This is a transcript of episode 157 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

How giving work to your boss positions you as the driving force, not the bottleneck—and more methods and mindset shifts to change the perception “gee, that tech team sure is slow”.

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Listen to the episode on SoundCloud or Apple Podcasts.


Listen to this section at 00:14

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

Jeffrey: Hi Squirrel.

Squirrel: So we had a really interesting conversation earlier and I thought that maybe we could talk about that topic, which the topic of the conversation with the folks we were working with was how to drive. We don’t mean is driving a car, although I bet people are really excited about doing that since no one’s been allowed out of their houses for months. The issue of driving in your organisation, how to not be slow, not to be perceived as the bottleneck, the tech organisation always being slow to support the company’s goals, but instead be the driver, be the one pushing and making progress.

Jeffrey: Oh, that’s great. I’m really excited to talk about this because I feel like I’ve been talking about it a lot recently with various different people. And actually I’ve been in a position where at the moment I’m supposed to be driving a project, hopefully am driving a project and got advice from other people about, well, how do I do that? And I think it’s really important here, what we’ll talk about are things that are useful both for perception and for reality and I think that’s really important here. We’re going to be talking about ways to actually be more effective in getting things done. And as a nice side effect, it will also remove any complaints people might have about you or your department, your role as being a source of slowness, which is something that, as you said, is often things that people in our audience are probably used to, people in product management or technology, scrum masters are often told, “you’re getting in the way, your process gets in the way. You know what’s wrong with you? How come you can’t deliver what we need?” I’m sure you see these kinds of dynamics all the time in your consulting.

Squirrel: Absolutely! It’s one of the major reasons that people hire me is they say, “Squirrel, can you come and sort out our tech team? They’re too slow.” And I know immediately that I’ve got a relationship problem and a trust problem and all the things that we’re about to talk about are going to come up. And that’s great business for me. But it’d be wonderful if fewer people had this problem. So we can certainly talk about it. As a matter of fact, I’m going to say more about it at the end, that I’m teaching a workshop to non-technical people about how to deal with their tech folks in exactly this kind of situation. So that’s something very much on my mind as well. What should you do if you’re the bottleneck? People are telling you, “hey, the bozos over there in tech, why don’t you get moving, get out of first gear.”

Demand Support and Radiate Intent

Listen to this section at 02:47

Jeffrey: This is great. And I say the most important thing to do, if you want to go faster, you want everything going faster is counterintuitive and it was you need to be more demanding of support. And what I’m thinking of here is, something like in the book Art of Action, we talked before about briefing and back briefing. And very often what happens is people are waiting to be told, they’re waiting to be given a brief. “I just want them to explain what they want, you know, delegates stuff to me and I’m already I’m here waiting and ready to receive and go and do my thing. But I can’t move ahead until I’ve got my briefing from them where it lays out what’s the goal here and what are the constraints.”

Squirrel: And we heard that so clearly from the folks we were talking to in the conversation that inspired this, they were saying things like, “well, they haven’t signed it off yet. We haven’t got the green light. They have a process they want us to follow. We’re not sure what the next step is.” You want to do the opposite of all of those things and want to have the opposite of that thinking completely, which seems very counterintuitive. We’re going to talk more about what that looks like.

Jeffrey: Yeah. And the idea here is that rather than just waiting passively and this is where slow and delay comes from, instead we’re going to invert that and be proactive. And what that means is filling in the gaps as far as you know. And you can instead of waiting for the briefing, you give the briefing. And in a sense, you’re saying “here is my understanding of the briefing that has not actually been spelled out for me. But here’s my my perception of it. And based on my understanding that I’ve just explained, I’m intending to go do these things.” So you are in a position of giving both the briefing and the back briefing, you’re laying out your understanding of the mission and your plans of how are you going to do it. And we’re using here something that we’ve talked about before, the key principle here is radiating intent. And I want to be clear about that. This is not the same as what some people advocate, which is, “oh, just go do things.” they would say, “don’t wait around, go and do it.”

Squirrel: Ask for forgiveness and not permission. Yep. I’ve been guilty of saying that before.

Jeffrey: And that’s right. And the thing is that’s not terrible advice that very often that advice within it has a lot of the same lesson. What it says is that very often action is better than inaction, and that is actually what we’re saying as well. But what we’re doing is a step further and saying, “the action can be communicating what action you’re going to take. And that communication is hugely important because you are giving a chance for people to interject. You’re giving you’re giving a reason for them to interject now, because you are setting the agenda and saying, “look, this is what’s going to happen. And here’s the reasoning and if I’ve got anything wrong, now is your time to let me know.”

Squirrel: “Because I’m headed this way.” And a wonderful response you could get is, “oh, my God, don’t do that.” That’s a response that should fill you with joy.

Jeffrey: Yes.

Squirrel: It’s an opportunity to learn that you had the wrong direction. And wouldn’t it be great to know that now and not a week from now or a month from now or a year from now?

Managing Fear to Optimise for Learning

Listen to this section at 06:06

Jeffrey: Yeah, I think that’s one of things that makes this really hard. And there’s several things that makes this, what we’re advocating, hard. And I think this is the first one, which is we don’t really want that correction in a sense we’ve spent the time thinking about what would be the right thing to do and we’re attached to our plan, you know, we’re attached to it. We want to do and it feels bad to be told, “no, you’re wrong that’s not the right thing to do”. It feels like, “oh, my gosh, that’s a judgement on me. I’ve just wasted time. I’ve wasted energy.”

Squirrel: I’ll look bad in front of my boss.

Jeffrey: I’ll look bad, exactly. They’re going to wonder what’s wrong with me. And my experience, though, is that that’s not actually a fatal problem. It’s not that’s not going to- be even if people perceive that of like, “oh, you made a mistake”, that actually my experience is that’s not a problem in practise because people are happy to just correct you and they’re not thinking as much about you. In fact, I could say if you follow our advice, you might be someone who they say like, “you know, if I want something done, I’ll give it to Jeff because he’s going to get it done. He’ll have to check in. I need to give some oversight. I need to make sure to keep on the right path. But man, stuff’s going to get done.”

Squirrel: And that’s the perception you’d like to have to that you’re not the bottleneck. But what we worked on with the folks that we were having this very informative chat with is imagining what kind of response you might get, because I bet a lot of our listeners are right now thinking, ‘oh, my God, what I might do is go to my boss and say, I’ve been waiting for your sign off, but I’m not going to wait anymore. I’m going to do this thing. Here’s where I’m going. Now’s your chance to stop me and oh, my God, what will happen?’ And so the little psychological exercise we did was to imagine what is actually the worst possible thing that could happen. And if your boss is really the kind of person who would not only insult you and scream at you, but also fire you, then then maybe that’s not the right step to take. Maybe you need a new boss. Yeah, but most of us don’t work in those situations. And in fact, the people we were chatting with definitely do not. And so when we asked them this, they said, “well, you know, I guess he could fire us, but he wouldn’t do that. No, no, that’s really a joke. That wouldn’t happen.” So we said what would actually be the worst possible thing? And it was answers like the ones that we were just describing that are actually super informative and helpful.

Squirrel: It was it was hard for them to at first see how valuable those answers were. But they were things like, “you’re really heading down the wrong path. You can’t do it that way. You need to do it this way or these are my expectations. You must meet them. You were going to not meet all of my expectations. You must do it this way. I’m telling you how to do it.” And the trick is not that those are necessarily wonderful answers or the answers you want to hear, or that they are the ones that will obtain in the future that you will have to agree to them. None of those things are true. But what’s wonderful is if somebody comes back to you and says “that’s the dumbest idea ever”, even if they express it that strongly, they already thought that, that was already true. You just didn’t happen to know it yet. And you have a choice of finding it out now or later. And now is a thousand percent better because you can do something about it. Whereas later, unless you’ve invented a time machine, you’re not going to be able to.

Jeffrey: That’s right, and that idea of inviting the bad news early is I think part of what makes this difficult is because people are acting as though the choice is between, having the bad news be true or the bad news not be true. But in our experience, my belief is that that’s not the choice you’re making. It’s whether you find out the news now or later. That’s the choice. And if you frame the choice that way, then suddenly becomes a lot easier to say. You know what? Let’s bring that forward. Better to find out sooner rather than later.

Squirrel: There are people out there who are not testing there are countries that are not testing for coronavirus, and they’re imagining that somehow that means that there are people have less coronavirus. That’s not the case at all, that the fact is, people are going to be dying in your hospitals as a result of having this disease. And you can find out about it now and build more hospitals and do things about it. Or you can hide your head in the sand. That’s the kind of harsh way to put it. And it is just such a natural human action that even when threatened with death, people are still much more likely. They have a tendency to to avoid the conversation, avoid learning the information.

Jeffrey: That’s right. And that’s the key word here, because what we’re saying is we’re optimising for learning and what we’re not doing is optimising for comfort. Like this is not a comfortable conversation that were describing, but it is a really effective one in that you’re generating a lot of information in a short period of time.

Making the Default be Action

Listen to this section at 10:56

Jeffrey: One thing so far, we’ve just kind of focussed on that, the things that might go wrong. But I think there’s something else that we should add, which is a really positive thing. We said it might go wrong, we actually, look at this as a game like it’s good to learn this information. But there’s another valuable thing. It’s not just about learning, but it’s also that the decision gets made sooner, that you get action sooner. What I’m thinking of here is that when you or when I go and do this, I do try to live this, when I put out a plan like this and say this is what I’m intending to do, what I’ve done is I’ve used a principle that you hear described in the book Nudge, which is I’ve made the default action to be a good choice.

Jeffrey: And what I mean here is that now, by default, if people don’t engage, if they don’t answer, if they don’t care, then you know what’s going to happen? We’re going to get this action that I planned that I think is good and I think is going to advance our mission. And that’s so different than very often when people aren’t following these principles. The normal action is nothing. The normal default action. We have a meeting, we discuss something, people talk about things that might happen, things that might be good in the future, the things are said but there’s no real commitment. There’s no clear next steps. There’s this real lack of clarity of what exactly might happen and when. And so the default actions end up being nothing. There’s there’s delay, there’s uncertainty. And often there’s fear. There’s fear of like ‘this doesn’t seem to be going anywhere’. You may not feel that fear, but odds are that someone else and probably the people in charge of the company, the people higher up, they almost certainly have that fear. And that fear is not a good thing to be out there.

Squirrel: And it often comes back to you. As that second order effect.

Jeffrey: Yes.

Squirrel: Where you hear later not “I was afraid” or I lacked trust that you would be getting this done” or something like that. What you hear is, “gee, those tech people, they’re really slow. They never get anything done. They’re always the bottleneck.”

Jeffrey: That’s right.

Squirrel: And that’s the perception that someone gets when they observe that there’s this delay and lack of commitment and lack of drive.

Jeffrey: Yeah. Now, if we if we invert this, and instead you’re coming in and you are coming with your plan, what your actions are. And let’s say one more thing here, part of this demanding support has been demanding of other people and the role they have to play in you succeeding in what you want to do. And we had a great experience of this at TIM. One of the product managers got this kind of briefing about how he might work, not from me, but from his manager, who’s the head of product, and was being told very clearly said, “look, you need to be driving this. That means you need to be giving work out to other people. If you’re waiting on a contract that’s the bottleneck in this process, you need to be talking to the CEO every day. Where’s my contract? So if you’re waiting for the other founder, if you’re sitting at meetings, you need him to be there, make him know that. And it turns out he was in this experience where he was he was he was driving the founders to go in and get meetings set up, get these conversations happening, get this done.” And their perception of him was like, ‘wow, this is amazing. He’s really driving the project because when people know that you’re waiting on them, they’re not going to see you as slow they’re not going to see you as indecisive. It’s very clear you’re driving. And this is not a bad thing.

Jeffrey: This is just you’ve been very clear on what other people can do to support you in achieving your mission. And that’s the goal. You will achieve your mission faster if you can find more people to take some of the work. And that often means going to these other people and other functions, leaders in other areas and saying, “look, to get this done this is what I need from you.” And having that kind of clarity and this is a great example where the second best answer is no. Again, you can say “I need to get these people on the sales team. They need to set up meetings with me. I’m going to need five meetings from different clients. Can you talk to them about that in the sales meeting this week and have them commit to that?” If the sales manager says, “no, I can’t because, whatever reason. We are end of quarter. We’re getting stuff done. We can’t do this week.” You’re like, “fine, well, when can we get it?” Getting that “no” is, again, super valuable. It’s not the answer we maybe wanted, but it’s the second best one, which is it’s generating more information that we can bring into our plan. And that kind of pushing the pace is something I think that people can do much more often than they do. And they don’t because maybe they have never thought of it as a possibility or it’s that sort of fear of not liking the answers that come up. And we’re saying, go embrace those fears.

Radiate Intent then Take Action

Listen to this section at 15:58

Squirrel: So if we summarise then what we’re telling people to do, if they’re hearing, “you’re a bottleneck. Tech’s in the way, you don’t get enough done.” Share what you’re intending to do and then go do it without waiting for other people. Intent, share, radiate your intent so that it’s clear what you’re going to be doing so you can get feedback that may lead to painful learning, but then take action and go and begin delivering. Change your sprint, adjust your delivery time, start releasing software every day, whatever it is that you’re going to shift, do that, having radiated your intent and see what the fallout is, see what the result is. Part of doing that is likely going to be also giving direction to other people who are elsewhere in the organisation, maybe above you, which will feel very strange and uncomfortable, but will definitely lead to no one perceiving you as a bottleneck anymore, they may perceive lots of things about you. They perceive that you’re headed the wrong way, that you’re a loose cannon. There may be lots of things, all of which are likely to lead to even more learning as you discuss those topics. But you won’t be perceived as a bottleneck anymore because you will be taking that action and most importantly, others will be helping you. You’ll be going to other people probably outside the tech organisation, non-technical people who can help unblock you. And if they’re able to do that, they certainly won’t have the opinion that you’re standing in their way. They may think that they’re standing in their own way.

Jeffrey: It’s right. Which they would be.

Squirrel’s Upcoming Workshop

Listen to this section at 17:22

Squirrel: Indeed. All right. Well, if those ideas are helpful and useful to you, dear listener, please get in touch with us. One thing you could do, by the way, is you can come to this workshop that I mentioned earlier. I’ll give you just a little bit more about that. That’s a workshop I’m leading on the 25th of March. It’s called Decoding Tech Speak, Profiting from Technology Through Confident Conversations. It’s aimed at non-technical people who have to deal with us techies and helping them to understand what they could be doing, in fact, to help us, just as we were talking about. What sorts of things could you work on to define your commitments with your tech team? How can you give greater clarity to your discussions with your tech team? How can you not be afraid of tech speak? And so if you’re interested in those topics, you want to spend a half a day with me. That’s something you can sign up for links in the show notes. You can just go to and you’ll find it there. In addition to that, Jeffrey and I are starting to line up some workshops for the summer. Might even be in person, who knows? But right now they’re online. So watch out for announcements about those.

Squirrel: You can get in touch with us at where you can find our Twitter and email and all those kinds of wonderful things and argue with us if you think that we’re wrong, tell us what you’d like us to talk about in a future podcast. And of course, we love it when you hit the subscribe button, because then we’ll be back next week with lots more exciting ideas and we’d like to hear from you. So please come back next week. Hit the subscribe button and we’ll see you then.

Squirrel: Thanks, Jeffrey.

Jeffrey: Thanks Squirrel.