Quick question. How many deals did you lose this year?

Not leads that ghosted after one email. Real deals. People who got on a call, saw a price, maybe got a proposal, and then said no. Or said "let me think about it" and have been thinking about it ever since.

Now the harder question. How many of those people did you actually call and ask why?

If you're like most owners I work with, the answer is zero. Maybe one, if you count the guy you bumped into at Publix who told you he "went another direction" while staring very hard at the cereal.

We spend thousands on ads to figure out what people want. We buy books on sales psychology. We hire consultants (hi). And the people holding the exact answer we need are sitting in the CRM marked "Closed Lost," and nobody asks them a single question.

That's nuts. And you can fix it this week.

My contrarian take for your Monday: your lost deals are worth more than your won deals. The people who said yes are biased. They already bought, so they want to feel good about it, and they'll mostly tell you what you want to hear. The people who said no don't care about your feelings. That's exactly why you need to hear from them.

So why doesn't this ever happen?

It stings. Nobody wants to dial a stranger and hear "your price was too high" or "honestly, the other company just seemed more organized." It's like calling your ex to ask what you did wrong. Educational. Also terrible.

You think you already know the answer. Ask any owner why they lose deals and you'll hear one word. Price. And they're usually wrong. Price is what people say because it's polite and it ends the conversation. "Too expensive" is the business version of "it's not you, it's me."

You think it'll be awkward for them. It won't, if you do it right. Most people are flattered to be asked. Nobody asks for their opinion on anything anymore except the survey at the bottom of the Home Depot receipt.

And you're busy chasing the next deal. That's the real trap. You keep pouring fresh leads into a bucket with a hole in it, and you never once look at the hole.

I've made a lot of these calls, for my own businesses and for clients. The real reason almost always lands in one of six buckets, and price is rarely the biggest one.

The first four are fixable. Number five is a follow up date on your calendar. Number six is either a positioning problem or a sign you're talking to the wrong people.

Picture a landscaping company that loses about half its estimates. The owner is positive it's price, so he's been knocking ten percent off every bid to stay competitive. Then he finally calls eight people who said no. Six of them say some version of the same thing: "We never heard back after the estimate."

The estimates went out by email and sat there. No call. No text. Nothing. He wasn't too expensive. He was invisible. And that ten percent discount was solving a problem he didn't have while costing him real money on every job he did win.

You only find that stuff out by asking.

Pull a list of every deal you lost in the last six to nine months. Not cold leads who never answered. People who got far enough to see a price.

If you run your pipeline in Go High Level, filter by your lost stage and export it. If your CRM is a spreadsheet and a pile of sticky notes, fine, start there. No judgment. Okay, a little judgment.

Pick ten to fifteen names. Mix them up. A few big ones that still hurt, a few you thought were a lock, and a couple that went silent for no reason you can explain.

Ten calls is enough to see a pattern. Twenty and you'll stop arguing with it.

Who makes the call matters. If you're the owner and you weren't the one selling, you're the perfect person. "I'm the owner and I'm trying to get better" opens doors a sales rep can't. If you were the one selling, it still works, you just have to try harder to make them feel safe being honest. Or get someone neutral to do it. A friend who runs a different business is a cheap version of a research firm.

Don't call out of nowhere. Send a short text or email first. Something like this:

"Hey Sarah, it's Dan from [company]. You looked at working with us back in August and went a different way, which is totally fine. I'm trying to get better at what we do and I'd love ten minutes of your honest feedback. No pitch, I promise. Would Thursday or Friday work for a quick call?"

Three things make that work. It names the time, so they know it's short. It says no pitch, and you have to mean it. And it says you're trying to get better, which is true and disarming.

Expect somewhere between a third and half to say yes, depending on how the deal ended. If someone says no, thank them and move on. Don't follow up on your follow up.

If they'd rather answer in writing, let them. Some people are more honest in a text than they'll ever be on the phone.

Fifteen minutes, tops. Record it if they're okay with it, and ask every single time, because some states require everyone on the call to agree. I use Fathom for this. It records, transcribes and pulls the highlights, so I can actually listen instead of scribbling.

Open like this: "Thanks for doing this. I'll keep it to fifteen minutes. There are no wrong answers and you can't hurt my feelings. I'd honestly rather hear the ugly stuff."

Then ask these, in this order, and shut up after each one.

Pay attention to question three. Sometimes the answer is "nothing." That's a huge insight. You didn't lose to a competitor. You lost to the couch, which means your real competition is inertia, and that's a whole different sales problem.

Question five is the money question. People can usually point to the exact moment. "When the proposal took eight days." "When your guy talked over my wife." "When I couldn't figure out what the $1,200 setup fee was for." That moment is your fix.

Question eight is the bonus round. It's where people finally say the thing they were too polite to say earlier.

A few rules.

Don't defend. Ever. If they say something unfair, say "That's really helpful, tell me more." Defending yourself on this call is like arguing with the ref after the game is over. You lose twice.

Don't sell. If they say they're ready to buy now, great. "I'd love that. Let me have someone reach out tomorrow." Then finish your questions. Pivot into a pitch halfway through a feedback call and you'll burn every bit of trust you just built.

Dig on vague answers. "It just didn't feel right" isn't an answer. "Totally fair. What was it that felt off?"

Thank them like you mean it. A $25 gift card or a handwritten note goes a long way. They just gave you consulting worth a lot more than that.

The calls are worthless if they turn into a nice folder you never open again.

Drop every transcript into Claude or ChatGPT and ask it to sort each reason into the six buckets, pull the direct quotes for each one, and rank them by how often they show up. I run both through Galaxy.ai so I'm not paying for five subscriptions. Takes about ten minutes, and it'll catch patterns you missed because you were on the call and your ego was too.

Then take the top two patterns and fix them. Not all six. Two.

What that usually looks like:

If speed was the problem, set a rule that every estimate gets a phone call within 24 hours and a text at 48 hours. Build it as an automation in Go High Level or Make.com so it doesn't depend on somebody remembering on a busy Tuesday.

If clarity was the problem, cut your proposal to one page. What you'll do, what it costs, what happens next. Put the fine print in an attachment for the three people who'll actually read it.

If trust was the problem, add proof in the middle of the process, not just on your website. A short video from a past client sent the day after the estimate. A one page case study about someone in their exact situation.

If fit was the problem, that's a marketing problem, not a sales problem. You're attracting people you aren't built for. Tighten up who your ads and content are talking to.

If price really showed up, check whether you're showing the value before you show the number. Or whether you need a smaller first step for the folks who aren't ready for the whole thing.

This next part surprises people. A good chunk of the folks you call will come back.

Not because you pitched them. Because you did something nobody else does. You called, you listened and you didn't get weird about it. That tells them more about how you'll treat them as a client than any sales call ever could.

And some of them went with the other guy, and it's not going great. You'd be amazed how many of these calls end with "honestly, we're not thrilled with who we picked." Leave the door open: "If anything changes, you know where to find me." Then set a reminder for 90 days out. Clay is great for this. It keeps track of who you talked to and nudges you when it's time to reach back out.

The timing is perfect right now, too. We're about ten weeks from the end of the year. A lot of the people who said "not right now" back in the spring are about to plan next year's budget. A thoughtful, no-pitch call in late October is the best thing that could land in front of them before that happens.

The week looks like this.

Monday or Tuesday: Pull your lost list and pick fifteen names.

Wednesday: Send the ask.

Thursday and Friday: Run the calls. Ten minutes each, fifteen at most.

Next Monday: Sort the answers and pick your two fixes.

That's maybe four hours of work. It's the cheapest research you'll ever do, and the only kind that comes straight from the people who already decided you weren't the one. Go find out why. Then fix it.

Talk Soon,

Dan

Dan Kaufman

Founder, Dead Simple Growth and Pinnacle Masters

P.S. Reply with LOST and tell me about the last deal you lost and why you think it slipped away. I'll tell you the one question I'd ask them if I were making the call.