This is Part II of The Profile, a 6-part fiction series about a CEO, his unconventional coach, and the dating app that reveals why his team doesn’t trust him. New parts publish every two weeks. You can read Part I here.
It’s rainy today, and the drops streak down the 12-foot tall windows in David’s office. The clouds half obscure the skyscrapers and David feels exposed as the coach sits across from him. He’s kept his phone out of sight this time, hidden in the top drawer of the cabinet behind his desk.
“What happened last week?”
“I cancelled.” He says this in a tone he hopes comes off as flippant but probably sounds more like defiance.
She seems unfazed, leaning back in her chair, as if they were discussing the bad weather. “But here we are, two weeks after we first met. Why did you reschedule?”
Trying to be flippant wasn’t working because David was mad.
“This is bullshit, you know?”
“What is?” She didn’t look offended.
“Tinder? I mean, come on.” He stands, fully, pacing to the window. “This is a waste of my time. You want me to swipe through photos like some…” he stops himself, trying to maintain a level of civility. “I’ve got a company to run. Real problems. A board that’s breathing down my neck about retention. And you want me playing games on my phone?”
She’s swiveled in her seat, watching him walk from one side of the office to the other.
“What’s next, are we going to analyze my Candy Crush strategy?” His voice rises. “I’ve spent fifteen years building this place. I know how to lead. I know how to read people. And you’re sitting here asking me to…what? Learn about myself from a dating app?” He turns back to her, and he feels something raw in his expression. Naked. “I rescheduled because the board told me to. Because apparently I need ‘executive coaching.’ But this? This is ridiculous.”
She waits. Lets him finish. The rain, white noise on the glass, fills the silence between them.
“Are you angry?” she asks.
“I’m pissed!” Her question enrages him.
“At me?”
“At…” he stops, regaining his composure. “At the situation.”
“What situation?”
“That I’m here. That I need to be here.”
“I understand.” She nods slowly. “And by the way? I completely agree. You’ve built something remarkable here.”
He feels pride flicker through his anger. His hand goes automatically to his watch. His fingers encircle his wrist and wiggle the band.
She continues. “Right now, you’re responding strongly to what I’m proposing. But let’s just imagine you do play along. What would it cost you?”
David’s still standing, but something in his posture has shifted.
“What would it cost me? My self-respect, maybe. Sitting here admitting I need... what, therapy? A performance review from someone who’s never run a company?”
“Therapy. Performance review.” She lets the words sit. “What if it’s neither?”
David notices she’s not defending herself. Weird.
“Look, you don’t know me. And you’re right, I haven’t run a company. So yeah…why should you trust this is worth your time?”
He stares down at her, grabs his watch again. Backs up a pace when he realizes she’s not backing up and his position might be physically intimidating.
“What would you need to make it worth it?”
“What I always need. Concrete deliverables.”
“Like what?”
“Oh, right, you wouldn’t know, because you’ve never run a company.” He sees her mouth twitch at his heavy sarcasm, and winces. Backs up another pace.
“Like what?” She repeats her question, poker faced once again.
“I need my exec team to stop second-guessing every decision I make. I need the board off my back about ‘leadership maturity’ or ‘retention’ or whatever buzzword they’re using this quarter.”
“How could we measure that?”
He sizes her up. Not a bad question. “Measure it? I don’t know. How about…fewer emails questioning my decisions? My CTO actually implementing what we agreed on instead of relitigating it in Slack because he won’t talk to my VP of Sales to her face? Not that it matters anymore since she’s gone.” He’s warming up to it. Measurement is in his comfort zone. He starts to pace around. “I walk out of here with something I can actually use. Not insights. Not awareness. A plan. Something that changes what happens Monday morning.”
“Okay. Fewer emails. CTO follow through. Something for Monday morning.” She pauses. David waits. Feels off balance because he doesn’t know what’s coming next.
“I assume you are familiar with how dating apps train their algorithms…every swipe teaches it what to show you more of.” He stares at her.
“And your own product does this with user behavior, right? Every click trains the system on what to prioritize, what features to surface, who gets what experience.”
“Great, you’ve done your homework.” He’s trying to lighten the sarcasm.
“Well, your organization works the same way. What do you think your team is optimizing for?”
He looks around, as if something in his immaculate office might provide the answer. “Probably what gets rewarded. Don’t we all?”
“What do you think?”
He feels the wheels turning, starts to feel the spark of something. Recognition. Connection between two things he’d never regarded as related.
She’s still talking. “You’ve got six sessions with me whether you want them or not. We can spend them resenting the board’s mandate, or we can figure out what you’re inadvertently training for.”
He’s listening. She smiles and gestures at his chair, inviting him to sit down again. He relents, settling down. Not surrendering, he promises himself. Just being open minded.
She takes a deep breath in, then slowly exhales. “How many employees do you have?”
“Last week we passed 500.”
“How many of them have Tinder?”
“Come on, that’s ridiculous.” David’s outrage flares again, and now it’s tinged with morality. He starts to rise again from his desk but changes his mind. “I’m not asking my employees if they’re on Tinder. Now that would be the end of the company.”
“You’re right.” She smiled again. He can’t tell if she was joking. “How about LinkedIn?”
He sits back down again, twisting his watch. “Probably all of them. We require candidates to share a LinkedIn profile when they apply. It’s part of our vetting process.”
“Interesting,” she says. “I’d like to hear more about that later.”
“Why can’t we just talk about LinkedIn?” He hears a plaintive tone in his voice and hates it.
“It’s too close.” She says it right on top of his questions and shifts forward in her chair. “When we look at something familiar - something we’re already experts in - we have a tendency to defend our existing patterns instead of examining them. But when we study behavior in a completely different context, the insights can be cleaner. They’re less contaminated by what we think we already know. We’re looking at human behavior here, not just organizational behavior. Sometimes you need to zoom out on the whole person to better understand them in one context.”
“What would you have done if I were a dating app user?”
“You weren’t, though.” She smiles. “Did you use Tinder since the last time I’ve seen you?”
“I deleted it,” David says.
“That’s OK. Do you want to download it again?”
“I deleted it…” his voice trails off. “But I re-downloaded it last week.” He feels like a kid, sheepish, especially when he has to turn his back on her to retrieve his phone from the cabinet, like he was hiding something.
To her credit she maintains her poker face.
“Why did you re-download it?”
“Because I’m single, and I’ve never tried it, so why not?” He shrugs, attempting casual. “I even paid for Tinder Plus so I can hide in another country, where people probably don’t know me.”
She nods. “OK. We aren’t going to swipe today, anyway. Let’s just spend some time talking about the photos you’ve chosen.”
He unlocks his phone, opens the app, and hands it to her. She scrolls slowly through his profile.
“Walk me through these,” she says, turning the phone so he can see. “What did you choose, and why? Let’s start with the sailboat.”
“I swapped some out,” he admits. “After I looked at other profiles. The headshot felt too corporate. Too stiff. So I added that one from the sailing trip last summer - someone I was dating at the time told me I looked really good in it.” He slowly reaches for his phone screen, and swipes to the next photo. “I put this one in, I was just walking in the city a few weeks ago. I took out the one from the conference stage. It felt like I was trying too hard.”
“Trying too hard to do what?”
“To impress people. To look successful.”
“And the sailing photo doesn’t do that?”
He pauses. “It does. But differently. It’s more... casual success? I don’t know.”
“And the picture in the city?”
“Well, everyone’s been to New York, right? At least anyone I’d want to date.”
“Anyone you’d want to date has been to New York?” She looks at him neutrally.
“I mean, it shows they’re cosmopolitan, I guess. They travel. Or they live somewhere worth visiting.”
“So that’s what it shows about you?”
“Well, yeah.” He stops to think, confused for a minute. Was he picking the photos to show who he was or send a message to the people he wanted to pick him? What was the difference?
“What did you see in the other profiles that made you change yours? For example with swapping out the corporate headshot.” It’s like the coach read his mind.
“It was in the profiles I found interesting,” he clarifies, his thought process lining up. “People looked…” he searches for the word. “Approachable. Like they were actually enjoying themselves, not posing for their LinkedIn profile. There was this one woman who had a photo with her dog, just laughing. Nothing fancy. And I thought, that’s probably getting more right swipes than my corporate headshot.”
“What made you think that?”
“Because it’s real. It’s not trying to sell anything.”
She pauses, watching him. “No?”
He shifts in his chair. “Well, yeah. I mean...myself, I guess. So you have to think about what works.”
“Mm.” She waits.
The silence stretches. He looks at his phone, then back at her. “I guess I was... adjusting. Based on what I saw working.”
“Working as in…”
“I felt like I was matching more with women who I actually wanted to talk to.”
“OK.” She nods, pauses. “What else adjusts based on what works?”
He knew she was going to go there, and he fights his urge to respond sarcastically. The question sits there.
“My team?” he says slowly, trying to play the game, trying to hide the slightly mocking tone that he’d wanted to use.
She nods, still quiet.
“They watch what I…” He stops. “What I respond to. What gets traction.”
“And then?”
“Then they give me more of that.” He looks at the phone in his hand. “More of whatever I responded to last time.”
“Like?”
“Like... safe ideas. Polished presentations. Numbers that look good.” His jaw tightens. “Shit.” This wasn’t so bad. Or actually it was.
She waits.
David grows frustrated, shaking his head, not liking what he thinks she’s implying. What he was implying. “But that’s just... I mean, that’s prioritization. I can’t engage with everything.”
“No one’s saying you should.”
He’s quiet for a long moment. “So they’re…” He doesn’t finish.
“They’re what?”
“Watching my patterns. Learning what gets through.” He sets the phone down, face down, so he doesn’t have to look at it. “The same way I was watching those profiles.”
“What does that mean for what reaches you?”
He exhales slowly. Doesn’t answer right away. “I don’t know. That’s the problem. I don’t actually know what I’m... selecting for.” He pushes back his chair, gently this time, and gets up. Looks out the window. Peers at the buildings, half obscured in clouds.
She speaks again. “You mentioned retention issues. Who’s left recently?”
“VP of Sales quit two weeks ago. Right after our last meeting, actually.”
“Why?”
“She said... I don’t remember exactly. ‘Growth opportunity elsewhere’ in her exit interview, something like that.”
“Do you have the actual notes?”
He pulls out his phone, slacks his CPO. Waits while the typing indicator appears, then disappears, then appears again. The notes arrive. He reads them.
His face changes.
“What does it say?”
He reads aloud, his voice flat: “I got really good at meeting his expectations. Maybe too good at it. I stopped paying attention to what I was seeing that he wasn’t. That’s on me - I chose that dynamic. But it showed me what I actually want: to work somewhere I’m being paid to bring my full judgment to the table. Where we’re both being pushed to think harder.”
The room is quiet.
“What do you think about that?” the coach asks.
“She learned my algorithm.” David rubs his eyes, wiggles his watch. “And maybe that’s on me, not on her.”
She gives him a minute, then sits up straighter.
“Here’s what I want you to do this week: Notice your swipe patterns in meetings. When someone speaks, pay attention to your internal reaction, and then pay attention to your response. Are you approving or redirecting? Then we’ll get to - what pattern are you teaching?”
He nods, already thinking about it.
“Also,” he adds, feeling like confessing, “Jim from the board emailed yesterday. He wants to come visit Thursday. ‘Understand the culture challenges,’ he said. Set up one-on-ones with three of my directs.”
“What was your response?”
“I don’t know. I mean, I don’t have a choice. I could try to prep them? Tell them what to say to…” He stops. “Yeah. I hear it. I was about to say ‘tell them what to say to make it sound good.’ Fuck.”
“Sounds like we’ll have a lot to talk about next week,” she says. She stands. “Assuming we’re on?”
David nods, meeting her eye. He doesn’t offer his hand. His fingers are still working at his watch band - a tell he can’t quite control yet. “We’re on.”
Brillant piece on leadership blind spots. The insight about teams learning to game approval patterns really captures someting most leaders dunno they're doing. In my experience managing a small tech team, I noticed the same thing where people stopped bringing up edge cases once they learned I prefered clean status reports. The exit interview quote about becoming 'too good' at meeting expectations is the uncomfortable truth nobody talks about.