This is a transcript of episode 298 of the Troubleshooting Agile podcast with Jeffrey Fredrick, Douglas Squirrel.

Is your tech team choosing safety by doing everything, or do you dump more than you do?

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Safe Choices are Less Valuable

Listen to this section at 00:14

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

Jeffrey: Hi, Squirrel. You were telling me you had some interesting reading. Can you tell me more about that?

Squirrel: I sure did. And it’s related to last week’s episode, especially when we talked about outsourcing risk and having real results. And what happened was that a client sent me somebody else’s report on the company I was about to investigate. So I often do these reports and evaluations of companies someone is going to invest in or companies that someone is heading and they’re not sure how they’re performing. And I assess that not only their technology, but their product strategy and their approach to the market and so on. But I don’t get a lot of feedback on these. In other words, I don’t get a lot of competitive analysis because I do mine, but mine is private and other peoples are private, so I don’t know how other people do this. So I got the rare privilege of reading someone else’s. Someone sent it to me as part of our discussion about me doing a similar thing for them, and I was shocked by how safe it was.

Jeffrey: Safe?

Squirrel: Yeah, it was. It didn’t have anything challenging in it. And the main way the person had assessed the team was through metrics you could get from tools like Jira and from GitHub. So number of pull requests, how many lines of code were in each pull request, number of tickets resolved per sprint and things like this and very pretty graphs. And the person drew conclusions about the team from these things and said where there were strengths and weaknesses but didn’t seem to have talked to anyone. Now I suspect the person did. It was just obscured by this kind of overall safety. But it led me to think more about the outsourcing of risk. We talked about last time that it’s very easy for someone to say, “Well, hey, you just tell me what to do and I’ll do that. And as long as I have a list of tasks and I’m working through them, it must be okay.” And not to be accountable for results like improved conversion rates or lower churn or more profit.

Jeffrey: Right. Activity metrics are safer.

Squirrel: Exactly. And this person had used activity metrics to evaluate the team. So from outside. And that’s just really foreign to me because that’s not at all how I do it. Now, I look at those sorts of things and those are valuable inputs, but I’m looking for threatening and challenging and difficult conclusions, which come largely from the interviews I do and the interactions I have with people which sometimes don’t make those people happy and don’t always make me happy. But the result is that I’m making challenging, opinionated recommendations, which again, people don’t always agree with and don’t always take my advice. And I’m not always right for sure. But it seems to me that the this particular report I was reading was one that felt so safe in a way that I observed many people setting goals and evaluating teams not only in this formal way, but in their day to day work. I just wonder how that strikes you, Jeffrey.

A Searing Moment of Insight

Listen to this section at 03:46

Jeffrey: It’s actually it’s really interesting hearing you describe it this way, because what it made me think of is, if I heard this right, you know, you’re taking a risk. So you’re making this contrast. You are making risky recommendations where in a sense that you might be wrong about it. But if you’re right, then you’re giving them concrete, high value things they can they can change and make different. What it reminded me actually, of is talking with our friend Benjamin Mitchell back when we were doing our conversational dojos, when you and I were learning conversational skills. And what I remember there was we talked about the difficulty of learning and kind of the risk of when we would examine our own conversations, we might discover something that was unsettling. We have a conversation where we were pretty sure coming into our analysis that the other person, you know, was a bozo. But then it turned out, oh, look, no, I’m the bozo. I’m making these mistakes. I’m showing this lack of skill.

Jeffrey: And Benjamin had a, what I thought was, a really interesting saying. He said he was talking about how he had tried to share these ideas of conversational analysis with colleagues before and hadn’t been very successful. And he said, “as it turns out, that not everyone is looking for that moment of searing insight”. And it strikes me that’s what you’re kind of describing. Here, which is the sort of risky analysis, risky conversation, but with a potential reward and, but that it’s safer to not do that. But, if we really want to get better, if we really want to have a better result, we’re going to need to do the unsafe thing. I know actually, that’s what I’m just back from a houseboat trip and I’m going to be coming back to the office and I’m expecting to have a lot of difficult conversations with people about how we’re going to prioritize. I mentioned, I think in our past episode that it’s OKR season and that’s why we were talking about results.

Squirrel: Objectives and Key Results (OKRs) for people who might not know that term.

Jeffrey: Exactly.

Squirrel: So you’re setting goals for the coming quarter, I assume?

Jeffrey: That’s right. And an important part of it is, we have goals we want to achieve. But the difficult conversation part is like we’re going to have lots of good ideas, but we’re going to need to say no to some of them.

Squirrel: Probably most of them.

Jeffrey: Well, yeah, exactly. We have lots of good ideas. Most of them probably won’t make it onto the proposal list. And of the ones that do, even those, even that short list, we won’t be able to do all of them. Or rather it’d be easy in the goal setting to say to and essentially be safe in our conversations and say, sure, let’s try to do all of them. We have 17 good ideas. How could we not do these good ideas? Why would we not do a good idea?

Squirrel: Oh, and Jeffrey, it’d be okay if we if we didn’t get to all of them. I mean, we’ll just try all of them. And, but because there are 17, we’ll just try all and we’ll make everybody happy that we tried and, you know, some of them won’t work out and that’ll be okay. Isn’t that a good way to set goals?

Jeffrey: Well, no! It’s not. This is the normal way. That’s the safe way, because it’s safe short term because we avoid those difficult conversations. But the lack of focus means that we’re unlikely to progress on any of them, or the progression will be accidental. So we won’t end up with what we’ve chosen to end up with. We’ll end up with kind of an accident of what happens versus what doesn’t. And that lack of control ends up being a huge problem in most of the teams I’ve ever dealt with. The lack of focus really undermines the company’s ability to get where they say that they want to go. They’re just not willing, in a sense, use this terminology. They’re not willing to have the risk and of the conversations to define what’s really important and what’s not. What are the things that are are outside of the focus.

Squirrel: And here’s the crucial idea for executives, your team or teams that are taking these safe options, when they take the safe option, that’s worse than failure. That’s worse than picking 1 or 2 really key areas of focus and not making progress on them. And there’s two reasons why that’s worse. One is the team learns that safety is better and doesn’t take risks, and that’s almost certainly not what you want. And second, you miss the opportunity to have a moment of searing insight, to have a very significant value result. And if you do that across all your different teams, then some of them will have this significant success and some of them won’t. So it winds up at the team level being the same result. But we’re going to try a number of ideas and some of them won’t work out, but you wind up with much better results from the teams that do have success and organizational learning that taking risks is a good idea.

Jeffrey: You often talk about this. It’s not just like it’s you have the yes list and that maybe list, right? You, I think, go further and say we need to have this is the not doing list.

Squirrel: Oh, yes. That’s extremely important. So that’s the idea of negative space, which have the feeling we’ve talked about at least once. But I don’t think we’ve we’ve gone into it in much depth. It’s an idea I learned from my wife, who is the world’s only blind art historian. She’s just incredible. And when she describes art, she often talks about how there’s a vase of flowers or a street scene or something, and there’s bits that are not being painted. There are bits that are not being shown, and they’re typically black, or there’s a curtain behind the vase of flowers or something like that. And what’s there you think is not important. But actually if you if you were to cut out the main subject of the painting, if you were actually to take scissors and cut it out and take it away, you’d wind up with a painting of nothing. You’d wind up with a shape there, which is the reverse of whatever you’re drawing. And that’s called the negative space.

Squirrel: And turns out in art history, that has great importance. Now, please don’t ask me to explain that. But it has tremendous importance for product decisions and team goal setting. You need to expressly put things in your negative space. I make people do this when I have them write what I call a napkin strategy, have them describe what their company is trying to accomplish and what it’s expressly not going to do. So a common one that I pick up is, well, yeah, are you going into Africa or are you going into China? Are you moving into into those markets? Now, some people say, yes, that’s my focus.

Squirrel: I’m absolutely you know, sub-Saharan Africa is our next frontier. I say fantastic. Are you also trying to do China? Are you also trying to do Australia? And if people say yes to all of those things, I start to get worried that they haven’t defined their negative space. And I’m picking locations, but you can also pick market segments, technological innovations and other things. And what I’m looking for, if the organization is successful, is the ability to to be explicit about and communicate vigorously what that negative space is.

Squirrel: Now, that’s risky because you got somebody who says, “My God, we just have so many opportunities in China or the United States or wherever it is I’m moving into. And why aren’t we attacking that?” Just like you said, why don’t we try all 17 ideas? The mark of an effective technology team or technology organization or company or organization is that it’s able to make those negative space choices explicitly and clearly and to say we’re putting our bets in these areas because no organization can do everything. And it would be better if we failed at these and learned something from them than if we tried that safe option. If we did everything, if we just wrote a bunch of reports that made it sound good and we got our sprint goals done, but we didn’t make any progress on these important business goals.

Negative Space or Where’s Waldo/Wally

Listen to this section at 11:48

Jeffrey: You know, when you describe negative space, what came to mind for me was I was trying to imagine, well, what’s a picture I’ve seen that didn’t have negative space? And you know, what came to mind for me is, Where’s Waldo? Have you ever seen one of these?

Squirrel: Yeah, I have. Oh, that’s a great example!

Jeffrey: And for people who don’t know. So Where’s Waldo? Is this-

Squirrel: It’s actually called something else in Britain. I can’t remember… Where’s Wally? I think. But you go ahead.

Jeffrey: Okay. So you have this character. You have this character of this person wearing a distinctive shirt and hat and they’re in a picture and you need to find them somewhere in this picture. But the point is that this is difficult because the picture is chock a block with different things to look at. And I’ve seen other kind of puzzle pictures like this where you need to find objects hidden in it. And what makes it difficult is there is no negative space. Everything is jammed together and you have to look all over to find Waldo. And it’s a puzzle. And just suddenly, you know, your corporate strategy should not be a game of Where’s Waldo find the important element out of all these other things. Because I will say this. The thing that hurts me is when you’re describing people will often pay lip service to, you know, this is our priority, this is our strategy… And we have 17 other things we’re going to do.

Squirrel: They’re all priorities. Yeah. So we have a lot we’re doing a lot here. That’s why we’re busy. That’s why we can’t have any, any strategic time here because we’re too busy doing all these important things.

Jeffrey: That’s right.

Squirrel: That’s when you say, “hang on a second. You’re being safe by doing that. And you would do better to take more risks.”

Jeffrey: Right? So this this idea of negative space in your strategy and I now have this new image should not be it should not be a puzzle to figure out what your priorities are. And the the only way they can stand out is if you’ve defined those, you’ve given them space by moving other things away and defining those those things that you’re not doing, that not doing list is just as important as your as you’re doing list.

Squirrel: That’s what we’d advise listeners to do. So if you’re struggling with this, no matter where you are in the organization, you can actually do this even if you just joined it and you’re straight out of university, or it’s even easier, but more and more effective perhaps if you’re the executive. But you can do this at any level. Define for yourself what is the negative space of the organization and have conversations about that. And if you then refer back to that and say, “hang on a second, I think that is actually it may be something that marketing really wants, but it’s in our negative space, isn’t it?” That kind of language and that definition helps when setting the goals that, for example, you, Jeffrey, are just about to do this week?

Jeffrey: Yep. I have something new to try with people this week, in explaining the importance of what we’re doing.

Squirrel: Excellent. Thanks, Jeffrey.

Jeffrey: Thanks, Squirrel.