I’ve had reason to think again about the oft provided career guidance about “being comfortable with ambiguity”. It first showed up for me when I began working as a manager. This was right after the dotcom boom so automation and the widespread use of software was still a newish thing so to speak. This led me to think, young and naive as I was in my career, that as long as leadership could just clearly communicate their really clear goals, life is easy for everyone and we can make huge jumps in progress.

After becoming a manager for a while I learned a lot in a very short time. One of those lessons was that leadership wasn’t avoiding communicating the goals clearly as much as they were wrestling with what they should be. That didn’t mean they were ineffective, but rather that the problem being solved had to be framed very very carefully and thoughtfully.

I also witnessed how the environment’s rapid pace of change impacted this. Large upcoming changes, like the Affordable Care Act caused organizations to speculate heavily on what it would mean for the business but they were often wrong. Not because the leaders or people trying to predict these things weren’t smart but because it hadn’t ever happened before. Our organization, wisely at the time, focused on helping managers with navigating change with their teams using William Bridge’s and other frameworks. There was also a lot of openness and grappling with the fact that there are unknowns and embracing that was hugely beneficial. Compared to when I started, where it was basically implied and expected that leaders would have the answers, this was a breath of fresh air and often empowered teams to find the right way to evolve with the times.

Now the business and even entire industries can evolve almost overnight. The most challenging form of ambiguity that I experience these days seems to take the form of questions around identity and principles. What are the meaning of our core values in times like these? How do missions of different business units that are in flux kept whole, or do they stay whole? What would it mean to lose a large book of business in support of a totally new business strategy?

The re-imagining of industry and business, with radical amounts of automation at the core, doesn’t stop at company boundaries. Divisions, departments and even individuals are looking at how they change their tasks, functions and roles. This will automatically lead to the questioning of fundamental assumptions and values, especially when it happens across divisions. Whereas in older models holding all the divisions and teams in harmony may have been the desirable outcome, now embracing of disruptive change means that’s often not even a goal anymore. There is a story that Jeff Bezos, on being challenged about the chaos inside of Amazon in its early days responded that it didn’t matter if Amazon didn’t know everything that’s going on, only that Barnes and Noble had no idea.

How do old strategies for coping with ambiguity apply in this kind of environment? Do they even? What new strategies are needed? After wrestling with this for a few years I’m coming to feel that there are two essential skills to cultivate..

The first skill is empathy. Understanding the perspectives of everyone around you and involved in the changes that are happening is priceless. Empathy is especially necessary because people aren’t robots and the changes have an emotional impact. Is the person in finance stressed out because they need to process twice the accounts receivable in the same amount of time with a new set of tools? Is the person in IS steadfast because their mission is to ensure stability of systems? Are our customers happy with the status quo or going away to competitors because we don’t offer what is needed anymore? With empathy you can understand different viewpoints of the same issues, especially when they are conflicting. If you only see your perspective or side of the story or your part of the mission you may wind up sewing the conditions for conflict and time wasted. Empathy makes you a better and more valuable teammate who can help chart new courses in a sea of chaos.

The second skill is curiosity. The days of working a widget line and knowing that you’re building the right thing are long gone. In its place is a constant circle of build, measure and learn with emphasis on learn. What do your customers care the most about? What are they willing to pay for? How does my industry work? How do we measure success? Are those measures the right ones? The curiosity must be driven and focused. One of the very most important questions is “What are the right questions to ask now?”. Asking questions without actually learning anything doesn’t help. How do you reflect on what you learned? How do you place it in your own personal body of knowledge in a way that you can act on what you learned? All of this makes the assumption that you already know how to build and measure. Good execution is now just a given but consistent curiosity ensures you don’t drive the wrong results or miss as many opportunities.

I believe that these two skills together best prepare us for dealing with high ambiguity environments where there is a lot of uncertainty. Understanding the perspective of others and constantly learning how things work make it easier to generate useful predictions or act in a much more adaptable way. Curiosity keeps you learning, asking the right questions learning from everything you do. Both makes it easier to recognize when your role is changing and how best to transition. Lastly and most importantly they continue to grow you as a person and professional.

Old Apple Trees