but talking to a friend recently who’s in the muck and bullets of it all reminded me that not much has changed, in fact it’s gotten harder. But having distance from the swiping and hearing her stories reminded me that the more I coach leaders, the more I see the same patterns that show up on dating apps. We just wear suits instead of selfies.
And the constant search for “the one” who can finally make everything easier.
Because, like dating, leadership is all about relationships, connection, trust, communication, and follow-through.
And just like dating, when those things slip, so does the spark.
Here’s what the apps can teach us about leading people and what to do differently if you want something that actually lasts.
It’s the dating-app classic the ultimate non-question. It sounds like connection, but it’s really filler.
Leaders do the same thing.
Randomly checking in with one-liners “All good?”, “How’s everyone doing?” isn’t communication. It doesn’t surface real challenges, it doesn’t build trust, and it certainly doesn’t help anyone grow.
In both dating and leadership, small talk masquerading as care gets you nowhere.
If you’re pushed for time, ask this instead (in work not on hinge):
What’s been most frustrating or energising for you this week?
That question gets you under the surface where connection (and performance) actually live.
Because good leaders, like great partners, don’t talk to fill the silence. They talk to understand.
No one joins a dating app hoping for a lifetime of witty small talk - they want to meet up IRL.
The same goes for leadership. Endless emails, Teams messages, and status updates don’t build connection. They just create the illusion of it.
You can’t really know how someone’s doing through bullet points and emojis. The real work happens in one-to-ones, eye contact, tone, pauses, the stuff that never fits in an email thread.
Try this: if your calendar is full of group calls and updates, carve out one 20-minute face-to-face a week that’s about the person, not the project. You’ll learn more in that half hour than in a month of inbox ping-pong.
On dating apps, chemistry is everything. You either click or you don’t.
In leadership, clarity is the chemistry it’s what makes things click between people.
In my Good to Great workshop, I take leaders through what it actually takes (and costs) to create clarity and they’re always surprised.
Leaders dodge clarity for two reasons:
- They’re time-poor and haven’t thought the goal through properly.
- They don’t actually have clarity themselves.
Either way, it shows.
People want to talk with someone who resonates with them.
Try this: When you delegate a task, set the relationship up for success. Get clear on what success looks like to you then ask the person you’re working with to repeat back what they’ve understood.
You’ll find most “performance issues” aren’t about capability, they’re about confusion.
On the apps, you’ve got the ultimate cop-out, just un-match and disappear. No explanation needed, and you hope you don’t bump into them IRL (not advisable, from experience).
But in company-land, you don’t get that option. “Un-matching” isn’t a phrase HR has caught on to just yet.
And yet leaders do it all the time.
Nothing said after a missed deadline.
No mention of the negativity that’s crept into every meeting.
Just silence followed by low appraisal scores months later.
It’s feedback by avoidance, and it kills trust faster than a bad first date.
Try this: Build a simple, standard feedback framework into every 1-2-1:
- What's going well
- What I'd like you to stop or start doing
- What could be even better
Make it two-way so you get feedback too.
Do that consistently and you don’t just fix performance, you shift culture.
A like here, a “how’s it going?” there but never actually committing to anything real.
A like here, a “how’s it going?” there but never actually committing to anything real.
Leaders do it too.
A half-hearted “we’ll get you on that course soon,” the occasional “you’re ready for bigger things,” or a vague promise of progression that never materialises.
It keeps people hanging on, hoping, waiting.
But just like in dating, after a while they get the message: you’re not really invested.
Try this: If you value someone, show it with action:
- What's going well
- What I'd like you to stop or start doing
- What could be even better
Because dangling potential without delivery doesn’t motivate – it demoralises. People don’t want breadcrumbs; they want a meal.
The search for “the perfect one” is exhausting in love and in leadership.
Great leaders know the best hires rarely tick every box.
They hire for curiosity, adaptability, and emotional intelligence the things you can’t teach.
Try this:
When hiring or promoting, ask yourself: “Is this person still learning?”
If the answer’s yes, you’ve probably found a keeper.
You don’t go on a date hoping to rewrite someone’s personality (at least, you shouldn’t).
Yet too many leaders try to “fix” their people instead of understanding them.
Influence comes from connection, not control.
Try this:
Spend less time managing and more time observing.
What actually motivates your team praise, autonomy, challenge, humour?
Lead from that.
After a while, dating apps get… exhausting.
The endless swiping, small talk, and “what do you do?” exchanges start to blur together until you’re scrolling out of habit not hope.
Work can feel exactly the same.
The constant emails, Teams pings, and performance check-ins can make you cynical like you’re stuck in a professional version of “Tinder”.
Take a break.
Log off. Properly. Don’t check your emails.
Spend time with people who don’t care about your job title.
You’ll come back clearer, calmer, and probably a bit more fun to be around.
Do something where you don’t have to make a single decision.
Because connection in work or in love doesn’t thrive on constant availability.
Sometimes, the most productive thing you can do is pause.
The parallels are endless because the principle is the same: people don’t want to be managed, they want to be understood.
They don’t need leaders who perform empathy once a quarter, they need leaders who build it daily.
Dating apps just made the truth impossible to ignore: connection without effort is an illusion.
Whether it’s your match or your team, the work is in the follow-through.
– Sinead