honest club

Honest coaching for designers, creatives, and people in tech.

👋 Hey, I'm Andrew. I spent twenty years in product design, the last stretch leading teams. Now I coach the people I used to work alongside, from the inside out.

Book a free discovery call →

25 minutes. A real session, plus a look at how we could work together.

Who I coach

My people.

I work best with people who feel things deeply. Big emotion is not a problem to be managed here, it is the material we work with. It is what lets us get past the tidy version of the story and into the kind of change that actually holds.

Coastal hills meeting the ocean

Product designers & design leaders

ICs, managers, and directors wondering if this is still the work they want, or how to lead without losing themselves.

Coaching for designers
A path through misty hills

Creatives

People whose work is personal, who feel the gap between what they make and what they're asked to make.

Coaching for creatives
A coastal sunset with a bird in flight

People in tech

PMs, engineers, and managers navigating reorgs, burnout, promotions, or the itch to build something of their own.

Career coaching
Kind words

What it's like to work with me

Andrew has an astute, human-first approach. He connects with you deeply before working toward solutions for whatever you're facing.

AI Product Designer

Andrew embodies the best of what a design culture can be: the person who most clearly represents the values, history, and heart of a design team.

VP, Design

The energy Andrew brings to every room is contagious. Working alongside him made the whole team better.

Senior Director, Design

Andrew is a tremendous part of the cultural fabric of any org he's part of. His presence is felt long after he's moved on.

Senior Design Manager

Andrew is a wonderful person in this world. Watching him grow, and being trusted to grow alongside him, was a gift.

Staff Designer
What I offer

Ways to work together

Coaching runs one on one, in a small group, or inside a company. One on one, the difference is not how hard but how far you want to climb. We work pricing out together on the call.

One on one, over time

Best for most people

Monthly Coaching

A 55-minute session every other week, for whatever you are working through. Month to month, cancel anytime.

12 sessions over six months

6-Month Package

For the long climb: the whole shape of how you work and live.

Book now
One 55-minute session

Single Session

For one decision or conversation, no ongoing commitment.

Book now

Groups and companies

In person, in San Francisco

Honest Sessions

Morning coffee, a simple lunch, or an early dinner, depending on the session. A small group, a structured conversation, and the transition you are actually in the middle of. Tickets stay at five dollars or less.

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For companies, founders, & teams

Coaching inside your organization

Design and product teams carry a lot and have few places to be honest about it. I become that place. Clearer decisions and fewer quiet exits tend to follow.

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What I believe

How I show up for you

Misty rolling hills
01. Honesty

Real talk over polished talk

We tell the truth about what's working, what isn't, and what you actually want.

A quiet path leading to the ocean
02. Listening

I'll talk your ear off later. First, I listen.

I slow down to hear what you're saying, and what you're not. Then I walk alongside you.

Tall redwood trees
03. Inner work

Start on the inside. The title catches up.

Roles and titles shift when something inside shifts first. We start there.

Soft green Japanese maple leaves
04. Champion

I'm your loudest fan in the room.

I root for you, push back when it helps, and remind you who you are.

The path

What the work looks like

  • 01

    A free 25-minute call

    No prep needed. We talk, you get a feel for how I work, and at the end I'll share how coaching with me works so you can decide if it lands.

  • 02

    We get honest

    We choose the shape, monthly, six months, or a single session, and start saying the true things out loud, including the parts you have been carefully talking around.

  • 03

    The change holds

    Roles and titles shift when something inside shifts first. In my experience, that shift shows up around the eighth session, so we stay with it until you can hear yourself clearly without me.

Twenty-five minutes, no cost, and you get a real session out of it. We will talk through packages and pricing there too.

Book a free discovery call →
About me

Hey, I'm Andrew

Andrew Tolentino, life and career coach, laughing in San Francisco

I've spent about twenty years in product design, the last five or so leading teams, mentoring designers, and helping people grow into the work and lives they actually want.

I'm a professionally trained life and career coach and a Co-Active Practitioner (CAP). It's a coaching method that's curious, direct, and human, and it fits how I already work.

Outside of coaching, I'm a deeply creative person. I run Cake Therapy, my home bakery, and spend time throwing pottery and shooting film photography. Making things keeps me curious, and it shows up in how I coach.

There is a longer version of how I got here, and why I left my job to do this.

Fair warning: I'm loud, I laugh a lot, and I get genuinely excited about your stuff. Bring your whole self, because I'm bringing mine.

  • Co-Active Practitioner (CAP)
  • 20 years in design, 5+ leading teams
  • Baker, potter & photographer
  • Based in San Francisco
Read my story

Come say hey!

Free 25-minute call. It doubles as a sample coaching session, so you leave with something either way. We'll talk through packages and pricing there too.

Book a free discovery call →

Not in tech? Most of my clients are, but the work is human. If something here resonates, let's talk.