In my last blog, I talked about the work I was doing at Wikimedia, the Foundation that brings the world Wikipedia. I highlighted just a small number of the ways leadership there is more complex than at any of the other organisations I support (and leadership in most organisations is more complex than most of us can imagine). In these next blogs, I’d like to talk a little about leading through complexity.

One of the things that matters, of course, is your capacity to hold and understand complexity. I write about that idea a lot as I think about adult development (click here and read about it in my book Simple Habits for Complex Times.). Adult development describes, among other things, the ability for each of us to hold the shades of grey complexity brings with it. Leadership is filled with shades of grey, so it matters that we can see those different shades.

Adult development teaches you that the shape of the world transforms as we grow. It describes the forms of mind through which we see the world, and seeks to understand the ways we grow over time. Each developmental shift brings us the ability to see more grey. Over time we can move from the more socialised form of mind (in which we have a sense our choices as coming in to us from the outside world) to the more self-authored form of mind (where we pick up the pen and write our own story). Over time some people (not so many) grow to the self-transforming form of mind where the world is interconnected to such an extent that most of the black and whites connect in a field of grey.  Too abstract? Let me give you an example about why this matters for leaders, and especially why it matters for leaders in complex systems like Wikimedia.

Say you are a leader who is faced with a conflict between two people who report to you. Juan says Shawna undermines his decisions on projects they share; Shawna says Juan never makes decisions but just hedges all the time, leaving her to manage the difficult issues. In a simple world, you could either decide one of them was good and the other bad (and tell them so) or you could separate them so that they no longer shared work. Alas, in a complex world, even if you did believe that one was right and one was wrong, you probably be fooling yourself if you believed that simply telling Shawna to not undermine Juan’s decisions would fundamentally change her behaviour. And the more complex your work is, the more difficult it is to segment cleanly so that Shawna and Juan never need to work together.

If you had a socialised form of mind (and odds are you do have at least partially a socialised mind, because most studies show more than 50% of adults have at least one foot in this sensemaking system), this conflict may look like something with a Right answer and you might agonize over trying to find out what that Right answer might be. With this form of mind, your clues are likely to come from outside you, so you might check with experts or rely on key management theories. At this stage in your own sensemaking, it’s hard for you to transfer from one context to the next, so you might struggle to find exactly the right case study to give you guidance. Once you’ve decided what to do, you’ll probably expect that the Right answer will lead to the Right outcome and you might be surprised that the fairly simple sanction, reward or reorganization approach you’ve taken didn’t work well. You might even try the same approach again, harder, because 1) you don’t really understand why it went wrong and 2) you don’t really have a suite of additional choices anyway.

If you had a self-authored form of mind (and you might be on your way to this world though less than 30% of adults have fully arrived here), this conflict might be something you’d have to scan your own values and principles about. You’d be able to draw from a wide variety of internal resources about this, checking to see what other situations (either from your own experience or from anything you’ve heard or read about) had anything in common with this one. Instead of deploying a single solution and expecting it to work, your more nuanced understanding of the world would let you cobble together a series of solutions, all aligned with your own self-authored values and principles. If one approach doesn’t work, you can create another, and then another—all stemming from the same basic understanding of the situation. You might feel very stuck if your own principles compete on this issue.

If you had a self-transforming form of mind (which is pretty unlikely, as less than 5% of adults are even on their way towards this way of understanding the world), the whole situation would be filled with grey—and would be filled with opportunities for many different kinds of action. You’d look at the conflict between the two people, sure, and you’d wonder about what they were each protecting that made this conflict so severe. You’d also look to the system, though, at the larger drivers that made these sorts of behaviours crop up in these two people. You’d look at yourself and what you as a boss were doing that might encourage this. And from this whole web of interconnections, you’d have an enormous variety of choices for action. If one didn’t work, you’d learn from it—about yourself, about the conflict, about the system—and you’d be able to try a wholly different approach. Others watching your actions might not even understand the thread that held them together, but they would be able to see that you had more choices than most people, and might even refer to your “intuition” as kind of “magical.” What they wouldn’t understand is that it was just the way you understood the world and its connections that allowed these solutions to arise.

Why does this matter at Wikimedia? Or really why does it matter at any of the many different kinds of organisations I work with? Because even the most simple organisations I work with are no longer simple. The ones who develop and sell products have gotten so big, and their product lines so interconnected, that the organisation is really a global web rather than a neatly defined set of orderly silos. The service organisations are offering service in a much more complex world, and their clients are no longer interested in simple solutions—they have created apps or call-in centres in Dubai to handle those. And Wikimedia operates inside a community that is a community in a new way, networked in a new way, and more diverse than any other community I can think of. All this in an organisation of less than 150 people. See what I mean?

But you’ve seen the numbers above. If we need to grow to handle complexity, and if complexity is all around us, what do we do about that? Well, that’s what my book is about, it’s what my work with The Leadership Circle 360 is about, and it’s what my whole firm is about. We need ways of thinking about the world that help us grow, and we need ways of thinking about the world that helps us handle complexity before we grow. Watch this space for all of that…