Wild Leadership Problems and How to "Solve" Them

If you want to change your culture, put your computer away.

The job of a leader is to identify and shepherd change. One of the best tools to make change happen is surprisingly easy to do, effective, and free. However, it also takes wisdom, hard work, and empathy to execute.

In his classic book, The Effective Executive, Peter Drucker shared eight primary leadership skills: 

1. They ask, “What needs to be done?”

2. They ask, “What is right for the enterprise?”

3. They develop action plans.

4. They take responsibility for decisions.

5. They take responsibility for communicating.

6. They focus on opportunities not problems.

7. They run productive meetings.

8. They say “we” more than “I.”

That is, leaders spot what needs to change (1); judge whether it's realistic (2); form plans (3), decide (4); communicate why change matters (5); explain its benefits (6); execute (7); and support their teams (8).

But how do leaders do this in the face of an increasingly complicated world?

One tool is decidedly non-technological: the humble checklist.

Let me explain.

Leaders Are Paid to “Solve” Wild Problems

As economist Russ Roberts says in his best-selling book Wild Problems, there are two types of problems human beings solve: wild and tame problems. 

A tame problem is "How do I get from New York to Chicago?" They have clear, correct, knowable answers. For example, getting from New York to Chicago is complicated, but with a map or mobile phone app, you can find a solution, and the outcome is fairly predictable. 

A wild problem, by contrast, has no clear answer. And the act of solving the problem changes you, like being in the wild; the outcome is unknowable. Wild problems include whether to have children, who to marry, or whether to move to Chicago.

“Solving” wild problems changes who you are.

I put quotes around "solve" because you don't solve wild problems. Instead, you research, go with your gut, and act.

Charles Darwin and His Wild Problem

Roberts used one of history's greatest scientific thinkers, Charles Darwin, to illustrate a wild problem. In his 20s, Darwin began to grapple with a decision to marry or not. He journaled about this wild problem, and Roberts researched his original entries.

Roberts summarized Darwin’s thinking in his book, below.

The list shows the naturally naïve view a 20-year-old has of marriage — "it's better than a dog" and "having someone to take care of the house" are laughable attempts to describe the reward of a relationship that changes you.

Wild Problems, Russ Roberts

In Darwin's list, the negatives outweigh the positives. By my count, 13 to 9.

Finally, upon reflection, Darwin married. By most accounts it was a long and fruitful union. Darwin matured into one of history’s great scientists, and I’m pretty sure the wisdom he drew from his relationship had something to do with it, more than the “charms of music and female chit-chat.”

Wild Business Problems

Wild business problems include questions like: will this salesperson build customer trust and confidence? Should I fire or hire this VP? Should we launch a new product?

Like Darwin's decision to marry, wild business problems are risky… making them changes your organization… success or failure is uncertain. Yet, as Drucker suggests, solving wild problems is the job.

As I wrote in Checklist Culture Change, the humble checklist is a crucial tool to help lead the way through solving wild problems. 

The Checklist Manifesto

Since 1970, over 70,000 medical procedures, 6,000 diagnoses, and 4,000 drugs have been discovered. As a result, we know more about how the human body works now than ever. That's the good news.

The bad news is choosing among those thousands of options is a wild problem, even for the best-trained doctor. For example, studies show that 50% of 150,000 post-surgical deaths are avoidable each year.

Twenty years ago, Harvard medical student Atul Gawande observed the impact of wild problems in healthcare. He learned that good medical outcomes weren’t happening at hospitals with the best students. Instead, they happened at hospitals with the best process. 

Gawande dove in. He discovered that the best hospitals repeated the same process over and over to the point where they developed a simple, systematic, easy-to-follow system of using checklists before and after surgery. He shared his findings in his best-selling book, Checklist Manifesto.

The use of checklists to solve wild problems isn't a new idea. In 1935, sparked by a rash of deadly airplane crashes, the aviation industry decided to improve safety systematically.

Their solution: pre-flight checklists.

Here's a checklist for the Cessna 172. This list isn't from 1935; it's from today: checklists work and are standard practice in aviation today. Ask any pilot, and they'll tell you!

A wise, thoughtful, effective list looks obvious. And that's what makes them work.

Gawande's team set out to design checklists to make surgery safer. Their "safe surgery" checklist systematized pre-surgery procedures. Some items were as simple as "wash your hands."

It worked. In one study, checklists reduced surgical patients' complication rate by 36% and deaths by 47%. And results replicated over and over.

Although checklists are becoming accepted in the medical community, it's been a slog: some doctors resist checklists as overly simplistic; staff is overworked; using lists takes leaders with passion, humility, and a willingness to fail — they're tough to find.

But checklists work. And they're spreading.

Checklist Culture Change for Business Leaders

Here’s how to practice checklist culture change in business.

ONE: DESIGN LISTS TO BE READ OUT LOUD. A good list is simple. A good test of simplicity is to read it out loud. Does it make sense? Easy to follow? Clear?

For example, here's what pilots do when an engine fails in flight. The list has six steps: "Turn the Fuel Shutoff valve ON" and "Turn Auxiliary Fuel Pump ON" are among them. 

TWO: COVER ESSENTIAL FAILURES AND MISTAKES. My favorite step on the Engine Failure Checklist is the first: FLY THE AIRPLANE!  The designers of this list knew that when an engine fails, it's easy for pilots to panic. So the first job is first on the list: keep flying! "

So when you’re designing a checklist for a change process at work, start by listing obvious mistakes to avoid. For example, Rick Tacelli, one of the best salespeople I know, used this checklist before meetings:

It's a simple list, but do you always put yourself in someone else's shoes before each meeting? Do you always debrief and discuss what you could have done better? Do you always review action items?

Rick’s recipe emphasizes empathy, connection, and putting others first. Many novice salespeople, and even some experienced ones, miss these steps. A list like this makes salespeople better, even experienced ones.

THREE: INCLUDE COMMUNICATION BREAKS: Sports teams have time outs and halftime. Sales teams debrief after key meetings are essential. Surgeons hold “Morbidity and Mortality Conferences” every week.

Good lists have communication breaks. For example, Rick reviews the sales plan before each call and debriefs after. Time-outs ensure good habits are reinforced.

FOUR: NAME YOUR LIST. USE PAGE. NO COLOR. LESS THAN 10 STEPS. DATE AND SIGN IT.

Simple is hard!

FIVE: APPOINT LIST CAPTAINS. When installing checklists in new hospitals, Gawande appoints Checklist Captains to help define, refine, and apply lists. 

A captain's job is to edit and refine the list and make it their own. 

Then, they hold daily, weekly, or monthly meetings to discuss, improve, and adjust lists.

Everyone's busy. Schedules, deadlines, and distractions abound. Strong Checklist Captains keep things on track.

SIX: TEST, LEARN, ADJUST. Good lists evolve. Gawande recommends putting lists into action, observing their success and weakness, and updating them as a team. Eliminate confusing or redundant steps. Some problems are easy to fix, and others are impossible.

It sounds easy, but being open to change and admitting mistakes is the essence of leadership — the list is a living manifestation of that openness to adjust and fix what doesn’t work.

Six Steps to Culture Change

Checklists are a proven catalyst for change. 💡

Learning to make, use, and lead with them takes ten minutes to learn but a lifetime to master. ☯️

Try using them to solve your wild business problems. 🐺