Last week, 10 people started at our company on the same day, right in the middle of our all-company onsite in Miami. I’ve worked at startups where 10 people were the whole company. 🤯
All week I kept coming back to the same question: What do I hope those 10 people pick up about how we work just by watching us? And how do I make that true for the next 10 people, too?
After 16 years in startups, these are the 11 things I’ve seen great teams do differently:
1. They tell you they’re stuck while there’s still time to help. They’ve already taken a real shot at fixing it, and they know asking for help won’t get them a lecture.
2. They disagree in public and resolve in public. They have the debate in front of the team so people can hear what you each weighed, what changed your minds, and why you landed where you did.
3. They do the work today. If a 5min call can get someone unstuck this afternoon, why are we scheduling it for Thursday?
4. They say “we” when they win and “I” when they fail. They are accountable for their actions every time.
5. They keep their word on the little stuff. When someone says “I’ve got it,” you can close the mental tab.
6. They trust people to make decisions that matter. They'll never most fast enough if they micromanage every easily reversible decision.
7. They never settle on hiring. They’ll keep a role open for months, then fight like hell for the person they want.
8. They make the hard call before the team pays for it. If you keep letting someone treat people badly or leave their teammates to pick up the slack, you’re telling everyone else what’s acceptable here.
9. They meet people where they are. One person needs you to sit with them through a first draft, and another needs you to hand them the problem and leave them alone. Pay attention to what gets the best work out of people.
10. They take the work seriously and themselves lightly. My favorite coworkers can have a hard conversation in the morning and spend an objectively unreasonable amount of time on a stupid prank in the afternoon.
11. They remember what matters to you. Your kids’ names, where you went on vacation, and that thing you told them about your mom that they remember to ask about a week later.
What would you add?
https://t.co/Wz9BWYYJ7V
I turn 39 today. I also missed every goal I set last year.
47 book agent rejections. No TEDx talk. Missed my subscriber target.
In the interest of full transparency, I did acquire a cat.
For anyone whose birthday arrived before their imagined success:
https://t.co/ZbEog3lnxt
Everyone offers “just be authentic” as the answer to building a personal brand, growing your career, and becoming a thought leader.
Um, okay. Let me get that out of my unorganized sock drawer.
I’m striving for something else. and it starts with a different question.
What I’m practicing, how to try it, and why my ego would still prefer a six-figure book deal:
https://t.co/MiMkNEZv3f
Most people use AI to solve their work problems.
I think that’s the wrong first step.
I built a prompt that makes ChatGPT figure out if you even have the right problem first.
It will question your version of events, argue the other person’s side, tell you what you’re contributing, and occasionally deliver the deeply offensive news that the problem might be you.
Rude. But useful.
https://t.co/uSxcM97Am6
I’m one year sober today.
A few things people told me about quitting drinking that turned out to be bullshit:
“You won’t miss the taste.”
I do. Prosecco is delicious. We don’t need to lie to each other.
“Quitting will be really hard.”
It wasn’t.
“You’ll feel amazing.”
Eventually. First you’ll feel everything. And apparently there are a lot of feelings you haven’t had to deal with in years.
“You need a rock bottom.”
You can also just stop on a regular Tuesday. No dramatic final drink. No promise that it’s forever. No intervention. Extremely anticlimactic.
“Your social life will suffer.”
Nope, mine got crazier.
“You’ll save so much money.”
I have incredible news for the THC and beauty industry.
Anyway, I wrote about my first year sober and somehow turned it into a vendetta against Brad Pitt.
https://t.co/eaFLMbtzDM
I have a fake male assistants who negotiate my rates for me.
I name them after men who have wronged me personally.
This is called healing.
https://t.co/2juDEEC7eb
Can you come back from hating your job?
I think you can.
I wrote about what employees can try before quitting, what managers can do when someone starts pulling away, and how to figure out whether the job still fits.
Because disengagement doesn’t always mean it’s over.
https://t.co/TwjkZnmjOB
I stopped trying to achieve work-life balance and developed a significantly less marketable system:
Rotate the Suffering.
Something always gets less of you. Just don’t let it be the same thing forever.
https://t.co/SEbZl3x1WX
If my career disappeared tomorrow, I know exactly how I’d rebuild it:
• Join a startup. The earlier, the better.
• Stop asking mentors what I should do.
• Choose the "difficult" boss.
• Stay longer than is comfortable.
• Take access over title. Every time.
• Say yes before I’m qualified.
• Refuse to pick a lane too early.
• Learn how the business makes money.
• Tell my career story like my best friend would.
• Trust my gut before I have the data to defend it.
What would you add to this list? https://t.co/iUUWktfyVd
I think everyone should work at a startup at least once.
If only to learn that “I have absolutely no idea how to do this” is not a reason to say no.
A little delusion might actually be a career advantage.
https://t.co/etuTjHQX5f
For years, I thought I wasn't "executive material." I wrote about the leadership philosophy I accidentally built after 16 years in startups.
Leading From the Corner https://t.co/uCpxq5dRsi
Someone recently told me that a lot of my writing is about wanting more.
My first thought was, "How dare you."
My second thought was, "You're right."
New essay: I Refuse the Assignment https://t.co/DVN00PClbB
New on Substack: Arguments I've Won in the Shower, Vol. 1: Why We Should Buy the House
The argument against buying it is that we can't afford it.
The argument for buying it is that it has a ballet barre.
I think the choice is obvious.
https://t.co/iYh5DJbIlH
I’m Woo Woo and I Don’t Care Who Knows It - 10 slightly unhinged things I do that make my life better (and make me $18k in one week).
https://t.co/SIZFyLVKWZ
I re-read my blog from 2011 this morning and discovered that 24-year-old me had unlimited internet access, zero self-preservation instincts, and surprisingly good material. https://t.co/lmgP4DJSBG
I've spent 16 years in startup operations learning how to justify decisions. Turns out the most important ones in my life rarely arrive that way.
https://t.co/BVtFOC2TwE