At some point, you begin to lead. This is very different than managing. The difference can be summed up with the phrase, “leaders make their own problems”. I’ll explain that in a bit, but first, let me tell you a story.

When I first realized I was missing something

When I first became a director, I had a conversation with another Director named Jim.

Jim: “So, you’ve been in this role for a month now. Have you figured out your vision for your organization?”

Me: [What is he talking about?]

I realized I was used to taking direction from others, and I had become a sort of “execution” focused manager. I didn’t have any idea what my organization needed. I had no idea what the future should look like. I was managing my organization, not leading it.

Interrogate yourself

I brought this up with an executive coach I was working with at the time. He encouraged me to set time aside every week to really think deeply about my area of the product.

At first, it was hard to preserve the time I set aside. In my busy schedule, it seemed luxurious to save a couple hours just for thinking. But it quickly became some of the most valuable time I spent each week.

I would spend time each week thinking amount my organization, about the product, about how things were going. I researched other products that competed with mine. I spent time using the product. I thought critically about our technical and product failings.

I ended up developing a better sense of what possible futures I could create. I started to see possibilities that were invisible to me. I started to learn how to lead.

Mental models: try and catch them all!

At around this time, my manager challenged me to start using more mental models in how I assessed my organization. He suggested looking at the situation from the point of view of:

• A systems thinker. (this was my default)
• An architect
• A product manager
• A designer
• Etc.

Most leaders use their own experience as their main mental model. Being able to add new mental models to your toolkit makes you more flexible. Each mental model can alter what you think the future should look like. And what the present should look like. It can also inform you of the actions you should take to make things happen.

As I started developing a habit of looking at things from other mental models, I began to see blind spots in my previous ways of looking at the world.

Interrogate yourself with what exactly?

Each week, I sat down and looked at an evolving set of questions. I would go through the list and write answers to the questions on the list. Here is my list of questions:

Review high level objectives

• What are the results that are needed? What needs to be true in a year? X needs to be Y by Z. What would need to change for that to happen? What are the implications of that need?
• How are the teams performing? On time, hitting the mark, right characteristics? How are they performing AS a team?
• Where are things on the path to fail?
• What’s the worst thing that could happen?
• Is there anything I think my boss is making a mistake on?
• Can all of my reports take over my job in 1-2 years?
• What seems like it’s not working right now?
• What’s going well that could be turned into a repeatable process?
• What should I worry about?
• What do my managers need?
• What does my org need?
• What do I need?

Review progress against objectives

• How on track is everything?
• How long should the rope be for all of my objectives? Agree to them with other people. For ex: when should we expect reliability to improve?
• Review team health
• Review progress against goals.
• How are team members doing against their goals?

Identify next actions

• What actions should be taken?

I found writing down the answers to these questions to be tremendously helpful.

If you’re an external processor, you might find it more useful to talk with others about these questions. For me, I did a bit of both. I found a few other people that I would talk about these things with. But I found the private thinking time valuable — it gave me more material to test with others in conversation.

Leaders make their own problems

A leader is a person that asserts a future for a group of people.

If you want to lead, you have to learn to make your own problems. You want the problems you’re working on to be partially something you’ve generated. Because that is really the role of a leader: to scout out the upcoming terrain and prepare a group of people to navigate it. While you don’t need to do all the scouting yourself, your need to have a way to make sure the future is explored and thought out.

Hopefully, you’ll find this post useful to develop and approach to navigating that future. If you’ve found other methods to do so, please share them with me!

Thank you

Jim Ruppert helped me see that I didn’t have a vision for my organization, and his gentle nudge helped me expand my horizons. Robert Goldmann helped me learn the perspective I needed to lead better. He helped me develop some of the questions on this list. Alex Kroman challenged me to consider things through multiple mental models. Thank you to George Sudarkoff for feedback on the post and some minor edits. Image by Arek Socha from Pixabay