Frequently Asked Questions

“Gray’s ability to reflect my behaviors in a non-threatening way was eye-opening. He helped me see that my own behaviors were the only thing standing between me and where I wanted to be.”

What does a typical coaching engagement look like?

During our initial consultation I’ll gain a better understanding of your situation and provide some options on how we might best work together. While each individual circumstance is different, a typical engagement may last six months and include an initial discovery session, an in-depth 360 review, and bi-weekly coaching sessions. Together we’ll identify goals and aspirations that truly matter, figure out what’s holding you back, and chart the course towards the outcomes that you desire. I very rarely work with anyone for less than three months.

What kind of clients do you work with?

I work with high performing clients that are building thriving businesses around customer-centric products.

Typically my clients are sitting in the CEO, CPO, or CTO seat, or are key members of their leadership teams. These leaders are aiming to make a significant impact in the world and their products have the potential to shape our future. I am energized by proving my support and amplifying their success.

My clients typically fall into one of two zones: (1) senior leaders at established tech companies, or (2) c-suite executives at earlier stage companies that are scaling. While day-to-day coaching needs differ, the common thread is that both are scaling themselves as leaders and delivering meaningful business outcomes.

Are you a “Leadership Coach” or a “Product Coach”?

I am a leadership coach with deep experience driving business outcomes through leading product development teams. I view my role is to help you do you very best thinking and to show up at your best, not to tell you what to do. That said, I do hold strong opinions around the science and art of building products and I am happy to share those with you. If you are looking for product expertise, it’s extremely likely that I have personally lived through a situation similar to the one you face, and I have also led or coached several others through something similar as well. I can offer up approaches I’ve seen work for others and share the pros and cons of each. Clients have told me that this helps them make efficient and confident decisions.

Perhaps a client of mine put it best when he said, “In addition to leadership coaching, Gray has direct expertise in the science of building products and driving massive business impact. You’re not going to find anyone else in the industry like that.”

I’m not feeling like a “high performer” these days, though I used to be. Does it make sense for us to work together?

I am energized by helping drive meaningful outcomes for my clients and their businesses, and so I only work with clients who are motivated to do the hard work necessary to achieve real change. We’ve all felt stuck at some point in our careers and lives, and that is completely understandable. Here’s the test: are you truly ready to put in the energy to get unstuck, to get back to a place of motivation and excitement? If so, let’s talk.

What is involved in the coaching process?

Together, we establish a strong relationship built on care and curiosity, which allows us to delve deep into your true aspirations. We clarify goals that resonate with you and identify both internal and external barriers that may be holding you back. With this understanding, we chart a clear path forward, outlining actionable steps to make meaningful progress. Throughout this journey, I provide consistent accountability, ensuring you stay committed, take decisive action, and tackle the hard work necessary to unlock new levels of imagination, productivity, and leadership.