There are roughly three kinds of coaching that work.

The one everyone knows: sit down after the hard conversation, debrief, figure out what you'd do differently. Done well, it's irreplaceable for long-term growth. The smartest coaches I know are doubling down on this, not running from it.

The second: a structured relationship. Regular sessions, a specific leadership challenge, a curriculum you're working through together. The gold standard for deliberate development.

Then there's a third kind. Almost nobody talks about it, because until recently it was essentially impossible to scale.

Think about a shooting coach working with Jalen Brunson. They don't just meet in the film room. They watch him play. They catch a hand position or a moment of hesitation in real time and intervene. A nudge. A micro-correction that lands before the habit hardens. That's not retrospective. It's not strategic. It's something different: coaching that happens during.

This form of coaching, intimate, real-time, and context-aware, has never been practically available to most leaders. Even at the C-suite level, having a coach present across your actual working environment is vanishingly rare. And here's my honest read: 80% of what goes sideways in management isn't a coaching problem in the traditional sense. It's a context problem.

It’s simple misalignment, a lack of curiosity, a tense moment that could have gone differently with one well-timed nudge from someone who actually knows what's happening.

Last year we tried to address this with a Slack integration. You could bring the problem to Ren, describe what happened, and get a coaching response. It worked technically. But something felt off.

Every time someone used it, they had to initiate. Explain the backstory from scratch. It felt less like having a coach and more like filing a support ticket.

We shelved it. But not just for the reason I thought at the time.

Yes, the model was wrong: we were asking people to bring the conversation to coaching, instead of the other way around. But the technology wasn't ready either. The level of nuance, orchestration, and genuine coaching quality that real-time intervention requires? We were still wrestling with all of that in Ren's core brain. It took until late 2025 to get it right.

Now that we have both, we could ask a different question.

Years ago, I watched a teammate slip a sticky note to a leader mid-meeting:

"Don't ask any more questions. Just wait." 

She knew him. She knew his tendencies. In that split second, she gave him the one thing he couldn't give himself: permission to stay quiet.

That's the audacious goal. So we asked: what if Ren could just be there?

Not to monitor. To share context. Present in the actual channels where work happens, so when you need a gut-check, you're not replaying the tape from memory. Ren already knows what happened. It's the difference between a GPS guiding you in real time versus someone telling you where you should have turned yesterday.

That's v2. It starts rolling out next week.

One thing we've already learned: the value isn't just that Ren can offer a response. It's that Ren is working from the same reality you are. Not your version of what happened. What actually happened.

That changes the conversation entirely.

— Jonathan

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