This is a transcript of episode 282 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

Vague instructions from the Board or CEO are the norm, and in fact mean great opportunity. Listen to this episode of Troubleshooting Agile to discover why there’s no recipe that gets the right answers to executive problems, with Squirrel & Jeffrey!

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Read the previous episode in this series here.


Listen to this section at 00:11

Squirrel: Welcome back to Troubleshooting Agile. Hi there, Jeffrey.

Jeffrey: Hi, Squirrel. We are picking up from last time where we were talking about being self-critical and the idea that you can’t just follow steps. You made the point that this is a part of the process of becoming an executive: dealing with that uncertainty. What did you have in mind with that? Can you expand a bit?

Squirrel: Sure. I have loads of clients that I help with this transition. Not only technical people: salespeople, marketers, you name it, I coach them. A universal problem that people making that transition, who are new to the executive suite have, is that suddenly the rules are much more fluid and in fact they’re expected to make up some of the rules, but they don’t know that. It reminds me of when I would talk with my physics friends at university. We’d all be trying to do some physics problem in a physics course, and I was a mathematics major and then a mathematics graduate student. I would take the differential equation or whatever it was and follow some steps to get an answer, which might be -2 million. And they would say, “Squirrel, I really think the temperature at the surface of the earth is not -2 million degrees.” And I’d say, “But that’s the answer! Look, it solves the equation! It gives the right answer, it balances.” And they’d say, “Yeah, but it doesn’t match reality.” This is often a challenge for the type of person who has been a very successful individual contributor by following a set of rules. If an engineer, it might be they have taken a requirements, have something written down, have something that they’ve learned about from a product manager, and done a super job making a piece of software that does whatever someone told them. Now they’re in charge of doing the architecture for a piece of software, and that’s a completely different mode of thinking. Suddenly you have to deal with physical reality and you can’t just follow the steps. Same thing happens if a salesperson is used to taking a deck that someone has given them with a bunch of very good arguments for why you should buy whatever it is, and they’d gone off to do a wonderful job building relationships and explaining the product and getting people across the line to buy. But the person has not become good at actually defining what that product should be, and changing the decks, and telling others and fighting with them and arguing with them to get them to make a different product that would sell better. This kind of shift is very difficult. I’m often telling people, you can’t just follow the recipe. You have to be the chef now, coming up with what should go in and making variations, and that is a real shift. It’s really difficult to switch into that level of—using our term from last week—self-criticality.

Jeffrey: Yeah, that’s a good point. The interactions change entirely in sort of what you’re getting from your boss. Your boss has changed and now instead of working for a line manager of some sort within a discipline and domain, you’re now dealing with a sort of CEO person who’s a generalist and is looking across the whole business, and really may not be a specialist in what you do. But more importantly even if they were, they’re kind of expecting you to run things. So you’re going to get some directions from them, but they’re not going to be what you would have had from a line manager who’s essentially responsible for what you’re doing. That’s I think one of the big differences that people miss when they’re getting these things. They end up having results that they need to be accountable for, not just an obligation to follow these steps, although sometimes you get steps, and sometimes those steps don’t make sense. And then what do you do? I’ll tell you what you can’t do if you go in as an executive: go ahead and just follow the steps that you were given and get a nonsensical result.

Squirrel: “The earth is -2 million degrees. We all ought to get parkas, move in with the penguins.”

Jeffrey: Yeah. That’s not going to fly with most of the CEOs I’m aware of.

Where the Sidewalk Ends

Listen to this section at 04:30

Squirrel: No. And this reminds me of a wonderful article which we’ll link in the show notes by Ben Horowitz, if I remember right, about the psychology of being a CEO. It applies just as strongly to anyone in the executive suite or anyone who takes this kind of direction. One of the things he observes about the founders and CEOs he’s worked with is that all the way through university and school before that and their early jobs and so on, they’ve been rewarded for following the steps really well. So when when you’re taking a class in trigonometry, the teacher doesn’t say, “Boy, you’ve done a great job looking at things that aren’t triangles. We’re very interested in four-dimensional triangles, glad that you did that.” The teacher says, “Do the darn sines and cosines and tell me what the hypotenuse is and stop bugging me about the 12th dimension.” But when you get to running your own startup, in Horowitz’s case, what you find is number one, there aren’t any steps anymore. Number two, most people fail because there aren’t any steps. You’re inventing something new. If you want to use the Cynefin framework, you’re in the complex domain. There are no signposts. There’s no rule book that you can follow, and there’s no rule book when you’re in the situation you’re describing, Jeffrey, for the CEO giving you the direction either. The direction you might be getting from someone else plus your own knowledge is completely insufficient. And that’s by design. That’s how it should be.

Jeffrey: That’s where the opportunity comes from.

Squirrel: Exactly. So Horowitz says, they’ve been getting 100 or 99 on every test all the way through this point, and nobody tells them that the mean score on the test they’re now doing is 22. And so they feel really terrible that they can’t figure it all out and do everything, when that’s not the expectation. I was just seeing it this morning with one of my clients. He was problem-solving. He said, “I just need to figure out what the CEO is thinking. My boss is thinking X and I have to solve for X.” And I said, “Stop thinking that way! There isn’t an X, your boss doesn’t have one. Come up with an approximation, something that could match physical reality. Maybe the earth is 20 degrees, maybe the Earth is 25. Wait a minute. Is it Celsius or Fahrenheit? These are the sorts of things that you can be looking at and experimenting with. That’s how you make progress here: by defining the problem yourself, and redefining it. The vague instructions you may get from someone else are actually an opportunity.

Jeffrey: Say more about that. I was thinking the opportunity is in terms of a startup where there’s the unknown and that’s why it’s an opportunity: no one else has figured it out. If someone else figured it out, well, they would have already have the market. But I think you have something else in mind when you’re saying the instruction from a CEO is an opportunity. Say more about that? What is the opportunity when a CEO gives you vague instructions?

Squirrel: It’s an opportunity for you to define something better than what the CEO was thinking, because by definition, if you are in an environment in which everything is perfectly well understood, it’s simple or complicated in Cynefin terms…link in the show notes. It’s a framework for understanding how complex things are and how they relate. But if it’s simple or complicated and you can just follow it, it doesn’t fit for an executive. There’s no reason for there to be an executive there. There may be people who have those titles and all they do is put the numbers in the spreadsheet and get the number out and they never have to look at how it works or what the formulas are. I don’t think of them as executives. They’re not the ones I’m talking to. Most of you who are listening to this, you are either at that level or you’re headed that way. You’re operating in an environment of uncertainty. You’re operating in a complex domain. And when you get vague instructions, that’s a signpost that gives you some idea of what to do in the complex domain there’s no guidance, but here you’re getting some. But it would be wrong just like if I were to tell you, Jeffrey, I’d like you to come see me here in England, and you were trying to guess the precise route that I was suggesting. Which airport should you go to and what train should you get on that would take you here to see me, that would be silly. I’d like the outcome of “Jeffrey being here in my house” and I’m happy with however you get there. If you’ve got a private helicopter, sounds good to me. I’ll see you in a while, get on a boat. But the point is that the details and the execution are not defined for a good reason. They aren’t known. So when you’re out there searching for X, when you’re searching for what the the secret hidden message is, it’s not like in school where that was true, right? Your teacher might give you an assignment and say, figure this out. You were supposed to get the teacher’s answer. That’s not the case here.

Jeffrey: As you were saying that, one thing that occurred to me is that this is not just a property of executives. This is actually a property of the highest-performing employees I’ve worked with at every level, which is they’re the ones who are considering better answers. There might be better ways of doing things. And it’s not a case where I as their manager or anyone else could tell them in advance what to do, but they’re out there taking ownership of things and embracing the uncertainty and inventing better outcomes, better routes than than we knew about before they headed out to go find them. So that’s really what came to me especially when you said “maybe you’re going to get a better answer than your boss.” That’s a good thing. And taking that kind of ownership is the opportunity at every level. The people who are looking at the imprecision as the opportunity are the ones who have high agency and end up making a tremendous contribution.

Squirrel: They’re certainly the ones that are most successful when I coach them.

Jeffrey: Absolutely.

Squirrel: All right. Thanks, Jeffrey.

Jeffrey: Thanks, Squirrel.