How Coaching Actually Works

What if I'm not sure coaching is right for me?

The best way to determine if coaching will be valuable is to experience it directly. I offer a free introductory session where we can:

Discuss your specific challenges and goals
Experience my coaching approach firsthand
Assess our potential chemistry and fit
Explore what a coaching engagement might look like for your situation

There's no obligation, and even this initial conversation often provides insights you can immediately apply.

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: With 4+ years of coaching and 100+ leaders across 60+ companies, I've refined 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.

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 does a standard coaching relationship look like?

While I adapt to each client's specific needs, here's the typical structure:

We meet every other week for 45-60 minutes (more frequently during critical periods, less often when you're in crunch mode)
Sessions happen virtually via video call
I'm available between sessions for unlimited async support (document review, quick questions, reviewing important emails before you hit send)

This cadence provides enough space to implement what we discuss without losing momentum.

How do sessions actually work?

Each session is focused on making tangible progress on your most pressing leadership challenges:

We begin with a brief check-in (about five minutes) to get context on how things have been going since we last spoke
The majority of our time is spent tackling specific challenges you're facing
You bring topics that are top of mind
I bring observations and potential areas to explore based on our ongoing work
Together we prioritize and work through them one by one

While individual sessions focus on immediate needs, we'll identify recurring patterns and develop strategies to address the underlying systems, not just the symptoms.

How should I prepare for our sessions?

There's no formal preparation required—just show up ready to engage. Some clients prefer to:

Send a brief agenda a day before our sessions
Jot down challenges they've faced since our last conversation
Come with specific situations where they want feedback or guidance

Others simply arrive and talk through whatever is most pressing. I'll help guide the conversation either way, so the only real requirement is being fully present during our time together.

What are some real examples of 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 actually 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

Is there homework?

Sometimes. Certain development areas require progress between our sessions, but:

We decide together what makes sense given your current workload
I won't assign work when you're already overwhelmed
Any "homework" is directly relevant to your actual job, not busywork

The most effective coaching happens when you can apply concepts in real time to your day-to-day challenges.

How do we measure success?

Success looks different for every leader, so we'll define what matters most to you. Common approaches include:

Progress on specific goals from your performance reviews
Improvement in areas identified through 360 feedback
Periodic check-ins with your manager (with your knowledge and consent)
Your own satisfaction with how you're handling previously challenging situations
Concrete outcomes like improved team retention, faster product delivery, or better cross-functional collaboration

We'll establish clear indicators at the beginning of our work together and revisit them regularly.

What about ROI?

Leadership coaching delivers both tangible and intangible returns, though I've found that the most valuable outcomes are often the hardest to quantify.

While studies have found impressive statistics—like the frequently cited 788% return on investment from a MetrixGlobal study and evidence that organizations with strong coaching cultures report 51% higher revenue than similar companies according to coaching statistics research—these numbers only tell part of the story.

If you need to build a business case for coaching, 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
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.

How is coaching different from therapy or mentoring?

While there can be some overlap, these approaches serve different purposes:

Coaching is forward-looking and action-oriented, focused on developing specific leadership capabilities and achieving professional goals. Our work together centers on your effectiveness as a leader.
Therapy typically addresses psychological health, emotional processing, and healing from past experiences. While coaching might touch on emotions and behavioral patterns, it's not designed to treat mental health conditions.
Mentoring usually involves an experienced professional in your field sharing their knowledge and career advice. While I bring product and design leadership experience to our relationship, coaching goes beyond advice-giving to help you develop your own solutions.

I'm careful about maintaining appropriate boundaries and will refer you to other resources if your needs would be better served by therapy or mentoring.

What about confidentiality?

Coaching works best when you can be completely honest, which requires trust and confidentiality:

Everything we discuss stays between us
I don't report back to HR or your manager without your explicit knowledge and consent
The specifics of our conversations remain private even if your company is paying

This confidentiality creates a safe space for vulnerability and authentic growth.

How long do coaching engagements last?

The duration varies based on your needs and your company's approach:

Some organizations build coaching into executive compensation as an ongoing benefit
Others provide a year of support to work through typical annual challenges
We can design shorter engagements focused on specific transitions or challenges

My commitment to clients doesn't end when the formal engagement concludes. I keep in touch with former clients and provide complimentary ad-hoc sessions for as long as they're helpful.

Isn't having a coach kind of embarrassing?

Not at all. Having a coach doesn't mean you don't know how to do your job. The most successful people in virtually every field work with coaches:

Elite athletes have multiple coaches even at the peak of their careers
Fortune 500 CEOs regularly engage executive coaches
Acclaimed musicians continue taking lessons throughout their professional lives

Leadership coaching is about optimization and growth, not remediation. It's a sign of ambition and self-awareness, not weakness. The best leaders recognize that having an objective thought partner provides perspectives they simply can't get from inside their organization.

Consider this: your company is investing in coaching because they value you and want to maximize your impact. They see your potential and believe in your growth—that's something to be proud of, not embarrassed about.

In my experience, leaders initially concerned about perception quickly find that mentioning they have a coach actually enhances their professional reputation. It signals to others that you take your development seriously and are committed to bringing your best to your role.

Schedule a free leadership chat