The Other PMF: Wes Kao’s Framework for Founders Who Want to Communicate — and Lead — Better

Tactical advice for founders on mastering “personality-message fit": leaning into your natural communication style.

Outline

There was a time when Wes Kao thought that to be a leader, she would have to change. Leaders, she believed, had to look and act a certain way — serious. Buttoned-up. Formal.

When she co-founded Maven, an online cohort-based course platform, Kao was thrust into an executive role, and she quickly began unlearning her preconceptions. The company culture that emerged organically at the startup helped her reflect more deeply on how a leader should speak or behave. “We weren’t serious or corporate for the sake of it,” she says. “It allowed us to be ourselves, and care about the quality of the ideas that we were sharing.” This suited Kao. “I think I’m a pretty professional person,” she says, “but I don’t think I’m the most formal person.”

Back then, Kao was still figuring out her leadership style. She would often notice, in meetings or at events, that one of her co-founders would make a comment that Kao felt she could never get away with.

“He would say certain things and people would love it. If I said something similar, I just knew it wouldn’t land the same way, and vice-versa.”

This observation planted a seed that would bloom into Kao’s own unique communication framework: personality-message fit. If you shape your message to suit the tone, style and quirks of the way you naturally communicate, Kao argues, rather than adopting an approach that feels forced, connection with your audience will come effortlessly. This might be in a hard conversation with your co-founder, on a call with a prickly customer, or when pitching a room of potential investors.

“I don't think that we, as founders or leaders, can change 180-degrees, even if we want to,” Kao says. “We've all seen somebody pretending to be Steve Jobs, or trying to be Mark Benioff, and it’s not landing. It's better to know, ‘this is how I am, this is the constraint, and these are the levers I have to pull for people to better understand me.’”

It’s about more than simply being authentic. “That word gets thrown around a lot,” Kao says. “I don’t know if I believe there’s one true way to be ‘authentic.’ We can be different versions of ourselves in different settings, in different contexts, with different people.” Charisma, too, is a concept so broad and abstract it’s hard to translate into actionable steps. What Kao is talking about is more strategic. “You see founders of all types, styles, and idiosyncrasies being successful,” she says. “It’s more about what makes you you, instead of trying to copy someone else and having those tactics fall flat. There's a lot of things you can do to evolve, grow and get better in the way that you communicate.”

In this conversation, the executive coach and entrepreneur, who in addition to Maven co-founded the altMBA with bestselling author and marketing trailblazer Seth Godin, shares how founders can develop personality-message fit, first by finding their own voice, and then by learning how to make it land with others.

Part 1: Personality

Self-reflection is the “personality” side of finding personality-message fit. Before thinking about an audience, you need to understand yourself: how you show up, what feels authentic, and where you naturally shine.

Do an internal audit

When it comes to personality, disposition, and temperament, Kao says “it’s important to understand what your baseline is.” Ask yourself how it feels most natural to you to present in different settings, from pitching in a boardroom to mingling at an event, or speaking to a large group versus in conversation with a few people. Does it feel natural to joke, or be more reserved? To lead with data, or begin with a story? To hold attention with practiced pauses, or exuberant energy? “How do you react to things?” Kao asks. “Where does your head naturally go? Then, if you want to make adjustments, you can — but you have to know your baseline.”

Armed with that information, you can adjust the delivery of your message accordingly. Kao gives the example of an executive coaching client who is relatively inexpressive; she could barely tell when he was happy or upset. Kao’s advice to her client was not to learn to emote more, or force himself to make more animated facial expressions, which would only feel contrived. “If you want people to know how you feel,” she says, “you need to amp up other levers. Instead of trying to be high-emoting, or relying on your facial expressions or tone of voice to do the heavy lifting, you can turn up the enthusiasm with the choice of the words you use.”

By deliberately choosing language that signals energy (phrases like “I’m very excited” or “this has me feeling fired up”) Kao’s client was able to show conviction without faking it. Kao says it’s about finding subtle ways to make your intent clear, even when your delivery is naturally understated.

Practice the 30-second prep habit

In Kao’s experience, most communication issues can usually be traced back to the same root: a lack of preparation. “It’s the biggest bottleneck to clear communication. We often jump from one meeting into the next, and answer Slack messages in between. I think people just don't put enough thought into their communication.”

And while you would undoubtedly prepare for a high-stakes meeting, you might not prepare for a quick Slack huddle or a walk-and-talk. But Kao says smaller moments of communication also require preparation to be fruitful. “When you’re speaking in real time, your brain is doing a bunch of different processes at once: processing, thinking, connecting it to past context, formulating a response, and then saying it out loud, all in milliseconds. If you aren’t clear about what you’re trying to say, it’s going to be confusing.”

Drawing on the data you have from your internal audit, Kao recommends spending as little as 30 seconds asking yourself a few clarifying questions before a conversation. “A couple of moments can make a big difference. It allows you to speak up on a call, or in a meeting, in a way that gets your main point across much better.”

Kao suggests jotting down notes, or simply reflecting. “Instead of sharing whatever comes to mind, start with your ideal outcome, and work back from there.” Questions to ask:

What is my ideal outcome?
Who is the recipient?
What does this person need to know, and what do they value?
What’s my main point?
What’s my secondary point?
Who are other potential stakeholders involved?
What are the levers that I have I could potentially pull?
What are any sensitivities that I need to be mindful of in this situation?

Part 2: Message

Finding your personality-message fit requires more than self-reflection. You’ll also need to conduct research in the field — to try different approaches, adapt them to your audience, and see what actually lands. “You can’t pontificate in your own mind endlessly and then come to a breakthrough. You can’t know what’s resonating until you go out and try. You have to get reps,” says Kao.

Learn to read the room

Some people seem born with the ability to sense a shift in energy, or spot confusion before anyone speaks up. “They're naturally better at this,” Kao says. “Better at noticing the reactions of others and asking themselves, ‘Was that the reaction I was hoping for? If I approach it this way, am I going to get the reaction I'm looking for more?’ But it’s a skill you can get better at.” Kao advises approaching reading the room as a muscle you can build, not a talent that either you have or you don’t.

“I take an experimental, iterative approach, and it's very much first principles based. I’ll try a bunch of different things along the way to see, does that feel natural for me or does that feel off?”

Go deeper on feedback decoding

If you receive feedback on your communication style in a more formal capacity, such as from your co-founder or an investor, Kao warns against rushing to make changes without first probing for specifics, especially if the feedback is vague. “Three months later when you check in with that person, you might find that what you thought they meant was not what they meant at all.”

Don’t accept vague feedback at face value. Ask follow-up questions until you can define what the other person means. Kao gives an example of the common piece of feedback founders get to be more strategic. “You might ask, ‘when I did this thing, would you say that that was strategic, or did it not feel as strategic? What are some examples from my peers that you feel are strategic?’”

Kao warns that not everyone is skilled at providing specific feedback, so it might take a few attempts to glean the information you need. “They might not be able to share more specifics if you just ask them point blank. You may need to ask indirectly. Draw that information out of them.”

Once you’ve gathered examples, read between the lines. “You might notice a pattern; maybe a peer always starts with context, or they’re great at stack ranking what matters most,” she says.

The result of feedback on your communication style should be that you have clear, actionable steps to take to make changes. “It’s your job to unpack it, clarify it, and get to that next level of specificity so you can fix the right things,” Kao says.

“You might normally start talking in a chronological way about what happened starting from the past three months up until now,” Kao says as an example. “That is going to be confusing for someone who is hearing about this for the first time.” How you could shift your approach based on feedback is to frame the topic up front, and tell your audience directly what you need from them.