Dealing With Ambiguity and Murky Questions

One of the biggest differentiators I see among people is their ability to deal with ambiguity. We coach people to work with clients or bosses to understand what expectations are, but I worry that we go too far or the message is taken too literally. A professional that wants a dynamic career has to be able to balance understanding expectations with an ability to create a path on their own.

I really struggle to articulate what I mean because there certainly is an “it depends” quality to this discussion. What I’m talking about here is the ability to face a murky situation and make headway. I am NOT suggesting people ignore or not seek feedback on direction. But often you are being asked to figure it out because people don’t know the answer. If they did, they wouldn’t be asking you.

I want to talk about several different ways this struggle can play out.

Thought Process

First there is the situation where people really want to put effort into the problem, but there are cognitive reasons they are floundering. I would cluster the “flounderers” into two broad (and unscientific) categories, linear and abstract thinkers.

Linear thinkers want to know the straightest line to the answer and put together a clear Gantt chart and work plan to grind out the answer. The problem is often that the question isn’t even clear. There’s a natural iteration and struggle in projects or situations that are fuzzy. You have to be willing to work the situation, material and people through some fuzziness and not know exactly what the output will look like. You have to be willing to remain patient and positive while working through rounds of starts and stops etc.

The abstract folks are often the opposite of the linear gang. They are so focused on all the interesting combinations and permutations of the problem space or the situation that nothing ever gets committed to print and lots and lots of interesting conversations result in little if any progress. There’s often a reluctance here to “commit” to any specific path because we might not know and there could be a “better” or more ideal answer etc.

So what’s the solution? Recognize your own style and that of the group/team you’re working with. Commit to putting your ideas in print, but recognize that it will iterate A LOT the more ambiguous the question. I’ll talk more about iteration below. My generic answer to most of these situations is to put a timeline on it and start committing ideas to print and circulating them to others for iteration.

The iteration cycle is critical and often where people fall down. They mistake being asked a question with needing to answer it by themselves. Getting good thoughts in front of people early leads to more cycles of improvement and depth in the final product.

Lack of “Appropriate” Effort

The second scenario is when people either aren’t really trying or don’t know what “trying” looks like.

A common situation that I see is a basic lack of understanding of how hard it is to get things done and the level of effort (my “appropriate” above) truly required. People often want to know the straightest path to “the answer”, not understanding there are no straight paths. You will burn up a lot of time on some paths that don’t play out, but that is unavoidable. We can use tools to limit it and improve productivity, but the iteration I talk about is staying on the problem and continuing to push even as some solution paths don’t pan out.

Generation and iteration are the keys here, along with having a personal sense of stick-to-itiveness. You need to be unwilling to settle for weak answers. I see people stop at the first obstacle or early on when there are ways over, under or around the obstacles. Merely finding some web content and pasting it into PowerPoint isn’t what I’m talking about. You have to challenge yourself to keep asking why does this matter?, what are the implications? etc. You’ll often have to go create data and analysis.

I’ll conclude with those who don’t really try and dismiss them summarily. If you aren’t committed to a problem or situation, you won’t solve it, the end. So you need to decide are you in or out and owe teammates or colleagues clarity if you’re not in.

So, how this can play out in career path?

Most people I work with say they want to be challenged and have lots of responsibility, but often want to be told what/how to do it. In my experience it rarely works that way. You need to be comfortable with charting a course if you want success in organizations. There is rarely an algorithm to spit out answers to difficult situations. People who succeed regularly solve these problems by sticking to them in creative ways. Get to the point where you are open to feedback, but in lieu of it are able to proceed confidently on a course of your own devising and sticking with it until the problem is solved.

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