My 4 Favorite Questions

At some point in the last two decades of my professional career I noticed a shift. Early on I believed that my value in any of my enterprises, or in the ones I supported, came from having the right answers to increasingly complex questions. The more questions I was asked, the better the day. The more often I hit the target with a good answer, the more valuable I felt I was.

Then, as the complexity and sophistication of my work and of our challenges grew, the more often I realized that finding the right answer eluded me. It was quite unrewarding. I spent more time and energy in search of correct, powerful and keen answers and packaging them so that they would leave my teams with awestruck clarity. It was a great feeling but decreased in frequency, occurring less often than I liked. This approach also set me up to argue my point. While I was (and am) quite good at that skill, it usually left the team feeling less—rather than more—engaged.

Then, oddly, as increasing complexity advanced, and as the skills and competencies and commitments of my team grew, I found that I needed to ask better questions. This shift was freeing. And it was surprisingly invigorating. I found that if I changed from answering to asking and then from asking surface questions to asking deeper, more catalytic questions, our strategies accelerated, our teams engaged more deeply, and our passion (and fun) increased. And, I slept better.

Looking back I’ve found some questions are reliable starting points for me. They have become my 4 Favorite Questions.

First: What problem are we trying to solve? It may not come as a surprise to you, but it did to me, that the presented problem is rarely the problem worth solving. Asking this question is clarifying. And when we identify the problem, we ask what is the problem that created that problem?

Second: What opportunities does that core problem create? This is a fun one. Most often I found myself thinking that the work was to solve the identified problem. Boom! Done! Next? But, a few years back I began to realize that every problem brings something else to the party: An Opportunity. If not for the problem, this Opportunity would not exist. This question takes the toxicity out of simple problem solving.

Third: What have we tried already? What have we done that obviously isn’t working? Why are we still doing it? Who cares? What is working? What is not?

Fourth: What would you do if I were not available? This is both instructive and entertaining. Most of the time, with a smile, I can say, “You are probably correct in that approach.” It is also humbling as it occasionally reveals my inadequacies and over-controlling nature as a leader.

In every case these 4 Favorite Questions have resulted in far better engagement, more innovative solutions and greater alignment in my team. Try them on for size. They may help you, too.

Maybe it’s Me

Nathan looked down at his notepad and slowly rotated his pen. It had been an intense three days. Twenty people gathered for frank conversations about the future of the organization. Each person as passionate and engaged as the next. Each with a long history, long memories and a lot invested. Each with a dawning awareness that this was a pivotal moment. Grow or die? Will the storied organization shake off a downward spiral of decay or transform itself and flourish?

Every human endeavor faces this question. In fact, all of nature faces it. Leadership teams, investment firms, extended families, subcultures, streetwear brands, tech firms, political parties—and even ideas—all face this question. To delay the answer is to choose decay.

Day three of the discussion resulted in a list of nearly thirty “must do” opportunities, each compelling and crying out for investment, attention, passion and leadership. Each ripe with potential. Each pointing to groups of people with needs begging to be met.

But four years ago unresolved conflict between investors, stakeholders and leaders emerged. Like an obnoxious, immature narcissist drunk on attention, the conflict took center stage. Since then it has droned on sapping energy and optimism.

Representatives of both sides are few in number and have become increasingly unrepresentative of the whole. They are out of step with the values that undergird this great company. As has been true throughout history, the majority—that large, quiet middle—is irrelevant. Even worse, members of the quiet middle are deluded believing their silence excuses them. It doesn’t. They will remain silent. Shortsighted protection of the current state, even as it drifts slowly to decay, is paramount to them. Their silence is their voice. What we permit we promote.

“Maybe it’s me.” Nathan was asking as much as answering. As the executive leader of the organization he is right to wonder. And he is correct when he concludes that it is him. It is not totally him. But it begins with him. His leadership matters. Leaders get there first. It is on Nathan’s shoulders to get to a new place first if the organization is to grow. It is his responsibility to give people a reason to follow.

His question was authentic and free of manipulation. The room was still. No one spoke for a long moment. They knew the answer.

When we as leaders are faced with that question, the answer is always “Yes, it’s me.” It’s me because leaders get their first. Leaders are the first to humble themselves and ask for forgiveness, the first to engage, the first to sweat, the first to face the gaps between dream and reality, the first to be unselfish. Leaders are the first to have the uncomfortable conversation. They are the first to praise. The first to admit their own mistakes. The first to recognize their own deficits. The first to celebrate team wins.

Yes Nathan, it is you. Then, when you get their first, you will give others a reason to follow you. They will.

In the next few months we will see the result of Nathan’s choice. If he has the courage to get there first, to give those around him a reason to follow—to get up early, to suffer, to engage, to choose adventure—then we will follow.

Perhaps you are Nathan. Your family is waiting for your leadership, or your team, or your company. Your friends are waiting for you to lead with that idea and to finally give them a reason to quit their dull jobs and create something new. Your community is waiting for you to give them a reason to follow.

Maybe it’s you.

What a Dummy!

You’re just a big dummy!

We all paused. Spoons, forks, drinks hanging midway between table and tongue. Rex meant it. Well, he partly meant it. He was describing a conversation he had with someone he leads. The rest of the leadership team laughed and added color commentary to the account. I participated, to be frank.

I wondered later (probably a lot later… my bad) if I had done what the subject did, would I have also been a big Dummy? Of course not. I would have made the best decision I could at the time. My intentions would have been unselfish and pure. The Dummy’s…. not so much.

If I walk by a sink full of dirty coffee cups, it’s because I have important things to do and important people to see. If Dummy does it, he’s lazy. If I miss a deadline, it’s because quality takes a little longer. If Dummy misses the deadline, he’s a poor planner. You may see my point.

Don’t be surprised. There’s a name for this common practice. We call it “attribution error.” Whenever an expectation is missed, I attribute pure motives to myself and polluted motives to someone else. I attribute the best of all values, drives, habits or priorities to myself. The worst to Dummy.

Then I compound that thought error with another one. I add a “predictive error.” I inaccurately predict what I would have done, or what I would do if faced with the same situation in the future. “I would never do that! I would wash the dishes, show up on time, pick up the litter, meet the deadline. I’d never do what Dum-Dum did.”

Attribution and Prediction Errors are the tools of over-confident and uncurious minds. They lead to dead ends. They are the precursor to dreaded confirmation bias: a mental calculation that sets me up to only see what I expect to see, to only see what confirms my current beliefs. Finding what I’m looking for is a relief, if it’s my white SUV in acres of cars in front of Costco. Or, if it’s the face of a friend in a crowd. But finding what I’m looking for in support of incomplete or incorrect assumptions is lazy at the best and tragic at the worst.

Next time you hear confirmation bias or attribution error or predictive error (even coming out of your own face) challenge it by saying, “Well, I may have done the same thing under certain circumstances.” That opens up the possibility that we can learn from mistakes more quickly. Get and stay curious throughout the conversation. Attribute good intention to the Dummy. Assume good intent. Doing so will help you see underlying, sometimes irresistible forces at play.

The Oldsters called this grace. Not a word we use much any more. But they were on to something. Next time, after the laughter, rolled eyes and tongue clicking subsides, I think I’ll wonder aloud, “Well, could have been me.”

Built for the Storm

The flatscreen caught my attention. I’m not a fan of broadcast or cable TV. It bores me. Thirty minutes and I feel like my brain ate a bag of candy, and a pizza, and drank 2 liters of Coke. But this time I stopped, stood and watched an entire re-run of America’s Biggest Loser. You know the show: It captures contestants as they work valiantly to change their physical health by losing weight. A lot of weight.

At some point and upon hearing the back-story of the largest mobile man I had ever seen, I muttered, “How did that happen?” Another person overheard and said compassionately, “One bite at a time.” She had no judgement, no malice, no mockery in her voice.

Part way through his exercise routine—a 15 minute walk on a treadmill set on level 1—the contestant complained, “I can’t do this!” He was suffering and wanted to quit. His trainer shouted, “Keep going! You were made for this!” So he kept going. And kept complaining. I followed up later and found that he lost all of his target weight and has kept it off for nearly two years. One bite, one step, one decision at a time.

Yankee Flyer—Montague Dawson

A dear friend just completed a year marked with deep struggle, personally and professionally; the kind of struggle that combined would crush most people I know. Yet his humor is in tact. His relationships are strong. His perspective is fresh. His creativity inspiring. After our last conversation I found myself asking, “How did he get that way? How did he become so resilient?” He became resilient one choice at a time.

Donnie Q and I talked about him today. Donnie said, “He’s built for the storm isn’t he?” That phrase intrigued me. Some people see themselves that way. They imagine themselves well suited for wind, rain, high seas and the intensity of a significant life. They have thought of themselves that way for years. Their hourly choices reflect that image.

Others I know see themselves as delicate, fragile, perpetually in search of calm seas and sandy shores, deserving of all the soft things a wealthy culture can offer. They weather storms, but barely. They complain bitterly while doing so. They see looming adversity as a forecast of some fundamental flaw in the world, in their family, in their friendships, in themselves. They see the cold blast of challenge as something to be avoided at all cost.

How do you see yourself? When you look in the mirror do you see someone built for the storm? When you listen to your inner narrator, does he or she say, “You’ve got this. You’re built for this!” or mutter something else?

Our daily choices reflect how we see ourselves and how we see life’s challenges. Our small choices—the ones other people wouldn’t even notice—all add up to make us who we are. They spring from a clear image. Do you see yourself as someone built for the storm? Or, as someone built for perpetual vacation in a calm port with sandy beaches?

Riding in the Rain and the Unexpected Consequences of Discomfort

I’m happy we live in an economy that results in rich layers of comfort. I like my furnace. I like my Redwing riding boots and Grifter gloves. I like my warm rain jacket and smooth Baker six speed transmission on my motorcycle. I like a tankless water heater, my microwave and my iPhone. I love my million-position-adjustable heated and cooled leather seats in my Range Rover. They make me comfortable.

But to be frank, the best things in life spring from the struggle at edges of life. When comfort fades and it is replaced by challenge, adventure, significance, even intense skirmish, then I’m truly alive.

Yesterday I awoke to an unseasonably cold and rainy day, even for Seattle standards. I was tired, cold, irritable. Knowing that the reported temperature of 48 would be a “real feel temperature” of 32 when in the wind on my motorcycle, I still decided to ride rather than drive. And, I picked the bike with no fairing or windshield. Simply because it’s more fun to ride.

Dawning rain proof-ish gear and winter gloves, I set out. When I arrived nearly 30 minutes later I was cold and soaked around the neck, wrists and legs. It was the best ride of the week! I felt every drop, every gust of wind, every slip of the tires and every revolution of the engine. It was an intense beginning to a wonderful day.

We face the “comfort or adventure” choice daily. Sometimes several times a day. And I’ve found that significance never follows comfort. It’s always found on the other side of intensity and struggle, regardless of the scope. And so I choose adventure over comfort every time I see the choice. Best of all, I surround myself with people who live their lives similarly.

This banner hangs in our shop (Rottweiler Motorcycle Company). It’s a daily reminder that regardless of the delightful advances achieved by a civilized society, the pursuit of comfort is a slow death. So, lean into discomfort and challenge. You will be happy you did.

I Have the Controls

One of my lifelong adventure goals is becoming a reality. I’ve started ground school and flight school to obtain my Pilot’s License. The first surprise was learning that it’s not even called a license. It’s a Certificate. How dull. A small letdown but I got past it.

I’m several hours into flight school in a Cessna 172. It was manufactured when I was in high school back in the day. It’s well maintained and has updated Garmin Avionics but it is still a lot like flying my red 1968 Mustang convertible. It’s loud, jerky, uncomfortable, underpowered and endearing in every way.

Aaron is my Certified Flight Instructor. Out of respect for his achievements, he is actually a CFII, not just a CFI. Look it up.

He’s smart, funny, engaging, one-third my age, with a degree is physics and never makes me feel as uncoordinated as I act. I understand and love physics. But experiencing the laws of flight and gravity while sitting behind the controls of a plane at 3500 feet in turbulence is a new adventure. I’m learning (very slowly) how to spot and recover from stalls, how to take off and land in a stiff crosswind and how to navigate over the vast forests of the Olympic Peninsula. It is a blast.

Early in my very first flight Aaron gave me the controls, said “You have controls” and expected me to repeat, “I have controls.” The significance of that exchange was not lost on me. I knew that I was flying the plane. I had control. Within the predictable laws of physics and the unpredictable bi-polar disorder-like tendencies of the Seattle weather systems, I have control. Sort of.

He has also repeatedly said, “Fly the plane. Make it do what you want it to do.” A tall order for a novice like myself. But, I have control. When my altitude is too low, I have control. When the wind is pushing me off course, I have control. When turbulence bounces us up and down 100 feet in two seconds, I have control. When taking off and climbing to pattern altitude, I have control. When embarrassing myself on a radio call (saying I’m in my Range Rover instead of a Cessna for example), I have control.

The idea of Control in the midst of complexity is interesting to me. I have complete control over just a few things, but those few things make all the difference. With the Cessna, I have control over pitch, power, direction, altitude, timing. But not over other airplanes, or over weather patterns or the FAA, or my stomach. Knowing what I have control over, and employing it with finesse, is the key to becoming a good pilot (so I’m told. I have yet to experience it.)

You may be tossed by turbulence or experience pressures from systems and people outside your control but remember you have control. You have control over at least three things. First, you have control over how you look at life and how you see yourself; you have control over your perspective. Second, you have control over whom you trust and rely on. Third, you have control over your behaviors at any given moment.

So, take control. Don’t blame the weather or other pilots or the plane you’ve been given. Fly the plane. Fly your life. (See how I mixed metaphors there?)

Our life is a beautiful adventure. So fly it. Sometimes you won’t have the finesse required, but you can still take control and fly. Sometimes you will cause others around you to experience a little motion-sickness. Maybe they will even gasp a little and yell at you. But you have the controls. So fly your life.

So, I am flying an old Cessna 172. Aaron is helping me learn so that I can fly my Cessna 412c. He is patient and I have a long way to to. And so far he has only raised his voice in excitement twice in our many hours together. He gasped once when I unintentionally put the airplane into a spin (yes, a spin) and screeched once when I botched a crosswind landing (no damage to the plane, just a massive adrenaline rush and a scratch in my ego).

But, I’m flying.

No Honeymoons in War

Few things in life and work really matter. Very few. Fewer than we think.

Practicing the discipline of setting the right priorities, and then cutting the number in half, is vital. It is also elusive. And incredibly difficult.

If you’re working to have a significant impact, if you are driven by a purpose that is bigger than yourself, if that mission is likely to fail, but worth the attempt, then you will be perpetually challenged by choosing between competing priorities. These choices will not be easy. They will be like choosing between going on your honeymoon or pushing through the next big battle.

“There are no honeymoons in war!” John shouted. His senior team laughed. They were doing the mental math that such exclamations elicit. And, judging by their grimaces and downward glances, coming up short. Most were thankful the impossible choice was not theirs but that of an absent team member.

How do we make such difficult choices? Most of us aren’t good at it. Many of us make the choice based on a prediction of the emotional responses from others we care about. One choice will make three people angry, the other only two. One choice will make one very important person smile and several dozen others rage.

Some of us choose based on a fuzzy image of the risks and benefits each path may create. We choose based on past experience and on the advice from others who have faced similar dilemmas.

Some of us choose based on our own comfort levels. This choice is better than that one because it’s familiar territory and we are good at it. It is comforting.

But, is there a better way to make impossible decisions?

We’ve studied people who are good at such choices. They do three things:

They return to values: They remind themselves, and others engaged in the choice, what really matters. They force the choice between good, competing values.

They return to principles: They remind themselves of the fundamentals and of the principles that undergird their work. They use the “this SO THAT that” way of communicating. They say it again. Aloud. These are our guiding principles. These are our fundamentals. They are crucial and timeless. And there aren’t many of them.

They time travel: In making difficult decisions people who are really good at it project themselves into the future and imagine the best outcome. This is the vision, the goal, the result they seek? This is the answer to “Why are we doing this?” They travel days, weeks or even years into an uncreated future and envision the end-state. They answer in great detail what success looks like and why it’s so important.

Armed with clarity about values, fresh thinking about the fundamentals, inspiration from the vision, they decide.

Then then then act. With full hearts.