How coaching works
Everything you need to know about working together, from logistics to outcomes. No corporate speak. Just honest answers to the questions you're asking.
Why coaching works for product and design leaders
Product and design leadership is uniquely challenging. You're caught between stakeholders who want everything yesterday, teams who need clearer direction, and strategies that change faster than you can communicate them. You're translating user needs into business outcomes while defending decisions to people who measure everything in metrics.
Most leadership advice focuses on frameworks and processes. But the real challenges don't have playbooks. They're about the human dynamics and organizational forces that make or break those frameworks. That's where coaching comes in.
Coaching provides what your organization can't: a confidential space to think through complex decisions, an experienced perspective from someone who's navigated similar challenges, and structured support for developing the capabilities your role demands. You're the expert on your own situation; I help you develop your own solutions while building the leadership muscles you'll need for whatever comes next.
What to expect in your first coaching session
The best way to determine if coaching will be valuable is to experience it directly. I offer a free introductory session where you can see how coaching actually works.
Your first session is designed to give you a real experience of coaching, not a sales pitch. Here's exactly what happens:
Context setting (10 minutes)
We'll discuss your current role, recent challenges, and what prompted you to consider coaching. This helps me understand your situation and what you're looking for.
Working session (30-40 minutes)
We dive into a real challenge you're facing right now. You'll experience my coaching approach firsthand: asking questions, offering frameworks when helpful, and helping you develop your own insights and action plans.
Reflection and next steps (10 minutes)
We discuss whether coaching feels like the right fit for you, what ongoing work might look like, and any questions you have about the process. There's no pressure. I want you to make the best decision for your situation.
Most people leave this first session with at least one actionable insight they can apply immediately, regardless of whether they decide to continue. There's no obligation, and even this initial conversation often provides value you can use right away.
Free session • No sales pitch • Immediate insights
How coaching sessions work
Once we're working together, each ongoing session follows a similar rhythm:
- • Brief check-in (about five minutes) on what's happened since we last spoke
- • You share what's most urgent or challenging right now
- • I offer observations and patterns I'm noticing from our work together
- • We prioritize and tackle the highest-impact issues first
Beyond addressing immediate needs, we'll track recurring patterns and develop strategies that address root causes, not just symptoms.
What good coaching feels like
As one former client put it: good coaching sessions leave you with "calming clarity with a bit of anxiety." You should feel like there's a lot of clarity about what needs to change, but some anxiety because now it's on your plate to actually improve and make things different.
What a coaching relationship looks like
I adapt to each client's specific needs, but here's the typical structure:
- • Bi-weekly 45-60 minute video calls (more frequent during critical periods, less when you're heads-down)
- • Unlimited async support between sessions for document review, quick questions, or reviewing important emails before you send them
This rhythm gives you enough space to implement changes without losing momentum.
Coaching vs therapy vs mentoring vs advising
While there's some overlap, these four approaches serve fundamentally different purposes. Here's how to think about which one you need:
| Coaching | Therapy | Mentoring | Advising | |
|---|---|---|---|---|
| Primary Focus | Future performance and leadership capability | Mental health, emotional healing, past experiences | Career development through shared experience | Solving specific problems with expert guidance |
| Time Orientation | Forward-looking, action-oriented | Processing past to improve present | Sharing what worked in the past | Immediate problem-solving |
| Who's the Expert | You are (coach helps you find your answers) | Shared expertise (you + trained professional) | Mentor is the expert sharing their experience | Advisor is the expert giving recommendations |
| Approach | Asks questions to prompt self-discovery | Clinical process with professional training | Shares wisdom and guidance from own career | Provides direct advice and solutions |
| Best For | Leaders wanting to develop their own capabilities | Addressing psychological health or emotional challenges | Learning from someone who's been there | Getting expert answers to specific questions |
| Example Question | "How do I navigate this stakeholder conflict?" | "Why do I always avoid conflict?" | "What did you do when you faced this?" | "What should I do in this specific situation?" |
The Bottom Line
Many successful leaders work with multiple types of support. Coaching focuses on developing your own leadership effectiveness. Therapy addresses psychological well-being. Mentoring provides field-specific wisdom from someone who's been there. Advising solves specific problems with expert recommendations. They're not competing approaches. They serve different needs at different times.
Common coaching topics
Coaching conversations span a wide range of leadership challenges. Here are some actual examples from past sessions:
- • Refining an all-hands presentation to more effectively communicate your product vision
- • Transforming your 1:1s from mechanical obligations to productive conversations you look forward to
- • Practicing your upcoming board meeting roadmap presentation with feedback on both content and delivery
- • Building a hiring plan aligned with your team's evolving needs
- • Developing a career ladder that provides clear growth paths for your team members
- • Navigating a difficult conversation with a stakeholder who keeps changing requirements
- • Balancing tactical execution with strategic leadership as your role evolves
What makes my coaching approach different
There are a lot of great coaches out there, and you'll get the most out of the experience if you find someone you feel comfortable with. My approach is centered on a few core principles:
Real-world experience
I've literally been where you are, having led product and design teams across startups and enterprises. I'm not learning theory from a textbook. I'm drawing on two decades of leadership experience (successes and failures).
Efficiency-focused
I'm obsessive about not wasting your time. Our sessions are structured to deliver maximum value in minimum time because I know your calendar is already packed.
Proven track record
Since 2020, I've coached 100+ leaders across 60+ companies, refining my approach through extensive practical application.
Tailored, not templated
While I have frameworks and tools at the ready, I resist the urge to force-fit your unique challenges into pre-fabricated solutions. You can get that level of support from a search engine or LLM.
That said, finding the right coaching fit is deeply personal. It comes down to whether you can be authentically vulnerable with someone and whether their style resonates with you. If you want more guidance on this, .
Investment and ROI
Who pays for this?
Typically, your company covers coaching as part of professional development. Most organizations have Learning & Development budgets specifically for leadership support like this. Companies invest in coaching because it's both good business (better leaders = better results) and helps with retention (people tend to stay where they feel supported).
If your company doesn't have a formal coaching program, some clients expense coaching through their personal development stipends or negotiate it as part of their compensation package.
What about ROI?
Leadership coaching delivers both tangible and intangible returns, though the most valuable outcomes are often the hardest to quantify.
Studies report impressive numbers (788% ROI from MetrixGlobal, 51% higher revenue for companies with coaching cultures), but these statistics only tell part of the story.
If you need to build a business case, I can help you:
- • Identify specific metrics relevant to your role and objectives
- • Establish baseline measurements before we begin
- • Document improvements over time
Some clients have seen measurable improvements in team retention (reducing costly turnover), project delivery timelines, product adoption metrics, team engagement scores, and successful cross-functional initiatives.
The real value often extends beyond these metrics, showing up in your ability to navigate complex challenges with greater confidence and less stress. Our focus will be on the outcomes that matter most to you and your organization, not just the ones that are easiest to measure.
Looking for self-directed resources?
Beyond personalized coaching, I share and for product and design leaders.
Frequently asked questions
Ready to kick the tires?
I treat our first conversation like a real session. We'll dive into your actual situation so you can see if my approach meets your needs.
Here's how it works:
No sales pitch. I just show my value, and if it's what you need, you'll know.