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How My Coaching Works
7 min read

How My Coaching Works

How My Coaching Works

I'm asked by prospective coaching partners all the time what it's like to work together. I frequently hear questions like, how's your coaching structured or how does it all work?  Whenever I get the same questions over and over, I find it useful to put pen to paper. This helps me refine my thinking, share more broadly, and spark a dialogue.

This is my first attempt to publicly articulate how I serve my coaching partners. Before I dive into the details, I'd like to make a few important points.

First, I bring my full self to the coaching relationship. Yes, I'm a trained and ICF-certified coach but I'm also an advisor, meditator, father, recovering VC, AA sponsor, and more. You're getting 40 years of lived experience, 10 years as an operator, 10 years an investor, and 3 years as a coach. Most of the time, I show up wearing my coaching hat. Occasionally, I'll put on my advisor or investor hat if that's what you want or need. Bottom line: you're getting more than a coach.

Second, I don't view you as a "client." Instead, I see you as a partner. Our work together is a co-creation. I seek to build and cultivate a symbiotic relationship where we grow, learn, and thrive together. Our partnership is built on a foundation of trust, mutual respect, collaboration, and growth. Like in any relationship, we're going to bump up against our edges and hopefully go beyond them. I am committed to evolving collectively.

Finally, I'd like to underscore several of my core beliefs. I believe the world is rigged in your favor. That doesn't mean things will be a cake walk but I generally trust that things will work out for you. I also believe you will be successful whether we work together or not. My role is to help you gain greater clarity, awareness and perspective to help you go further faster. Lastly, I  believe that personal growth is essential for a fulfilled life. Investing in yourself is hands down the most important investment you can make.

If what you just read resonates with you, I invite you to continue to the FAQ below. To learn more about working together, feel free to contact me here. Godspeed.


Who is your ideal client?

My ideal partner is an early stage entrepreneur who wants to evolve into high performing CEO. I usually prefer them to have at least 4 FTEs though that isn't a requirement. I also work with "Leaders In Transition" and GPs at VC firms. If you would like more details, I wrote this post that captures who I serve.

How many clients do you work with?

I am purposefully keeping my practice small for the time being. I usually work with no more than 8-10 coaching partners at once.  That's why I view our initial conversations as a fit process rather than a sales process.

How long does a coaching engagement last?

My coaching relationships are open-ended and the duration is mutually determined. All I ask for is an energetic commitment for at least three months. I typically won't partner with someone unless I believe there is the potential to build a long term relationship. The average length right now is nine months. No coaching relationship should last forever.

Do you have a program or system?

I don't subscribe to a "one-sized fits all" or templatized approach to coaching. Context matters and is critical. While I draw on frameworks, case studies and other resources when necessary, I believe you are inherently wise and resourceful to determine the best path forward. My immediate goal is to help you develop novel perspectives and approaches rather than providing just advice or answers. I tailor the approach based on your situation, challenges, experiences, cultural norms, values and knowledge.

How do we kick off the relationship?

Before we get started, I send an on-boarding package which includes a standard coaching agreement, invoice for the first month, and "Discovery Questionnaire." We then kick off the relationship with a ninety minute "Discovery Session." During our first session together, we set our intentions for the relationship, dive into the questionnaire, agree on logistics, and address any final questions before moving forward.

What's a "Discovery Questionnaire?"

The questionnaire helps you get to know yourself better and set an intention for the relationship. It's designed to help you think deeply about who you are as a leader and human. This includes your values, habits, strengths, blockers, goals, and much more. The questionnaire also helps you clearly define what you want achieve together in the first 3-6 months. We review this document every few months to see how you're changing and progressing towards the future you envision.

How often do we meet?

I typically meet with each "coaching partner" twice per month. You can also text or email me at your convenience. I also make myself available for "spot coaching" if you need support in between sessions. Remember, this is a partnership. You can think of me as an extension of your personal board of directors. I'm available when you need me, not just when we have time scheduled.

Where do we meet?

Currently all of my sessions are virtual. Sessions take place over Zoom or phone. I don't prefer one medium over the other. I leave that up to you based on your preference. Each medium is a different experience with strengths and limitations.

How long is a session?

Coaching sessions typically last an hour, but sometimes go longer depending on your objectives and how much we're able to achieve in the allotted time.

How much time do I have to invest in coaching?

Like anything in life, you will get out of this what you put into it. Coaching includes not only the sessions but also the preparation and follow up. I would mentally prepare to spend at least two hours every other week. This could be more depending on the scope of the follow ups and action items.

When days and times do you coach?

I typically coach Monday through Thursday from 11am ET to 6pm ET. That said, I have flexibility if we need to work around your schedule, move things around or talk in a moments notice.

How do we schedule our sessions?

I’m flexible. For many of my "coaching partners," we typically schedule our next session in real time at the end of a session. I can also work with your assistant if you have one. You may also book appointments at your convenience using my Calendly link. I want to make this easy for you.

How do I prep for a session?

I send an email 48 hours in advance with prompts for you to contemplate and complete. This allows us to hit the ground running and make the most of our time together. Here are the questions I typically send in advance:

  • How would you rate last week from 1-10? Why?
  • What progress have you made since our last 1-1 session? Any big wins?
  • What have you learned?
  • What is your top priority right now? Why is it most important?
  • What challenge is keeping you up at night?
  • What are the 1-3 topics you would like to cover this week?
  • Anything I can do to help you between now and our session?

Can you walk me through a typical session?

A typical session has four phases. The first phase is a quick check in. This provides each of us an opportunity to share how we're showing up energetically and emotionally. After our check ins, we spend five minutes highlighting any key events, milestones and/or learnings since our last session. We then dive into the main topic(s) which takes the bulk of our time. Finally, we spend the last five minutes summarizing any action items, next steps, and accountability structures.

What happens after each session?

I send an email with detailed notes typically 12-48 hours after a session. These notes are structured in three sections — follow ups, your reflections and my reflections. Follow ups include specific next steps and timing. Your reflections include any notable quotes and questions that you surfaced. My reflections often include general thoughts, reframes, and questions for reflection. I maintain a coaching log in Notion so you can access the notes on demand and track our progress.

How do you provide accountability outside of the session?

Accountability is an important aspect to any coaching relationship. I provide different forms of accountability depending on your needs and desired outcomes. Some partners like simple nudges like a weekly text or email while others prefer a quick call to check in at the end of the week. When we set your action items, we also identify the right accountability structure for you.

How else do you help between sessions?

There are countless ways you can leverage me when we're not together. As I indicated above, you can always text or email me at your convenience. I also share curated books, articles and resources depending on your learning objectives. Additionally, I review important documents such as OKRs, pitch decks, sensitive communications, and much more. If you're not sure, just ask. I strive to be an expansion of your inner circle and active member of your personal board of directors.

If I need something in between sessions, how quickly do you respond?

I try to have a 24 hour response time. That said, if you have an emergency or a time sensitive deadline, I always encourage you to text me.

How can I provide feedback?

Every few months, we set aside five minutes at the end of a session explore what's working, what's not, or any changes you'd like to make to the coaching relationship. I can also send a brief feedback form in the event you prefer sharing asynchronously.

How long does it take to get results?

This varies from person to person. A number of partners have felt and seen the benefits during our very first session. That said, I would expect to see outcomes and results in one or two months. We should always know what success looks like and whether we are moving closer towards whatever that might be.

How much time do I have to make a decision?

Take as much time as you need. Coaching is a big investment of time, money and energy. I very much view this as a fit process rather than a sales process. Both of us need to feel energized and excited to work together. I sincerely want what’s best for you personally and professionally.

What's your fee?

I charge a monthly retainer rather than a "per session" fee. My average monthly rate is $2,000. I don't let money get in the way if there's a strong fit and desire to work together. I bill on the first of every month. I don't ask for large upfront payments or force you into a multi-month contract.

Do you take equity?

I will never explicitly ask for equity from anyone I coach. Several coaching partners have offered "advisor shares" after we've worked together for some time. If this conversation happens organically, I'm open to exploring. That said, I have zero expectations around equity and won't broach the subject.

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