Advising and 1:1 Executive Coaching
I typically work with founders and executives on setting a high bar of excellence, leveling up your strategic communication, and leading/managing lean teams with ambitious goals.
I offer 1:1 executive coaching and advisory consulting with monthly retainers. The clients that get the most value from working together tend to be series A and beyond.
My current and former clients include the CEOs of Section, Morning Brew, Poo~Pourri, etc. I draw from my experience co-founding two companies in the past fifteen years: In 2014, I co-founded the altMBA with bestselling author Seth Godin. In 2020, I co-founded Maven, an education company that raised $25M from Tier 1 investors including First Round Capital and Andreessen Horowitz.
If you’re interested in how I can amplify your growth, send me a note at wes at weskao dot com or fill out the form below. I’m looking forward to meeting you.
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, if an expectation is normal (for them to have for others, or others to have for them), etc.
They are often looking for a thought partner to figure out what to do and how to do it/how to say it. They want to be stronger communicators to maximize buy-in and minimize resistance from internal/external stakeholders.
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?
One of the most valuable parts of coaching is we can get into the specifics of your situation and I can share personalized suggestions. So it’s not just improving how you present to your CEO as a generic figure—it’s your particular CEO with their idiosyncracies, values, priorities, pet peeves, communication style, etc, and the specifics of what exactly you’re presenting. It’s not just how to appeal to your direct report—it’s how to appeal to a specific individual, given your specific dynamic, the specific behavior change you want to happen, and exactly what you want to say to that person. Through specifics, you learn generalities you can apply to other situations.
I’m fascinated by topics that are deceivingly basic. Topics that seem tactical or minor on the surface, and are usually spoken about in broad strokes, but underneath there’s more nuance than most people realize. I believe by unpacking what’s usually taken at face value, you’ll have a more accurate mental model of the world and gain an advantage in pulling 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. So I believe the way to stand out is by learning to see and act on what others miss.
I also care a lot about judgment. As you advance 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 and never “tell” 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 probably 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 do or say—until they try to execute. This is why it’s useful to practice the actual words you’re going to use. When we practice in real-time, I can see you in action, pick up on tacit information, and give you specific feedback on areas you didn’t even know you needed to ask about. The idea is for you to feel confident about variables that might shift in unpredictable ways in real-time, so you can stay present and keep your eyes on the prize.
It’s fun to be good at your job. I’m hoping working with me 1:1 will 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.