The Leaflet #109

1. resolve delegation anxiety 2. transitioning from founder to CEO 3. how to move forward when no one can agree

1. Resolve anxiety over quality when delegating

Imagine you’ve delegated something, and you’re worried about its quality. You’re watching the delegated work unfold at a lower quality level and wondering: is this worth it?

Here’s one answer to the dilemma.

I tend to feel okay watching something unfold at a lower quality level if I have the structural – or mental – equivalent of a clipboard.

I literally used a clipboard when I would watch someone lead a meeting in my organization. The clipboard meant: I’m paying attention, and I’m recording what needs to improve. The person I was observing knew ahead of time that this is what I was doing.

This matters because it norms the situation as a developmental experience. While I’m holding the clipboard and writing on it, everyone else in the room understands there’s an acceptable “lower quality” level in the moment — because this is part of someone getting better.

It becomes a constant signal: this person’s lower-than-mine performance is okay for now because we’re actively raising the bar. Around here, people take on new challenges and level up.

And you don’t have to have a physical tool. The “clipboard” can be any process you lean on—any shared frame that makes it clear what’s happening. Your “clipboard” could be, eg, a manager sitting on a Zoom call off camera. The point is to create a visible container for work that’s in progress: the stakes might be real, and the quality might be uneven, but you’re present, and you’ll jump in if needed. With this container in place, you communicate to everyone that improvement is part of the job here.

-ben

2. Transitioning from founder to CEO

There’s a transition you have to make: from being primarily a founder—incidentally the CEO—to being primarily the CEO, and only symbolically the founder.

That transition is a must.

Your meaning as a founder never goes away, of course. But everyone’s day-to-day interaction with you is primarily as the chief executive. And whether they say it out loud or not, they’re comparing you to someone who is extremely technically proficient at that job—someone who isn’t you—someone who could come in and run the thing exceptionally well.

Many founders (myself included) operate with an unspoken belief that we don’t need to be that person, because we have so much “juice” from the founding story: the vision, the origin, the purpose, the credibility.

And people will love that when you’re making speeches. They’ll love it when they see you on podcasts. It will be a major reason they say they love working there.

But their day-to-day experience — like, if you could poll every hour and 23 minutes to ask “how’s it going?” and get the average of those responses — will be about their experience of you as an executive, not as a founder.

Behaviors that are appropriate for founders — like forcing something through when it needs to be done — carry different meaning in the CEO role. And often, that meaning is reliably more negative.

-ben

3. How to move forward when no one can agree on the plan

The silver bullet with any sort of loggerhead disagreement with a report where you suspect that you’re correct, but you’re not fully clear on how to assert that, or you don’t feel like you have the data to back it up yet, is just to say:

I’d love to ask you if we could try it for X amount of time.

And at the end of X amount of time, I’m going to put a reminder for us in our one-to-one to hit the refresh button and check if this is still good, or if you think this is still worth doing.

I’ve seen this work in so many different situations where otherwise we’d hem and haw in trying to make a decision.

-ben

COMPELLING QUOTES

Avid blogger Zvi Mowshowitz on feedback:

A rule for game designers is that:

1. When a player tells you something is wrong, they’re right. Believe them.

2. When a player tells you what exactly is wrong and how to fix it? Ignore them.

3. Still register that as ‘something is wrong here.’ Fix it.

People are very good at noticing when things suck. Not as good at figuring out why.

Deeply human polymath Cate Hall on your elephant and rider:

Ultimately, you can’t go anywhere without your elephant. Sure, the rider can imagine it controls everything — that it’s capable of endless achievement, that it will never rest again, that it doesn’t possess humiliatingly normal needs. The rider, gifted with imagination, can pretend it is an infinite being, right up until the moment the elephant stops playing along.

Writer John Brinckerhoff Jackson on the use of “landscape” as metaphor

We should not use the word landscape to describe our private world, our private microcosm, and for a simple reason: a landscape is a concrete, three-dimensional, shared reality.