Sales and dating

There was an executive at a company I wanted to work with so badly I day-dreamed about it endlessly.

The main challenge was that I didn’t know them, so I stalked them on socials to find out which industry events and conferences they were attending, and I showed up at every single one too.

Here are 3 stages of a sale, and what each one looks like done well and done badly.

The awkwardness is nearly identical in both worlds. You’re interrupting someone who didn't ask to be interrupted, and you can feel the cringy moment in your gut when you realize you might be the person they’re hoping to escape.

In dating, it's the job title, salary, the workout routine, and the summary of your last 3 relationships. In sales, it’s the awards, the logos you have worked with, the years in business, and your special way of doing things different than your competitors, all said before the other person has been given a reason to give a crap. Credentials are what you reach for when you have nothing true to say about the person in front of you, which is exactly why I was wearing mine around my neck.

Not “you’re so beautiful,” which could be said to anyone in a crowded bar and gets nothing but an eye roll in response. A remark about the book they’re carrying, or the thing you overheard them say to the bartender, while not perfect, at least proves you were paying attention. In outreach, that’s why “I really love what you are doing” fails, because it invites the reply “oh yeah, what exactly do you love about it?”, and if you don't have that answer, it’s just more spam in the inbox. One credible observation about their business beats 4 paragraphs of introduction.

Effort aimed at yourself reads as performance. On more than one occasion, an agency showed up with a bloated proposal and a beautifully cut sizzle video, you could see the hours that went into every page and edit. To be honest, it made our decision harder, because the argument of why them was buried, plus it was painfully clear the founder had frame-f’d every element. They set out to show us everything they could do, and what came across was how high maintenance they'd be to work with.

Other agencies came into the pitch and let the right people present the right parts. The money person took the ROI question, the tech lead took feasibility, and the account manager took brand and operations. The founder was obviously still in charge but didn't need to prove it by answering everything herself. The proposal was short, the answers were clear, and they won the contract. I’d assume both agencies had put in the same effort behind the scenes. But one aimed at us, and the other aimed at themselves.

You don’t ask someone to marry you on a first date (at least not in this century). What got me comfortable with cold approaches was shrinking the goal. I’m not trying to close anything. I’m trying to find out whether there’s a conversation worth continuing, and that one adjustment changes how long you talk and how fast you let them speak.

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Everyone knows this date. You answer their question and watch them wait for you to finish so they can get back to their own material. 90% of discovery calls are that date. The owner logs on to Zoom knowing what they intend to sell, asks about the challenges, waits for the phrase that connects to the offer, and starts presenting.

You can't tell whether someone is listening just because they look attentive. You can tell by whether anything they hear changes what they’d say next. If they raise a priority you hadn't considered, you follow it there instead of steering it back. If your explanation doesn't land, you stop advancing the script. If their answer proves your assumption wrong, you say so while you’re still in the meeting.

On a date, it’s the exes who were all somehow crazy and to blame. Your date has never once been at fault in their own story. For an agency founder, the blame for a project gone wrong is the exec who can’t make the call, the five people who give feedback with nobody deciding, or a deadline that can’t move sitting next to an approval process nobody can hurry. Never their firm. What people leave out tells you more than what they volunteer.

Nobody wants your origin story at hello. They want to know why you see things the way you do. When people ask me why I do this, the answer is short. I sat in the buyer’s chair for decades and watched talented agencies lose because they made the decision hard, and then I built an agency and made every one of those mistakes myself under pressure. So I mentor founders who are excellent at the work and have never been taught how to sell it.

There’s a moment in dating when you sense the person deciding to agree with an opinion they don’t share. Suddenly they’re free every night. They never disagree or have a point of view. Yet you can feel them disappearing anyway.

I mentored an owner through the business version of that on a vendor response for a major entertainment company. Every one of his answers promised adaptation. We can work in your tools, your workflows, your restrictions, and your preferences. I told him, I know you want to please, and I know you want to get to work, but this is too flexible, and it reads as desperate rather than confident.

Eager is interested, responsive, and prepared, while desperate gives things away before anyone has asked. Watch it happen in pricing. The owner shares the fee, the prospect pauses to think, and before a word is spoken, the owner lowers the number or adds scope. The prospect was only thinking, and now they’ve learned that silence gets them a discount.

Someone can admire your work, enjoy your company, and work for a logo you’d love without being right for you.

So ask yourself whether you want the work or the association. If the honest answer is the association, you’re not choosing a client. You’re buying a reputation, and you’ll pay for it in project hours. Arm candy has a business parallel, and that version is worse, because you can’t end it at 2 in the morning by not returning a text.

I took one of those. They were the hot new brand everyone was buzzing about, and their logo did exactly what I wanted on my website. Up close, they were arrogant, difficult, not as bright as their reputation, and not especially talented once you could see the work being made rather than publicized.

There’s a reason none of that registered while I was chasing them. The Gottman Institute’s research on couples says: When you’re bonding with someone, you minimize the bad and maximize the good, which is why the earliest warnings are the hardest to see. An agency founder chasing a logo they want is doing the same thing to themselves.

You can usually tell in the first discovery call. They want a detailed proposal and won’t discuss budget. They expect original thinking before any commitment. They won’t bring in the people who approve the work. The deadline is fixed, but the decision process isn’t. None of that is something you can tidy up later. That’s the client showing you how the whole project will go.

When it ended, my whole team told me they’d known from the first meeting. Then the other agencies who’d worked with them before us surfaced with identical stories. Every one of their exes could have warned me, but I never asked a single one, because I was too flattered to have been chosen. So before you sign the trophy client, call someone they’ve worked with. Not for a reference, but for the truth. What surprised you? What would you do differently? What do you wish you’d known upfront? Comparing notes with the exes is unseemly in dating, and it’s ordinary diligence in business.

When I’m the one ending it, the language is simple. Based on what we’ve talked about, I don’t think the way I work is right for what you need, and I’d rather say that now than take your money and spend 6 months fighting something we both saw coming. Nobody has ever been offended by that. Most people are relieved somebody finally said it.

A no becomes a later yes only if coming back is comfortable. Acknowledge the timing or the fit, leave the door open, then leave it alone. Half a dozen anxious follow-ups have never saved anything.

I don’t really walk away from people anymore. I stay in their orbit, and they stay in mine. There’s no hostility, because there was nothing to resent, and there was nothing to resent because I was useful and honest the whole way through. They comment on something I post, they ask for an introduction, or they turn up in NYC wanting to grab a coffee. Plenty of them will never buy anything from me, and that’s fine.

When a date says it, it’s a consolation prize. In business it’s an asset, because friends refer you, recommend you in meetings you’ll never hear about, and call years later when the budget finally exists.

Most agency owners think sales discipline means getting better at saying yes. It mostly means getting better at recognizing the no you should have said a few conversations ago.

The company I chased for a year never became a client. The one I did land taught me the same lesson from the other side, and everyone around me could see the mismatch long before I could.

Every founder leading with their awards is wearing that lanyard. Every proposal that opens with fifteen years of experience is wearing it. Every one of us has spent an evening looking past someone who might have mattered, because we’d already decided who we wanted.

You knew all of this at 21. Then you started a business and forgot it the moment somebody attractive caught your eye.