Herding Cats... and Solving Complex Problems

Most people are looking for a simple answer when they ask, “What do you do?”

I have never had a simple answer.

Over the years, I have worked in product development, institutional finance, stakeholder coordination, and complex project execution.

Depending on the setting, I have answered that question in different ways. At one point, I used to say, “I make change.” 

Later, I started saying, “I herd cats.” That answer usually gets a laugh, but the truth is, it is probably the most accurate one I have ever given.

Because that is what complex work often feels like.

It is not just strategy. It is not just execution. It is not just leadership. It is taking a moving set of priorities, personalities, constraints, regulations, and unknowns and somehow bringing them into alignment.

It is getting people, institutions, and ideas moving in the same direction, even when they all begin from very different places.

That is the work.

What I really do is take complicated challenges and break them down into smaller, manageable actions. I look at problems as puzzles to be solved. The more complex, the more interesting. I have always been drawn to the situations that others dismiss with phrases like, “We can’t do that,” or “That has never been done before,” or “That’s not how we do it here.”

To me, those statements are not conclusions. They are invitations.

When people ask where I start, the answer is straightforward: I start with the rules.

I start with the laws, regulations, requirements, and real-world constraints that define what is possible. Then I read. I study the framework. I look for the pressure points, the pathways, the conflicts, and the opportunities. Long before AI tools existed, that was the process. And despite all the new technology available today, it still is.

Yes, I use ChatGPT. But I use it the way I think these tools are best used: to refine, polish, and sharpen what I have already worked through myself. You still have to own the information. You still have to understand the facts, the structure, and the consequences well enough to stand behind them.

That matters because complex work is never static.

I am involved in projects right now that require coordination across multiple stakeholders, agencies, advisors, and decision-makers. Everyone has a role. Everyone has a concern. Everyone sees the problem from a slightly different angle. The challenge is not just creating momentum. The challenge is creating alignment.

That takes work. It takes preparation. It takes communication. And maybe most importantly, it takes humility.

I do not know everything, and I have learned that pretending otherwise is one of the fastest ways to fail. Some of the best progress I have ever made came from asking questions, inviting critique, and listening closely to people who understood a piece of the puzzle better than I did. Regulators, risk managers, technical experts, community stakeholders — they all matter.

One of the most important lessons I learned came from a risk management executive at a bank where I worked. She was responsible for reviewing new product development and, in many ways, protecting the institution from its own blind spots.

Before one committee meeting, I had walked her through a proposal in advance and felt confident I was prepared. Then, during the actual meeting, she raised questions I had not anticipated. I was caught off guard. I remember feeling frustrated and deflated because I thought we had already covered everything.

Afterward, I went to her and asked what had changed.

Her answer stayed with me: new questions always come up. Then she added something even more valuable — that I should never assume preparation means every issue has already been discovered.

She was right.

Preparation matters, but it does not eliminate uncertainty. In complex work, new information surfaces, conditions shift, and unexpected obstacles appear. You have to be able to adjust without losing momentum. In the end, that proposal was approved, and more importantly, it was stronger because of the questions that challenged it.

That lesson shaped how I work to this day.

The skills you develop today are rarely limited to the job in front of you. More often, they become the foundation for what comes next. But that only happens if you are willing to rethink your assumptions, stay open to challenge, and keep learning as the work evolves.

So what do I do?

I take on complex problems. I break them down. I bring people together. I ask questions, listen carefully, adjust when needed, and keep moving until the path forward becomes clear.

In other words, I herd cats.

And when the cats are stakeholders, regulators, agencies, advisors, partners, and competing priorities, that is not just a joke.

It is a skill.