No lazy thinking: How to train your team to think rigorously and systematically

If you're a leader, you got to where you are because you think strategically and are killer at execution. You simply can't get very far without being good at both.

Now that you're in charge of people, though, your ability to increase impact depends on how well you manage OTHER people. You need your team to become smarter, sharper A-players.

Unfortunately, sometimes smart people (like you) accidentally traumatize their teams....

You say you want your team to think harder and stop just doing exactly what you say. But every time they have a question, you just answer it. Or worse, you give them a wrist slap for bringing you a new idea.

I get it. You already don't have time to do your own job, so you definitely don't have time to clean up everyone else's mess. But each time you give your team a wrist slap for stepping outside the box, you discourage them from trying new things.

So you have a dilemma: You want your team to think like an owner and bring you fresh ideas—AND you want those ideas to be defensible.

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Wes Kao
How to upgrade your career with marketing strategies [YouTube]

I want to share a Facebook Live recording I did recently that might be relevant if you want to increase your personal credibility.

What we’ll cover:

  • Why it's a mistake to save your questions until the end of an interview

  • How to use marketing concepts (FOMO, turning bugs into features, social proof) to get people excited about your ideas

  • How to even out the power dynamic during an interview

  • Why the “negotiation” started before you walked through the door

  • How to stay agile and hit on your hiring manager’s pain points

Check it out “How to upgrade your career with marketing strategies” on YouTube.

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Wes Kao
Do things your Future Self will thank you for

Every time I have to explain a process to new team member, I search in my Google Drive first. Why?

I’m a documentation and playbook nerd. If I’m repeating the same conversation more than three times, I create documentation—it saves time and energy for all parties involved.

At moments like this when I find my own notes, I say, "Thanks Past Wes! You just saved me an hour."

You might debate whether a certain task is worth your time. If so, the framework of thinking about your Future Self is a useful litmus test.

The Future Self concept is about much more than documentation though. First, let’s take a step back.

Why you can't trust your Present Self

For the sake of this exercise, let’s assume you have three selves:

  • Your Past Self

  • Your Present Self (this is you, right now)

  • Your Future Self

Sorry, but your Present Self can't be trusted. Humans are notoriously bad at estimating time, we are influenced by our immediate surroundings, and we overemphasize the negative.

Your Present Self cares about what's going on in this very moment. How you feel, if you're hungry, what Shauna said to you in the elevator, or Brad's attitude at your meeting.

Your Present Self feels elated when your new campaign is getting lots of engagement. Then an hour later, feels panicked because the metrics are plateauing.

Based on how you feel from day to day (or even hour to hour!), you could feel productive or like a waste of space. These ups and downs are unproductive, obviously. So how do you get out of your own way?

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Wes Kao
Technical leaders make these 3 common storytelling mistakes

I recently had the privilege of giving a talk for Backstage Capital and their amazing early-stage portfolio companies. My talk was called “Storytelling for Technical Founders” and I shared how technical leaders can tell better stories.

Here are a few common mistakes and takeaways:

1. Over-reliance on technical details

Real-life is non-linear, but stories are linear. Therefore, stories are always a simplification.

You definitely want to tell the truth, but don’t feel guilty for leaving out details in order to prioritize your overall narrative arc. I’ve coached plenty of founders who were afraid their audience would call them out for speaking in broad strokes. The paranoia of getting called out is real.

Your audience doesn’t mind. They want to be wooed, entertained, and taken on a journey — in addition to learning about your product and story. What about the subject matter experts who might have a specific question about your technology? They’ll ask. And you’ll be ready to answer and impress them with your substance.

Anytime you feel the urge to say, “Well, technically…,” you are about to kill a good story.

Remember: What gets someone in the door isn’t necessarily what gets them to stay. 

For example, think about J.Crew stores. They show colorful window displays and front tables with a rainbow assortment of t-shirts in salmon pink, lemon yellow, neon orange, and cerulean blue. 

Nine times out of ten, I walk in and end up buying a basic color (white, black, navy, grey). Most customers do this — that’s why retailers plan the inventory accordingly and have stockrooms full of basic SKUs.

But if they put only the most basic stuff on display, you would probably keep walking and never enter the store.

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Wes Kao
Your team should be getting 20% smarter every year [ActiveCampaign podcast]

Whether you're a changemaker within an organization, or a startup CEO running your own company, your ability to do great work is directly tied to your team's performance.

You realized this when you transitioned from an individual contributor to a people manager. But it's likely a lesson you're constantly reminded of.

Almost every week, I hear a founder say, "I'm the bottleneck for everything. How do I get my team to be as smart as I am?"

Of course, when I hear that, I have to remind them to simmer down: "If your team were as smart as you are, they would be your boss, right?"

Poking fun aside, the next question is: "What are you doing to help your people get better at their jobs?"

The answer is usually nothing.

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Wes Kao
Read your messaging in a robot voice

My obsession with messaging is based on my personal experience editing hundreds of pages of copy for myself, my direct reports, and my clients. When your brand is on the line, you're incentivized to make sure copy gets your audience to take action, achieves the outcome you want, and represents you well (so you don't invite a flurry of customer complaints).

In other words, if you're a leader or changemaker who uses words to persuade, this post is for you.

I want to tell you about what I call the robot voice method.

Do you have a friend who sounds cold via text? In person, they might be the nicest, warmest people. Then you'll read their text. You pour your heart out, and they reply with "Ok.”

And you think, “Wow, do you secretly hate me? Are we even friends??”

This is a classic example of coming across differently than you intended. You might have great intentions, but no one will care. They only care about how they feel when receiving your message. This matters because how they interpret your words impacts how THEY act. It can either spiral upwards or downwards from there.

This is why it's important to understand the constraints of your medium. The medium we're talking about today is written text: email, Google Docs, memos, SMS, Slack, FB posts, tweets, etc.

When you’re in person, you have all kinds of clues that add to your message:

  • Facial expression

  • Mood

  • Tone of voice

  • How fast or slow you’re talking

  • Pitch of voice

  • How somber vs light you sound


All of these show sincerity and trust. They help your recipient understand your message.

But when you convey messages with the written word, you only have text.

Cold, hard text.

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Wes Kao
To drive growth, focus on increasing desire—not just decreasing friction

As a marketer, salesperson, UX designer, or product leader, part of your job is to reduce the friction involved if someone wants to buy something from you.

For example:

  • Make the button bigger

  • Use brighter colors

  • Write shorter copy

  • Put everything on the homepage above the fold

  • Add the call-to-action button everywhere on the website

  • Send reminder emails about the sale

  • Use monetary incentives, e.g. discounts, bundles, promotions, and reverse promotions ("The price goes up next month!”)

The underlying assumption is, “If I make this easier (or cheaper) for you, you’ll eventually want it.”

But this logic is fundamentally flawed.

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Wes Kao
Activation energy and why it matters for product launches

If you mix diluted hydrochloric acid with carefully measured strips of magnesium, you’ll get hydrogen...

You need a certain amount of each chemical though. If you don’t, the reaction won’t happen. You’ll get silence.

Activation energy is a term I learned from my friend Yuki, a biochemist who grows meat from cell cultures in Petri dishes. It’s “the minimum quantity of energy needed in order to undergo a specified reaction.”

Many projects take a level of activation energy before you start to see feedback—negative or positive. Maybe you’re an inch away from seeing a result, maybe you are a mile away…

So what can you do?

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Wes Kao
Be your own mentor

No one is coming to save you.

[Cue panic and running around in circles.]

I remember the first time I realized no one knew the right answer. It was simultaneously alarming and liberating.

Heck, I sat ten feet away from the most famous marketer in the world.

One day, we were discussing growth strategies. He stopped and said, “Wes, you should decide. I don’t have the answer. If I did, I’d just tell you."

Up until then, I thought our usual rigorous line of questioning was his way of teaching me to have a stronger point of view. Kind of like the Socratic method, if Socrates were a battle-hardened Navy SEAL in Special Ops.

“Oh God,” I thought. “If he didn’t have the right answers, who would? What hope do any of us have?”

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Wes Kao
People don't trust their own judgment

Why do people buy bestselling books?

Why are there laugh tracks in sitcoms?

Why are we suspicious of restaurants that are empty?

All of the above are examples of when we look around to see what people around us are doing…. To help us decide what we should do.

We feel pressure to fit in with our peers, to do the right thing that is expected of people like us. This means taking social cues from others, and using those social cues to give context to what we think is cool (or not).

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Wes Kao