We don't know what we don't know

Photo by Cats Coming.

In the before-times, we used to do in-person intake interviews for every single participant in every single one of our programs. Yes, really. And the most common sentence coming out of those discussions was "I don't know what I don't know." Not about teams, or skills, or hard conversations, or motivation, or career paths. The number one thing we heard from bosses was that they lacked the understanding to even get started. Let alone, to make headway on the learning.

This thing. Where you sometimes know exactly what's not working but not how to fix it. And sometimes don't even know the name of the thing to be able to look up a solution. We know this pattern well.

When we founded RSG, we knew how to build things people loved and also how to get the word out. But neither of us had ever done sales. We had worked with super talented sales people, but knew next to nothing about how they did what they did.

We were so ignorant that we lacked the terminology to be able to even look up the answers to Very Basic Questions. But this was not the place for ego. We spent about a month of trying and failing to get to answers on our own. And then we sent three text messages to friends who had all done B2B sales. We had a proposition:

Let us pick your brain about sales and we'll buy you ramen or pizza. Your choice.

Two ramens and one pizza lunch later, we had the fundamentals in place. Had we become sales experts over the course of three lunches? Absolutely not. But had we gone from utterly clueless to slightly less embarrassing? Yes.

This early unlock saved us a ton of heartache and time. We went from "I don't even know what questions to ask" to "I now know the next three things I need to do" over the course of a week and a half. Eventually, we figured out that the way we learned sales generalizes to a bunch of other areas as well.

Draw two circles

The process is simple to describe, and hardly unique to us. You've seen this advice a hundred times before.

Find three experts in a thing.

Be specific in your ask for their time.

Buy them coffee, or ramen if they'll let you.

There's nothing untrue about this basic format, that's not the problem. The problem is that, in practice, it often doesn't work. There's too much unspoken here. Too many assumptions baked in about how to prepare, and how the conversation will go. This is how to draw an owl, only instead of wasting paper it wastes your professional network. You might do these things and have a phenomenal, brain-opening conversation. But a more likely outcome is that you'll end up frustrated, and embarrassed that you wasted your person's time.

It's recoverable, though. There's a good version of this process that is much more likely to actually work. We just need to say some of the unspoken bits out loud.

If you already know it all, why are we here?

The core of how we have made this process work for us — from sales, to books, to events, to asbestos remediation — is vulnerability of a very specific kind. The specific thing you need to do is to push through the discomfort of someone seeing your ignorance. You need to get very clear and honest about what you don't know, even when you feel like you should.

This is very hard to do. In a professional context there are strong incentives to represent more depth than you actually have. And if you're someone whose competence gets questioned regularly, because of racism or sexism or some other awfulness, admitting ignorance is not an option. One way or another, many of us learn early to hide the fact that we don't know... everything.

And so, even with acknowledged experts who want to teach us, we reach for the cop-out. Safe, thoughtful-sounding phrases like, "I think I'm pretty good at this but I'm always looking to improve." Or, "I have a working understanding but would love your perspective." Stop us if these sound familiar.

What happens if, instead, you lean fully into the admission? Call it a journaling prompt. What's the core issue here? "I keep getting this wrong so I need to start over from the basics." Or, "I've actively resisted learning about this thing because it seems gross/beneath me, but that's ignorance I'd like move out of now." Or, "I'm embarrassed because I should have learned this years ago." Scarier, right?

This is where the good stuff lives. The questions you ask from this place might be shockingly basic. Your broken assumptions will be obvious. Your lack of fundamentals will be visible from space. But your questions will be honest. You will be able to have core beliefs challenged, or disposed of wholesale. Write those questions down. They're 9000% better than those safe, thoughtful-sounding dodges.

Play fair

Lowering your shields enough to get to real questions is the hard part. But once you have those in hand, there are still a few other mistakes to avoid. And they're tricky, because they sound like good ideas:

Making the conversation do double duty. Wouldn't it be delicious if one of the experts you learned from was your boss' boss' boss? You could learn from a real pro, get some face time, and also show them how dedicated and promising you are! No. Those ulterior motives will wreck your ability to admit what you don't know. And it's also unlikely to work. Any executive worth learning from can clock that shit a mile away. That doesn't mean you can't learn from leaders in your org. But you know in your heart if you are engaging genuinely to learn, or whether you're playing games. Don't play games.

Asking for a free version of someone's day job. Many senior people will make time, and not charge, for an earnest and vulnerable ask. It's often rewarding for senior folks to mentor someone who's genuinely putting in the work. But do not ask DEI consultants to give you free DEI training. Do not ask sales trainers to give you a version of their $10k course for a bowl of noodles. If you want to ask a teacher what it's like to teach, have at it. If you want to ask a teacher to teach their subject to you, pay tuition.

Draw the rest of the owl

The point of all this preparation was to get you here. With a list of good, honest questions. With experts you can talk to without trying to prove anything. Your only real job now is to ask your questions, and to listen.

Listen deep. Listen not just for the answers to your questions, but to the implied models for how they approach the problem. Most experts have developed systems for how they think about their work, but they are famously bad at articulating them. Those models leak out, though, in the way they word things, in the way they break down problems. When you ask the second and third person your questions, and you see the patterns that emerge, you'll have found something really important. Play those patterns back to them, and see if they agree.

At the end of three conversations, you will get it. At least, a bit. You'll have new stuff you want to dig into, but it will be more well-formed, easier to google, and it will plug into a lattice you've already built. You'll know what you don't know.

Whatever that thing is that you've been meaning to get better at for years. You are three proper conversations away from cracking it open. It's still early February. If you get to work now, you can have those questions answered before spring.

- Melissa and Johnathan