Hiring a design mentor can be a shortcut to clarity and an accelerator to career growth.
It can also turn into an expensive loop of “good conversations” that never change what you do Monday morning.
If you are a senior IC or a new design manager, this checklist will help you hire a mentor who fits your actual problems: choosing what to optimize for, building evidence, and translating “next level” into real behaviors.
Name your problem area first, as senior IC problems and new manager problems are different
A lot of mentoring fails because the mentor is solving the wrong problem.
If you are a senior IC, you might need:
- A sharper scope: what you own, what you influence, what you stop doing
- An impact story that holds up in promos and interviews
- Stakeholder strategy for high-stakes, cross-functional work
- A plan to move from “excellent execution” to “decision ownership.”
If you are a new design manager, you might need:
- A way to delegate without quality dropping
- A feedback cadence that does not turn into avoidance
- A system for prioritization, decision-making, and communicating tradeoffs
- Help leading through ambiguity without becoming the team’s bottleneck
Decide what “better” looks like in the next 90 days
Do not hire a mentor for “growth.” Hire for outcomes.
Good 90-day outcomes for a senior IC:
- A promotion-ready narrative with 3–5 evidence points you can defend
- One case study (or portfolio story) rewritten to show scope, decisions, and outcomes
- A stakeholder plan for one initiative, with specific conversations scheduled
- A clear “role definition” for your next level, mapped to behaviors you can practice
Good 90-day outcomes for a new design manager:
- A delegation plan for 2–3 workstreams, with ownership and check-in rhythm
- A feedback system: what you do weekly, what you do monthly, and how you document it
- A decision log or planning ritual that reduces firefighting
- A clearer operating model with PM and engineering so you are not negotiating everything from scratch
If the mentor cannot help you make outcomes concrete, you will default to “more effort,” which is not the problem.
Ask how they will diagnose your situation (not just advise you)
The first call should not feel like a podcast.
A good mentor will ask:
- What are you optimizing for right now?
- What is the constraint: time, confidence, politics, unclear expectations, or missing evidence?
- What is happening in your org that makes this hard?
- What have you tried already, and what did not work?
If they jump straight to “here’s what you should do,” they may be selling a framework rather than helping you.
Make sure they can work at your level
Generic advice sounds smart, but doesn’t move careers.
Look for mentors who consistently do at least one of these:
- Create tradeoffs: help you say no, narrow scope, and choose the few bets that matter
- Build evidence: help you document impact beyond “one metric” and turn it into a narrative
- Train behaviors: role-play hard conversations, meeting facilitation, stakeholder updates
- Define the role: translate “Staff,” “Lead,” or “Manager” into decision ownership in your company
If you leave sessions inspired but not more decisive, your growth will not compound.
Pressure-test the cadence against your real week
You are not buying motivational talk, but a support system that creates career-development momentum.
Before you commit, align on:
- Session cadence and duration
- What happens between sessions (async check-ins, document review, accountability)
- Whether they will review tangible artifacts: promotion packet, role definition, portfolio story, 30/60/90 plan
- What “success” looks like at the end of the first month
If their process assumes you have 5 extra hours a week, and you do not, it will fail.
Red flags to watch out for
Consider walking away if:
- They sell a universal “leadership mindset” without getting specific fast
- They make everything about confidence instead of decisions and evidence
- They promise outcomes they do not control (“promotion in 8 weeks”)
- They do not ask about constraints, stakeholders, or expectations
The one question that makes the decision obvious
Ask this before you pay:
“If we worked together for 90 days, what would we build, and how would we know it’s working?”
A good mentor will answer with concrete artifacts and behaviors.
A weak mentor will answer with vibes and coaching lingo.
The easiest way to see if I’m a good fit for you is schedule a short 30-minute call using the contact form. See you soon!
