This is a transcript of episode 273 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

Can it really be more effective to throw out the plan? This week on the podcast, Squirrel talks about his late-night escapades at improv classes and why he’d prefer to travel to Mars in a starship, not a rocket. Join Squirrel and Jeffrey to find out how you can use improvisation to benefit your business.

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Listen to the episode on SoundCloud or Apple Podcasts.


Listen to this section at 00:11

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

Jeffrey: Hi, Squirrel. You recently had an event where you talked about improvisation for executives. Tell me more about that.

Squirrel: Well, this is part of my Squirrel Squadron, where I get tech and non-tech people together and we talk about anything to do with making technology more profitable. One of the things that struck me, partly inspired by our conversations here, was how much we can learn from improv theater. Have you ever done improv theater, Jeffrey?

Jeffrey: I’ve not, though I recently read the book Impro and found it really interesting; I definitely felt there was stuff I could apply there in the future.

Squirrel: Oh, great. We’ll have a link in the show notes for the book, and for a recording of the event. The thing I covered was three areas in which I thought executives of all kinds could benefit from making up more stuff, being more improvisational. Two of them we’ve talked about, one I don’t think we have. I talked about “yes, and” which we definitely did an episode on a while ago. Just a couple of weeks ago, we talked about how valuable rehearsing was, how important it is to try things out, roleplay, practice your conversations. But the third one we talked about was having no script. The idea that actually it would be beneficial to any team not to have a detailed plan for the next six months saying who would be doing what on which day, and that’s quite a radical view. I wonder what you think about that, Jeffrey.

Sounds Scary

Listen to this section at 01:50

Jeffrey: Well, it’s interesting. I think the idea of working without a script makes people very nervous. I often hear from executives that they want to make sure that they keep people busy. “We have to make sure that we’re constantly feeding the team, that there’s something they’re going to be busy on.” So I think that a lot of people would be nervous about that.

Squirrel: “And we have to be sure it’s the right thing they’re busy on. We don’t want them doing the wrong thing.”

Jeffrey: That’s often the second concern that people have. But the first thing they’re concerned about is that there’d be nothing at all. I think the script that lays out what people are doing over that period of time kind of addresses both things. So that’s the thought that comes to mind is I can see how people would be very uncomfortable with that. And yet I know for myself that actually I’m kind of the opposite, which is if I have everything laid out to the point where it’s trying to say what everyone’s going to do over the next six months, that makes me nervous because I don’t have a lot of faith in those scripts.

Squirrel: Precisely. We had someone in the session who’s a chief operating officer and works with a lot of people on operational tasks and works with technologists and creates a lot of Gantt charts and spreadsheets and detailed plans. And when I said this, she said, “Oh, that would be wonderful because I don’t believe those things anyway. But people in the rest of the business really want me to create them. And then of course we never deliver to them. So what could we do instead?” And we had a great discussion on an earlier episode about having no estimates, which we talked to Vasco Duarte about, and methods for very frequent feedback so that you actually build trust and you know what you’re going to be doing next in the short term and you know that you’re working in the right direction long term, although you don’t know the details of it. How’s that work out for you, Jeffrey? I know you do a lot of that.

Jeffrey: Well, in this past week we had sort of a stressful delivery. We had a deadline on Wednesday and we delivered the software to test run on Tuesday, the day before the big launch. We had to make a change Tuesday night and actually have the big launch on Wednesday. We were a bit nervous and really didn’t like working up to the deadline in that way. So luckly our retrospective was on Thursday, and we were talking about what would have made a difference. No one said, “You know, what would have made the difference is a precise script of everything we wanted to do with all the estimates.” But we did say an agreement on the critical path would be valuable. So we had the feeling there was a bit too little shared understanding of what needed to happen. That understanding was unevenly distributed and that inhibited our ability to get together. So in no way do we want a Gantt chart, but we did want agreement on what the key steps were going to be and in what order. So knowing the overall flow would have been very useful to have at the start, but we didn’t need every step spelled out. How does that relate to improv and the kind of scene-setting that you’re thinking of?

A Bearing in the Storm

Listen to this section at 05:27

Squirrel: Well, it relates perfectly, and I can tell a story about that which you’ve just triggered. I was doing improv theater at university, not professionally in any sense, it was drunken late night review theater, very funny stuff with a lot of crazy people. I remember doing the first show of the year, where we had the details worked out enough that we knew we were going to tell first year students: “Part of your assignment is to come up on stage and participate.” Well, a bunch of them did, and we didn’t expect that. So I’m in the wings watching these extra actors appearing, trying to perform, and drunkenly staggering about the stage. I said, “What on earth do I do?” And someone who was actually in the theatre department said, “Well, this is live theatre. Go out and follow the plan that you had.” And I went out and it was great. They played along. The whole audience was in stitches. It worked out very well. My job was to shoot some of the actors with a water gun and I’d just shot some of the freshers. Served them right for coming up to the stage. But the point is that we had an understanding. I had a water gun in my hand. I knew that the next thing I was going to do was go out in my soldier’s uniform and perform this action. I just had to adjust it to the event that was occurring. In the same way, I think your team would have still discovered late that there was some extra step, there was something more they needed to do, but with a framework they would have been able to anticipate that better. They would have been able to work to it better. They would have been able to adapt to the situation. If they’d tried to write it all down at the beginning, they probably still would have missed this step. They probably still would have missed this item if they tried to list the 17 things they had to do on Tuesday evening all in a row. They would have missed number 18. Am I missing something there?

Jeffrey: Not at all. We have a lot of feedback in our process so we definitely would have both missed things from the script, and if we were trying to work too tightly to that, we would have definitely come unglued, especially if we tried to replace feedback with the script. You know, hearing us describe this, I’m actually reminded a bit of how we do these episodes, which is we often talk beforehand and set the scene and have an overall plan, but we definitely don’t have a script.

Squirrel: Yeah, I didn’t tell you that story because I only thought of it as you were describing your end. So we didn’t talk about that beforehand. You didn’t know I was going to tell that story from university.

Jeffrey: Yes. I think it’s interesting how that comes up, that the combination of having the overall plan and reacting to what comes up allows us to have greater value for less effort than it would be if we tried to script the whole thing out.

Precise Foreknowledge and Freedom to Respond

Listen to this section at 08:44

Squirrel: Exactly. You know, there’s an analogy I often use with my clients, which we might find entertaining here. So there’s two ways of getting to Mars, and one is the way that we actually have. Elon Musk is using it, and maybe he’ll go there and maybe he’ll stay there. I don’t know. But that method is to strap yourself into the top of a rocket, bring a book, because you’re not going to be doing anything for a long time. Then when you arrive at Mars, you get out. That’s the simple method of getting there. But you don’t need any windows or anything because you just blast the rocket off at just the right time. You maybe do a couple correction burns, but the plan is set. You can’t do anything else. Much more interesting and in every science fiction show, Star Trek is the most obvious, but everyone has this characteristic that actual rockets don’t have, which is your starship can change direction and change course. Often they’re going to, you know, Betazoid 27 and they decide that Alpha Mir 12 is much more interesting halfway along. The fact that you can react to something, you can see an asteroid halfway to Mars and say, “Oh, that’s interesting, let’s stop off at the asteroid,” gives you much more flexibility, but much less certainty. On the rocket you know precisely to the nanosecond when you’re going to arrive and when you can get out. With the starship you might get interested in a comet on the way. Giving up that certainty requires a level of trust that you might not have. I think that was what was trapping my COO in my session. She was saying, “You know, it’d be lovely to do without this, but other people demand it.” Well, I would claim that the reason they demand it is she and others in the tech team haven’t built enough trust. And there are lots of ways to do that which we cover in our book and elsewhere. Once you get that trust, the uncertainty actually is an advantage because it lets you do more flexible things. It lets you discover stuff, for example in your case, stuff that you would never have guessed beforehand.

Jeffrey: That’s right.

Squirrel: Thanks, Jeffrey.

Jeffrey: Thanks, Squirrel.