Most mentorship fails in a slow decay of calendar invites, until both people are relieved it stopped.
I wrote a version of this in 2018, drawing on years of mentoring designers from underrepresented backgrounds, and later through Andreessen Horowitz. I've had several more years of it since, on both sides. The original five points still hold. What I'd add is why they fail, which is the part I skipped.
1. Meet them where they are in their career
The most common failure, and I have done this myself, is a mentor answering the question they find interesting rather than the one that was asked. Somebody wants to know how to handle a specific piece of feedback from their manager on Thursday, and you give them a framework for career narrative arcs.
Speak at their level, about their situation, in language that matches where they actually are. And be concrete about where that is: a striking number of designers have no idea what level they're operating at, because nobody has ever told them plainly. Helping someone locate themselves is often the single most useful hour you'll spend with them.
Then tell them what the next level requires, and be clear which parts of getting there are outside their control. Pretending advancement is purely meritocratic is a way of making people feel personally responsible for structural problems.
2. Teach them to ask better questions
The skill that separates levels, at every level, is question quality, not answer quality.
A junior designer asks whether the button should be blue. A senior one asks what happens to the rest of the flow if this action becomes the default. A lead asks whether we should be building this surface at all given what we learned last quarter.
And the factors a good question has to hold have expanded. It used to be aesthetics, ergonomics, usability, data, technical constraints. Now it's also business model, ethics, inclusion, what the thing does at scale to people who never chose to use it. That's a harder discipline than it was when I started, and I don't think we've adjusted how we teach it.
You can hand someone an answer and solve their week. Teach them the question and you've changed what they can do without you. That is the actual goal, and the reason mentorship should end.
3. Relationships and allies are not a soft skill
Talent is not sufficient and pretending otherwise is a disservice. Relationships are how work gets funded, and how it survives the first person who objects to it. Someone who does not know this will do excellent work and watch it get shelved, and conclude the problem was the work.
Be specific here. Which people in this organization need to know what you're doing? Name the ones who'll be in the room when your project is discussed and you aren't. And work out who has been burned by something adjacent and will object for reasons that have nothing to do with you.
This is not cynicism; it's the operating system, and it's disproportionately invisible to people who didn't grow up around it, which is why it belongs in mentorship rather than being absorbed by osmosis from people who already had the map.
4. Teach them to advocate for themselves
Most designers I've mentored underclaim. They describe a team outcome when they drove it, or list what they made without saying what it changed.
The fix is mechanical, not attitudinal. Keep a record as things happen: what you did, what changed because of it, who else was involved. Not a brag document, an accurate one. Almost nobody can reconstruct this at review time, so they default to vagueness, and vagueness reads as a weak year regardless of how strong it was.
If you're mentoring someone from a background where self-advocacy carries a social cost (and for a lot of people it demonstrably does), say that out loud. The advice "just talk about your work more" lands very differently depending on how it's received when you do.
5. Show them a path, not a destination
The worst thing a mentor can do is present their own career as the route. Mine involved three companies of my own, four as an executive, a move to California and a move back, and almost none of that is repeatable advice. It's a sequence of specific circumstances I responded to.
What transfers is the reasoning. Why I took a role, what I was optimizing for at the time, what I'd weigh differently now. The decisions are portable. The path isn't.
Why it decays
Now the part I left out in 2018.
Unclear termination. Nobody agrees what "done" looks like, so the relationship runs until it's awkward. Set a horizon (six sessions, one specific goal) and renew deliberately if it's working. Ending well is not failure; it's the design.
The mentor is getting something they haven't admitted to. Being needed is pleasant. If you're honest, some of what makes mentorship rewarding is being the person with the answers, and that incentivizes dependence without anyone intending it. Watch for it in yourself. I have caught it in myself.
No preparation. Thirty prepared minutes beat ninety unprepared ones. If your mentee arrives without a specific question, the session becomes pleasant catch-up, and pleasant catch-up is what a relationship decays into right before it stops.
None of which is complicated. It's just easier to write five tips than to admit that most of the difficulty is in the maintenance.
What mentorship cannot fix
The five points assume the problem is one a mentor can reach. Often it is not, and I think a lot of mentoring energy gets spent in places where it cannot possibly work.
A mentee with a manager who does not give feedback, on a team with no clear levels, in a company where promotion runs on visibility, does not have a mentoring problem. They have an employer problem, and an hour a fortnight with a sympathetic outsider will not touch it. What that hour can do is help them see it clearly, which is worth something and is not the same as solving it.
I have watched organizations use mentorship as a substitute here, and it is an efficient substitute because it looks generous. Pair the underserved people with senior volunteers, run it for a year, report participation. Nobody has to change how promotion works or how feedback is given, and the burden of navigating a structure that disadvantages someone has been handed back to that person, now with a coach.
So the question I have learned to ask early is what the mentee is actually up against. If the answer is a skill or a blind spot, mentoring is the right instrument. If the answer is the shape of the place they work, the useful thing I can offer is a straight account of what I think is happening, an introduction or two, and the observation that leaving is a legitimate move rather than a failure of resilience. I have given that advice more often as I have gotten older, and I have not once regretted it.
Adapted and substantially expanded from notes I wrote in 2018. I've built design and product teams at Honor, Lyft, Grammarly and Pitch, mentored founders at Rockstart, and mentored designers from underrepresented backgrounds, including through Andreessen Horowitz.
© 2026 Renato Valdés-Olmos