Write a letter to the board

I recently sat on a promotion board. Everyone  in the military says that at some point, you should sit on a promotion board — and with good reason. The handful of times I’ve acted as a gatekeeper have been enlightening both as an evaluation writer and as a person subject to gatekeeping forces. 

It’s like meeting the Wizard of Oz, when the illusion of an all-knowing authority disappears, revealing that the gatekeepers are just regular people, like me, doing their best to uphold a standard.

Which is why people need to write a letter. 

Any gatekeeping process comes down to two types of data: quantitative and qualitative. That sounds obvious, but if I’m a high school kid applying to college, all the stuff I’m doing, from producing A’s, B’s and C’s, to playing varsity soccer or volunteering at the soup kitchen—it all ends up a data point. I don’t mean to sound jaded when I say that you can see everything you do as data, on a personal level there’s more to it. But remember that people are terrible mind readers, and to a stranger who only knows you on paper, it’s just data.

I can’t think of a scenario that is purely quantitative or qualitative. Both types of input factor in to some extent, even in something as straightforward as making the U.S. Olympic track team, for an extreme example. At first it may seem like the only factor that matters is speed. But even in elite sports if an athlete has a history of doping or is unpopular with the public or whatever, that stuff plays a role. People have to like you, or at least tolerate having you around to coach you, play with you, etc. Since people have to find you moderately compelling, knowing how to tell your story is helpful. 

And as I say this, I think of the times that I applied for a job without a cover letter. I repeat: people are terrible mind readers. They don’t know what your deal is and are not going to bother to string it together for you. You have to string it together for them. 

So what makes a good letter? First, you want to pick your best story. Hint: it’s probably not the first one that comes to mind for you. “Best” means most relevant to the thing you’re trying to do. 

The next thing you want to do is put your best story in a logical narrative that’s easy to understand. Emphasis on the word logical, and the phrase easy to understand.

The third thing you want do is make sure that by the end of that letter (no longer than one page), the reader has no questions about you as it relates to what you’re asking for.

The truth is that none of it is easy. Even with all these great AI tools, people are still terrible mind readers. That includes you. You will also fail to guess at what someone will want to hear as they read your letter. But it’s more than worth a try. Saying nothing is no data at all. You’re your best advocate for whatever it is you’re trying to do. Writing a letter already says that you care enough to say something. So just send the letter to whomever it may concern.