Posts in Leveling up
Build your personal credibility, not your personal brand

I hate the phrase “personal branding.”

Remember school projects? There was always that one kid who didn’t do much work, but was great at presenting. The teacher thought they did all the work. Personal branding reminds me of that person, now all grown up–and still talking their way through life. Ugh.

Most of us are not good at “personal branding.” A lot of good people are too busy actually doing the work to spend energy managing the optics of that work.

Unfortunately, this means well-deserving people often get the least credit.

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Give your boss context when you ask for approval

“Can you give the greenlight on this?”

“Can you approve next week’s social media post?”

“Can I get an approval on this Facebook ad creative?”

Depending on your role, you might ask your boss for approval once to several times a day.

Even directors and vice presidents need to check in with their bosses. And if you’re creating anything new, it makes sense to get your boss’ buy-in each step of the way.

We can’t force our bosses to approve our work, but we can embrace that it’s our responsibility to get better at securing their greenlight.

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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.

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Everything takes longer than you think, so plan accordingly

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.

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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.

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Leveling upWes KaoLeveling 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.

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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.

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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."

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