• Table of Contents (expand me!)

There’s a lot of variability in what you get from different coaches. So what can you expect from working with me? How do I approach coaching?

Who I Coach

• Most of my clients are founding CEOs of startups.
• I also work with several founding CTOs, COOs, and CFOs.
• I begin working with most of my clients when they’re at or near product-market fit, but my current list of clients ranges from companies with ~10 employees all the way up to 500+.
• All of my coaching relationships are 1:1. Sometimes I work with pairs of co-founders, but we meet separately.
• Occasionally my work with a CEO or executive extends to facilitating off-sites, retreats, or group trainings.

Client-Specific > Rule-Driven

“Every founder is dealing with the same challenges, but they deal with and experience those challenges in different ways.” — Amy Buechler [1]

Amy’s quote encapsulates how I think about coaching so wonderfully. Because every founder is dealing with the same challenges (hiring, selling, shipping, performance management, board meetings, co-founders, etc.), it’s dreadfully tempting to think one can publish a manual, curriculum, guidebook, or “one-size fits all” approach to becoming a successful founder or CEO. But since every founder responds to, copes with, manages, and experiences these challenges in such different ways, that’s impossible. Instead of giving you a book to read on how to ski, I’d rather we strap the skis on, get on the chairlift, and we’ll use any challenge on the way down the mountain as an opportunity to learn and improve. That said, for the readers out there, I periodically update Andy’s Coaching Curriculum for Founders with resources under specific headings.

Another way flexibility plays into my approach to coaching is that I can switch between a few different “hats.”

• The Coach Hat: I primarily wear the “coach hat,” which involves asking lots of questions, to help you better understand the challenges you’re facing and eventually develop your own solutions.
• The Founder Hat: Far less often, I’ll put on my “founder/advisor” hat where I’m happy to share best practices I’ve seen work first and second-hand. I’ll usually do this by asking questions to “diagnose” what’s going on, and sometimes I’ll have a “prescription” in the form of an article, excerpt from a book, video, etc. for you to read to help you approach whatever challenge is at hand.

I find that clients love it when I put on “The Founder Hat,” because I’ve curated an extensive library of very specific and useful resources for different scenarios, but I also try to be cautious not to offer advice or problem-solve too soon, as that’s an easy way to end up solving the wrong thing or rob you from the opportunity to learn to self-coach without me—the last thing I want is to foster a dependent relationship.

Emphasis on Managing Yourself

Peter Drucker was wise when he said,

“Executives who do not manage themselves for effectiveness cannot possibly expect to manage their associates and subordinates. Management is largely by example. Executives who do not know how to make themselves effective in their own job and work set the wrong example.” [2]

While it will be your responsibility to drive the agenda, I will encourage you time and time again to focus on what you can control instead of trying to control other people. This will mean understanding your thoughts, feelings (emotions!), gut instincts, and how they lead to behavior that works for you or against you. I highly recommend all clients read Drucker’s Managing Oneself. [3]

Focus on Treating Root Causes & Preventing “Re-injury”