How Do You Solve a Problem That’s Never Been Solved Before?

MOLLY WOOD: The best leaders step confidently into the unknown and bring their teams with them. Today, I’m talking to Dr. Britt Aylor, Director of Leadership Development at Microsoft, all about a framework for tackling new challenges, like the transition to AI, that are changing the way we work. Dr. Aylor is an expert in something called adaptive leadership. She got her doctorate in education from Harvard University, where she worked closely with Professor Ronald Heifetz, who’s a founding father of the adaptive leadership framework. Dr. Aylor joined Microsoft from the Broad Institute of MIT and Harvard, specifically so she could lead the charge in scaling adaptive leadership across the organization.

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MOLLY WOOD: Dr. Aylor, thanks so much for joining me.

BRITT AYLOR: Yes, thank you so much for having me.

MOLLY WOOD: All right, let’s jump right into the framework, because it seems like adaptive leadership, for lack of a better way to put it, is kind of a thing right now. [Laughter] What is it, and why is it suddenly so relevant?

BRITT AYLOR: Adaptive leadership is about leading on complex challenges with no existing solutions that, therefore, require us to navigate high levels of ambiguity, problem solve in the unknown, and mobilize stakeholders across the system to collectively engage in creating a solution. I do think it is a thing right now, and I think a lot has to do with us advancing into the AI space at a very accelerated rate. That in and of itself is an adaptive challenge.

Everything is going to be different. Everything is already changing. So, therefore, how do we operate effectively in the unknown? And adaptive leadership is a framework that lends itself really well to build that adaptive capacity in people, to problem solve in the unknown, and to operate with each other in a new collective intelligence capacity. For me, what is central to this style is a certain mindset. Of course, there are skills and capacities to build, but it really starts with shifting your thinking.

MOLLY WOOD: In your research you’ve come across two distinctions within the adaptive leadership framework. Can you tell us what those are and how to think about them?

BRITT AYLOR: One is around the what. What challenge are we grappling with at the moment? Is it technical, or is it adaptive? And technical challenges, first of all, have nothing to do with technology. What we mean are challenges that can be very complex. However, they have existing solutions and there’s a pathway we can follow. So we have a clear right and wrong, and moreover, we have deep expertise that we can leverage. In contrast, adaptive challenges are a completely different universe in that they are very complex. And what makes them especially taxing is that we have to navigate these really, really high levels of ambiguity. So it’s not so much even the complexity of the challenge; it’s actually the really high levels of ambiguity, because where do we start? Oftentimes we don’t even know what the challenge is. Asking the right questions is much more important than thinking, what are the solutions? Because chances are, we probably don’t yet have the solution. And so we really have to leverage the questions. And again, those questions may not naturally come to us because we may be in an old paradigm around how to solve a challenge that may seem similar, right? But that is actually more in the technical territory. And we know that applying what works in the technical to adaptive doesn’t work, and it actually creates boomerang challenges. I like to talk about Groundhog Day, the movie where you wake up in the same day, day after day. And that’s how I picture people feeling when they’re grappling with the same challenge, which is an adaptive challenge, and they try one technical fix after another. The challenge may go temporarily away because the temperature is lower, the symptoms are addressed, but the root causes are actually not identified and treated. 

MOLLY WOOD: Can you give us some examples of technical challenges versus adaptive challenges? 

BRITT AYLOR: A technical challenge could, for example, be building a plane or a rocket ship. Hugely complex, takes deep, deep expertise to do that. And the fact is we know how to build planes that can fly in the air. When the first plane was constructed, that actually was an adaptive challenge because we did it for the first time. Our technical challenges, chances are at some point they were adaptive, especially if they’re complex. But then as we learn our way forward, they actually move into the technical territory. In contrast, an example of an adaptive challenge would be, how do we address global warming? There’s the scientific perspective, there’s the global governance perspective, and then the question of, how do we reverse the effects we’ve created from a scientific perspective?

And then, even if we have that, how do we then engage globally, right, to get the buy-in across the critical stakeholders, to engage in a process that probably will require some cost, making some tough decisions. So that is in the territory of an adaptive challenge. We like to often operate in what I call more of the comfort zone, which works actually really well with technical challenges, because with technical challenges, we have the expertise and the solution pathway, so it’s just about executing. So we don’t need in-depth brainstorming. We don’t need involved decision making. We can leverage the solutions we have. But in the adaptive space, it’s a deep investment. And also, what I like to amplify is it’s an investment, and honestly, trying to operate an adaptive territory with technical ways of operating is actually a sunk cost. We need to first invest in growing adaptive capacity in our people. 

MOLLY WOOD: It’s my understanding that you joined Microsoft, in part, specifically to scale adaptive leadership across the organization. And you didn’t just focus on executives, right? You may have started with Jared Spataro, who leads AI work at Microsoft, but then you worked with his whole team—managers and even individual contributors. Talk to us about that experience.

BRITT AYLOR: The most powerful way of actually having adaptive leadership come alive is when it can function as a closed circuit, when it’s not just the most senior leaders that understand adaptive leadership, but moreover, their direct reports and then the direct reports below that, so that the entire organization can have the same language and the same concepts, and therefore have the same decision-making framework of, how are we operating together? And what is needed in this situation? And so we started with the senior most leaders. And then we went to the other layers—we went to the management team, and then we did an event where all of Jared’s people were in the room, and moreover, they were in person in the room, which creates such a powerful learning environment. Adaptive really lends itself to in-person learning. A lot of this work is deeply emotional, because, again, change is difficult for people, in particular because it often leads to loss. It’s actually not change that people resist, it’s the loss element. And so that is one angle, for example, that we worked with Jared’s larger organization to really think collectively through, what does it mean to adapt? What does it mean to lead for change in this age of AI? And what will that take? And at the heart center of adaptive leadership, you know, the first level is understanding the language, understanding the concepts. And then the second level is really diagnosis. We need to diagnose. Are we in technical territory? Are we in adaptive territory? And that also leads us to the second distinction, which is authority versus leadership. Distinguishing between exercising authority that you have by virtue of the formal role you are in, versus leadership—and we actually define leadership as a verb. That activity can be executed from anywhere within the hierarchy. You do not need to be in a formal role that sanctions you with formal power.

Leadership is actually a self-chosen activity that can come from anywhere in the system. And the way that it maps to the context we’ve been talking about so far is that with technical problems in the world of the known, where we have existing solutions and deep expertise, authority is actually our go-to mechanism for leading. So there’s big, big value in authority, and organizations exist to a large extent to execute on the deep expertise on technical work that we do. Nine times out of 10 when I ask people, what does leadership mean to you? Even though there’s this excitement around leading for innovation, they actually give me the answer for authority, which is, I determine the situation and then I go to our expert solutions, and then I delegate and kind of deploy my team in the way that it makes sense. And I’m like, yes, that is an excellent way of operating in the world of technical and known. Leadership starts where authority ends. When we enter this world of the unknown, where we don’t know what the answers are, and that’s where it’s all about change and leadership and the adaptive framework. The primary activity of leading is navigating through this change territory, and doing that moreover with all of the stakeholders who are connected to the adaptive challenge. So adaptive leadership is never an activity of one. We always exercise leadership with other stakeholders who need to be part of the solution in order for it to stick.

MOLLY WOOD: And that feels like it goes to the heart of answering that question, too, about why it’s so important to do this training, to do this knowledge sharing at every level, because it sounds like what you’re saying is everyone can contribute to leadership. 

BRITT AYLOR: You know, in the day and age of complexity that we are living in, we need the collective intelligence of everybody to come together. We have no chances of solving the adaptive challenges we’re facing nowadays if we rely on even just the genius brain of one. That equation, maybe it worked in the past at times. In the future, I think it is all about plugging into each other’s collective intelligence and amplifying that. And there’s a whole skill set around that, right? Some people find adaptive leadership an emotionally challenging territory because it’s often engaging with people who have a very, let’s say, at times an opposite point of view to your own, right? And that’s where we need to channel growth mindset, because it’s actually being deeply curious about that other perspective rather than being threatened by it. So instead of going, like, right and wrong, being like, That’s so curious. Let me understand more where this stakeholder’s coming from, because they might actually see something I am not. So it’s being deeply curious and kind of taking our ego out of it too. 

MOLLY WOOD: You brought up this idea of change and the fear of loss, and that actually gets to a key component, I think, of adaptive leadership, this idea of psychological safety. I want to ask you about what that means in the context of the workplace, and how business leaders, especially as you’ve alluded to in a time of a lot of change, can ensure that they’ve built a culture that feels psychologically safe. 

BRITT AYLOR: Part of the process that makes innovation possible is smart experimentation. The understanding has to be failure in the service of learning will be part of actually delivering success. I think that is a really important element to focus on. When we talk about psychological safety, when we decide this adaptive challenge or this capability solution, whatever it is, we want to build that in the innovative space that we do not yet know how to do. We are okay with a certain amount of failure, assuming we design smart experiments, but then learning and recovering quickly from failure, I think, is the other capacity that we are going to have to build in ourselves. And then, moreover, the overlay of the leadership at the top saying, We have decided this is really important to get us to this innovation, and therefore, we are expecting and understanding that a certain amount of failure and learning along the way is an investment we need to make. If that is explicitly understood and agreed, it creates psychological safety. I think actually that is a big unlock for being able to lead adaptively. But what often holds people back, I have found, is this fear around, What does that mean if I start to lead in adaptive ways? Because one of the frontiers we have, which is actually an adaptive challenge, is what are the metrics for being successful in this adaptive space? How do you measure incremental advances towards your innovation? The horizon can be very long on adaptive challenges. Again, going back to thinking around the adaptive challenge of global warming, we are talking years here, right? We’re probably talking decades. And so how do you even start to then parse out what is the timeline, and what do we consider success? And having those be measurable milestones that are acknowledged. 

MOLLY WOOD: Well, so adaptive leadership is having a moment because of AI, but I wonder, can the unknown challenges that come with AI actually help us become better adaptive leaders? 

BRITT AYLOR: I do think that AI will help us to navigate both the world of the known and the technical problems we’re facing, as well as the world of the unknown and the adaptive challenges. First of all, probably in the nearer future, a lot of the things that are in the technical realm, AI will actually start to be driving. A lot of that work will probably be increasingly done by AI. And so, I find it exciting. By AI being able to step into, increasingly, that technical expertise known world, it really frees us up to do what is uniquely human, which, I think, is operating in that frontier of knowledge space. Using collective intelligence, I think, AI will be able to help us connect with each other and also manage the knowledge. 

MOLLY WOOD: If you had to give organizations some advice about how to proceed in times that are uncertain and how to take on this challenge of learning adaptive leadership, what would you say?

BRITT AYLOR: I think central to all of it is really starting to become very diagnostic, building that capacity, and then making a conscious choice and forming kind of a strategic picture around, what is the ratio of the work that falls into the world of the known versus the world of the unknown? I think top of mind of all our leaders should be thinking around, what is the ratio? And moreover, how am I going to shift gears between the two? And, building on that, how am I going to signal to my people that I’m shifting gears? If we uncouple what we talk about as leadership into the function of exercising authority versus leading for innovation, those are two fundamentally different ways of operating and showing up. And those expectations are very different. In order to—again, looping us back to psychological safety—in order to create psychological safety, we as leaders need to be very clear, as clear as we can be, of, are we operating in technical territory, and therefore, I’m going to show up in my authority role, because the solution path is clear and the game really is high efficiency and effectiveness. Let’s perform to the max versus signaling, Hey, I actually don’t know what the solution is in this innovative, adaptive space. And therefore I’m actually asking all of you to lean in. I’m asking for collective brainstorming. I am willing to make that investment of time and energy, because that’s the only way we’re going to navigate our way forward. And I think if leaders can provide that clarity—what is the territory I’m asking you to work in?—I think it will provide a fundamental psychological safety. But if there’s not clarity on, Hey, what territory am I working in, it can actually be very risky doing brainstorming and investing in innovation when, No, actually my leader above me wanted me to just execute on what we know how to do. So, being very clear on that distinction, I think, will go a really long way.

MOLLY WOOD: Dr. Britt Aylor, thank you again, Director of Leadership Development at Microsoft. We really appreciate the time. 

BRITT AYLOR: Yes, thank you so much.

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MOLLY WOOD: And that’s it for this episode of WorkLab, the podcast from Microsoft. Please subscribe and check back for the next episode, where I’ll be speaking with Bryan Hancock, who’s the global lead of the talent management practice at McKinsey. We’ll be talking about why managers hold the key to unlocking AI. If you’ve got a question or a comment, please drop us an email at WorkLab@microsoft.com, and check out Microsoft’s Work Trend Indexes and the WorkLab digital publication, where you’ll find all of our episodes, along with thoughtful stories that explore how business leaders are thriving in today’s new world of work. You can find all of it at microsoft.com/WorkLab. As for this podcast, please rate us, review us, and follow us wherever you listen. It helps us out a ton. The WorkLab podcast is a place for experts to share their insights and opinions. As students of the future of work, Microsoft values inputs from a diverse set of voices. That said, the opinions and findings of our guests are their own, and they may not necessarily reflect Microsoft’s own research or positions. WorkLab is produced by Microsoft with Godfrey Dadich Partners and Reasonable Volume. I’m your host, Molly Wood. Sharon Kallander and Matthew Duncan produced this podcast. Jessica Voelker is the WorkLab editor.