I was too drained to write a delicate message. My agent wrote it in my voice.
It also coached me on my own blind spots, unprompted.
Hey Titans 💪🏻
Recently I wrote about building a file that describes how I lead in Most managers can’t describe how they lead. Your agent should.
The whole point of that piece was to answer a question most managers stumble on: put your leadership style into words your agent can actually use.
I realized that I ended the article with a promise but without proving its value in real-life scenarios.
Today I am sharing how I managed to write a delicate message to my clients on a late Friday evening, shielding one of my engineers so that he can navigate a difficult life situation and had me enjoy the following Saturday without the need to decompress.
The file loads itself, every session
Here’s the setup, because it matters for what comes next.
The file isn’t something I paste in when I remember to.
It’s loaded automatically.
Two files do the work: the deep-dive profile itself, plus a global instructions file that tells every new Claude session to read the profile before it coaches me on anything to do with communication, conflict, or my team.
So I never think about it; every session already knows how I lead before I’ve typed a word.
6pm, out of the meeting, out of gas
One of my engineers - call him Wei - ran into a demanding personal situation. The kind that urgently needs a big chunk of someone’s time for a few weeks, no way around it.
At the same time, three stakeholders across two projects were each pushing to be the priority. Every one of them had a fair claim.
I had to write to those stakeholders and get them to agree on which project was the real P0. Without it reading as “we’re dropping your work.” While protecting Wei and not putting his personal situation on display.
That’s a tightrope; the wrong tone in either direction and I create a mess - a stakeholder who feels deprioritized, or an engineer who feels exposed.
And it was past 6pm. I’d just walked out of the 1:1 where Wei told me what he was dealing with, and I was spent. Writing something this careful - warm, precise, protective of a delicate situation - is exactly the task I’m worst at with an empty tank at the end of a long day.
So I asked my agent to draft it.
What the agent handed back
Here’s the message I got back - genericized enough that I can share it here:
Hi <stakeholder names>,
Reaching out to get us aligned on priorities for Wei over the coming weeks.To share some quick, transparent context: Wei is navigating a demanding personal situation related to <the actual situation> right now that urgently needs a significant amount of his time over the coming weeks. He’s doing exceptional work, and I want to protect both his wellbeing and our delivery for you…
He’s currently fielding two major asks from your side:
- <project A>
- <project B>
To protect his focus while we keep delivering, could the three of you sync and agree on which of these two projects should be our primary focus right now?
Wei remains fully committed to giving his best, and we deeply appreciate your partnership and flexibility while he handles what’s in front of him.
Let me know what you decide is the P0 ask so I can guide his focus. Thanks for your support and understanding!
— Leszek
Make no mistake - I proof-read it several times looking for what to fix.
I changed almost nothing.
It handled the tradeoff with grace, it protected the engineer without exposing him, and it moved the decision to the people who should own it. It sounded like me on my most composed day.
I sent it and started my weekend.
Under usual circumstances, that message would have eaten my Friday evening and followed me into Saturday while I tried to decompress from it. From that standpoint alone I consider it a good result delivered by the agent: a competent message, drafted in seconds, in my voice, protecting my weekend from work-related stress seeping in.
There’s more I appreciated about that message.
It explained its own reasoning to me
Under the draft, unprompted, the agent had appended this:
Coaching Note: By framing this transparently as a partnership tradeoff rather than a pure delay, you lean into your Strategic / Analytical strengths. It gives the stakeholders the objective data (two projects, limited bandwidth) and invites them to solve the optimization problem with you, rather than feeling like work is just being dropped.
The agent explained its own reasoning back to me in the language of my documented leadership profile. Strategic and analytical.
The exact strengths my data distilled down to.
It knew that framing a hard ask as an optimization problem is how I actually operate at my best - and it told me that’s what it had done, and why it works.
That’s only possible because the profile is loaded every session. Without it, I get a well-written email from a generic assistant. With it, I get my email, plus a mirror held up to my own leadership style while I’m still in the middle of it.
The same file guards my worst version
Now the flip side - my profile doesn’t only list what I’m good at.
It documents my blind spots in plain terms.
Two of them: “pivot shock” - when I swing from warm coach to cold analyst too fast and suddenly start telling people what to do. And running hot - getting too intense under pressure, into the “prove and perform” mode, which is exactly the state I was in when I sat down to write that message.
The same file that writes in my voice also guards against the version of me that shows up under that kind of pressure. If I’d drafted that stakeholder note myself, in the moment, it would have come out sharper. More “here’s the constraint, deal with it.”
Less partnership, more decree - not what I’d want to hear, if I were on the receiving end of that message.
The agent already knew that about me.
So it steered toward the version I’d want to have sent, not the one I’d have fired off at 6pm with my jaw tight.
Yes, I still own the judgment call; thankfully, the guardrail was there before I needed it, not after.
The reply that told me it worked
One more thing, and it’s the part I keep coming back to.
As I write this, one of the three stakeholders has replied. The answer was better than I hoped - they agreed one project should sit below the other…
…the exact call I needed someone to make.
But the priority ranking wasn’t what stayed with me - they responded to Wei as a person. They acknowledged what he was carrying and made clear his wellbeing came before any timeline.
That was so great to see. The first reply sets the tone for the thread, so I expect the others to follow. But the best part was watching a busy stakeholder care about the human in the middle of the tradeoff, not just the deliverable.
What this changes, every day
My leadership-style file stops being a document and becomes a coach who’s worked with me for years.
Every session, it starts already knowing how I lead, where I’m strong, and where I get myself in trouble. I don’t brief it. I don’t paste context. I just ask, and what comes back is calibrated to me.
Building the profile was step one. This is what it buys you: an agent that drafts in your voice, protects your people the way you would, and coaches you on your own reasoning while you’re still inside the hard moment.
Have you written down how you lead in a form your agent can actually use - or is it still living only in your head, where it’s no use to anyone under pressure?
— Leszek
Great idea - it also happened to me to use AI when I'm tired or when the communication needs to be crystal clear because it’s political. But I haven’t created my leadership style document but will do it now!