A single champion can often inspire an organization to shift to the product operating model—especially if that champion is the CEO or CPO.
But that’s only the first step. Your transformation will get stuck without support from people throughout your company.
Over the past few months, I’ve been discussing this topic with Hope Gurion. We’re reflecting on what we’ve seen after years of coaching hundreds of teams and companies. When has transformation worked? What are some pitfalls and antipatterns to look out for?
If you haven’t seen the previous posts in this series, you might want to start here:
- First, we considered how to determine if your organization is ready for change.
- Next, we revealed the most common mistake we see companies making when they get started with their transformation.
- Then we shared advice on how to select your pilot team to trial the change.
- And in the most recent edition, we offered advice on building the skills pilot teams need to succeed.
Let’s do a quick recap of the last discussion in the series before we dive into today’s topic.
When the first phases of transformations work, it’s generally because the pilot teams themselves have the right skills and knowledge. This includes:
- A clear understanding of the business context—how does your company make money and how does their work contribute?
- Regular interactions with customers and the ability to synthesize what they learn via opportunity mapping.
- Quick ways to evaluate if their proposed solutions will work—typically via assumption testing.
- The ability to shift between discovery and delivery continuously.
But pilot teams don’t work in a vacuum. They need support from their own managers and other leaders throughout the company.
Today, we’re looking at what leaders and stakeholders need to do to best support pilot teams.
You can watch the video or read a lightly edited transcript below.
Full Transcript
Teresa Torres: Welcome, everybody. I’m Teresa Torres, and I’m back with Hope Gurion recording our next video in our org transformation series. Today, we are going to talk about the role of leaders and stakeholders in supporting our pilot teams to help our teams be successful.
Previously, we talked about how to choose pilot teams. Last time, we talked about how to upskill our pilot teams. This is really all about how we make sure our pilot teams become bright spots.
Hope, do you want to give the overview of what we’re going to cover today?
3 Ways Leaders and Stakeholders Can Support Pilot Teams
Hope Gurion: Yeah, there’s really a few things that we want to make sure our organization close to those pilot teams does:
- The first is we want to make sure we’re aligned on the outcomes the pilot teams are working toward.
- We want to help those direct managers or leaders over those pilot team members to know what’s different about working in an outcome-oriented environment, as well as the stakeholders that might be outside of the product/technology/design part of the org to know what they need to do differently.
- And we want to show how transparency and collaboration works differently with these pilot teams.
Teresa Torres: I love this topic because I think one thing we see a lot is org transformations get framed as: We just need to train our teams and everything will change. And we forget that actually the rest of the organization also has to change.
And so we’re starting to dig into that a little bit today.
Let’s talk about buy-in from leaders and stakeholders on these teams, our pilot teams being outcome-driven teams. What does that look like?
1. Getting stakeholder buy-in on pilot teams’ being outcome-focused
Hope Gurion: The first is making sure that we do want to move from just dictating features to build. So the first is, are we interested in any teams being outcome oriented? And are we willing to look at a couple of teams to try it and see how it works for our organization? So that sort of buy-in on doing any pilot teams.
But then the next is, what is the outcome that each of these teams is working towards? And so we want to make sure that whoever the people are, whether it’s the direct managers—the head of design or the head of engineering or the head of product or a group product manager, whatever the layers are—we want to make sure that the people directly managing the individuals on the pilot teams agree that the outcome that the team is working towards is a meaningful outcome.
But it’s not just their direct managers. If those pilot teams also have a key stakeholder that is going to have a point of view about what is a good outcome for the product team, then that stakeholder also needs to have a say in what that outcome is that the team is working towards.
So that’s sort of foundational. What is the outcome? Why is that the right measure of success for that team?
Teresa Torres: I love that you highlighted two parts to this. It’s not just alignment around the outcome. There also has to be this belief that this is the way we want to work. And this gets at the very first video we recorded about org readiness, where we talked about how the CEO has to feel pain and urgency around shifting to working this way.
We actually need that all the way down the layers to the product teams, that’s your pilot team.
And I think what people underestimate—I’ve seen this a million times, I’m sure you have, too—where you have an executive that’s driving the change. But all humans don’t change at the same pace, so maybe the middle manager, maybe your director of product is still working on their own change process, and they’re not fully bought in.
And so now your team is hearing one thing from their immediate director and a different thing from their senior executive, and it can be really disruptive and is not going to lead to a successful pilot team.
Hope Gurion: The last thing you want is your pilot team getting mixed messages from their leader, and then either their direct manager or their key stakeholder is completely contradicting everything they’re supposed to be working on in the pilot team.
Teresa Torres: We see this sometimes in our large company trainings where we hear somebody say, “Yeah, I get it, but my boss thinks it’s the flavor of the week.”
And we’ll get into that kind of topic in much more detail in a future video. So stay tuned on that.
2. Leaders need to commit to learning how to manage by outcomes
Teresa Torres: Okay, our second area to look for is just to be prepared that your leaders—again, the people in the hierarchy, the org chart above your pilot teams—and any stakeholders that are involved in deciding what to build, are going to need some support while these pilot teams go through this process. Do you want to talk more about that?
Hope Gurion: If we have alignment on the outcome that the team is working towards, there’s going to be new ways of working together. Because if what they know is: “I tell you what to build and you go do it and please do it yesterday,” what is the role of the stakeholders and managers?
Managing by outcomes is very different from managing by outputs. And we can’t assume that our leaders and stakeholders who’ve never worked this way will immediately know what to do. So we want to make sure that these pilot teams also create an opportunity for these direct managers and stakeholders to learn what it means to manage by outcomes.
They may need support in the form of coaching from either the head of whoever’s leading the transformation in the company or from outside people who can help them learn how to manage by outcomes, how to ask questions, how to get curious about the evidence that the team is using to make those decisions, as opposed to just being dictatorial.
Teresa Torres: What I love about this is it’s surfacing how complex this change can be. And this is exactly why we start with pilot teams.
You don’t want all your managers in your organization and all your stakeholders going through this messy change at the same time. It’s chaos.
A few years ago I gave a talk at Business of Software about what changes when we manage by outcomes. But it really just gets into exactly what you said about, how do we ask questions rather than dictating outputs?
I’ll also highlight the reason why coaching might be a good option here is that there’s often sort of that messy emotional response of like, “I’m giving up control. There’s a lot of uncertainty. What do I do if this pilot team isn’t successful? I’m still on the hook for their outcome.” So it’s that kind of stuff you’ve got to be prepared for.
3. Encourage pilot teams to be transparent and collaborative with their decision-making
Hope Gurion: It can be high stakes. And that’s why the next thing that we recommend is that these pilot teams really learn how to be very transparent and collaborative with what they’re learning and involve their direct managers and their key stakeholders in their decision-making process.
This is not about like the power center shifted. It’s about how we show our work in a way and show the evidence about why we think this is the next right thing to do that brings the necessary people along, because we all agree if we do this thing, it’s moving us closer to that measure of success that we described in our outcome.
Teresa Torres: Yeah, this showing your work part is so important. And I think it’s easy to frame it—people think, “Oh we’re a pilot team, and we’re piloting being empowered. And that means we get to make all the decisions.”
I don’t think I’ve ever seen a product team at any organization get to make all the decisions. Really what an empowered product team does is they go do the exploratory discovery work and they bring the trade-offs and what they’re learning back to their stakeholders and together they make decisions.
So it’s not about: “Leave me alone, I’m going to hit my outcome however I want.” It’s about: “I’m going to go do the legwork. I’m going to go learn what our options are. I’m going to bring them back to the table and we’re going to have a good conversation.”
And I think that’s the piece that’s really missing. And so our pilot teams need to learn how to do that. Our leaders and our stakeholders need to know they’re now getting new information from teams and they should trust that information. And then we’re jointly discussing decisions and deciding how to move forward.
Hope Gurion: One of the things that I often mention to pilot teams going through this who have skeptical stakeholders, which most of them do, is: Find out from your stakeholders what types of decisions they most want to be involved in. Because for a lot of them, it might be they’re worried about a team going too far down a road that is difficult to unwind.
And so it could be at the solution ideation stage where they want to be involved. They want to contribute solution ideas or they may want to be involved in the choosing of the opportunity to solve to make sure the team doesn’t inadvertently choose a low-impact opportunity.
Understanding and using these pilot teams to really explore when do stakeholders or leaders want to participate in the decision or at least have a chance to review the evidence that is driving that next decision helps create the future set of rituals and ways of engaging that aren’t going to fit for that organization before you scale.
Teresa Torres: Yeah, and that might even change from leader to stakeholder. And so one of the things our teams need to learn is how to have those conversations and set those rituals, even though you may not have a universal rule across your company of: We always check in at this point.
Because some leaders like the uncertainty and want to see all the cycles and want to go on the learning journey with you. And some want to just know what you’re going to build. And so we have to adapt how we share our work.
Stay Tuned for Future Sessions on Resistance and Challenges from Pilot Teams, Leaders, and Stakeholders
All right, this has been great. This video is almost a teaser for what’s going to come next, because next we’re going to record a couple videos about what type of resistance and challenges are going to come up from your pilot teams. And then we’re going to look at the same topic for your leaders and stakeholders.
We’ll dig in a little bit more into the complexity of what you can expect during pilot teams.
But don’t let this overwhelm you. Our goal with this series is to show this is a whole org transformation. It’s not just your product teams that are transforming, but there are ways to scaffold all this and to get support and to make it very doable. We just want people to go in with eyes wide open.
All right. Thanks, Hope.
Hope Gurion: Thank you.
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The post Preparing Leaders and Stakeholders to Support Product Operating Model Pilot Teams appeared first on Product Talk.
Preparing Leaders and Stakeholders to Support Product Operating Model Pilot Teams was first posted on June 18, 2025 at 6:00 am.
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