Navigating The Gray: How Leaders Make the Best Decision When Faced with Ambiguity

One of the areas where I’ve seen new leaders struggle is the art of "navigating the gray": cutting through the ambiguity that comes with complex situations in order to make a decision.

Over the years, I’ve heard:

  • “How did we handle this exact same situation in the past?” (Answer: There has been no “exact situation.)

  • “Where’s the process on how we deal with this issue?”(Answer: Nowhere. You can’t write a process for every issue that occurs at an organization, assuming it will happen regularly.)

  • “Who knows what we should do? ”(Answer: You. You are the person that is probably closest to this problem that can determine what to do next.)

Circa 2014 When I became an HR Director, it was now my responsibility to make recommendations with large implications for the organization. And like most (women especially), I did not want to make a decision unless 100% sure it was the right decision. I remember thinking, “How did my boss always seem to know what to do???” And furthermore, seem very confident in how to move forward?

When solutions are not clear-cut it can become paralyzing, especially when others are looking to you for the answer. What I learned is that there is never really one right decision, but instead what could be the best decision to make in the face of ambiguity.

The conclusion: moving successfully through the gray requires practice.

The more we flex this ambiguity muscle, the better we become at making a decision with the best outcome based on the knowns (and unknowns).

Use these key strategies when you find yourself in the gray:

  • Embrace Uncertainty. Acknowledge that ambiguity is a natural part of leadership. Cultivate a mindset that sees uncertainty as an opportunity for growth and innovation rather than a threat. This can help overcome the desire to be risk avoidant or get unstuck from the limiting belief of having to be right.
    Ask yourself: What will I learn from this that will help me be an even better leader?

  • Start Small. Practice makes progress. Establish challenging yet achievable goals where you practice decision-making and accept the consequences, whether positive or negative. You can also reflect on past experiences involving ambiguity and use them as learning opportunities. Learn from each decision to make better ones in the future.
    Ask yourself: What is a challenge I could use for practice where the stakes are not so high yet still pushes me out of my comfort zone?

  • Remain Calm. When faced with ambiguity that has greater impacts for your organization, your team will look to you for stability and guidance, as well as how you process making decisions in these unclear circumstances. Project confidence by communicating openly and transparently about the ambiguity at hand. Share what is known or what is uncertain; answer questions and listen to any concerns.
    Ask yourself: How can I keep my composure during this difficult time for the benefit of my team?

  • Make it a “We” Problem. The best decisions are usually not made alone. When you value diverse perspectives and input, this can lead to more comprehensive problem-solving. Promote critical thinking skills for your team by encouraging them to ask questions, challenge assumptions, and explore various scenarios. This can build trust in on your team in their ability to handle ambiguity, and you can even delegate authority to capable team members to make decisions within their areas of expertise. When you come up with the solution together, the team takes ownership and pride in its execution.
    Ask yourself: Where can I lean on my team’s expertise that will help us make the best decision?

A personal example:

I have had team members come into my office and say, "Megan, I need your help. I have Problem X." Then they pause for my response. Sometimes, the expectation of the leader is to say, "Oh yes, I've dealt with that. Here is how you solve Problem X." Most likely I will say, "Oh yes, that is quite the problem and I haven't dealt with that either." The next sentence is crucial. Instead of launching into my insights first (which is challenging to do when you list one of your strengths as a problem solver!), I ask, "What is your recommendation?" Even if it may not be the final decision, use this as a coaching opportunity to see their thought process and help develop their critical thinking skills further by working on it together as a team, and not turning their problem into a "me" problem to solve.

  • Seek Expertise (Not Advice). When dealing with particularly complex or specialized areas of ambiguity, tap into subject-matter experts. This is not asking for advice on how to solve your problem; rather, it is filling the informational gaps you need to make an informed decision.
    Ask yourself: What do I not know enough about to help make this decision, and who can provide me this information?

  • Balance Patience and Persistence. Resolving ambiguity may take time. Be patient in your efforts to gather information and input, and also persistent to move yourself towards a decision before its too late.  As its almost the start of football season, I am reminded of a saying a CEO I know once said: “let’s not get all the way down the field and then fumble on the one-yard line."
    Ask yourself: When will I feel confident in having enough information where I can make a timely decision based on the current circumstances?


Bottom Line:

Leaders don't always immediately know the answer. Effective leaders view ambiguity as an opportunity to learn, grow, and lead their teams through challenging situations, rather than something to be avoided at all costs. Many successful people (e.g., Oprah Winfrey, Steve Jobs, Stacey Abrams, Michael Jordan, Sara Blakely) faced ambiguity head on, turned adversity into motivation and used their experiences to fuel their determination, resilience, and creativity.

Once we see ambiguity as a worthy adversary in our pathway to success, we not only feel confident but also excited about overcoming the challenges we will face as leaders.

Want more tips and resources on how to move through ambiguity? Here are some of my favorites:


Bottom line:

If you are a working parent: this is not a deficit but an advantage. You may need to be more explicit and intentional when and where you draw attention to these skills (especially if you have a boss who may not have the same experience to draw from). Continue to advocate for yourself by showcasing your elevated talents strategically without having to put in late nights (hint: dinner with the fam is MUCH MORE important!).

Want more resources on how to do that? Here are some of my favorites:

If you are an organizational leader: creating a flexible work environment that keeps working parents engaged and thriving will pay off tenfold. Don't forget, the early years of childhood can be the most challenging AND they don't last forever. Working parents won't forget the support organizations provided during the time they needed it the most. So help these parents give their best at work so they can do the same at home.

Learn more about how to support parents here:

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