Milestone map
Milestone map
3 milestones
Establish a mentoring agreement and document the mentee's starting point
1–2 weeks
A mentoring relationship without shared goals is a series of chats. Before starting, agree in writing on what the mentee wants to achieve, the timeframe, the session frequency, and how you will both know progress has been made. Document the mentee's starting point — their current skill level, their immediate challenge, and one specific goal for the mentoring relationship. This baseline is what the M3 outcome evidence will be measured against. The agreement does not need to be formal; a shared document or email exchange is sufficient.
Proof required
Share: (1) the written mentoring agreement or summary (goal, timeframe, session frequency, and success definition), (2) a description of the mentee's starting point covering current skill level, immediate challenge, and one specific measurable goal, and (3) the mentee's confirmation that the agreement reflects their goals — this can be a short written statement or email reply from the mentee.
What gets checked
- Goal is specific and measurable — 'get better at coding' is not measurable; 'complete a working CRUD web app and push it to GitHub within 10 weeks' is
- Starting point is documented with enough specificity that progress can be measured against it later — 'beginner coder' is not specific; 'can write basic Python functions but has never built a web app or used version control' is
- Mentee confirmation is in the mentee's own words — the mentor's paraphrase of what the mentee wants is not the same as the mentee's own statement
Resources
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What a verifier looks for
- Ask for the mentee's goal in the mentee's own words — if the submitter can only paraphrase what the mentee wants, the agreement was not co-created
- Ask about the baseline: what can the mentee do now, and how will that be measured against the goal at M3? — if the baseline is vague, the M3 progress evidence will be vague too
- Confirm the mentee voluntarily chose this mentoring relationship — captive or assigned mentees produce very different dynamics than self-selected ones; the distinction matters for how to interpret the outcome evidence
- Setting a goal that is too broad to measure — 'become a better developer' has no end point; goals that take longer than 12 weeks to assess are too large for a single mentoring engagement
- Skipping the starting-point documentation — without a baseline, M3's progress evidence is a claim without a reference point; document the starting point before the first substantive session
- Writing the agreement yourself and asking the mentee to sign off — the agreement should reflect the mentee's goals in their own framing; a mentor-authored agreement that the mentee passively accepts usually misses what the mentee actually wants
Complete 6 sessions and keep a documented progress log
6–10 weeks
Mentoring is built across sessions, not in a single conversation. Complete at least 6 sessions over at least 6 weeks (one session per week minimum) and keep a brief log after each session: what was discussed, what the mentee committed to doing before the next session, and whether they did it. The log does not need to be long — 5–7 sentences per session is sufficient. The pattern of commitments made and kept (or not kept, and the discussion that followed) is the primary evidence of a real mentoring relationship.
Proof required
Share a session log covering all 6 sessions with: session date, main topic discussed, commitment the mentee made at the end of the session, and whether the commitment was completed before the next session. If a commitment was not completed, include one sentence on what was discussed about it. You do not need to include sensitive personal information — summarise topics at the level of 'discussed career options in data vs. product management' rather than personal details.
What gets checked
- 6 sessions on 6 separate dates spanning at least 6 calendar weeks — 6 sessions in a single week is 6 conversations, not a mentoring relationship
- Each session entry includes a specific commitment the mentee made — 'work on the project' is not a commitment; 'push a working login page to GitHub by Thursday' is
- At least one session entry notes that a commitment was not completed and describes what was discussed — a log where every commitment was completed on time is either unusually productive or is being reported selectively
Resources
Depthgo deeper
What a verifier looks for
- Ask for the session log and review the commitment column — specific, time-bound commitments ('push code by Thursday') are the signal of a real working mentoring relationship; vague entries ('think about career direction') suggest the sessions lack structure
- Ask about one session where the mentee did not complete their commitment — how did the mentor handle that conversation? This reveals whether the mentoring relationship has the honest feedback quality that distinguishes effective mentoring from supportive chat
- Check the date spread: 6 sessions should span at least 6 weeks — bunching sessions together defeats the purpose of building sustained momentum
- Sessions without commitments — a mentoring session that ends without the mentee committing to a next action is likely to produce no change between sessions; the commitment is what drives progress
- Log entries written all at once at the end of 6 weeks — session logs written immediately after each session capture specifics that are lost after a few days; a log written all at once will read uniformly and lack the specificity of real notes
- Sessions that are too infrequent to maintain momentum — sessions more than 3 weeks apart allow the mentee to lose context and revert to old patterns; the minimum of one session per week is intentional
Document measurable mentee progress and reflect on your mentoring growth
1–2 weeks after completing 6 sessions
A mentoring relationship is complete when the mentee has moved measurably toward the goal defined in M1 and the mentor can articulate what they learned about mentoring through the process. For this milestone, document the mentee's progress against the M1 goal with specific evidence, collect a short written testimony from the mentee, and write a reflection on how your mentoring approach changed across the six sessions and what you would do differently in the next engagement.
Proof required
Share: (1) a comparison between the M1 baseline and the mentee's current state against the specific goal — concrete evidence (a shipped project, a score, a new skill demonstrated, a job offer received, etc.), (2) a short written testimony from the mentee (3–5 sentences) about what changed for them and what was most useful about the mentoring, (3) a 200–300 word reflection on how your mentoring approach evolved and one thing you would do differently next time.
What gets checked
- Progress evidence is concrete and comparable to the M1 baseline — 'the mentee improved' is not evidence; 'the mentee shipped a working app and has 3 GitHub commits from the last 4 weeks, compared to zero at M1' is
- Mentee testimony is in the mentee's own words and names something specific — 'it was really helpful' is not testimony; 'the weekly commitment structure meant I actually did the work between sessions instead of waiting for motivation' is
- Mentor reflection is honest about at least one mistake or missed opportunity — a reflection where everything went well and nothing would be changed next time is implausible
Resources
Depthgo deeper
What a verifier looks for
- Ask to see the M1 baseline document alongside the M3 progress evidence — the comparison between baseline and current state is what constitutes proof of progress; progress claimed without a baseline is unverifiable
- Ask for the mentee testimony document and confirm it is in the mentee's own words — ask the submitter whether they reviewed or edited the testimony before submitting; editing a mentee's testimony introduces a credibility problem
- Ask the mentor what they would do differently in the next mentoring relationship — a specific, honest answer ('I would establish the session commitment structure in the first session rather than in session 3') shows genuine reflective practice; a vague answer suggests the reflection was performative
- Progress evidence that describes the mentee's stated intentions rather than demonstrated change — 'the mentee plans to apply for jobs' is not progress; 'the mentee has submitted 3 applications and received 1 interview since the mentoring began' is
- Mentee testimony written by the mentor — the testimony must be in the mentee's own words, even if it is brief; a mentor-authored summary of the mentee's experience is not the same thing
- Reflection that credits all the mentee's progress to the mentoring — attribution is complex; honest mentors acknowledge that the mentee did the work and identify specifically what the mentoring contributed