Working with Manager Practice
The 'Working With Me' practice is the symmetric counterpart to the Manager README — written by the report ABOUT themselves, for their manager. It compresses the manager's learning curve about each report's working style into a one-page document: communication preferences, motivations, what stresses you out, how you receive feedback, and what you need from your manager to do your best work. The practice originated in remote-first cultures (GitLab, Buffer, Doist) where managers can't observe team members in person and need explicit signals. The discipline pairs with manager READMEs to create a two-sided contract: both parties have documented how they work, removing the mutual-guessing tax that consumes the first 90 days of any reporting relationship.
The Trap
Reports are reluctant to write 'Working With Me' docs because they feel high-status leaders shouldn't need accommodation. This is exactly backwards — the docs are there to make collaboration MORE efficient, not to extract special treatment. The other trap is using the doc as a wishlist ('I work best when not given deadlines') rather than as honest self-knowledge. A useful entry sounds like: 'I think best by talking out loud — I'll process aloud in our 1:1, but I usually don't expect you to act on what I say in real-time. Ask me 'is this just thinking or are you committing?' to clarify.' That's actionable. 'Don't give me deadlines' is decoration.
What to Do
Write your 'Working With Me' in five sections, each 3-5 sentences: (1) How I communicate best (channels, response times, sync vs async preferences). (2) What motivates me (specific examples, not abstractions). (3) How I receive feedback best (in private, with examples, in real-time vs after thinking, etc.). (4) What stresses me out and how I behave when stressed (so my manager can recognize the signs). (5) What I need from my manager to do my best work (be specific). Share with your manager in your first 1:1, then update annually. Have your manager pair it with their Manager README for the full two-sided contract.
In Practice
Hypothetical implementation patterned on GitLab and Doist practices: each new hire at a remote-first company writes a 'Working With Me' doc as part of their first-week onboarding. The doc lives in their public profile in the company wiki. New managers read all their reports' docs in their first week before scheduling 1:1s. Companies with this practice report cutting the 'getting to know you' phase from 6+ months to 4-6 weeks. Source patterns: GitLab Handbook, Doist 'Async Work' guide.
Pro Tips
- 01
The most underrated section is 'how I behave when stressed.' Naming the signs ('I go quiet on Slack and over-edit my docs') gives your manager a way to support you when you're not at your best — without you having to ask in the moment.
- 02
Update the doc when something changes. New caregiving responsibilities, new commute, new energy patterns from a life change — these matter. A 12-month-old doc is stale and the friction returns.
- 03
Read your manager's README and YOUR doc together with them in your first 1:1. The conversation reveals more than the docs do — and signals to your manager that you take working-relationship design seriously.
Myth vs Reality
Myth
“Writing one of these makes you look needy”
Reality
It signals self-awareness and operational maturity. Senior leaders read these docs and immediately upgrade their estimate of the report. The reports who refuse to write one are perceived as either lacking self-knowledge or unwilling to make their own work easier — neither is a positive signal.
Myth
“If my manager has a README, I don't need to write one too”
Reality
The asymmetry breaks the contract. A one-sided README puts all the burden on the report to adapt to the manager. A two-sided practice makes both parties responsible for the working relationship — which is the only sustainable design.
Try it
Run the numbers.
Pressure-test the concept against your own knowledge — answer the challenge or try the live scenario.
Scenario Challenge
You just got a new manager who has published a detailed Manager README. They've asked you to send them a 'Working With Me' doc before your first 1:1. You haven't written one before and feel awkward about it.
Industry benchmarks
Is your number good?
Calibrate against real-world tiers. Use these ranges as targets — not absolutes.
% of Reports With 'Working With Me' Doc
Remote-first or hybrid companies with documented people practicesElite (Remote-First)
> 80%
Healthy
50-80%
Emerging
20-50%
Absent
< 20%
Source: GitLab + Doist + Buffer remote-work benchmarks
Real-world cases
Companies that lived this.
Verified narratives with the numbers that prove (or break) the concept.
Doist
2015-Present
Doist (the company behind Todoist) is fully remote across 35+ countries. Every employee writes a 'Working With Me' doc in their first 2 weeks and updates it annually. The docs are public in the company wiki. New managers read every report's doc before their first 1:1. Doist publishes its async work practices openly and credits the two-sided documentation practice with cutting onboarding ramp time by ~40% compared to industry benchmarks for fully-remote companies.
Countries Represented
35+
Onboarding Ramp Reduction
~40% vs benchmark
Doc Update Cadence
Annual + life changes
% Async vs Sync Communication
~80% async
Doist's data shows the practice produces measurable ramp-time reduction in fully-remote contexts. The mechanism: removing 6 months of mutual preference-guessing from the working relationship. Hybrid and in-office companies see smaller but still meaningful gains.
Hypothetical Pre-IPO Startup (Anti-Pattern)
Hypothetical
Hypothetical: A 200-person Series C startup adopted Manager READMEs but did NOT pair them with 'Working With Me' docs from reports. Within 18 months, two patterns emerged: (1) reports felt the practice was one-sided — managers documented their preferences but didn't try to learn the team's. (2) Engagement surveys showed reports felt 'managed at, not managed with.' The CPO retroactively introduced the 'Working With Me' practice in year 2 and engagement scores recovered.
Manager READMEs Coverage
85%
Initial 'Working With Me' Coverage
0%
Engagement Drop in 'My Manager Knows Me'
-12 points
Recovery Time After Practice Added
6 months
Asymmetric documentation creates resentment. The Manager README practice REQUIRES the report-side counterpart to feel like a working contract rather than a manager imposing their preferences. Skipping the report side is a common mistake when companies copy the practice from public examples.
Related concepts
Keep connecting.
The concepts that orbit this one — each one sharpens the others.
Beyond the concept
Turn Working with Manager Practice into a live operating decision.
Use this concept as the framing layer, then move into a diagnostic if it maps directly to a current bottleneck.
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Turn Working with Manager Practice into a live operating decision.
Use Working with Manager Practice as the framing layer, then move into diagnostics or advisory if this maps directly to a current business bottleneck.