The Lost Art of the Prep Call

Foundations of a Customer Meeting - Part 3

Apologies for the delay in closing this trilogy out. Sometimes it takes just the right event to inspire action...and boy do I have the right event for you.

We had a crazy cool opportunity - an existing customer wanted to use our technology to solve a problem that we hadn't even considered it could solve! The salesperson put the cart in front of the horse on several calls in a row, with my Solutions Engineers steadily raising concerns about the quality of our engagement with the customer. Gong recordings showed they were right. After a quick chat with my business partner, who also shared my concerns, I asked the salesperson for a prep call before the next meeting.

"Why? Everyone knows what they need to do."

"Maybe I'm just out of touch. What's our agenda for the next call?"

"We don't need one. We're going to get together and the customer is going to ask us questions."

"How do we know we have the right people on the call for their questions?"

"Sally and Fred are really good. We'll handle it." (Full disclosure - I suck at making up fake names for real people when relaying real events)

The salesperson wasn't budging.

But Sally and Fred were the very people who'd raised concerns about our engagement, so I ultimately had to demand a call if the salesperson wanted to use my team members.

Six people joined the prep call (never a good sign) and within a few minutes it was obvious that not only did we need a prep call for the upcoming meeting, but also a strategy session on the deal in general. There were numerous open action items, risks, and activities that needed to be completed for a deal that was supposed to close soon. Our 30-minute call went an hour and (against the desire of the salesperson) we shared an agenda with the customer.

It was a good thing we did - the customer heavily marked it up and sent it back! We quickly adjusted and held a fairly decent conversation with the customer. If not for that huddle, that next call would have been one more disaster.

Why Prep Calls Matter (Yes, Even When...)

Look, I get it. Nobody wakes up thinking "I can't wait to have more meetings today!" Like seriously, have you seen my calendar?

Everyone's juggling multiple deals, and adding another 15-30 minutes to the schedule feels like a tax on productivity. But here's the thing - prep calls aren't just another meeting. They're an investment that pays dividends in three critical ways. Let me walk through the most common objections I hear as a means of emphasizing their value.

"We're already all on the same page."

This is the most dangerous assumption because it feels true. Your salesperson talked to the champion. You reviewed their notes. Maybe you're bringing in someone from Product who understands the specific use case. Everyone did their homework, right?

That's where the danger comes from. We assume we're all aligned because we're all professionals and we've done our homework - customer research, reviewed the attendees, read the background materials.

Here's the issue - people can prep individually and come to the conversation with completely different ideas of what success looks like. In my example above, everyone on our side had different expectations and those were different from the customers.

What you gain: Prep calls surface hidden misalignment before it costs you. It's the only time your entire team articulates their assumptions out loud in the same conversation. You might discover you're perfectly aligned - great, a 5 minute call! Or you might discover you're headed in completely different directions - and now you can fix it in private instead of in front of your customer.

Take the time; maybe y'all are all good and the call is quick. But a 5% chance you're not isn't worth taking on a transformational deal!

"We've done this a hundred times - we can handle it."

I get it, this ain't your first rodeo. You've fielded hundreds of tough customer questions, run this demo dozens of times, and can think on your feet brilliantly. You're a superstar! But here's what experience can't replace: being prepared for every tough question this customer is going to ask.

Every deal has predictable objections, sure, but every customer has their own angle, perspectives, and priorities that matter in HOW we answer the questions.

What you gain: Prep calls let you pressure-test your responses before it matters. When you role-play the tough questions with each other - when the SE challenges the salesperson's pricing strategy, when the salesperson asks "what if they bring up competitor X?" - you're not just practicing answers. You're uncovering gaps in your story, identifying weak points in your approach, and aligning on how to handle the hard stuff.

The prep call is where you say "they're definitely going to ask about X because they have Y" and align on the perfect response together. Individual experience gets you in the conversation. Team preparation wins deals.

"Everyone's got their section covered."

You've each built your portions independently based on your understanding of what the customer expects. But in doing so, we all make assumptions on the content to deliver and what not to deliver as well as what the others will be covering in their sections. And let's be honest - when the salesperson sends out the combined deck with 40 slides from 3 different people, how often do you actually review it?

Individual preparation and team readiness are different things.

What you gain: Prep calls identify the gaps and assign the work. This is where someone says "Wait, do we have an answer for their data residency requirements?" and you realize you don't know off the top of your head. Or "How do we respond when they ask about implementation timelines?" and there's an uncomfortable pause on the line. Or "What if their CTO joins?" and you realize your current plan won't work for that audience.

The prep call is your last chance to discover what you're not ready for and fix it. After the prep call, everyone knows their role, knows what they need to prepare, and knows what gaps to fill before the customer meeting.

The Real Value of Prep Calls

A prep call forces you to articulate your plan out loud. To defend your assumptions. To admit what you don't know. To surface disagreements that are easier to ignore. It's uncomfortable to discover mid-prep that you and your partner aren't aligned or that your strategy has gaps.

But that discomfort is exactly why you need the prep call. Better to discover the problems in private than in front of your customer. The temporary discomfort of a difficult prep call is nothing compared to the lasting damage of a botched meeting.

The best prep calls aren't comfortable - they're challenging. You're pressure-testing each other, raising hard questions, and surfacing risks. That's not a bug, it's a feature. When you walk into that customer meeting, you want to know that your team has already asked the tough questions of each other so you're ready when the customer asks them of you.

So how do you run a prep call that actually does this? Let's break it down.

Part 2: The Anatomy of an Excellent Prep Call

Prep calls aren't rocket science so what I'm sharing here isn't different or unique and there are doubtless better approaches. Even if you use a different structure, the key point is to HAVE a structure for the call. This prevents everyone from just talking randomly for a few minutes, high five'ing, then going back to work. Here's the structure I use:

Timing & Logistics:

• When: 2-3 business days before the customer meeting
• Duration: 15-30 minutes for most calls (scale with complexity)
• Who: All attendees on our side

The Structure:

1. Introductions & Expectation Setting

Setting the upfront contract for the prep call itself and getting the small talk out of the way puts everyone in the right mindset:

• Personal introductions of each team member
• What we're trying to accomplish in this prep call

2. Customer Overview / Update

Bringing everyone up to speed on the state of this customer and this deal by reviewing:

• Background of the customer up to this point
• Who's who in the zoo - key stakeholders and their concerns
• Recent developments or changes
• Review our hypothesis for what the customer's perfect outcome looks like

3. Align on the PGA for the Customer Call

This is the heart of the prep call - align on Purpose, Goal, and Agenda (from Parts 1 & 2 of this series):

• Write down and discuss the PGA
• What gaps do we have in our PGA that we need to ferret out ahead of the call?
• Does everyone understand and agree?

Ensuring that everyone is bought into the PGA is the most important portion of the prep call!

4. Pressure-Test the Plan

We're challenging our approach & assumptions here:

• What could prevent us from reaching our goal? (risks and gaps)
• What assumptions are we making that we need to validate?
• What is the next best outcome should we not achieve our goals? (Fallback position)

This is the second most important section and the key here is to challenge each other! Better to make each other uncomfortable when it's just us than to be exposed in front of the customer.

5. Next Steps and Action Items

Make sure everyone knows what they need to do:

• What do we have to accomplish to be ready for the call?
• Who has what action item?
• Any dependencies or blockers?

The prep doesn't end when you hang up. One critical step before you're done: get that agenda to the customer. Remember from Part 1 how customer feedback on the agenda revealed gaps we didn't know we had? Share it at least 2 days before the meeting so you have time to adjust based on their input. Then follow through on everything else - action items, risk mitigation, gap-filling. A great prep call only matters if you execute on what you uncovered.

Part 3: The Importance of Role Playing

An often forgotten but valuable step in an effective prep call is stepping into the shoes of our customers through role playing. This turns generic preparation into being ready for questions that are SPECIFIC to the situation and the people we're meeting with.

Back in my days at a high growth startup, we'd create customer cards for key stakeholders in important deals based on what we know about them (think baseball cards) and spend hours pretending to be that person challenging each other…even acting like that person. By throwing the toughest curveballs we could think of at each other from that person's perspective we were well prepared for the much less hard questions they would actually ask.

Here's what makes role playing actually work: you've stepped into the shoes of the other person and start looking at the world through their eyes. The goal isn't perfect answers - it's finding gaps. The hesitations. The misalignments. The places where the answer isn't as solid as it needs to be. Finding those gaps now, when it's just the team, means they can be fixed before the customer exposes them.

So what does good role playing look like? Get specific with the customer context:

• "You're their CTO who has already shared that their current vendor burned them with unrealistic implementation timelines. How do we assure him we won't?"
• "You're their CFO who is going to have to justify this to the board during cost-cutting mode, not investment mode - push back hard on our ROI assumptions. By the way, she's a fan of their incumbent."
• "You're their security lead who just dealt with a breach last quarter - grill us on data protection and make us prove our security posture is bulletproof."

Notice the pattern? It's not "what if they ask about pricing" - it's "what if their CFO, who's under pressure to cut costs, asks how we justify being 3x the price of the incumbent system they've used for five years?" The more specific the setup - who's asking and why they care - the better the preparation. Incorporating their personal mannerisms that the team has observed? That's mastery.

Walking into that customer meeting after role playing like this changes everything. The worst questions have already been asked. Nothing catches the team flat-footed. Everyone has already aligned on how to handle the hard stuff. That confidence shows - and customers notice the difference between a team that's prepared and a team that's winging it.

Conclusion

Remember that opportunity from the beginning? The exciting expansion into a new use case with an existing customer? We did the prep call. We found the misalignment. We sent the agenda and the customer marked it up. We showed up prepared for what we thought would be a good conversation.

The customer was "kind".

Not angry. Not frustrated. Just... kind. Polite. Professional. They thanked us for our time, appreciated our presentation, and a few weeks later let us know they were "exploring other options." Honestly, they had already moved on before our last call, we just didn't know it yet.

We lost the deal. I'm still slow burn angry over the loss because it was completely preventable.

Here's the brutal truth: one good prep call couldn't undo weeks of misalignment and missed expectations. By the time I forced that prep call, we were already behind. The damage from the earlier calls - the ones where we showed up unprepared, where we contradicted each other, where we didn't have answers to their questions - had already eroded their confidence in us. The prep call helped us avoid yet another disaster, but it couldn't repair what we'd already broken.

That's why you can't wait to start prepping together when things feel off. They need to be part of your discipline from the very first interaction. Not a rescue mechanism - a standard practice.

So here's my challenge to you: make your next customer meeting different. When the customer invite is sent, schedule the prep call. Make it non-negotiable. A few minutes to align, pressure-test, and identify gaps. Do it even when it feels unnecessary. Especially when it feels unnecessary.

Because the alternative - a "kind" customer who politely shares that they're going in another direction - is far more expensive than the 30 minutes you think you don't have time for.