Finding a path through uncertainty

If you find yourself at a crossroads and unsure of which route to take, read through this list before you make a decision.

Every leader can find themselves unsure of what to do. When I coach CTOs and VPs of engineering, I often hear phrases like, “I don’t know what’s expected of me,” or “I feel lost,” or “I wish someone would tell me what to do.” 

These sentiments can be compounded when you go a step up to the CEO level. While a CEO might have a board, a coach, a mentor, or a separate body of support, their remit is encapsulated by one broad statement: Make the company succeed. While the mission sounds simple, it’s also ambiguous. Without clear direction, leaders must grapple with this uncertainty. And though difficult to balance, these individuals aren’t alone in their feelings of discomfort and trepidation.

If you’re struggling with this, here is a simple recipe to find a path through uncertainty.

1. Write down your fears

Some level of uncertainty is actually a good thing. When we’re too sure of ourselves, we risk confidently going in the wrong direction. Uncertainty creates awareness of gaps in knowledge or understanding. When I’m coaching clients, I encourage them to specifically pinpoint what they are uncertain about. Try writing it down. Putting words to thoughts turns vague concerns into distinct issues that can be addressed. 

Here are some examples of phrases I’ve heard from engineering leaders that underscore this: 

• “I don’t know what technology direction we should choose for our product.”
• “I am uncertain about if I’m spending time on the right activities.” 
• “I am uncertain if I’m meeting my manager’s expectations.”

Think of this process of turning the unknown unknowns into the known unknowns. Until we know what we are uncertain about, we cannot find a way forward.

2. Consider your options

Now that you have a concrete statement in front of you, put on your problem-solving hat. For a moment, suspend the critic or the pessimist in you. Instead of thinking that you can’t do anything or that you don’t know what to do, focus on what you can do. Forget about whether or not they are good or bad ideas. Simply write down as many ideas or options as you can think of.

For example, if you’re uncertain about which technology choice to make for your product, evaluate the potential decisions or options you have in front of you.  If you’re uncertain about whether you’re spending time on the right activities, ask yourself which would be the most impactful for you to spend time on. If you’re uncertain about meeting your manager’s expectations, contemplate over what their expectations might be.

Now that you’ve listed your options, it’s time to find feedback to determine the best way forward.

3. Find feedback

After considering your options, you might worry about which one to pick. You’re naturally thinking about finding the “right” or “best” avenue forward, but remember that there is rarely a “perfect” answer. There is simply one choice that may be better than others or one with less painful tradeoffs. As you’re debating about which option or answer is best, remember you don’t need to decide alone. 

Although it can be lonely as a leader, you have people around you who can support you. You probably have a manager. Maybe you have a mentor. You have at least peers and people you’ve worked with for a long time. Turn to these people for feedback on your thoughts or prospects.

For example, if you’re unsure about whether you’re meeting your manager’s expectations, you might share a list with them and ask if you’re aligned on your current set of responsibilities. Invite them to share their thoughts on the list, if there are things you should or shouldn’t be doing, or things you’ve missed. 

If you’re in a situation where you’re skeptical about a technology decision, you might speak to a principal engineer or software architect and ask their opinion. Discuss how your choice would impact the tech team, or if you may have overlooked something. 

4. Make a decision (or bet)

Facing uncertainty can create analysis paralysis –  simply put, the fear of making a decision. For technical folks in particular, there may be a temptation to put off making a decision in the hope that you’ll get more information down the road. 

As a leader, making decisions is important even when the outcome is uncertain, as your choice will generate more information/data on the issue. In her book, Thinking in Bets Annie Duke suggests viewing her decisions like bets. We can’t control the future, and there’s always an element of luck when it comes to an outcome. A good decision doesn’t always guarantee a good outcome.

If you’re still struggling to make a decision, set a deadline for it. This may be the end of the week or month. 

Remember, not making a decision has negative side effects. The longer you wait, the higher the chances that teams make their own (misaligned) decisions, or delay progress while waiting for direction.  For example, if you’re deciding on a new technology platform choice, a team might wait for a clear direction instead of building a new feature to prevent rework or unnecessary work.

A path forward doesn’t need to be perfect

Navigating uncharted or uncertain waters is always scary. But, as a leader, it’s your duty to find a way forward. Pausing due to indecision won’t help you progress. Face your fears and write down what you’re uncertain about. With a concrete area of uncertainty, list out what options you have and then gather feedback about your preferred option. Finally, make a decision because you have a clear path forward, even if it might be unfamiliar.