Top Decision-Making Secrets Successful Leaders Use in Uncertain Times

As a leader, your ability to guide teams through ambiguity becomes a defining factor in your organization’s success.

Imagine this: You’re presented with a promising investment opportunity—but key market data is missing. The deadline looms. Make the right call, and you could fast-track your company’s growth. Make the wrong one, and you risk depleting valuable resources.

In finance, high-stakes decisions under uncertainty are the norm. Yet, the pressure can lead to decision fatigue or snap judgments that miss the mark.

By applying the right mental models and frameworks, leaders can make confident, strategic decisions even when the full picture isn’t clear.

Understanding Uncertainty and Its Impact on Decision-Making

Not all uncertainty is equal. Sometimes, you face known unknowns—missing information you know is missing. Other times, unknown unknowns—gaps you’re unaware of—can cloud your judgment.

These uncertainties trigger cognitive biases. You may overestimate risk, seek confirming data, or avoid decisions altogether—especially if perfectionism plays a role.

Recognizing and managing these mental traps allows you to make clearer, more confident decisions under uncertainty.

Preparing Your Mind: 4 Mental Models for Uncertainty

There are several mental models you can use for risk assessment and making decisions when faced with uncertainty. Here are four to try.

1. Use Probabilistic Thinking

Avoid thinking of the possibilities in terms of “yes” or “no” questions. Instead, ask yourself and your team open-ended questions that look at probability and rely on all the information you do have.

2. Consider the Opposite

Sometimes, you may be so focused on making a certain decision that you don’t consider what will happen if you don’t make that decision. Always take a moment to contemplate other choices.

3. Use Expected Value Decision-Making

Conduct expected value calculations to weigh the various potential outcomes of an investment decision based on probability and impact.

4. Assess the Possibility of Reversal

Consider what might change if new information emerges and uncertainty decreases. Could you adjust or reverse your decision? What would that process look like?

The OODA Loop for Uncertain Environments

You can also use the OODA loop to make decisions. This continual, never-ending framework developed by a military strategist is applicable to all decision-making environments.

The OODA loop, or the Observe-Orient-Decide-Act loop, requires observing to gather information, orienting yourself to the incoming information, deciding based on that orientation, and acting accordingly.

The loop continues as more information becomes available, but it ensures that you always make choices promptly, giving you a competitive edge.

3 Practical Uncertainty Management Techniques

Strategic uncertainty management can increase your decision confidence. Consider incorporating the following three techniques into your workflows.

1. Stick to Clear Decision Criteria

Identify the key information you need to make a certain decision—and set your criteria in advance. For example, when hiring for a role, define your non-negotiables. If a candidate meets them, proceed. If not, move on.

Also, consider creating a simple checklist with 3-5 must-have criteria for any decision. For budget decisions, your criteria might include: Does it align with our strategy? Can we afford it without hurting cash flow?

2. Conduct a Pre-Mortem Analysis

Walk through the various potential failures that could arise before making any decision. This can help you identify your team’s blind spots to be aware of and mitigate them in advance.

3. Use a Decision Template

A simple template can streamline how you document decisions, assumptions, and expected outcomes—helping you make choices faster and in a standardized manner.

Building Organizational Decision Capability

Apply these uncertainty management techniques across your teams to standardize deliberation while keeping processes flexible enough to adapt quickly. Encourage ongoing feedback and refine the approach as needed.

All the while, remember that workplace culture matters. Teams that feel psychologically safe make better decisions under pressure. Empower team members with the best information to make the calls, not just those with the most authority.

Personal Practices for Decision Confidence

As you strengthen your resolution around ambiguity, personal growth is essential. Get comfortable with imperfection, manage negative emotions, and stay grounded. Brief mindfulness practices, decision simulations, and reflection on your core values can all help you navigate complexity with clarity.

The Bottom Line

You can increase your decision velocity by implementing practical, easy-to-implement habits and frameworks. After all, uncertainty isn’t the enemy—it’s an opportunity for growth.

Pick one important decision you’ve been delaying. Use the minimum viable information approach to clarify what you need to know. Then, commit to deciding within a week—document your process, and let us know how it goes. We’d love to hear how these tools work for you.

Looking for tailored guidance on decision-making and leadership during volatile times? An Arootah Executive Coach can help you. Book a complimentary results call to explore how we can support your goals!