Problem: 7
Wednesday, 10 October 2018

I’m pinned.

I’ve maxed out my team leaders, and they’ve maxed out their teams. I’ve maxed out what Keats can do for me directly. I have many projects I want to delegate, but I’ve run out of delegation power and management bandwidth. I’m pinned.

And I’m not the only one who’s pinned. In their own problem landscapes, Kamron, Marshall, Erinn, Shane and Ric are all pinned to various degrees. Maybe if I figure out how to un-pin myself, I can figure out how to un-pin them, and vice-versa. Leverage is fungible: you find it anywhere, and you find it everywhere. Everyone is their own reinforcements, and everyone is reinforcing everyone else.

I began feeling pinned last quarter, but there was a lot of low-hanging fruit: easy, small, well-scoped, high-leverage projects that I could take on myself. So that kept me busy. Now the shallow oil’s been tapped, and I need to drill deep.

I can solve every problem in my problem landscape, but I can’t solve all of them at the same time. I would pick one, but they’re all-engrossing. Without a COO to run the company, I can’t commit to a full-on offensive. So my posture is balanced. I’m playing center: doing some attacking, doing some defending. I keep some energy in reserve to deal with any crises or reactive work that come up. I am doing some light networking and business development. I am pushing some management initiatives forward. And I’m investing in myself: getting organized, reading, doing research, going to the gym, thinking, talking to smart people, and setting myself up in NYC.

So, I’m pinned. What should I do?

One option is to wait. Overall, we’re making a ton of progress. Every quarter, we’re in a fundamentally different position. Why not “end turn,” and wait to see how the bets we’ve made pay off? “Just add time,” and see if, indeed, at T=2 I have more leverage than I started off with at T=1.

For example, our new website will be ready for launch by the end of the month. Then we’ll do our PR launch. That would be a good time for me to hit up my entire network and ask for help hiring a COO and an Executive Assistant. Two weeks isn’t that long. I could wait…

But I’m not very patient, because my company isn’t profitable yet. And I know I’m a high-leverage resource. Even though I can’t think of what I should be doing right now, it will be obvious in retrospect. And I don’t want to have to live with the guilt of knowing that I could have tried harder to find a way. There’s nothing less attractive than an overconfident leader who is wrong.

So my second option is to change the plan. As much as I would like to not continually second guess my decisions, and trust that my strategy will play out exactly according to plan, what if it doesn’t? Things rarely go to plan. But, on the other hand, I can’t continually change my orders: projects need to stay in flight and land. So I end up second guessing projects with deadlines that my team must hold as sacred. That isn’t very productive. I can only course-correct on a quarterly basis, and even then, most present-decisions are constrained by past-decisions. Trajectories have a momentum that is overwhelmingly powerful. This is what Sun Tzu called “hobbling the army” — in most situations, you can’t keep changing your mind. You have to commit your troops to a plan and watch them execute. You only get so many opportunities to adjust course.

My third option is to wait-actively. I call this the “prepare the way” option. In reference to Isaiah and Saint John the Baptist, Heidegger proposed this as a solution to waiting for God to return. If God exists, it seems that he has abandoned us. We must confront nihilism on our own. So maybe the right thing to do is to “prepare the way,” to wait-busily, to do as many smart, healthy, wise things as possible. To set everything up as well as possible. To be as organized as possible. To learn as much as possible. To be as strong as possible. To accumulate what Sun Tzu calls Shih, or potential energy. So that when the moment comes, we can explode into action. So that we’re attractive. So that we’re sending God the signal that we’re ready for him to return. If God comes back and asks, “What did you do with the time I gave you? Did you do this? Did you do that?” You want to have good answers, and prove yourself a good steward. Excuse the neo-Catholic existentialist philosophy, but you get the point.

I did this third option all of last quarter. I’m glad I did it. It was good. But as I mentioned earlier, I’m running out of small projects. And I’m restless: I somehow feel there’s a way through this labyrinth. There’s some way to un-pin myself.

This blog post comes to you because of this strategy. It’s the sort of thing you do when you don’t know what else to do. You start trying new things. And you hope that the trail of clues takes you to a new place, and eventually leads to a realization.

At first I felt guilty. Am I burned out? I was burned out and am still kinda burned out. But every time I came up with a well-scoped, high-leverage small project, I had a rush of energy and did a ton of good work. For example, in one day last quarter I did 50 1:1 calls with agents — in one day! Then I finished. That project ended. I had to return to the ambiguous in-between place, looking for leverage.

I don’t feel guilty anymore. One realization I’ve had is that this “pinning” dynamic I’m experiencing isn’t a hallucination, it’s real — and it has nothing to do with me being burned out. I wrote about this in “Finding More Leverage.” The problem is that I’m out of leverage. And I need to go find more.

Yay! I understand the problem now! I ran out of leverage. So now all I have to do is find more leverage. So… how do I find more leverage?

Finding more leverage is hard. It’s not obvious. There’s no formula. So I’m still stuck. But I’m stuck on a better question. That’s progress. Hmm…. How do I ask an even better question?

How about this:

Francis, you feel pinned. 
1. Describe your problem landscape in detail. Explain why you’re pinned. 
2. Then, describe what would need to happen for you to not feel pinned anymore. If a Genie showed up: what resources would you ask for?
3. Now, if you got those resources, what would you do with them? Describe, in detail, what projects you’d take on personally, and what projects you’d delegate, if you were fully supported.

That’s a much better prompt.

Okay, first, here’s how I see my job.

  1. I’m the CEO. 
    My primary job is to set the strategy, model, vision, and culture. EASY.
    My secondary job is to lead OFFENSE: fundraising and assist with hiring, sales, marketing and business development. HARD, BUT MY ZONE OF GENIUS. NEED AN ASSISTANT FOR THE SDR WORK AND OTHER SUPPORT SO I CAN FOCUS ON THE MEETINGS.
  2. I’m acting-COO.
    My primary job is to lead DEFENSE: run the company, directly manage team leaders, make sure the entire workforce is well managed and aligned, make sure that OKRs are hit, oversee all project-management, all systems, all structures, all tactics, and ultimately, execute the strategy as efficiently and effectively as possible. VERY HARD, NOT MY ZONE OF GENIUS. NEED A COO.

My problem landscape follows from this. I can’t go on the offense, because I don’t have a COO. Even if I did have a COO, I wouldn’t be able to do offense efficiently without an assistant (leveraging Keats) to source opportunities, set up meetings, run my funnels and oversee follow up.

So if a genie showed up, I’d ask for a COO and an Executive Assistant. That’s why I wrote this: “I’m hiring an Executive Assistant.” (I should write a companion post for the COO position.) Erinn is searching for both. We’ve had a few candidates that didn’t work out for various reasons. But again, I can’t just wait for these hires to happen. Waiting is bad strategy.

But let’s assume I get the hires, and continue with the exercise… If I got a COO and an assistant, what would I do with them? I should do this: “Describe, in detail, what projects you’d take on personally, and what projects you’d delegate, if you were fully supported.”

The job descriptions above outline what I’d do vs. what I’d delegate. As for what I’d delegate, “I’m going to start delegating in public.” I’m writing up all the projects I wish I could delegate. That’s the next step for me in finding my way through this labyrinth.

In writing this, I remembered an eerily prescient poem that I wrote in February of 2017 called The King. Read it. The King, in chess, is often the weakest piece. He is always pinned. The Queen is the piece you want to be. You want to hire a COO to be The King. After all, who wants to be King?