How to get better at problem solving

But how do you keep it cool? And how do you keep the birds from smacking into your windows? (Image by giovanni gargiulo)

“I am trying to learn problem-solving skills. Do you have any recommendations?”

I received this question on one of my very favorite topics from a reader of this blog. (Thank you!)

My answer is very simple: I learned problem-solving skills through solving problems.

Each problem required certain resources and tools to solve it. And then, once I solved it, I had those resources and tools to use on the next problem.

This makes it sound like my path was predictable and intentional, but it was not. In fact, I didn’t know that my entire career would be an exercise in problem solving. Whenever my work got to be too routine, I would change it up. Because I continually sought out novel situations and opportunities for growth and learning, I was always faced with fresh challenges. I continually encountered new problems to solve.

This life of perpetual twists and turns is not necessarily what I recommend — it’s just how I am. The downside is uncertainty, instability, frustration, and confusion. The benefit is some decent lateral thinking and the ability to make decisions quickly, one after the other.

When we’re stuck on a problem, it’s often because we’ve turned it into a dilemma in the classical sense: we’re only seeing two options, neither of them appetizing. With practice, we can learn to see additional possibilities. We can question the decisions that were previously made that caused us to arrive at this point. We can consider how we might free up resources that we didn’t think were available. With more options to choose from, we may find more attractive solutions to our problem.

Sometimes, our problem solving is hindered by lack of information. Instead of recognizing the gap and working (or simply waiting) to close it, we force a solution that is premature. With practice, we can learn how to deal with the discomfort of not having all the answers we need, whether that means that we must develop the patience to leave the problem unsolved for now or the courage to take the best course of action without the necessary information.

Another obstacle that hinders us from effective problem solving is our attachment to a particular solution. Unwittingly, we rearrange the facts to make our way the right way instead of carefully assessing the situation as it truly is. If we pay attention to the results of our problem-solving efforts, we have a chance to spot this pattern and correct it.

Absurdly, the arena where I have practiced the most problem solving is my email inbox. Think about it: Every email represents an incoming request from a person or entity. They are all calling upon you to take some kind of action. They want a meeting. They have a question, complaint, or idea. They want you to look at a document and give your feedback. They want to sell you something, or they want to buy something. Or maybe they just want to connect with you as a fellow human.

Confusingly, all of these varied requests are in the same place, side by side in little slivers of text on your screen until you click on them. That’s why David Allen’s first question is “What is it?” Almost every one of these digital missives represents problems to be solved our decisions to be made, even if that decision is to trash the thing.

I used to be caught off guard by this. I’d get an email from a client asking for a service that we didn’t offer, and I’d spend twenty minutes or two hours trying to figure out how we could offer the service without recognizing that I had chosen the wrong problem to solve. I was taking responsibility for solving the client’s problem just because this email was in my inbox, totally derailing my own priorities.

The problem wasn’t, “How do I find a sackbut teacher” or even, “Should I hire a sackbut teacher at my music school?” The problem was simply, “How do I kindly and politely say no?” I got really good at solving that particular problem. I also learned to accept the fact that I couldn’t act upon every idea that came my way, even the very good ones.

My master class in problem solving came in March 2020, when both Eclectic Music and The Little Middle School had to move online — while a critical member of our team was sick with the first wave of Covid.

We didn’t want to have to do it. It was a huge hassle and an inconvenience. We didn’t have all the information we needed — we actually acted before our local and state government did. We knew not everyone would like it. We knew it would cost us a lot of money. And yet, through the coordinated efforts of the team, frequent and transparent communication with each other and with clients, intense focus, and aggressive acceptance of reality, we were able to pull it off.

Earlier in my career, I’m not sure I would have had the wherewithal to act swiftly and decisively to solve the problem of a sudden pandemic. Because I had experience, I was ready. I was able to heed the wisdom of others, including key leaders on my team. I was able to see a variety of options and choose one, even though I hated them all. We thought ahead to the potential obstacles we’d face and how to deal with them. I could guide people who were scared and overwhelmed and empower them to make their own valuable contributions. It all came together.

I prefer problem solving when the stakes are lower. In those cases, it’s become kind of fun. But through practice, I’ve learned to handle more challenging situations with greater confidence and acuity. I believe that problem solving is a skill that anyone can learn, but like any skill, you can’t really learn it from a book. You get better at it by doing it.

What are some of your best approaches to problem solving? Have you seen this skill get better for you over the years? I’d love to hear in the comments.