Lonely leadership decisions are part of every leader’s job. How to handle tough choices, decide with partial knowledge, and trust your gut.

During my years working for an airline, many of my colleagues have undergone the upgrading course to become airline captains. It is widely known that this is the most important and also the hardest training a pilot can get.

When I met one of my colleagues for the first time after his captain’s upgrading, I asked him what it is like to be a captain. He said, without hesitation:

“As a copilot, I would look left to the captain when a problem came up. When I look left now, I only see the clouds.”

Although I am not a pilot, I love this perspective. You don’t have to be the President of the United States, the commander-in-chief of an army, or the CEO of a multinational conglomerate to know it’s lonely at the top. Airline captains, startup CEOs, and even single parents often have to make serious decisions without having anybody to turn to. That doesn’t mean they don’t have anyone to talk to, but in the end, their decisions are often very lonely.

Taking lonely decisions is easy when options are black or white, or when decisions don’t have huge consequences. To stay with the airline jargon: “Chicken or beef sandwich?” That’s an easy decision to take, with zero long-term consequences unless you are allergic to either chicken or beef. And if you are, the decision is easy to take, too.

Black or White? No, Grey

Let’s change worlds and dive into the grey areas of life. As the Founder & CEO of Yonder, a B2B SaaS company, most of the decisions aren’t as black-and-white as chicken or beef.

Promising Features

Shall I promise a certain feature to be developed and available by a certain deadline? What happens if I don’t promise it? Will I lose customers? What happens if I promise it but don’t make the deadline? Will competitors win over customers from me? How can I promise a certain feature before I know all the technical details to be considered?

Merging Teams

What happens if I merge two teams? Will efficiency and collaboration improve, or will we just shift the hectic? How will the affected team members react to the proposed reorganization? Are there any signs that some aspects of the reorganization will create new problems?

Saying Goodbye to Colleagues

How do I tell a person that it’s time to leave? Some people are great for the jungle phase of a startup, but they aren’t for the more structured dirt track or even highway phases. When did you notice for the first time that this person — although having contributed to the success of your company — is not the right fit anymore? How are you going to tell the person, and what specific facts will you use in this unpleasant meeting? Have you thought about the reactions in the affected team?

Finding Investors

How do I get the commitment of a lead investor for a financing round? Is everybody hesitating because the valuation is too high, or because growth is too slow? What will happen with my existing investors if I agree on new terms with a new lead investor? Will everybody start following once I have that new lead investor, only for the round to be oversubscribed? Or will nobody follow, with the round eventually dematerializing and leaving me out in the rain? And if that’s the scenario, was my agreement on new terms with that new lead investor the root cause, or something else?

Anticipating Problems

What do I do if a customer doesn’t pay their overdue invoices for months? Factoring and debt enforcement are easy in your home country, but how about far-away countries such as Saudi Arabia or Malaysia? And before you start debt enforcement and threaten to suspend SaaS service, can you find out what’s the true reason why a customer doesn’t pay? Are they unhappy with your service, corrupt, overly bureaucratic, or close to bankruptcy?

No Right or Wrong Answers

Twist and turn those questions the way you want, there is only one certainty: There is no right or wrong answer to them. Even with all the thinking, talking, and decision-making methodologies in the world, nobody can guarantee that your decision will be right in the rearview mirror.

I can guarantee you two things only: First, if the decision proves to be a good one, everybody will expect you to pass the kudos to the team, and stand back. Second, if the decision proves to be a bad one, everybody will point their fingers at you.

Let’s return to aviation. An airline captain in a troubled situation needs to make a decision within the shortest possible time, using only the information he or she has available at that time. It’s easy (and pointless) to debate after a safe landing (or — God forbid — a crash) what should have been done differently, had the captain known X or Y.

The same goes for product development, hiring and firing, and fundraising. Always assume decision makers have good intent, but respect the fact that they operate with partial knowledge, and they too are human and hence will make mistakes.

Listen to Your Gut Feeling

Retrospectively, many big problems I had to deal with brewed slowly over time. They brewed because it’s easier to delay a lonely decision than to make a bold decision with an unknown outcome.

However, whenever problems exploded in my face, my inner voice always told me that I would have known for a long time that I would have to solve the problem with a bold but lonely decision.

Even if you’re an analytical person, always listen to your gut feeling.