This is a transcript of episode 277 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

Are you pushing alone or pushing together? On this week’s episode, we take a closer look at how to be helpfully demanding and how to identify removable discomfort, with a story about helping a product manager who’s “pushing” for progress toward a quarterly goal.

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Listen to this section at 00:11

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

Jeffrey: Hi, Squirrel. So I had an interesting conversation today that I thought would be worth discussing on the podcast: someone who was following our advice found a situation that had them a bit concerned. Would you like to hear about that?

Squirrel: I sure would, tell us.

Jeffrey: So the episode of advice he was following was about how to be helpfully demanding, and I felt in our conversation he was being helpfully demanding in asking about a certain feature, that in the OKRs, they’re being worked on, for delivering this quarter, and he felt engineering-

Squirrel: Hang on a second, we should probably remind listeners what helpfully demanding means. Jeffrey, can you just remind us?

Productive Insistence

Listen to this section at 01:02

Jeffrey: Yeah, we talked about different ways to have conversations that were shorter, and part of it was about how you could be helpfully demanding about getting things done sooner with less waiting and therefore less waste. The correlation here was about disappointing people helpfully-

Squirrel: Oh yes, one of my favorite phrases! Demanding helpfully meant that you were explaining why the demand was there and what sort of external reality was driving your demand.

Jeffrey: That’s right. Exactly.

Squirrel: So you don’t just say “I need it Thursday just because I feel like it.” You say “I need it Thursday because we have a demo to the client on Friday.”

Jeffrey: Exactly. The canonical example that we cite and I love as inspiration is Toyota Kata, where one of the steps there they go through is to say “When can we see the results? Today is not too soon.” It sort of reminds people that we can move quickly on things, not everything needs to be scheduled out weeks in advance. This is the kind of conversation this person was having. Engineering was saying, “Well, we need to have this architecture discussion.” And he said, “When can we have it? We want to make sure that we’re able to get this done in this quarter, and so I’d like us to get started.” They said, “Well, we can’t have it before by before Wednesday because Wednesday we have this other thing we need to do.” He’s like, “Great. Does that mean we can have it Thursday?” When he described this conversation to me, he used language that I thought was very worthy of discussion. One thing he said is “I was pushing really hard.” Second, he said, “I had the feeling that people were uncomfortable.” I thought both of those were interesting, because the pushing he was describing was that helpful demanding part. He was pushing for clarity as opposed to being arbitrary and pounding the table or anything like that. He was just saying, “What’s the soonest reasonable date we can do it?” And the second thing was the discomfort. When I heard that I thought, “Yeah, maybe they should be uncomfortable because here we are at the end of April, you’re a third of the way through the quarter already. That might be an uncomfortable situation.” So that’s what I was thinking about. It reminded me a little bit about the phrase accidental complexity versus essential complexity.

Squirrel: Oh, from Brooks’s No Silver Bullet where he talks about how some software projects are just hard, and you’re not going to be able to speed them up by adding more people, for example, which was his famous dictum from Mythical Man-Month.

Jeffrey: Yes, exactly. And it occurred to me that when you’re looking for clarity and you’re being helpfully demanding, you’re clarifying the importance of something that can have people feel uncomfortable. But there’s a certain amount of that discomfort that’s essential. “This bad thing will happen if we don’t have this done and time is passing and we are getting closer to that deadline.” What do you think?

Together in Discomfort

Listen to this section at 04:24

Squirrel: Reminds me of someone I’m coaching who has a very standard norm in his team, it’s an engineering practice probably all of our listeners use. I don’t want to give too much away, so I won’t go into what it is. But he has something that he asks his team to do and everybody except one guy does this practice and it’s been known for a long time that this practice supports good engineering and efficiency and all kinds of things. So he said to me, “Squirrel, how do I fix this guy?” And I said, “Well, you don’t fix him. The first thing you do is go find out what what’s driving him, what’s his emotion about this practice?” And it turned out that this person has experienced this practice badly and it has slowed him down and he feels frustrated by it. Therefore, the main emotion that he has is frustration. I’m of course helping my client to introduce the idea that maybe this person should fall in line, which may or may not be comfortable. That’s not going to be a fun conversation. That’s what we would call, I think, the classic definition of a difficult conversation. It’s going to create some discomfort for both parties, and that is healthy. That’s why I said “good” when you said there might be some discomfort in this conversation. That’s what I would expect. However, the homework that I had my client do is going to help him remove what’s removable of the discomfort. I think that’s important. So in my my client’s case, he’s going to be able to talk about the frustration, jointly design some solutions that might work, might mean this person does the practice in a different way. It might be that the person leaves the company. There could be lots of different outcomes, but they can work on it together and my client can empathize and use the language that this person uses to acknowledge their different views because they’re unlikely to agree, but at least they can speak the same language. At least they can come up with solutions that work for both of them rather than just pounding the table. And it seems to me that in your story, there’s removable discomfort. There are things that your product manager there could be doing that would increase curiosity and transparency. I wonder what you think about that?

Jeffrey: I think that’s exactly right. I really like that because that was actually part of my advice back to him: “If you sensed they were uncomfortable, that sounds discussable. That sounds like you should say, ‘Hey, I get the sense you’re uncomfortable. Is that right?’” You know, test that. I think you’re exactly right to ask “What could we do to remove it?” There’s a central discomfort and there’s removable discomfort and you want to know the difference between the two, because if it’s something like the person says, “Well, we could do Thursday, but I’m going to be getting my teeth filled in the morning and I’m worried I’m going to be very out of it in the afternoon. Could we put it off till Monday?” Like that might be fine.

Squirrel: Or we could cancel whatever’s happening on Wednesday and do it sooner, you can jointly design solutions even better. But the key thing that happens when you’re not being curious—and curiosity is what I didn’t pick up there—is just as I heard the person saying, “Wednesday? No? Okay, Thursday?” I could imagine him just continuing on with “No? How about Friday? No? What about Saturday?” He’d keep going.

Jeffrey: That’s right.

Drive on the Road, Not the Map

Listen to this section at 07:43

Squirrel: And I never heard any curiosity. Whereas what I’d like to hear is “Tell me more about why we haven’t got to it today.” “What’s wrong with Wednesday?” “How do you think about the quarterly deadline?” “Do you do you know the quarterly deadline exists?” Doing some coherence busting, the person might not be aware that there’s a quarterly deadline or might have forgotten! That wouldn’t be good, but we’d sure like to know that so we can fix that, right? Suddenly, whatever’s on Wednesday might seem less important. So there are lots of things that your product manager could be doing here to respond to the discomfort. All of us are going to have that, we’re all poor at having these conversations, including very much you and me, Jeffrey. What is very valuable to do is to listen for that discomfort, observe that discomfort, make it discussable, and then look for ways to remove what you can. But if the person just says, “Oh, I wish we could get rid of this deadline,” that’s a discomfort we’re not going to be able to remove, as I assume that in your company, these deadlines are set somewhere else. Maybe it’s your deadline, Jeffrey, and these these two can’t really affect it. So if that’s the case, then empathy would be more useful. “Yeah, that would be interesting, but I don’t think that’s an option. What can we do that is actually feasible?” And having that discussion and the empathy for the essential discomfort would allow you to remove the removable discomfort.

Jeffrey: I love that as a pre-planned action. I got to say, I think the penny dropped while you were talking, in regards to the tell here. “How would I know that I should bring in that curiosity?” If you feel like you’re pushing. So if I think back when he said “I was pushing hard.” Maybe it sounds like you’re not curious. That’s part of what it “I’m pushing” means.

Squirrel: It should feel more like we’re pushing.

Jeffrey: Yeah! Or “I’m clarifying.”

Squirrel: I’m clarifying so I understand better. And then the two of us are pushing. We’re saying, “Gosh, maybe could we could we do early on Wednesday before the other meeting starts. Could we bring somebody else in who’s not going away on Wednesday? Could we delay your tooth filling? What could we do?” It should feel like you’re both doing it together.

Jeffrey: “Push together.”

Squirrel: If it feels like you’re butting heads and pushing against each other, there’s probably some removable discomfort.

Jeffrey: Fantastic. I really hope our listeners hear this. I thought this would be valuable because it’s one of those things that might happen to you if you’re following our adivce.

Squirrel: It should. If it doesn’t happen to you, you’re not following our advice correctly. So if you’re not experiencing discomfort in your conversations, you’re not having difficult ones. So go try to have some discomfort. Thanks, Jeffrey.

Jeffrey: Thanks, Squirrel.