Startup trek, episode 13: Angel One

Season 1, episode 13, “Angel One”

Lesson: dress for the culture of the people you’re meeting

This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each.

Riker and an away team visit Angel One, a planet ruled by women, to search for a missing crew. Men on Angel One experience much of the things that women on today’s earth do: there aren’t many of them in positions of power, and they’re expected to wear skimpy and flashy clothes. Riker dresses the part for his meeting with the planet’s leader, Beata, with a sparkly blue draped top that shows most of his chest, leggings, and ear jewelry. Troi and Yar think it’s hilarious but Riker does it to adhere to Angel One’s culture. It ends up being the right move because he gains Beata’s trust quickly.

The takewaway here? You’ll generally do better with a group if you dress more like that group. Interviewing at a startup? Don’t wear the business suit. Interviewing at a law firm? Time for the business suit.

Job seekers are coached to err on the side of rigidity, but that backfires in the startup world. Interviewers want to know the real you. You come in sweating in a suit and you look like an alien. It’s the apparel equivalent of starting an email with “dear sir or madam.”

I experienced this firsthand when I went to my first startup job interview ever in a Brooks Brothers suit. Let me put this into perspective for you: this was a job listing I’d found on the Boston Craigslist “legal services” section, in an office located above a bar in Central Square in Cambridge, with three employees (one sitting on an exercise ball), one dog, and two rooms. This suit was light gray with pink pinstripes, tailored, and fresh out of my law school jobs. I hated it and it wasn’t “me” at all, but you’re always taught to dress “professionally,” even if you look like a clown and it’s totally inappropriate for the context. So yes, I showed up like that, was quickly horrified, let them know I’m usually much more comfortable in Converse and hoodies, got the job, and never wore that suit again. It’s in my closet, lest I have an emergency where I need to pretend to be extra professional.

I got the job in spite of that wardrobe misjudgment, but if I’d done more research on what startup culture is usually like — especially at a tiny, super early stage company — I could have avoided that and shown up wearing something that better reflected who I really was.

The reverse is also true. Something I learned from my time in courtrooms: if you’re on time, sober, and wearing something moderately professional, you’ve already eclipsed half of the other people in the room that day. It’s amazing how many people show up to court in pajamas thinking the judicial system is looking to do them favors. A button-up, ironed shirt or dress goes a long way in how you’re treated. It may seem unfair, but it gives you an advantage in your dealings with court staff.

We’re a long way from the glittery spandex drapery atop Riker’s hairy chest, but hopefully you get the point. Speaking of which: