I’ve been watching people coach lately. Mine and other people’s. Inside teams, on calls, in coaching sessions, in the small handovers that happen between desks. And the same pattern keeps surfacing, in versions large and small.
We give directions. We rarely take the walk.
A direction is the polite, efficient gesture — the link in chat, the screenshot with an arrow, the “have a look at this, it explains it well”. It assumes the person on the other end has the time, the focus, and the confidence to follow the trail to the end. Most of the time, they don’t. Most of the time, they were asking because the trail is exactly what they’ve been struggling with.
Taking the walk is different. It means putting down what you were doing, getting up out of your chair (literally or in the digital equivalent of it), and going with them. It is slower, it is less elegant, and it is the thing that almost always works.
Why this hits hardest with Copilot right now
The reason this is sitting on top of my mind is what I’m seeing inside Microsoft 365 rollouts. Copilot is now embedded across Outlook, Word, Excel, Teams, OneNote, Loop — every surface a knowledge worker touches. The interface is right there. The documentation is right there. The training videos are right there.
And the gap is still enormous.
That gap isn’t a documentation problem. It’s a companionship problem. People know Copilot is in their email. What they don’t know is what to type when they actually have to reply to a customer who is upset, or summarise a three-week Teams thread, or pull the relevant lines out of a contract sitting in SharePoint. They need a person beside them the first time. Not afterwards. Not in a wiki. The first time.
When you sit next to somebody — sharing a screen in Teams works just as well as sitting at the same desk — and you open Copilot in their inbox, in front of their actual unread emails, two things happen. First, the prompt becomes specific. Generic prompt libraries are useless; their prompt for their email at this moment is electric. Second, they see you make a mistake, refine it, try again, and get somewhere usable. That’s the part documentation never teaches.
The handover is part of the coaching
The other thing I’ve come to value is the handover. Coaching isn’t finished the moment somebody can do the thing once. It’s finished when they have somewhere to go the second time.
In Microsoft 365 that means leaving a trail the next person — or the same person on a different morning — can pick up. Pin the prompt you just shaped together into a Loop component the team can see. Drop a note in their Teams channel calling out what worked. Connect them with the colleague who is already three months ahead. The point is that the next time they reach for help, the path ahead is already lit.
What I’m trying to do less of
I’m catching myself in the act of pointing more often than I’d like to admit. The instinct to send the link is strong; it costs me nothing, it looks like I helped, and it gets the conversation off my plate.
But the version of me that other people actually need isn’t the one with the curated bookmarks. It’s the one prepared to push the chair back and say, fine, let’s go and look at it together.
That’s the coaching that compounds. Everything else is signage.
CIAOPS 