Why A-players make assertions

Early in my career, I worked with some of the smartest people at the Gap headquarters in San Francisco. I was bright-eyed and excited to be there, so I’d spend time after work putting together “trend boards” about styles that were trending in the market.

“I’m seeing a lot of high-end designers using plaid.”

“Leggings sales have been steadily going up while pants sales stayed constant.”

“A lot brands are beginning to offer active wear this year.”

I would pat myself on the back when I pointed out an insight. I thought everyone else would pat me on the back too.

This wasn’t the case.

Insights are only a start

One of the senior merchants–my manager's manager–was a brilliant woman named Susie Park. Every time I knocked on her door to show her a mood board, she would say,

“And? What should we do? What are you suggesting? What action should we take?”

I rarely had a good answer. It was frustrating because I thought I had done my part, but each time, I was asked what we should actually do with the information I found.

I didn’t understand this until years later: Susie was trying to help me see that an insight alone isn’t enough.

An insight is just a start. It shows that you’re curious, you’re observing, you’re noticing what’s going on around you, you’re picking up on shifts in the wind.

But the next step is what actually moves the needle. The rare, courageous thing to do is to develop an assertion.

What’s the difference between insights, suggestions, and assertions?

When you point out an insight, you’re calling attention to an observation, something you noticed and wanted to remark on. In response, your colleague could say, “Hmm interesting. That’s nice to know.” They carry on with their day. You carry on with yours. Nothing changes.

When you make a suggestion, you’re putting forth a recommendation. You’re proposing a few different options to choose from. But you’re still not on the hook because your boss ultimately decides what to do. And the person who decides holds the emotional burden of that decision.

When you make an assertion, all of a sudden, things get real. You’re on the hook because there’s more of you in what you’re positing. You’re now advocating for your point of view and trying to convince others to support you.

Assertions have three parts:

  1. A bias toward action: You aren’t just pointing out a fact in a vacuum. You’re connecting dots, interpreting the situation, and positing what your team should do with this information to move forward. An assertion has to answer, “So what?”

  2. Personal conviction: You believe in this enough to look someone in the eye and try to convince them to do this. There’s an element of advocacy built into assertions.

  3. Ownership: You are willing to take responsibility for trying this idea. You’re going to be the go-to person responsible. You’re saying, “If I were in charge, here’s what I would do, here’s where I would go, here’s what I’m betting on.”

Assertions require your point of view

A fact, as a standalone, is just a fact.

A fact, interpreted by you, is given meaning about what the implications are.

It’s not about isolated facts here and there–it’s those facts, as interpreted through YOUR LENS. This includes your background, the accumulation of your experiences, your values, your interpretation of the data, your instincts, your sense of judgment. All of these help you form an assertion that takes an insight to the next level.

Think of it this way: if you just had to follow directions down to a tee, your manager could hire someone on Fiverr. They’re a lot more affordable than you are. And what’s even more affordable? A robot.

Any repeatable, clearly defined task can be done better by AI than by a human. We want you to do the job that only humans can do. Connect dots. See patterns. Come to a conclusion about what you think this means–and what we should do about it.

One event could be experienced by ten people, who come up with ten different assertions.

One person could experience an event, and come up with ten possible assertions…. The hard part is picking the one you want to stand behind. We want to hear what you pick and why.

If someone ignores an insight or suggestion, you can shrug your shoulders and walk away. But an assertion demands action. In or out, yes or no. It’s about forward motion.

graphic_insights suggestions assertions_wes kao.001.png

Making assertions in times of uncertainty

You might wonder, “Do I have to be 100% certain before I make an assertion?”

No, you’re not claiming to have all the answers. When you’re building something new, the work is messy and no one has the right answer.

The fact that no one has the right answer is precisely why assertions are so valuable.


First, there’s no historical precedent about what to do. You don’t have a baseline to say you exceeded the results from last quarter, or explicit sign posts to let you know if you’re doing a good job.

Second, when you’re doing something new, you can’t just copy what someone else is doing. You have different assets, levers, and constraints than the organization you want to copy. So even if you literally did exactly what they did, you’d get different results.

But somehow, the project has to move forward. Assertions help move your project forward even when you aren’t 100% certain of what to do.

You want to be mindful that your language reflects your intent, meaning, and level of certainty. It’s irresponsible to say you’re certain when you’re not.

Here’s a simple framework for creating assertions:

“Based on my insight of X, I believe that Y is true. To go a step further, given X and Y, I think we should do Z. I think it’ll work because A and B. If it doesn’t work, there’s a risk of C happening, and I’ll take care of that by doing D.”

You’re saying, “I’m willing to look you in the eye and fight for this idea to become real. I’ve done the rigorous thinking about how this would work. And I will take responsibility if it goes awry.”

Don’t just ask questions. Try to answer them too

Many people ask a smart question, and stop there.

Asking smart questions is a start, but it isn’t enough. That’s step one. Step two is asserting your answer to said question.

When you just ask a question, it puts 100% responsibility on the other person to respond with their assertion.

Let’s assume you are tackling a problem with a non-obvious solution. It's a problem with multiple variables and complex parts that influence each other. Any change to the system could have unintended consequences.

The stakes feel high.

For hard problems like this, your counterpart has likely asked themselves smart questions many times before. If all it took were a question, they would have figured it out already.

Don't just ask questions. Professionals and A-players ask great questions, then assert how to answer those questions too. They don't claim to know everything, but they do have a point of view about how to solve the problem they just presented.

When you assert an answer, it moves the conversation forward because it helps fill in the blanks.

Share what you think we should do. You can do this by bringing your assertions, your hunches, your recommendations, your interpretations. It will help your team find better solutions faster.

The bottom line? Questions are good, but a question followed by an assertion is the next level. When you bring a question, be open and ready to share your take on it.

Why assertions take courage

When you share an assertion, you could end up being wrong. Or your peers or boss could disagree with you.

We don’t like when people disagree with us. We don’t like being wrong. So we come up with all kinds of "rational" excuses about why we had an insight or suggestion... But stopped short of an assertion.

“If I had spoken up, it wouldn’t have mattered anyway.”

“I have a hunch, but I need more data before I can say anything out loud.”

“Who am I to assert what we should do? The leaders here know better than I do.”

Asserting is a generous thing to do because it gives other people something to work with. Even if someone disagrees with your assertion, you’re adding value because it helps your team come to a better understanding of the challenge or proposed solution.

Insights are a dime a dozen. Suggestions are a bit better, but still let you off the hook. Assertions are the realm of professionals who navigate ambiguity and rigorous thinking.

Assertions make an idea real. The sooner the ball gets rolling, the sooner you can iterate to make the idea better.

You can be the person who’s gets the ball rolling.

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Wes Kao