“I can’t believe I haven’t heard back from them. They loved our product when we demo’d it to them. They couldn’t wait to get their hands on it, they told me. Why am I having to follow up for the fourth time? This is driving me crazy!”

I hear the above a lot. The demo crushed. The prospect told us they’d circle back with their team to figure out when to schedule the next call. And then…silence.

The deal didn’t die because the product was wrong. Or the pricing was off. It died in the white space between two stages of your sales process.

 

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, we’ll cover the essentials needed for a sturdy sales process, and the factors to consider when you go about designing it. You’ll walk away with the necessary tools to start engineering your process from scratch, and the things to look out for as you take it to market for refinement. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your third installment.

Last time, we laid out the Lego blocks. The non-negotiables. The components every B2B sales process needs in some shape or form.

This week is about the synapse between steps in your sales process. And how to cross it to connect the stages together so the whole thing holds together.

Because here’s the thing: you can have every component right and still lose deals. Constantly. You’ll watch qualified prospects evaporate between stages. Meeting show-up rates that look like an empty restaurant on a Tuesday night. Agreements that sit in inboxes for weeks. And you wonder why your beautifully crafted process isn’t producing closed deals.

The answer is often the same: the connective tissue is weak. Or missing altogether.

So, let’s talk about it.

Selling the Next Step

If you’ve ever talked to me about sales for any length of time, you’ve heard me preach on this topic. Selling the next step is the bridge between the stages of your sales process. And this bridge has to be value-laden. Heavy with reasons the prospect needs to show up to whatever comes next.

Not, “Hey, can we get something on the calendar for next week?”

That’s not selling the next step. That’s begging for it. And it gets you exactly what pleading gets you in sales: maybe a meeting, perhaps a no-show, definitely no momentum.

Selling the next step means making the next meeting feel like must-see TV. The prospect should walk away from the conversation thinking, “I’d be an idiot not to show up to that.” Anything less, and you’re rolling the dice on whether they prioritize you over the seventeen other things screaming for their attention.

Let me tell you how I learned this lesson the hard way.

Enter Fitz

Back at Whitetruffle, the first sales hire I made was a guy named Chris “Fitz” Fitzgerald. I knew I’d recruited the right person within his first few days with us. Fitz handed me a book with a bright red cover, as he got to our sales desk one morning. “You’ve got to read this”, he said.

The book was The Challenger Sale. I devoured it over a long weekend. I now gift it to every new client that signs up for our coaching.

Fitz was a student of the game.

At this point, I had already built out our sales process from scratch. I had a playbook documented. We also had a go-to-market motion that overwhelmed me with sales calls. It’s why we hired Fitz in the first place. Part of his onboarding was handing him the playbook. Walking him through every stage, every script. And making sure he was set up to succeed.

A few weeks in, I noticed something.

Fitz had a no-show problem at our Account Optimization Call.

As context: the Account Optimization Call was a fancy name for our trial onboarding call. At Whitetruffle, we sold through a 14-day credit-card-activated free trial. The qualification call came first: a 15-minute conversation where I’d get prospects excited about the service and qualify them fully. From there, the Account Optimization Call was the forcing function that got them on our trial.

I’ll get to why that call came to exist in a second. But back to Fitz.

His no-show rate was hovering above 50%. Half of his qualified prospects were ghosting the very next meeting. We weren’t recording Zoom calls back then like we do today. We were taking sales calls over our iPhones. But Fitz and I shared an office. So I started listening to the back end of his qualification calls. Particularly the part where he was selling the Account Optimization Call.

Two things stuck out:

One. He lacked assertiveness.

Two. He wasn’t laying out the value of the next call clearly enough.

The prospect was asked to give up another 30 minutes. And they couldn’t fully see why it mattered to them. Why they’d benefit from attending.

Within a week or so, Fitz’s show rate went from sub-50% to 90%+. The industry standard you should benchmark against for any sales meeting that’s been booked.

His funnel was fixed. He started hitting quota. And he became a strong contributor to our sales team.

The whole episode was a stark lesson for me in just how much downstream damage a poorly-sold next step can cause.

Selling the next step is one example of a much larger principle: controlling the sale.

Losing control of the sale happens to the best of us. It’s interpersonal by nature, so it’s never fully controllable. But every degree of control you give up is variability you’re injecting into your sales process. And variance is the enemy of repeatability.

I learned this one the hard way too. Long before I hired Fitz.

Flash back to early Whitetruffle. I was tasked with building out our sales motion from scratch. I went to one of our silent cofounders, Mike Morrell — a mover and shaker in The Valley — for advice. Mike’s read? Perhaps we didn’t need a demo given our price point and the deal velocity we were seeking. “We might not need a full enterprise motion,” I remember him saying.

So I kept it simple. A 15-minute discovery call to get folks excited and fully qualified. At the end, I’d say something like, “Great, what we’ll do is send you a link to sign up for the 14-day credit-card-activated free trial. We’ll be monitoring your account during the trial, and we’ll reach out if we need to course correct. If you’re satisfied at the end of the 14 days, you’ll convert into a paying customer. You can of course cancel anytime during the trial.”

Sounded clean. Felt right. Should’ve worked.

Guess what actually happened?

Two-thirds of fully qualified, excited prospects never signed up for the trial.

For weeks, I was beside myself. Banging my head against the walls of our sales lab. These were folks who had told me, on the call, that they needed to hire engineers. That they had open reqs. That they wanted to get started. And yet most of them were vanishing the moment the link hit their inbox.

That’s when I had to accept one of the harder truths about human nature in sales: people don’t do what they’re supposed to do.

Even when it’s in their best interest. When they’re excited. Or when they told you, twelve minutes ago, they would.

It becomes our job to herd the cats. To tighten the screws. To control every variable we possibly can. Because anything we leave to chance is something the market might gleefully steer away from us.

As a last ditch attempt to stop the bleeding on my hemorrhaging funnel, I instituted the Account Optimization Call. The same one Fitz would later have to learn to sell properly. The pitch was: this is a 30-minute call where we walk you through the product in your own trial instance and set you up for success for the first 14 days and beyond. You hold onto the wheel. We guide you through the product in real-time. And by the time we’re done, you’re fully briefed on every bell and whistle of the service.

It worked. Overnight, fully qualified prospects were now showing up to our scheduled Account Optimization Call.

Here’s the kicker. About a third of the people who showed up to that Account Optimization Call hadn’t yet started their trial. Their credit card information hadn’t been entered. So I’d say, “No problem at all. We’ve got 30 minutes. More than enough time to walk you through the product. Why don’t you grab your CFO’s credit card. Or use your own business card if you’d prefer. Sign up for the free trial right now and we’ll get you set up.”

Our funnel was instantly fixed. We had just found a way to control the sale.

Selling the next step and forcing functions like the Account Optimization Call are just two of several things you can institute to control the sale. Let’s run through some others.

Recruit all stakeholders to the group product demo. Assuming you obtained the buyer journey during discovery (and you did, right?), you know who the stakeholders are. You know who’s going to weigh in on the decision. Who controls the purse strings. Now, you’ve got to get them in the room for the product demo. Each stakeholder has different pain points. Different concerns. Different reasons that might block or champion the deal. The demo is your shot to address all of them at once. Don’t waste it by demoing to your champion alone and hoping they’ll relay your message faithfully. Make sure you can expose all of your stakeholders to your product’s value.

Book the onboarding call before the agreement is signed. This one is where I see folks consistently leave money on the table. You get the verbal close at the proposal review. Prospect’s agreed to move forward. Junior rep’s instinct? Send the agreement. Wait for the signature. Then book the onboarding call.

No bueno.

Book the onboarding call, as a kind of double close, and then send out the agreement for signature. Make the onboarding call the forcing function for the signature. “Great, I’ll send the agreement over today. Let’s get the onboarding call on the calendar for next Tuesday so we can hit the ground running. We just need the contract executed before then so our implementation team can prep and take care of you guys from here on out. Can we make that happen?” You’re obtaining a commitment from your prospect that the signature will be done by the time you meet next. Without it, agreements sit in inboxes. And time, as you’ve heard salespeople say since the dinosaurs roamed the earth, kills all deals.

Arm your champion when you can’t get in the room. I don’t love having someone else sell on our behalf. But sometimes you can’t get the CEO, the CFO, the big boss in front of you, no matter what you do. When that’s the case, you arm your champion with everything they might need to represent us well. ROI calculator they can run their boss through. Marketing collateral tailored to the decision maker’s concerns. A one-pager addressing the specific objection you know is coming. Whatever you’ve learned about the decision-maker during discovery, build the ammo to match. Your champion is going to walk into someone’s office and try to do your job for you. The least you can do is give them a fighting chance.

Drive the success narrative during a pilot or free trial. This one deserves its own episode — and it’s getting one next. For now, just know this: if you’ve got a prospect in a paid pilot or a free trial, you can’t afford to let them define success for themselves. You drive that narrative. More on that in our next installment.

That’s enough for this week. We covered the connective tissue between the steps of your sales process — selling the next step — and the broader discipline it’s a part of: controlling the sale. As mentioned above, next episode, we’ll zoom in on something that determines whether your pilots and free trials ever convert into paid contracts: driving the success narrative. Most founders assume the product will speak for itself during a trial. And yet, the customer comes to a verdict. And if you’re not the one shaping it, someone or something else will. We’ll get into how you can provide expectations. All while talking about one of my favorite topics: restaurants. See you soon.