How Coaching Works

As your strategic advisor, executive coach — and occasional secret weapon — I’ll help you elevate your leadership so you can take yourself, your team, and your company to Point C and beyond.

But more than that, my ultimate goal is to give you - a unique leader committed to creating an extraordinary life - an experience that unlocks your full personal and professional potential for all of the Point Cs to come.

Grounded in decades of experience across entrepreneurship, innovation, media, and leadership education, my approach is shaped by real-world lessons from helping hundreds of leaders navigate growth, change, and reinvention.

Here’s how our coaching journey unfolds — from our first session to your Point C:

Our First Session

You need to feel like you can establish a rapport with an executive coach before committing to one. That's why I skip the consultation and offer a real, free first coaching session so you can decide whether you’re ready to make the personal and financial investment to reach your Point C. Our first 50-minute Zoom call is on me.

We’ll dive into your personal and professional goals, define the Point C you want to reach, and determine a pace that fits your needs and budget. You’ll get a feel for my coaching style, and together we’ll establish the norms that will guide our work.

If it feels like a mutual fit—and you’re ready to make the commitment—you'll choose a coaching plan, we’ll schedule a regular coaching rhythm at a consistent day and time, and continue the journey.

Moving Towards Point C

We’ll meet weekly, biweekly, or monthly for 50-minute sessions over Zoom — whatever cadence supports your goals and budget best.

  • Everything we discuss is confidential, even if someone else is covering the cost.
  • You own the agenda. I’ll hold you accountable to your goals.
  • Each session blends coaching, strategic advising, and hands-on prototyping. Together, we’ll challenge and refine your strategies, approaches, and ideas in real time—so you leave every session with clarity, confidence, and a clear next step.

This is a safe space to experiment, learn new tools, role-play critical conversations, and prototype the culture you want to build — and the leader you want to become.

Maintaining Momentum Between Sessions

To help you maintain momentum between sessions, I offer one round of asynchronous feedback between each coaching session.

You can send me a Loom video (10 minutes or less) walking through a challenge, idea, or prototype you’re working on. I’ll respond with targeted feedback to help you move forward.

If something big comes up between sessions—or you want to prep for a high-stakes moment—I’ll do my best to make time for a live emergency session.

As a coaching client, you’ll also maintain full access to The Idea Bucket—my weekly newsletter and archive featuring one visual framework, supporting one act of leadership, that brings you one step closer to building the subculture of innovation you want.

Deploying Me Strategically

As we coach together, you may recognize key moments when you want to deploy me, who will have become a trusted outsider, to accelerate your impact inside your organization.

As a coaching client, you’ll have priority access to hire me for additional services, including:

  • Facilitating strategic offsites, meetings, and retreats
  • Teaching workshops or leading user-centered design bootcamps
  • Building and running internal accelerator programs around your top initiatives
  • Assessing your culture’s capacity for innovation and experimentation
  • Expanding coaching to include your broader leadership team

Being a trusted outsider means I can speak truth to power—and bring unique insight grounded in global best practices. With the structural advantage of operating outside your organization, and the network advantage of working across a wide range of leadership and strategy challenges, I help cut through the noise, name what’s really going on, and offer clarity, perspective, and challenge in ways those on the inside often cannot.

Your Strategic Advisor

As you can see, this partnership goes beyond traditional coaching.

I’ll be your trusted strategic advisor—during sessions, between sessions, and in the moments that matter most: a secret weapon you can deploy to help your team fail faster, learn quicker, and succeed sooner. It’s a role I’ve played for many leaders - hear how they describe the experience.

Now, let me introduce myself — so you know who you’ll be partnering with.

My Story