This is a transcript of episode 281 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

You can be your own “devil’s advocate” to boost the quality of what you produce. Listen to this episode of Troubleshooting Agile to learn how and why to be self-critical, with Squirrel and Jeffrey!

Show links:

Listen to the episode on SoundCloud or Apple Podcasts.

Read the next episode in this series here.


Listen to this section at 00:11

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

Jeffrey: Hi, Squirrel.

Squirrel: So you were telling me you got some astonishing results from some of the folks on your team, and that led you to learn some interesting things about being self-critical. Tell us more?

Jeffrey: Yeah. I was talking to someone and we were reviewing some numbers they put together on usage, doing some analysis that was going to inform some product feature work. Looking at the table, I was trying to make sense of it. I was trying to understand what all the numbers meant, how they related. They’d presented their conclusion, they thought, “Well, this is really clear. Here’s the data that backs it up.” But I said, “You know, I’m bothered by something. I’m looking at this column where you talk about a rate, but then I look at the number and it’s 6000.”

Squirrel: Hey, that sounds like a good rate! 6000 sounds like a big number! 6000 what?

Jeffrey: Well, you know, it was supposed to be a click-through rate, and that just seemed really high. I had really had trouble imagining that all the users were opening that message 60 times each. I don’t think that was happening. So there was a number that didn’t make sense when you try to compare it to reality. When I asked the person about it, they said, “Oh! I have to go back and look at this. I’d asked other people to generate these numbers for me, and I missed that. I’ll do it and get back to you.” And it was interesting because then we ended up having a conversation about being self-critical. The really interesting thing, why I thought it’d be worth talking about in the podcast, is I ended up having the same conversation I’d had just the day before with someone else who had been working on a completely different report who had asked for advice. So I thought maybe, maybe it’s more than just these two people, right? You know, one is one is something, but two people in two days makes me think that this is maybe a bigger topic.

Isn’t “Critical” Bad?

Listen to this section at 02:11

Squirrel: Wonderful. So what do you mean by self-critical? I don’t think you mean that these people who presented figures that were nonsensical should go and get out a wet noodle and flagellate themselves. I don’t think you mean “beat yourself up.” You must mean something else.

Jeffrey: No, something different. I wanted to make it very practical. Actually, listeners who know about our technique for analyzing conversations will spot a similarity here, because when we do that, we talk about self-distancing, which is to say you want to be able to view your conversation as though it was someone else.

Squirrel: Not social distancing, but self-distancing. We all know social distancing. Self-distancing is a little different. It’s looking at yourself as if you were a different person.

Jeffrey: Exactly. And the point I was making is that to be self-critical kind of is an unnatural act. Our normal cognition and cognitive biases will tend to miss errors in the things that we’re creating. That’s really a challenge when we want to improve. So the advice I gave them was to have this kind of separate step and as far as possible, try to put yourself in the mindset of a different person entirely, so that you’re coming to it as a critical person. I used a couple of different analogies. One, I said imagine you’re that mean kid in high school who’s just trying to make themselves look smart and everyone else look bad in front of the teacher, you know. “Well, what does that mean? Do you even understand what that means? Where did that come from?” You know, trying to catch you out. I use the analogy here of the devil’s advocate, which I think is a great concept that came from the Catholic Church, actually, that when they were considering making someone a saint, there was someone who would take on the role of the devil’s lawyer arguing against it. There’s a great example they talk about on the Wikipedia page where they hired someone outside the church to be interviewed as a critic of Mother Teresa when they were going through that beatification process. So be your own devil’s advocate. Put yourself in a different mindset where you can view this as a work of a different person, as a way of trying to find the mistakes that someone else who is not already familiar with what you meant will see. That’s the key thing, the challenge is you knew what you meant when you wrote the document, when you created the table, when you created the presentation. If you read it as yourself, you’ll be thinking about what you meant. You need to kind of role play yourself into a space where you’re not that person who already knows the answer.

Getting Into the Mindset

Listen to this section at 05:02

Squirrel: This reminds me of one of my favorite exercises which I don’t get to use it enough: the six thinking hats. Now I can never remember which hat is which, but we’ll link in the show notes and you can go look, it might be the black hat or the purple hat-

Jeffrey: The black hat is the critical one.

Squirrel: So what you do is you’re working on a problem as a group, and the thinking hats are worn by all the members of the group at the same time. So everybody puts on the green hat and then the blue hat. But the black hat is the one where you all play devil’s advocate. You think, “How could this fail? How will it not work? What will be a catastrophe as a result of it?” One thing that people also do is they’ll do a pre-mortem, not the post-mortem after the patient has died, but the pre-mortem before the project, looking for all the things that might go wrong with it. So these are two areas where this kind of critical thinking really in the true critical sense, being a critic, being an advocate of the negative point of view, finding problems, can be very helpful.

Jeffrey: Absolutely. And I thought exactly the same thing as far as the six thinking hats, that we already know the value of a critical thought process and we also know that it kind of takes some amount of rituals to get us into that space, because it’s not a natural thing to do. So now bringing that down to a personal level, how can you adopt that mindset in a way that you can be self-critical and find the mistakes in your own work when you don’t have someone else available to critique it for you? Or maybe as a first step, you know, before you bring it to someone else. That process of seeking to understand, because otherwise you can easily fall into this scenario where you’ve done all the steps and you have an answer. The answer just doesn’t make sense in the world, which is what I encountered here.

Squirrel: That has happened to me loads of times. I’m often coaching people on exactly that problem where they’ve followed the steps and the steps aren’t the right steps. That’s one of the transitions to being an executive, one of the most difficult to follow. But maybe that one is a separate topic. Jeffrey, should we get into that next week?

Jeffrey: Yeah, I really like that idea. I think you’re right, because we can take this from sort of a small scale of working on a bit of a deliverable to what happens when you need to operate at a higher level, where as you said, it becomes less formulaic and you need to be all the more aware of what you’re doing as you go along. That sounds great.

Squirrel: And not being formal is actually a good thing. So we’ll talk about that next time. Thanks, Jeffrey.

Jeffrey: Thanks, Squirrel.