1:1 Executive coaching
I work with a select number of clients through monthly retainers. This allows you to build real momentum toward your ideal outcome--we dive into your specific situation and you’ll implement changes between sessions.
The areas I specialize in are:
raising your team’s bar of excellence
improving your executive communication
developing your executive presence
increasing your ability to influence
delegating to ICs while maintaining high standards
My current and former clients include the CEOs of Section, Morning Brew, Poo~Pourri, etc, among other talented individuals, including director and VP-level folks at companies like Amazon, Product Hunt, Chanel, State National, Vercel, and leaders at startups funded by Sequoia, Accel, Bessemer, SV Angel, Kleiner Perkins, etc.
If you’re interested in learning more, fill out the form below.
What kind of operator gets the most from working together?
If you’re curious if we might be a fit, I've noticed a few patterns among my clients:
They are usually folks who are too hard on themselves and take too much accountability, not too little.
They are self-aware and intellectually honest. I find intellectual honesty to be one of the most attractive traits in colleagues—I can't stand people who squirm out or delude themselves.
They tend to be “player-coaches” who both manage a team and execute as an individual contributor (IC) too. They lead others, but need to balance when to delegate, when to get into the weeds, how to create leverage, etc.
They are direct and want someone to be direct with them. They want a neutral, objective third-party POV and gut check on whether they're justified in reacting the way they're reacting, and if an expectation is normal (for them to have for others, or others to have for them).
They are often looking for a thought partner to figure out what to do and how to do it/say it. They want to maximize buy-in and minimize resistance from internal and external stakeholders.
They're willing to put in the work. I often give "homework" to implement between sessions. You'll get the most from coaching if you're willing to come prepared and put in the work.
I'm a founder and operator at heart, so I'm aware of the dynamics, rhythm, expectations, etc of being on a team building something new with pressure to show growth each quarter. Here’s what clients have said about what it’s like working together.
What’s my approach to coaching?
In my experience, “concrete” eats “abstract” for breakfast. One of the main benefits of coaching is getting personalized insights, so I like going deeper and getting specific to your situation. We can all be unreliable narrators sometimes, so I will often ask for examples and validate what you’re sharing. I might point out if I see a situation differently, speak up if I disagree with your interpretation, etc, so we can get closer to the truth—and can therefore make more thoughtful, intentional decisions.
There are some coaches who only ask questions. If you’re looking for that style of coaching, I’m probably not the best fit. My approach is a mix of advising and coaching. I offer my point of view because I believe I can add the most value to you this way, and if I think something is good for you, I want to try to convince you. Obviously, I balance this with asking questions to get a better understanding of your situation and leave ample room for you to reflect too.
I’m a big proponent of building muscle memory via mock presentations, role-playing, drilling, etc in the safe sandbox of our sessions. I believe most people think they know what to do or say—until they try to execute it. This is why it’s useful to practice the actual words you’re going to use. This way, you will feel confident about variables that might shift in unpredictable ways in real-time.
FWIW My approach is less about confidence and mindset (though I believe those are important too), and more about practical techniques for getting more of what you want. My style is quite scenario-based and goal-oriented, where we discuss your ideal outcome, stakeholders involved, specific levers at your disposal, and strategize how to get the result you want.
It’s fun to be good at your job. I hope I have the opportunity to support you, and help you get even better at what you do. If you have questions, feel free to reach out at wes at wes kao dot com or fill out the form above.