1:1 Executive coaching

I work with a select number of clients through retainer engagements. This allows you to build real momentum--we dive into your specific situation and you get the space to 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 Chanel, State National, Vercel, Product Hunt, 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. When we are abstract and stay at a high level, we miss out on spotting potential levers or seeing data points that were there all along. If you say, “I did X.” I’ll say, “Can you show me screenshots or share what you said verbatim?” I want to get as close to primary data as possible because this allows me to read between the lines and pick up on rich tacit information—including both what’s said and unsaid. This allows me to get the most accurate picture of what’s happening, and help you figure out what to do and say to reach your ideal outcome.

• I believe you gain an unfair advantage by digging deeper into topics that are deceivingly basic. These are topics that seem tactical or minor on the surface, and are usually spoken about in broad strokes, but underneath there’s more nuance. By unpacking what’s usually taken at face value, you’ll have a more accurate mental model of the world and be able to pull levers other people don’t even know exist. Almost every category and function is getting increasingly competitive. Most individuals and organizations have the same growth goals and access to the same levers. The way to stand out is by learning to see and act on what others miss.

• After a certain point in your career, variables like skills and years of experience matter less, and your judgment matters more. Judgment can be contextual, subjective, and hard to learn, so with every essay, I try to break down the “why” behind what I’m saying so you see my thought process and can better form your own perspective.

• There are some coaches who only ask questions because the idea is they want to let you discover the answer. If you’re looking for that style of coaching, I’m probably not the best fit. My approach is more akin to a mix of personal advising and consulting. 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 out loud 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. I believe confidence comes from competence—and sometimes you’re not that confident because you’re not that good at the thing yet. My approach is quite goal-oriented, where we discuss your ideal outcome, stakeholders involved, specific levers at your disposal, and strategize how to get the result you want, assuming you are working with intelligent colleagues who have reasonable perspectives of their own.

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.