How Entrepreneurs Who Hate Selling Close Sales

Or: How startups sell accidentally on purpose

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Do you enjoy the sales process? The cold calls? The awkward pauses? The millions of different ways to hear the word NO?

For many entrepreneurs, myself included, we’d rather have a series of root canals than pick up the phone and face the possibility of someone we don’t know laughing or swearing at us.

Yeah. I’ve had nightmares like that.

In building and selling products for over 20 years, one thing Ive learned about startup sales: There are several misconceptions about what a sales call should be — from first contact to closing the deal.

Here’s how to avoid the myths and start selling accidentally on purpose.

As a founder or leader, forget everything you’ve learned about sales. A colleague of mine, Ricky Spero, co-founder and CEO of Redbud Labs, puts it like this:

“I didn’t get or enjoy sales until I understood how structured and gamified it is.”

Don’t look at sales as your job. For you, it’s a game. And the game comes down to two basic strategies: Play the right competition and come prepared.

For the former, that means you’ll need to stop practicing. In other words, avoid these two major mistakes most entrepreneurs make:

  1. Don’t sell to friends, sell to strangers: A lot of entrepreneurs will try to sell in a comfort zone, calling on people they know in order to get a few suspected easy wins under their belt. Friends, family, and associates aren’t customers, even when they buy. In fact, I don’t even practice my pitch on people I know, because the feedback they give me will always be skewed.
  2. Don’t sell to fans: Using that same comfort strategy, entrepreneurs will usually pick target customers who they believe give them the best chance at a positive response. Most of the time, this isn’t the customer who can make a difference to your top line.

So don’t play unless there’s a chance to win.

Your first step is likely going to be a cold call, email, or some other form of digital messaging, so your first objective is to avoid the vibe and the jargon that turns most people off, including you and your prospect.

Be brief.

Your goal is to get the prospect interested in exploring the possibilities of making their life richer and/or easier. So do your homework ahead of time, make some assumptions about how the value of your solution will impact their problem.

Then remember that you’re not a salesperson. You’re the person who can solve their problem. Introduce yourself as the founder or leader or whatever it is you are, and get them interested in talking about their problem.

Not your product. Not your company. Not a sale.

You want to learn from them and explore the solution they need, not the one you’re selling.

The only way you’ll truly crash and burn is if you back yourself into a corner.

If you’ve got a winning script that you believe is your best chance to sell the customer, your objective becomes getting to that script when the customer is ready for it, and not a second before. If your best pitch results in a blank stare, you’re cooked.

Be flexible.

Your job isn’t to close the sale, it’s to solve the prospect’s problem. Be prepared with an outline that will guide the prospect through every possible variant of their problem, as well as all their potential objections. Let them lead the conversation, address their pain points, and lead them to understand YOUR solution as THEIR solution.

But be wary that you can be too flexible. I once sat in on a sales call as a favor to a friend of mine, this was like 15 years ago. She started her pitch with a version of the question: “Here’s what we do. How can we help you get more business?”

His response was: “If you have to ask me that, you shouldn’t be here.”

Now granted, the guy was an asshole, but he wasn’t wrong. Don’t fall into that trap. Lead with options, but be prepared to pivot based on what the prospect tells you they need.

An effective slide deck can close a sale on its own. An ineffective slide deck can nuke the entire sales call on its own.

Be visual.

There’s a reason why a picture is worth 1000 words. People generally tend to learn more quickly in a visual format. So it kills me when salespeople fill their pitch decks with an ocean of words.

There are some concepts about any product I build that if I wrote them out, it would take pages to get the point across. The same effect is usually made with a single image: A funnel, a chart, a diagram, even a photo.

This is what your deck is for, to educate visually, save time, and increase focus.

There’s one exception to this rule. You should always have a second version of your deck that you can email to a prospect as a PDF. This version should have the bare minimum words needed to make your visuals understood. Don’t overdo it, they should want to hear from you to explain more.

But no matter how few words you use, make sure your deck also focuses on the customer, their problems, their goals, and their solution. Stay away from feature lists and bragging about your company. You don’t have to lean on stats to make you seem legit. An understandable solution is the sincerest form of legitimacy.

Every sales call should result in a close, just keep in mind that close might not happen on your schedule.

Be patient.

I said before, the prospect will tell you when the time is right for your script. If that moment isn’t coming, you’ve got two options: End the call or keep listening and guiding.

Back to my colleague Ricky for how to gracefully deal with no.

“As soon as I see the call is headed to a no, I slip into customer discovery mode. What do you do? How do you do it? Why is that hard? It gives the prospect a graceful out, I learn something, and it almost always leaves the contact warm enough that I can come back later if I think there’s a better fit or there’s some other opportunity.”

When a sales call doesn’t result in revenue, it should result in one of two things:

  1. You have a reason to come back to this prospect at a later date with a new opportunity for a better fit.
  2. You’ve learned something about your pitch that is keeping you from closing.

A new opportunity for a better fit comes in the form of news or new feature or value-add to compel the customer to be further convinced that they need your product.

The lesson comes in identification of friction that you’ve added to your sales process to kick the close further down the road.

There are a few reasons why we entrepreneurs do this.

One is that fear and loathing of sales. We subconsciously put artificial road blocks in our own way because we never feel like we’ve successfully communicated more value to the customer than the dollar figure we’re asking them to commit. That feeling never goes away, so like any other fear, you just have to make the blind jump.

Another reason is that we see and hear a lot of bullshit about sales tactics and we feel like we need to use those tactics. That said, one sales adage that is always true is that time kills deals. Anything you’re doing to extend the time between first contact and deal close is working against you.

So again, imagine everything you’d have to change about your sales cycle to be able to close the customer by the end of the call. Then start thinking about what you can do to start removing the barriers.

The goal of these learnings is not to close every sale at the end of every sales call, but to reduce the time and friction necessary to close any sale.

Hey! If you found this post actionable or insightful, please consider signing up for my newsletter at joeprocopio.com so you don’t miss any new posts. It’s short and to the point.

Written by

I’m a multi-exit, multi-failure entrepreneur. Building Precision Fermentation & Teaching Startup. Sold Automated Insights & ExitEvent. More at joeprocopio.com

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