

  1. Will your question lead to the product’s strengths?
  2. Will your question create positive momentum in the call?
  3. If the prospect answers your question negatively, will it help disqualify the prospect, or will it burn a potentially good lead?
  4. Does your question stem from a place of confidence or from a place of insecurity?

Strong questions will lead to your strengths, create positive momentum, further the qualification process, and come from a place of sincere confidence.


What’s the easiest way to ask better questions? It’s to stop asking stupid ones. Keep your eyes open for the Child’s Why, the Gotchas and the Backfires. If you’re able to remove these questions from your calls, your prospects will immediately treat your calls with more respect.

And for you, more respect doesn’t just mean a happier workday. More respect means more booked meetings.

Yours on the grind,


Your Ask

If you’re like many sales reps, making a strong ask might seem like the hardest part of your call.

After all, your ask is the moment when a single, well-phrased sentence could lead to a booked meeting with your prospect. A single, fumbled sentence could end your call. Sometimes, it feels like the build-up to your ask is so thick that—for just a split second—time slows down waiting for your prospect to answer.

And then…

“Actually, if you could just send me some information, that’d be great.”


This article introduces a strategy for making your ask the easiest part of your call.

Consider this: unlike most parts of your call, which require meticulous listening skills, nimble pivots, and a sensitive balance of persistence and respect, your ask requires none of these things. In fact, you can use the same structure for your ask every single time. After all, if you’ve gotten to the point of your call where an ask is truly the right move, then the hard work is behind you, because it will be obvious to both you and your prospect that an ask is the reasonable next step. All that your ask requires is that you incorporate the three S’s.

Simple, soon, and specific.

See if you can pick out three reasons why this ask—all to common—is weak.

“You know, there’s just so much more to our product that we really haven’t gotten into yet. What I’d really love to do is get some time on the calendar to dive into this in more detail.”

Before you keep reading, actually take a second and think about what you’d improve here. When you’re ready, see if any of the ideas below came to mind for you.

Here we go.

First of all, no one cares what you’d “really love to do”. Your ask should be about your prospect, not about you.

Second, “get some time on the calendar” fails to establish your solution as a priority. There are 365 days on the calendar. Pick one.

Third, “dive into this in more detail”. All this tells your prospect is, “We’re going to talk more.” How can you expect your prospect to give you a “yes” if you don’t make it clear what you’re asking?

Now consider this alternative.Woman in home office with computer using telephone smiling

“Because you care about improving pain X, do you have a few minutes available tomorrow to discuss a few strategies you can use to make that happen?”

Simple. “Because you care about improving pain X” is about as simple as it gets. You’re not selling trying to sell your product. You’re not describing features. All you’re doing is taking the challenge that the prospect posed to you, confirming that you understand its importance, and implying that the logical next step is a meeting.

Soon. If you usually ask to meet with your prospects “sometime in the next couple of weeks,” for example, your calendar will be filled with meetings 3 and 4 weeks down the line. If you usually ask to meet with your prospects tomorrow, however, next week’s calendar will be packed. This is known in psychology as the anchoring bias1, and it’s a shockingly effective way to create a sense of urgency in your sale. Also, did you know that a prospect that agrees to meet with you tomorrow is more than twice as likely to show up as a prospect that agrees to meet with you next month2?

Help your prospect keep your solution top of mind by scheduling for tomorrow, not for a month from now.

Specific. Tell your prospect exactly what she should expect if she says, “Yes.” A specific ask makes it easy for your prospect to picture what’s being asked of her, and as a result, easy for her to commit. A vague ask is scary, and most people say, “No,” to scary things.

Try experimenting with different asks keeping these three S’s in mind – simple, soon, and specific. Once you discover an ask you like, own it. Tweak it. Make it yours.

It won’t be long before your ask is the easiest part of your call.

Yours on the grind,



  2. According to independent data I collected (n = 81 meetings). January 2016.

The Upfront Contract

Why is cold calling is do damn hard?

I’ll tell you why.

Cold calling is so damn hard because your prospect hasn’t agreed to talk to you.

That’s why.

In fact, when your prospect picks up the phone, she hasn’t agreed to anything. She hasn’t agreed to be polite. She hasn’t agreed to listen. She hasn’t agreed to a freaking thing.

How much easier would your cold calls be, do you think, if at the start of every call, you began with the following rule in mind?

If you can compel your prospect to agree to something, no matter how small,
larger commitments will be more likely to follow.

Psychologists call this rule the “foot in the door” principle1.

You might feel like the whole purpose of your call is to elicit one big commitment: to convince your prospect to schedule a sales conversation with you. However, when you break down your call strategy, you’re really seeking a series of smaller commitments, aren’t you? The small commitments you ask of your prospect might include:

  • Allowing you to proceed with your cold call in the first place.
  • Honestly disclosing her business challenges and interests to you.
  • Agreeing that your product might align with her challenges and interests.
  • Opening her calendar.
  • Reserving time to speak with you further.

With this in mind, at the outset of your calls, seek overlap between these two categories of commitment:

  • What you would like your prospect to agree to, and
  • What your prospect will actually agree to.

This overlap forms your “upfront contract”—the set of rules you and your prospect establish for the remainder of your call.contract-1229858_960_720.png

And how do you establish an upfront contract? Baby steps.

For example, to begin your upfront contract, show respect for your prospect’s time by explicitly requesting it at the start of your call. Some cold calling experts also like to acknowledge that the salesperson’s call is unexpected. Some methods of requesting time include:

  • “Do you have a minute?”
  • “I know I’m catching you out of the blue here. Do you have a minute?”
  • “I know I’m an interruption. Do you have 30 seconds for me to tell you why I’m calling?”

If your prospect gives you the green light to proceed, ask your second upfront contract question (more on that in a sec).

If your prospect gives you a “No, I’m busy,” then try to engage your prospect by briefly stating the purpose of your call – which is to see if your prospect is involved in solving pain X – and ask when would be better for you to call back. If your prospect replies, “Some time next week,” don’t accept that response. Nail down a specific time to call your prospect, and tell your prospect that you’ll send a calendar invitation for 5-10 minutes on the phone so she can expect your call. When you call at the scheduled time, you’ll find that your prospect will pick up the phone about 50% of the time, and because you previously demonstrated respect for her time, you’ll start the call with a new level of mutual respect that will make genuine business conversation easy.

If your prospect gives you neither the green light to proceed nor a busy response (maybe you got, “It depends on why you’re calling.”), assume a green light. “It depends” means that your prospect is giving you the opportunity to earn her time. Respect that opportunity by proceeding swiftly with your conversation.

Never ask your prospect for time twice. Repeating a request for time undermines your confidence, wastes both of your time, and all but encourages your prospect to end the call.

When you ask for time, your goal is to show respect, not to grovel.

Now, onto your second upfront contact question. Relevance. Ask your prospect to confirm for you that the basic pains you solve apply to her. For example, you might say, “I saw your title online, and I figured that you might be responsible for training the new sales reps on your team. Is that right?”

There’s a side-benefit to this approach: your relevance question implies the purpose of your call, so in the previous example, when the prospect confirms that she’s responsible for training new reps, so also subtly agrees to proceed with a conversation in which training new reps is the topic.

Do you think that these two upfront contract questions – asking for time and establishing relevance – might help you keep your prospects on the phone and engage them in meaningful business conversation? If you hit the right balance between a) what you want your prospect to commit to, and b) what your prospect will actually commit to, you might be pleasantly surprised by the results.

Yours on the grind,