Advising and 1:1 Executive Coaching
I love working closely with talented operators, founders, and execs. It’s extremely rewarding to get into the specifics and give personalized guidance to ambitious leaders on unique aspects of your situation. Going forward, I plan to invest even more bandwidth into coaching.
I offer 1:1 executive coaching and advisory consulting with monthly retainers. The clients that get the most value tend to be series A and beyond.
Typically, the topics we’d cover include setting a high bar of excellence, improving your executive communication, increasing your influence, and managing lean teams punching above your weight class.
My current and former clients include the CEOs of Section, Morning Brew, Poo~Pourri, etc, in addition to talented director- and VP-level leaders. 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 First Round Capital and Andreessen Horowitz.
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, 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 and 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?
I believe “concrete” eats “abstract” for breakfast. One of the most valuable parts of coaching is getting into the specifics of your situation. For example, it’s not just improving how to present to a CEO as a generic figure—it’s improving how to present to your particular CEO. It’s not just how to appeal to direct reports in general—it’s how to appeal to the specific individuals on your team, given your specific dynamic, and the specific behavior change you want to see happen. This is why I’m a fan of digging into real examples. I want to get as close to primary data as possible, so I can read between the lines and pick up on rich tacit information—including both what’s said and unsaid. This creates a more accurate picture, which allows me to give you nuanced guidance and allows you to see your own situation with sharper clarity.
I’m fascinated by 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 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 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 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. 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 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.