Wes Kao — Blog

Your boss called. They want you to manage up.

Bosses are frustrating creatures.

They want you to take the lead… But when you do, they micromanage.

They say, “Ask me questions any time!” But they also say, “Can you try to figure it out on your own?”

They say they don’t want status updates. Then they come by your desk frantic asking what you’ve been doing for the past two weeks.

Basically, they want you to read their mind. Which isn’t great for you, because mind-reading is hard.

Luckily, there’s a workaround which is pretty darn close. And that is the skill of managing up.

Leveling up, Influence and PersuasionWes KaoOctober 15, 2019Leveling up, Influence and Persuasion

Everything takes longer than you think

The problem isn’t that you’re not working fast enough. It’s that your expectations were never realistic to begin with.

For example, I was on the phone with my bank recently. I thought it would take 10 or 15 minutes... It took 51 minutes.

Almost an hour.

Whether you are troubleshooting a technical issue, hiring to grow your team, or planning a party…

Everything takes longer than you think.

Why does this matter? Because every day, we have to estimate how long things will take.

If you get better at estimating timing, you’ll be less stressed in all areas of life.

Leveling upWes KaoOctober 2, 2019Leveling up

How to write your own job description (and invent your role)

Creating a new position for yourself--one that doesn't yet exist--sounds too good to be true. But many of us have done it, and I’ve personally done it multiple times. I want to share a few ideas that will help you do it too.

Maybe you’ve grown tired of your current job responsibilities. Or maybe you see an opportunity to contribute, but the role isn’t listed on your company’s careers page. You might think there’s nothing else you can do--except wait for your fortune to change.

Luckily, writing your own job description can be the solution.

This is your chance to get creative about what you would like to work on that adds value to your organization. Here are a few things to keep in mind to get a “yes” from your hiring manager.

Leveling upWes KaoSeptember 23, 2019Leveling up

Simplify first, not last

One common approach is to write a lot, then trim later.

But sometimes, that means you come up with something entirely different than if you had decided to write something short from the beginning.

Simplifying first is a strategy to help you surface options that are categorically better. By setting a different target, you play a different game altogether.

Leveling upWes KaoSeptember 4, 2019Levelling up, Writing, Efficiency, Positioning, Messaging, Rigorous thinking, Strategic

Asking questions = no skin in the game. If you ask a question, try to answer it

“I asked a smart question. My work here is done!"

Whoa there, not so fast. The hard part is just beginning.

There’s so much dialogue about why it's important to ask questions, but not enough talk about the flip side: why you should answer questions despite working with imperfect information.

Leveling upWes KaoAugust 21, 2019Levelling up, Rigorous thinking, Make your own map

How to win a job negotiation before it starts

Everything is a negotiation. Deciding what to have for dinner, what to watch on Netflix, who should do each part of the project… All of this is negotiating, and you do it every day. Negotiating is simply positioning your ideas to try to get the outcome you hope for.

Here’s the thing nobody tells you: The negotiation starts way before you walk into the room. By the time you are in the room with the person, they already have an idea of how much you’re worth. You already have an existing dynamic--and they are anchored on this. Given need every possible tailwind, here are things to keep in mind for your next negotiation.

Leveling upWes KaoJuly 25, 2019Career advice, Strategic thinking, Negotiation

How to sharpen your mental models over time

One day, Seth was making lunch at the office for the team. Guess what was on the menu? Scallops. I haven't liked scallops since I was a kid.

I said, "That looks great! I'm not a huge fan of scallops. I'll pass, thank you."

I've responded that way dozens of times over the years. It was habitual at that point to say no to scallops.

He said, "Really? Give them a try. They're fresh caught from a boutique grocer in Chelsea Market and they are delicious. Just cut a tiny piece and see if you like it. If you don't, I'm sure Alex or Willie will eat it."

Leveling upWes KaoMarch 6, 2019Mental models, Levelling up, How to

"Is this making me smarter?"

Here’s a litmus test for whether you should continue reading (or scrolling or watching a video).

Leveling upWes KaoJanuary 18, 2019Levelling up, Rigorous thinking

Unconventional career paths and taking risks [PermissionLESS podcast]

You might think your career arc should be a straight upward line. Maybe you’ve noticed by now it’s more of a non-linear squiggle.

I used to have a strict plan for what I wanted to do in my career and how it would look. Over the years, though, I’ve changed my thinking of what it means to take risk. It’s opened the door for lots of opportunities I never would have found otherwise.

Leveling upWes KaoDecember 12, 2018Podcast, Career advice, Levelling up

A framework for ignoring sunk costs: "New situation, new decision"

Ah, sunk costs. We all know we should ignore them. It's harder said than done, like most things in life.

I want to share a framework/mental model I've found helpful to think differently about sunk costs:

It's called: "new situation, new decision."

Leveling upWes KaoDecember 12, 2018Framework, Sunk costs, Levelling up