Why Coaching Has Become Structurally Impossible — and What That Is Costing You

A Director of Operations I know does her 1:1s in the car.

Eleven direct reports. Two open reqs she has been told not to backfill. A VP who wants weekly updates and a frontline that wants her in the gemba. By the time she gets to the parking lot at 5:30, the only block of time left in her day is the drive home — phone on speaker, wife knows not to call.

She is not failing. She is the engine room of a $400M business. And she said, half-laughing, half not:

"I'd love to coach my people. Tell me which hour."

That is what coaching being structurally impossible sounds like in the wild.

If you are reading this, you have probably had some version of that sentence in your own head this quarter. Maybe not out loud. Maybe not in those words. But the shape of it — I know I should be developing my team; I just cannot find where that is supposed to fit — is the quiet refrain of senior leadership in 2026.

You are not lazy. You are not avoiding the hard conversation. You are not insufficiently committed to your people.

You are running a job that grew without anyone noticing, inside an operating model that did not grow with it.

The gap between what is on your job description and what is actually on your calendar has become the territory where coaching used to live — and where it now does not.

The conditions that made coaching feel natural a decade ago have been quietly dismantled. Most leaders have not registered the dismantling because it happened in pieces, over years, through reorgs and remote shifts and span-of-control adjustments that each made local sense. Stack them up and the math stops working.

Two forces did most of the damage.

The first is player-coach model. Spans of control widened. Layers got cut in the name of agility. The leader who used to have six direct reports now has eleven or fourteen — and is also carrying two of the deliverables themselves because the team underneath them is short.

You are doing the work, leading the work, and developing the people doing the work. The math no longer maths.

Something has to give, and the thing that gives — every time, in every leader I have watched — is the development work. Not because it is least important. Because it is the only thing without a deadline attached.

The second is what hybrid did to relational bandwidth. The hallway conversation, the walk back from the meeting, the five minutes in the parking lot where someone said "hey, can I run something by you"

— those were not throwaway moments. They were where a lot of coaching actually happened.

Unscheduled, low-stakes, in the flow. They have been replaced by a thirty-minute Zoom slot every other Thursday with a recurring agenda template, and the substitution is not a substitution. It is a calendar artifact pretending to be a relationship.

Add the two forces together and you get the leader I described above. Eleven directs. No bandwidth. No corridor. The 1:1 happens in the car because the car is what is left.

You did not stop being a coach. The conditions that allowed you to coach got engineered out of the week.

This matters because of what it changes about the question.

The question is not how do I be a better coach. The question is how do I rebuild the conditions for coaching inside the constraints I cannot remove.

That is a different problem. It has a different solution. And the leaders who are figuring it out — there are some — are not waiting for the structure to give them their time back. They are redesigning the small handful of things that are actually theirs to redesign: how they prepare for the 1:1, what they capture between 1:1s, and how they carry the context of a person across the weeks when they cannot see them in the hallway.

The leaders who coach inside this constraint share a small set of habits. None of them are heroic:

• They treat the 1:1 as the primary unit of leadership, not the leftover thirty minutes after operations. They prepare for it the way they used to prepare for a board update — not with a deck, but with thinking. They walk in with two or three real questions, not a status template.
• They keep some kind of running record on each direct report. Not a performance file. A working memory — what is this person wrestling with, what did I notice, what did they say last time that I want to come back to. The leaders who used to hold this in their heads when they had six directs cannot hold it for fourteen. The ones doing it well externalized the memory before they realized they had to.
• They protect the boundary around the conversation. The 1:1 does not get bumped for an operational fire unless something is genuinely on fire. The signal that sends — to the direct, to the rest of the team, to themselves — is that this conversation is the work, not adjacent to the work.

None of that requires the structure to change. It requires the leader to decide that the half-hour in the car is not a coaching conversation, and to do something about it.

This is one place AI is genuinely useful — and one place it is dangerous.

• Useful: the prep and the memory. Drop your last 1:1 notes into an LLM along with a short standing context block about the person, and ask it for the themes worth following up on, the contradictions you might have missed, the unspoken question they were probably circling, and three questions worth asking next time. Pair that with a private Slack or Teams channel — visible only to you (and perhaps your direct report), one per direct report — where you drop observations, voice notes, the LLM's pre-brief output. Over time it becomes the longitudinal record your memory used to hold when the math of the job was different.
• Dangerous: the conversation itself. AI cannot coach for you. It can hold the context that used to live in your head. It cannot hold the relationship.

It is time to accept that you are leading inside a system that quietly stopped making room for it. That is real, and it is not the end of the story.

The leaders who build momentum from here are the ones who do not wait for the structure to change, but instead change the operating model of their conversations — starting with the one they are about to walk into.

That is the work. We are going to spend the next several weeks on it.

I created a custom Gem in Google Gemini that will take your meeting notes, provide coaching feedback and create the 1:1 coaching preparation for you. You can access it here.