What Mentoring Someone Into Tech Actually Takes

Two people sat across from me a year apart, both trying to get into tech, both convinced everyone else already knew a secret they didn't.

One of them, Rawan, went from catering and hospitality into product management and now runs eight products with junior PMs reporting to her. The other, Megan, went from commercial furniture into a full UX research portfolio, earned her certificate, and then took a job in a completely different field. On paper those look like a success and a failure. They're not. They're the same kind of win, and the difference between them is the whole point of this post.

The myth I want to kill

People think mentoring someone into tech is a funnel. Pour in a motivated career-changer at the top, run them through some courses and coaching, and a job offer falls out the bottom. If the offer comes, the mentorship worked. If it doesn't, it failed.

That framing is wrong, and it quietly hurts the people it's supposed to help. It makes the mentee feel like a conversion metric. It makes the mentor optimize for the wrong thing. And it treats the only acceptable ending as "got hired in the exact field we studied," which ignores the most valuable thing coaching actually produces: a person who can finally see the work clearly enough to choose well.

Let me show you what I mean with both stories.

Rawan: the pivot that landed

Rawan reached out after COVID cost her a hospitality job she didn't want to go back to anyway. She'd been calling the thing she wanted "program management" for three months and didn't yet know the difference between product and project.

We didn't start with theory. We built a real case study around a real product, week after week. She did the research a stakeholder would actually believe, found genuine user pain, and prioritized it. The turning point wasn't a framework. It was the moment she wireframed a feature she loved, realized it was far more complex than it looked, and killed it because the evidence told her to. That's thinking like a product manager, not just talking like one. The case study she built got her hired, and she's been leading ever since. (The full story is here.)

Megan: the pivot that redirected

Megan came to me as a new mom getting ready to re-enter the workforce, unsure what she wanted to do next. We met after her baby went to bed, week after week, for about a year. She tore down an app she already used, then designed her own from scratch: real personas, a journey map, two rounds of usability testing, and a moment that should sound familiar, she cut a feature she'd built once users told her they hated it.

She earned the Google UX certificate. Her work was genuinely good. And then a different opportunity came through a friend, and she took it. Not a UX role. (That full story is here.)

I'm not disappointed about that, and neither is she. Megan got a real look at the work, the skills to do it, and enough self-knowledge to decide it wasn't the path for her. The failure would have been two more years of "what if." Instead she has an answer.

The patterns underneath

I've coached more than 150 product managers, in classrooms, inside a giant healthcare portfolio, at defense software factories, and one-on-one with career-changers. The environments are wildly different. The patterns aren't. (I wrote those patterns up here.) Three of them show up in every single pivot:

Build real proof, not flashcards. Nobody breaks in on theory. They break in on an artifact they can put in front of a hiring manager and defend. Rawan had a case study. Megan had two. Make the thing, get feedback on the thing, make it again.

Meet people exactly where they are. That looked like an Instagram DM for one of them and a standing slot after bedtime for the other. The logistics of someone's real life are not an obstacle to the coaching. They're the container for it.

Coach the decision, not just the skills. The highest-value thing I can give a career-changer isn't a portfolio. It's the clarity to know whether they actually want the field they've been romanticizing. Sometimes that clarity says go. Sometimes it says go somewhere else. Both are the job working.

The honest scoreboard

So here's how I actually keep score. One landed pivot, running a full product suite. One redirected pivot, made with real information instead of fear. And more than a hundred PMs who walked away more precise than they came in.

If you measure mentoring by job offers, you'll miss most of what it does. Mentoring's real job is to hand people the work and the truth, so they can choose with their eyes open. The offer is nice. The clear-eyed choice is the point.

If you're standing at the edge of a pivot and you're not sure the field you're dreaming about is the one you actually want, don't wait for certainty. Go do one small piece of the real work. I'll help you build it, wherever it ends up taking you.