Most managers can't describe how they lead. Your agent should.
How to teach your agent who you are as a leader and put that to work every day.
In the previous article Don’t ask chatbot questions, start writing briefs I covered how to get started with your first agentic workflows: building your digital double, closing the feedback loop, and writing briefs instead of questions.
This one goes a layer deeper. You’ll build a single file — my-leadership-style.md that teaches your agent not just what you do, but how you lead.
It becomes the go-to reference for your agent before it acts on your behalf:
A Chief-of-Staff that protects your priorities → when the agent knows what you optimize for and how you make calls, it triages your day around your priorities, not a generic productivity template.
Communication that sounds like you → drafts, updates, and replies come back in your voice and at your level of directness, so you edit instead of rewrite.
An early-warning system for your blind spots → the profile names your failure modes (mine: intensity under pressure, and the “pivot shock” when coaching quietly turns into bluntly delivered critical feedback). You are providing the agent an early warning about them, so it can flag the message you’re about to send too hot, or remind you to signpost a hard conversation before a report feels blindsided. You stop paying for the same mistake twice - and that shows up directly in fewer damaged relationships and cleaner decisions.
Let’s get into it.
1. Find the data that already describes you
You don’t need to fill out a long questionnaire from scratch. Most of the evidence about how you lead already exists, but you just haven’t pointed the agent to it.
Here’s what I fed in:
My DISC analysis from 2024;
Transcriptions from my 1:1s - how I actually coach in my own words;
Journaling notes - the daily log of highs & lows;
A few strategy slides - how I convince the team, and the stakeholders.
Important: the quality matters more than the volume.
Strategy slides show how you think, written comms show your tone, transcripts show how you coach. Triangulating across all three is what stops the output from being generic.
Don’t over-collect. Grab what’s at hand and move on - you’ll refine it later.
2. Run the prompt
Open Claude (I use Opus 4.6 on medium effort), drop your data into the context, and run the prompt below.
Two things make this prompt different from “tell me my strengths”:
It uses the
AskUserQuestiontool to interview you first - filling the gaps your documents can’t show before it writes a single word.It returns your strengths exactly the way a CliftonStrengths assessment would - your Top 5 from the real 34 themes, each justified with evidence pulled from your data.
# Role
You are an executive leadership coach and organizational psychologist.
# Task
Distill my personal leadership style from the real evidence I give you, and write a Leadership Profile to a file named `my-leadership-style.md`.
# Step 1 — Interview me first
Before writing anything, use the AskUserQuestion tool to run a short questionnaire that fills the gaps my data doesn't cover. Ask about: my role and team size, how I make reversible vs. irreversible decisions, how I delegate, how I handle conflict / feedback / underperformance, what energizes vs. drains me, and the blind spots people have flagged. Do not write the profile until I've answered.
# Step 2 — Read my data
I'm providing some or all of: my DISC assessment, company strategy slides, emails / Slack messages, and 1:1 transcripts. Triangulate across them — strategy slides show how I think, written comms show my tone and directness, transcripts show how I coach and delegate. Cite specific behaviors as evidence, do not invent traits the data doesn't support, avoid creativity.
# Step 3 — Identify my strengths the CliftonStrengths way
Infer my Top 5 using the actual 34 CliftonStrengths theme names (e.g. Developer, Analytical, Strategic, Relator, Command), each mapped to its domain (Executing, Influencing, Relationship Building, Strategic Thinking). The output must read as if I had taken the assessment: for each theme, justify its rank using evidence from my data.
# Step 4 — Write `my-leadership-style.md` with these sections
1. Header — my role, an "Evolved Profile" archetype name, and a Framework Mapping line (CliftonStrengths + DISC).
2. Executive Summary — the 2–3 forces that define my leadership.
3. CliftonStrengths Top 5 — each with an italic nickname, a "How it manifests" paragraph, and a concrete "In Action" example from my data.
4. Leadership Frameworks in Action — 3 named models for how I operate (decision-making, delegation, change/routine).
5. The Shadow Side: Blind Spots & Vulnerabilities — 3 traps, each as "The Trap / The Impact / Mitigation."
6. How to Work with Me — "What to Do" and "What to Avoid" lists for peers and reports.
# Style
Be specific, direct, and evidence-based. Include the unflattering observations. No generic strengths-coaching boilerplate.
Important: don’t skip the questionnaire part - it’s the part that makes the profile truly yours.
Your DISC report and your 1:1s say a lot, but they can’t tell the agent what drains you or which blind spot has bitten you twice. Answer those five minutes of questions honestly and the output stops reading like a horoscope.
What comes back is a file that names your Top 5 strengths, the frameworks you actually run, your blind spots and a “How to Work with Me” guide you could hand to a new report on day one.
3. Put the file to work
A profile you read once and forget changes nothing. The point is to wire it into your daily workflow.
Save my-leadership-style.md as a Claude artifact, right next to your about-me.md. Now every agent you run starts from a model of how you lead - and you can point specific workflows at it:
Chief-of-Staff → “Given my leadership style, what are the three things only I can do today? Triage the rest.”
Communication → “Draft this update in my voice and directness. Flag anything that trips my blind spots.”
Decisions → “Pressure-test this call against my Shadow Side. Where am I about to over-index on speed or run too hot?”
That last one is where the file earns its keep - the agent knows the version of you that shows up under pressure, before it manifests itself in your work.
The premise of this article: you already have everything you need to describe how you lead. It’s sitting in your DISC report, your 1:1 notes, your slides.
You don’t have to get it perfect. Don’t worry if you don’t have the DISC report like I did - simply run the prompt, answer the questions, save the file.
Refine it the next time a workflow returns something that doesn’t sound like you.
One question before you close this tab: if your agent truly understood how you lead, what’s the first decision you’d want it to check you on?
— Leszek