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AI predictions for 2026
But now that we've spent a year vilifying people who use AI to enhance their content, I think "performative imperfection" is going to be the new trend of 2026. We're going to edit photos to enhance imperfections, not deemphasize them.
Claire Baker
2 min read


What were startups like in the colonial era?
And speaking of equal opportunity, pirates welcomed escaped sailors from marginalized identities, giving them opportunities for advancement that they never would have had in the navy or merchant marines. Lady-pirates could even become captains, like Ching Shih, who led a fleet of 1,200 ships and a workforce the size of Morgan Stanley. You could call it D-E-Aye-aye-matey.
Claire Baker
2 min read


How do I build AI workflows that my team will actually use?
If you build a workflow that requires more than half of their brain, they’re going to mess up. The best workflows can be done while driving in the 2-minute gaps between chat support responses from the corner of the couch with Dora the Explorer playing at top volume in the background.
Claire Baker
2 min read


Can I report my bad boss?
So your boss sucks. They play favorites. They make arbitrary decisions and everyone knows they have no idea what they’re doing. They change rules on a whim. You’re right. Your boss sucks. But they’re probably not doing anything illegal. They're just bad at their job.
Claire Baker
3 min read


My boss is a jerk. What should I do?
In most cases, your boss wasn’t evil. You just didn’t get along. Good thing you don’t have to anymore. Even if your boss did do something super illegal, you don’t always get justice. Even if you did get justice, it doesn’t undo the awful thing that happened to you. It’s better to get out of the situation. Keep the awful thing from happening in the first place.
Claire Baker
1 min read


Where do EAPs come from?
Maybe you’ve had this experience: You’re in crisis. You can’t work, so you call in. A well-meaning person you hardly know sends you information about the Employee Assistance Program (EAP). You look into what it covers and wonder how this could possibly help. The minimum CYA measure to guard against the wild things that people in crisis do.
Claire Baker
2 min read


What's the connection between office holiday parties and union busting?
A hundred years ago, in the heyday of unions, non-unionized businesses needed a way to make their low wages, long shifts, and poor working conditions look a little more attractive. So they did what lazy corporate wonks have done to increase morale since the beginning of time: They threw a pizza party.
Claire Baker
2 min read


How to write a handbook that people actually read
Your handbook should help people make decisions. Not just disciplinary decisions. The handbook should draw bright lines where possible, and give guidance for situations that are unclear. Your handbook should give guidance on the unspoken habits your organization runs on.
Claire Baker
2 min read


Do you have a chair-jacket?
For me, my chair-jacket is an asset. It ensures I won’t freeze in that one conference room with the overactive air conditioning. It gives me the freedom to wear lighter clothing to the office without worrying that I’ll be stuck in an uncomfortable situation.
Claire Baker
1 min read


Can we improve daylight savings time?
It may seem complicated at first, but if we can coordinate something as complicated and illogical as Daylight Savings happening across 6 US timezones, at a different time from the rest of the world, on random Sundays in November and April, I think we can handle this.
Claire Baker
2 min read


How to work with difficult people?
You may see them as a perfectionist. Overbearing. High maintenance. A control freak. Nit picky. Difficult. It’s exhausting. You may avoid them. Or resent them. Since strivers are often high achievers, they tend to land in positions of power, putting their unrealistic expectations on you.
Claire Baker
2 min read


What should I do while I'm waiting for a Zoom meeting to start?
When is it appropriate to send the “Is now still good?” message? It’s not like they’re going to see it. If they were attentive they’d be in the meeting and this wouldn’t be happening to you.
Claire Baker
1 min read


How do I deal with workplace burnout?
Hard work isn’t the only ingredient to burnout. All work and no play can even be invigorating under certain circumstances. But when hard work is combined with the following ingredients, it’s a recipe for burnout.
Claire Baker
1 min read


Do engagement surveys actually measure how people feel?
Do engagement surveys actually measure how people feel? Or just how much they trust you? What are people really responding to when they complete a survey anyway?
Claire Baker
1 min read


Should we prioritize authenticity or privacy at work?
That's what leadership looks like: Putting aside your own experiences and recognizing when it isn't about you. Because, as we explained in that meeting, bias has no place in the workplace.
Claire Baker
2 min read


Is it reasonable to require "startup experience" when filtering resumes?
Truth: Working at a startup is different from working at a BigCo Inc. Myth: There’s some magical secret to it.
Claire Baker
2 min read


Can I really be my "authentic" self at work?
We each have our own voice. Not that bland, polished, HR voice that performs respect by never expressing an opinion. Strong opinions on how companies’ decisions shape our lives in meaningful ways.
Claire Baker
1 min read


The Problem Solver
That’s what it feels like when I get pulled in to clean things up when someone’s been sloppy. The damage has already been done. Nothing I can do about that. But someone’s got to manage the fallout.
Claire Baker
2 min read


Why soft power gets better results
It takes strength to show calm, respect, and humanity to someone who isn’t giving it back or "did this to themselves." It takes discipline to hold space and structure until order is restored.
Claire Baker
2 min read


Is it underperformance or a need for accommodation?
Your organization isn’t a spreadsheet. You can’t just delete the cells with numbers you don’t like.
Claire Baker
2 min read
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