John Sterling

Do personality tests really matter? The answer is yes. DISC. Myers-Briggs. StrengthsFinder. All useful. But when I'm hiring a rep, I want to know their Kolbe. That's the one that shows me if they'll actually pick up the phone.

I had a rep once who was doing everything right on paper. Calls made. Emails sent. Pipeline full. Manager loved him. But he hadn't closed a deal in three months. When I sat down with him, the problem wasn't effort. It was that nobody had ever defined what "good" actually looked like past the activity numbers. He was busy. He wasn't progressing deals. That's not a rep problem. That's a structure problem. Most sales teams I see aren't blocked by talent. They're blocked by the fact that activity and accountability aren't connected. Reps know what to do. Nobody's built the system that shows them whether it's working. You can't coach effort. You can coach direction. If your team is busy but your pipeline isn't moving, the structure is the problem. That's fixable. Send me a DM and we'll take a look at it together.

What's something you believed about sales early in your career that you completely disagree with now? I'll go first. I used to think the best salespeople were the loudest ones in the room. Thirty years later I know the opposite is true. Drop yours in the comments.

Before every important meeting, do these three things: Know who you're meeting, not just their title. Understand their priorities, their pressures, what a win looks like for them personally. Know your numbers with whatever you're selling. Wether a product, a service, a business — be ready to answer any question without hesitating. Know what you want to walk out with, maybe that's a next step, a decision, a handshake. If you don't know what you're there to accomplish, you won't accomplish it. Preparation isn't a nice to have. It's a huge part of the job. The meeting starts before you walk in the room.

We were in a $10M deal that went down to the wire. Same product. Same price. Head to head with our biggest competitor. The CFO, a retired two-star Air Force general, had the final call. He didn't pick us because of the numbers.

Nobody gets trained on listening. We train reps on pitching, objection handling, closing. We coach founders on their story, their numbers, their valuation. But listening? We just assume people know how. They don't. The best rep I ever managed barely talked in a sales meeting. He asked a question, then got quiet. Let the prospect fill the silence. By the time he made his recommendation, the customer felt completely understood. He closed everything. Same goes for buying a business. The founders I remember most aren't the ones who had the best pitch. They're the ones who asked good questions and actually listened to my answers. Listening isn't passive. It's the most active thing you can do in a room.

The best first meetings never feel like meetings. They feel like conversations. No deck. No rehearsed answers. Just two people being straight with each other about what they've built, what they want, and whether this thing makes sense. I've been in sales for 30 years. I can tell within the first few minutes whether someone is talking to me or at me. Founders, you don't need a pitch. You need an honest story. Sales reps, your prospect doesn't want a presentation. They want to know if you understand their problem. Drop the performance. Have the conversation. That's where trust starts.

The biggest check isn't always the right deal. I've been buying businesses for a while now. And the thing I keep coming back to is this... the best exits aren't transactions. They're transitions. A founder spent years building something. Their name is on it. Their team is in it. Their customers trust it. That's not something you hand off to whoever bids highest. When I sit down with a seller, I'm not just evaluating the business. I'm starting a relationship. Because the closing is just the beginning. There's a transition, a handoff, a team that needs to feel good about what just happened. I want sellers to know what they're walking into with us. What changes, what stays the same, what we're building toward. No surprises. The deals that go well? Both sides felt like they were choosing each other. That's what I'm looking for.

The gap between good and great isn't always obvious. It shows up in the small stuff. How you handle stress. How you read a room. Whether you do the work or just go through the motions. Tag someone who needs to see this.

Recurring revenue looks great on paper. Until you see the churn. I've looked at plenty of businesses with strong contract revenue that were quietly bleeding customers out the back door. Annual contracts are attractive but churning at 20, 30% a year.That's not a moat. That's a treadmill. What I'm actually looking for when I buy a business isn't just recurring revenue. It's recurring revenue with a story behind it. Why do customers keep paying? Is it because switching is painful? Because the product solves something they can't solve another way? Because your team has relationships that go 10 years deep? That's what creates real value. Not the contract structure — the reason customers keep signing. Build something they'd never want to leave. That's what gets a buyer excited. And it's what gets you a premium.

Do you actually know why your best customers stay? Not your guess. Not "the product is great." What they would tell you if you asked them point blank? Most founders I talk to pause when I ask this. Longer than they expect to. That pause is information. If you can't answer it clearly, a buyer definitely can't. And that uncertainty shows up in the valuation. The founders who nail this question? They've actually had the conversation with their customers. Wild concept, I know. So let's hear it, why do your best customers stay? Drop it in the comments. I'm genuinely curious.

The moment you decide to sell your business, you become a salesperson again. And in my experience, most founders haven't sold anything in years. They've been heads down building, running the team, serving customers, keeping the lights on. Which is exactly what they should have been doing. But now the product is the business itself. And buyers need to be sold on it just like any other product. That means knowing your story cold. Not just the revenue number the why. How you got here. What makes customers stay. Where the real value lives. I've sat across from founders with genuinely great businesses who couldn't articulate why their customers loved them. Couldn't explain what made their product sticky. Couldn't tell me the one thing a competitor couldn't easily replicate. If you can't sell me on it, I can't buy it. You don't need a pitch deck. You don't need a banker feeding you lines. You just need to know your business the way a great salesperson knows their product. That's the whole game.

When the founder is the accountant, the salesperson, the support team, and the CEO — that's not a business. That's a job. And you can't sell a job. I've walked away from deals where the numbers looked fine on paper. Good revenue, real customers, product that worked. But every critical function ran through one person. Who handles the key accounts? The founder. Who knows how the system is configured? The founder. Who do customers call when something breaks? The founder. That tells me the business doesn't run without them. And the moment they walk out the door so does everything they're carrying. I want to buy something that can stand on its own. Something with a team behind it, not just a founder holding it together with sheer will. That's not a knock on founders who've built something real. It's actually the opposite. If you've built real value, don't let it be invisible to a buyer because it's all stuck in your head. Start delegating. Start documenting. Build the thing like someone else could run it. That's when it becomes something worth buying. And honestly, that's when it becomes a better business anyway.

Joe thinks asking for help is a sign of weakness. Junior knows the best decisions get pressure-tested first. One of them is still wondering why deals fall apart at the finish line. Which one are you?

Most founders lose the deal before diligence even starts. Not because the numbers are bad. Because the conversation was. I've sat across from founders with great businesses — real revenue, loyal customers, solid product — and walked away knowing we weren't going to do a deal. Defensiveness. Vague answers. A story that didn't add up. That's not a financial problem. That's a trust problem. And I can't buy from someone I don't trust. Here's the thing, I'm not just looking for a good business. I'm looking for the right founder. Someone I can work with through a transition, who's straight with me from the first conversation, and who cares about what happens after the close. That starts in the first 15 minutes. If you're thinking about selling, even years from now, the work isn't just cleaning up your books. It's learning how to show up in that first conversation. Buyers remember how you made them feel. Make it count.

The best salespeople I've ever managed had one thing in common with the best founders I've ever met. They listened more than they talked. Not because they were told to. Because they were genuinely more interested in the other person's problem than in what they had to say about it. In sales that gets you a second meeting. In business it gets you a company worth building. Same skill. Bigger stakes.

When I joined Datastream in the early days, we had 4 people and no real sales process. Just a product we believed in and a lot of cold calls. We were working hard but we were making it harder than it needed to be. The turning point wasn't hiring more reps. It wasn't a bigger budget. It was getting simple. Clear structure, a comp plan that actually made sense, and teaching people the fundamentals of selling instead of just throwing them at prospects. We went from 4 people to over 1,000. That didn't happen because we outworked everybody. It happened because we stopped overcomplicating it. The teams I work with today look a lot like we did back then. Small, growing, selling harder than they need to. No real structure, comp plans that don't align, reps who are willing but haven't been taught the basics. The fix is usually simpler than people expect. If that sounds like your team, let's talk. I have 2 spots open this month for new sales coaching clients.

Most reps hang up the first call with no plan for what happens next. Then they wonder why the deal goes cold. Before you get off any sales call, you should know exactly when you're talking again and so should they. Set it. Agree to it. Put it on the calendar before you hang up. Weekly checkins works best. And when you show up on time, every time, you're already telling the buyer something about how you'll run the relationship.

I want to hear from you today. Think back to the best follow-up you ever received from a salesperson — as a buyer. What did they do? What made it stick? Drop it in the comments. 👇

Most sellers walk into a meeting and spend the first 10 minutes talking about themselves. Their company. Their tenure. Their awards. The prospect is sitting there thinking: "When are we going to talk about me?" The best sellers I've ever seen flip it. They make the whole conversation about the prospect's problem — and they don't bring up their credentials unless they're asked. That's not a technique. That's respect.