If you do all three of those things—the culture, the skills, reframing experience—complexity-first stops being scary and becomes the obvious, attractive way to work for everybody.
Working complexity first is at the heart of our CAPED framework, but many leaders struggle when their teams resist tackling the hardest, most uncertain work upfront. Instead, teams gravitate toward quick wins that feel safe but create nasty surprises later. In this episode of the Humanizing Work Show, Richard and Peter explore why quick wins are such an alluring trap, why teams hesitate to go after core complexity, and how leaders can make it safe to work complexity first. You’ll hear stories, practical tools, and a surprising example from Microsoft’s AI history that shows the power of culture signals in enabling bold, early learning.
Show Notes
- CAPED: Complexity Aware Planning, Estimation, and Delivery
- Theresa Amabile, The Progress Principle
- Satya Nadella’s Email on Tay (coverage)
- William McGonagall’s “Tay Bridge Disaster” Poem
Learn More
- CAPED Certification. Interested in learning more about working complexity first to get early value, learning, and risk-mitigation for your high-stakes initiatives? Join us for our upcoming CAPED Consultant Certification workshop where we dive deep into how to make this way of working stick in an organization.
- Schedule a time to meet with us. If you’re a leader who resonates with this, we’d love to have a conversation with you about how it applies in your unique context.
Episode Transcript
Richard Lawrence: Welcome to the Humanizing Work Show. I’m Richard Lawrence, here as usual with Peter Green. We’ve been noticing something interesting as we’ve been explaining CAPED. Over the past year. We frequently heard from technology leaders like directors and VPs of IT or software engineering who get the value of working complexity first, but who say things like, “you know, I’d love for us to work that way, but my teams or my vendors don’t want to. They gravitate towards the work that they understand most and they put the complex work off for later. So how can I get them to want to work complex first?”
In this episode, we’re going to look at why people who are reluctant to work complex first often have good reasons for that, and then we’ll look at how do you create the conditions where that can change.
Peter Green: Now, this is a tricky problem, Richard, because we’ve been trained over the years to do things that are small and safe and likely to succeed. And so when we think of a big project, there’s gonna be some things that are complex and tricky, and there are gonna be a few people that gravitate towards that just because it’s interesting problem solving.
But by and large, if you think of how we’re going to prioritize the work, we often tend to grab what’s the easiest stuff first, what’s the quick win? And those can feel small, safe, sort of satisfying to make early progress. They give us a dopamine hit, right? You make a little bit of progress. Theresa Amabile studied this and wrote about it in, in her book The Progress Principle.
So those things are tricky and very alluring to go, “let’s go to this small, safe thing first. And so shifting to something like CAPED where we say, no, grab that hairy complex, difficult problem. That’s tricky to do well.
Richard: Right. But if you go with the quick, easy wins, kind of first, as, you know we talk about a lot, if you’ve listened to our episodes on CAPED and other related things, the easy first approach is a trap, because the complex things don’t go away. They don’t suddenly become less complex because you’ve done other things first. It just pushes that discovery and surprise, and a lot of times value, because value and complexity correlate, it pushes us out to the end. Which makes your delivery less predictable, not more.
That’s why it’s really common for things to look green up until about 90%, and then to go bad because we’ve put off the part that is least predictable until later.
Peter: Right. And in the old days, we used to just put big buffers in place to try and accommodate that. But what we’ve learned over the years, and what other researchers have learned, is that the only way really to avoid those nasty surprises at the end of a project is to go after the complexity early. Early complexity equals early learning and fewer late stage disasters.
Richard: I think this is why so many of the leaders we talk to who’ve been around a long time, who are seasoned with lots of projects, they’re resonating with the ideas in CAPED because they can see, oh yeah, I’ve been on the wrong side of that so many times, and it would be different if we went after the new complex, valuable stuff first.
Peter: And it’s easy to think about, well, this other department won’t allow us to do CAPED, or the business won’t allow us to do it. But it is interesting to shift the focus and say, what if the teams are hesitant to do it? What might cause that?
And I’ve seen this a lot of times with any kind of change, is that the leaders get pumped up about it, but then those teams are hesitant because in the past they’ve accumulated scar tissue around being punished for things like trying to estimate differently or trying to make a change.
And then they’re the ones that get the brunt of the punishment when things go wrong.
Richard: Right. And it can also feel like. If we go complex first, we’re taking on big things. Like, complexity and bigness feel like they’re inherently tied up. And then you don’t get that sense of quick wins and early progress, and you can anticipate that’s gonna be demotivating. We’re gonna be like jumping right into the end of the project death march at the very beginning. And who wants to do that?
So if you’ve had bad experiences in the past with taking on hard problems and getting in trouble for being wrong about it, if it feels like you have to take on too much at once and you give up the ability for quick wins, complexity first feels mostly like downside.
Peter: Yeah. So if you’re a leader in this situation, you can’t just say, “Hey everybody, let’s go complex first!” You have to prove that it’s safe somehow. And our favorite way to signal any kind of change like that is with something we call a culture signal.
What’s a culture signal? Well, we’ve talked a lot about this. You can check out past episodes, we’ll link to ’em in the show notes. But culture signals are leadership behavior that signal the downside I’m willing to take as a leader in order to get the potential upside of this new approach. So we call that a culture signal, and what they do is they create an opening for people to try things.
One of my favorite examples of this, sort of this related to this topic today is back in 2016, Microsoft was already experimenting with AI chatbots and they had one called Tay, T-A-Y, on Twitter. They had tested it out and Tay was supposed to sort of inherit the characteristics of people that were interacting with it so that it appeared to be a real person.
That was the goal of Tay. Within about 24 hours, Twitter users had discovered that this was a chat bot and that it would sort of mimic their language. And malicious users started manipulating it to make offensive comments and racist statements, and Microsoft was forced to take the bot offline, amid a huge public backlash.
So when this went off the rails, you can imagine Satya Nadella, who was the CEO at the time, could have managed the PR disaster there by saying, listen, we found the team that was responsible for this. We’ve removed the leader of that team. That would’ve been a logical, and probably comfortable, stance to take for Satya.
But instead, he very clearly sent a culture signal to that team. He wrote an email that was then shared, with the press a couple years after that to talk about Satya’s style, where he basically said, we’re willing to take the PR hit in order to get that early learning. He said to the team, be bold, take risks. This is the downside of that. We’re willing to do that in order to learn.
Nine years ago, and we’re sort of starting to see the fruits of that with AI really starting to work well for many of us, right? So you probably don’t need a huge PR disaster to send a culture signal. We hope you don’t need it.
In fact, you can be much more proactive about that by thinking about what are the downsides you’re willing to emphasize. This is the key of a culture signal. You have to be willing to emphasize the downside in order to get the upside of going complexity first.
Richard: What are some downsides that people might need to accept Peter in order to work complexity?
Peter: First, if you’re gonna go complexity first, that means you have less illusion of precision and certainty at the beginning, where you’ve mapped everything out, you’ve done inside view estimation and breakdown, and it looks like everything is gonna work the way you expect it to, which as we all know, is an illusion.
Psychologists call this the illusion of precision, right? So that’s one thing is that you, you’re not gonna be able to do that if you’re taking on a complex problem because you can’t map out all the steps. That’s the nature of complexity.
The other thing that’s inherent to the nature of complexity is that we can’t predict what the outcome will be. It’s why we’re testing things early. And so you have to be able to take a stand and say, “here’s what we’re trying and here’s what we think is gonna happen,” learn that you’re wrong, and then go back to those same stakeholders and communicate, “here’s what we learned, here’s how we’re pivoting,” and there’s always gonna be some downside communication that happens to that.
You have to be willing to create a container where you’re willing to do that, and you have to own it in the same way that Nadella owned the communication around the Tay disaster,
Richard: There’s a, a famous bridge collapse that, William McGonagall, widely considered the worst poet ever, wrote a poem about the disaster on the bridge over the river Tay and when you said, the Tay disaster, I immediately thought of the terrible William McGonagall poem about the bridge over the river Tay. Alright, totally an aside.
So we were talking about culture signals and how leaders need to send clear culture signals, but it’s important to be aware that culture signals are not enough. If you send a signal that you want people to do a thing, but they don’t feel like they actually can do the thing, well, they’re not gonna be motivated to do it.
Signals without skills fall flat because our brains tangle up ability and motivation. If we don’t feel like we can do a thing, we’ll convince ourselves the thing is not worth doing. And I think there are three practical tools or skill sets that teams need in order to actually work complex.
First one, how to find the core complexity. What even should we focus on? Two, how do we slice that into small testable chunks so we’re not taking on everything at once? And then to help mitigate some of the downside you mentioned on predictability, I think there’s a third skill about how do you forecast when things are still foggy, and that’s that reference class forecasting we’ve talked about in recent episodes.
All three of these are built into CAPED. We build in step-by-step tools like assumption and complexity mapping, feature mining, reference class forecasting. If you wanna send a culture signal about this, you need to pair that with some skill development that will allow people to actually respond positively to that culture signal.
Peter: Both of those are gonna be really important. I think both the, sending the culture signal and the skill building because those tap into what is motivating and what is demotivating intrinsically for people. So you’re gonna have to double down on both of those. Make it safe to try things, make it clear that you’re gonna take the heat for the downside. They’re not gonna have to. And then help people feel competent and like they can master these skills and actually get better at those skills over time.
And then you may have to surface some of those old wounds. If, if the team has scar tissue, you, you may need to go back. I’ve seen leaders apologize in person to teams to say, I know that you took the heat for that and you shouldn’t have. I’m sorry, we’re trying to change things now. You need to make it clear that this time is gonna be different.
Richard: Right. If you do all three of those things, the culture, the skills, reframing experience, complexity first stops being scary, and it becomes the obvious, attractive way to work for everybody. And that makes sense because it allows teams to go after the new and interesting things and to see early value.
And circling back to Theresa Amabile’s, work in The Progress Principle, it wasn’t just about getting things done, it was about getting meaningful things done. And Complex First does that.
Peter: If you’re listening and this idea is resonating with you and you wanna go complexity first and try to figure out how to make that work for your team and for other stakeholders, we’d love to have a conversation with you about it. Schedule a free consultation with us on our website, humanizingwork.com, and hit the contact us page.
Richard: Or join us for our upcoming certified CAPED Consultant Workshop where we dive deep into how to make this way of working stick in an organization. It really is possible to get early value learning and risk mitigation on your high stakes initiatives by working complexity first, and we’d love to help you do it.
Peter: And thanks for tuning into this week’s Humanizing Work show and we’ll see you next time.
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