3 Questions Leaders Can Ask Themselves to Sleep Well at Night

You wake up in the middle of the night thinking about what you do all day. Are we making progress? Are we closing the gap? Is the gap closeable? Is it the right gap? (There’s more than one.) Are we losing ground? What am I missing? Because what I don’t know may in fact hurt me, and everyone else. Is this going to end up where it needs to be, or am I going to lead this team right off a cliff? I’m putting in crazy amounts of time, Lord knows, but are we going anywhere, or not?

The Privilege of Leadership

Leadership has its privileges, no doubt, but also more than its share of anxiety. Somebody has to call the ball. If it’s you, then you probably got there because you’re capable, you care deeply about succeeding, and you know how to work harder than anybody. In fact you’ve had some real success, evident to you and others. You’re not a rookie.

So why does it sometimes feel so damn hard? Because it is. If it were easy, anybody would be doing it. But wait — everybody is doing it. It’s just that not everyone will be successful doing it.

What Success Means

So there, we said it. Success. Do you know what that means? Where is this destination you call success?

Managing an enterprise can have a lot of moving parts and pieces that operate differently under different conditions. Understanding those parts and pieces, and how they interact, can be complicated. It does not matter how many zeros make up the top line. Managing big things is a different game than managing small things — but both can be demanding on whoever is at the top.

Envision the Destination

What to do? A good place to start is to take a breath and focus on the present. Resist the urge to over-plan.

Planning can manufacture a false sense of control in situations where certainty simply does not exist. Try instead to envision the destination. Where do you want to be, today? When you have a clear view of the destination, you’re in a position to empower the team to find their way there.

Thomas Jefferson had the vision to explore the American West long before he became president. Once in office, Jefferson commissioned Meriwether Lewis and William Clark to reach the Pacific Ocean on behalf of a young country. He provided resources, authority, and his full confidence. But he could not provide a map. There were no maps.

But Jefferson knew what “there” meant, and why it mattered. He selected the best leader he could find and left the journey up to him. Jefferson called it a voyage of discovery. Russell Ackoff, management science professor at the Wharton School, would call this kind of thinking “idealized design.” Define the best possible destination clearly and work backwards to create the journey.

If you’re in a start-up, the destination may be more obvious — you’re giving birth to something that did not exist before. If you’re in a turnaround, the destination is survival, this week. The harder case may be what’s in between: deciding on the right destination from among what may seem like a lot of plausible options, none of them blaring at you.

Planning paradigms can help, not so much as a map, but as a way to get the team thinking together, creatively, about the destination and the possible paths ahead. The shared exercise of building the plan is usually more valuable than the plan itself.

So ask yourself, are you confident in your understanding of the destination, today? It needs to be a big enough target, worthy enough to command the motivation of people who have other opportunities. The Pacific Ocean in 1804 was not some village or a street address. It captured the imagination and devotion of explorers willing to make an extraordinarily arduous journey.

Apply Systematic Thinking

The journey, working backwards from the destination, requires systematic thinking, understanding your present position (St. Louis) and the resources available to move you forward (canoes, willing explorers, provisions). But first, the team needs a clear idea that Jefferson wants the Pacific, not Paris.

So, ideally, you and the team commit to the destination together and can envision success, standing on the shores of the Pacific Ocean, ankle deep in sand, waves crashing. Leadership creates and shares that vision. Once it is shared, the team can find any number of means to reach it.

There’s a big river called the Mississippi (a strength) and another nearby called the Missouri (another strength), but neither flows west — a significant challenge. There are tough explorers who would much rather paddle against the current for two thousand miles than navigate uncharted wilderness on foot — that’s their call.

Canoes are easy to come by. The team decides to go by river. Some believe there are enough connecting waterways to reach the ocean almost entirely by water. That will not turn out to be true, but they don’t know that yet. Give them all the provisions you can, cut them loose, and let them figure it out as they go.

Embrace Creative Leaders

Leaders have to be clear-eyed about the destination and thoughtful in the selection of team members who are qualified, flexible, and creative in how they navigate the journey. Jefferson knew Lewis and thought he was capable. Not perfect, but capable and willing. Lewis knew Clark and thought the same. Good people tend to know good people. Perfection is rarely the standard, but creativity, adaptability, and resilience are.

No one on that expedition knew they would meet Sacagawea, but Lewis and Clark were perceptive enough to recognize that she was multilingual and could communicate with the local people who knew the terrain. Putting a female, let alone a teenage Native American woman, in that kind of role was unconventional thinking for the early nineteenth century. But that is what capable leaders do when the situation demands it.

They stayed focused on the mission, moving towards the destination, as best they could, and improvised when the need arose. When they ran out of river, they walked. When they ran out of food, they ate tallow candles and eventually their pack animals. They did not give up.

I doubt they lay awake wondering whether they should have been heading for Paris. They probably worried about freezing to death in the mountains and just surviving one day at a time. But they knew the destination and kept moving.

What You Are Asking Yourself

If you’re in charge, there are many questions you need to ask yourself: is the destination clear to me? Is it clear to the team? They have to know where they’re going to know whether they’re moving toward it or away from it.

Are they the right kind of people for this journey? Do they have the initiative, the courage, and the motivation to get there without you calling every play? Do they know how to build on strengths? (If you can find a river, paddle.) Are they creative enough, and flexible enough, to find resources where others see only obstacles? Would they cook up the tallow candles and put Sacagawea out front when things get tough — or remain lost and starve? Do I have leaders who are focused on their roles, as well as creative and flexible if need be?

Jefferson had the luxury of staying in Washington. Most of us don’t. Steven Brandt, who taught entrepreneurship at Stanford, talked about the interplay of “doing, managing, and leading,” three roles that effective leaders must hold simultaneously, in different proportions depending on the moment. In smaller enterprises especially, the leader is often Jefferson and Lewis and Clark rolled into one. You set the destination, you manage the journey, and you’re in the canoe eating tallow candles when the food runs out.

The challenge is to hold all three roles without letting any one of them crowd out the others, to keep one eye on the Pacific while helping the team navigate the next river, and picking up a paddle if need be. Encourage your team members to use their initiative and step up when they can; every team member is a potential leader, and the leaders know how and when to be doers.

When leadership understands its role and can clearly envision the destination, does the team share that vision? Once you and your team share that vision, you can empower them to work backwards, design the journey, and let it evolve. Help them if you can. But the right team, all headed in the same direction, will often find paths that leadership never anticipated.

Three Questions

So the next time you wake up at 3am, ask yourself three things:

1. Do I know our destination?

2. Do I have the right team?

3. Does the team know where we’re going?

If the answer to all three is yes — you’ve done the most important work. The rest is the journey. Sleep well.