What to do when the path isn't clear

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Some people thrive on ambiguity. Most don’t.

I’ve seen team members who are highly productive when given clear direction but struggle the moment things get vague. Instead of pushing ahead and attempting to figure things out, they get stuck and wait for clarity that may never come. Sound familiar?

If you’re leading a team, this can be frustrating, especially in environments where ambiguity is the norm. So, how do you help your team build the confidence and skills to work through uncertainty instead of freezing up?

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Don’t just throw them in

A common instinct is to force your team into ambiguous situations and hope they figure it out. It kind of works… but can also erode trust. Team members who aren’t ready for this level of autonomy may feel abandoned rather than empowered.

The better approach? Teach them how to handle ambiguity.

Here’s how I help my team navigate uncertainty:

Give them a framework, not just freedom. Ambiguity doesn’t mean "figure it out alone." Teach them structured approaches:

• Break the problem into knowns and unknowns.

• Identify risks and assumptions and write all of them down.

• Map out a few possible paths forward. You don’t have to capture all of them, but the idea is to see what’s possible beyond option #1.

Encourage proactive questioning. Team members who struggle with ambiguity often default to waiting for answers. Instead, push them to ask better questions:

• “What is the actual problem we’re trying to solve?”

• “What would success look like?”

• “What’s the smallest step we can take to move forward?”

Model decision-making with incomplete information. In real-world projects, we rarely have all the answers upfront. I guarantee you deal with ambiguity all the time in your own role. Show your team how to make reasonable decisions with the information available. Encourage them to take a small, reversible step instead of waiting for certainty.

Normalize discomfort and support them through it. It’s uncomfortable for me too! I like having a clear path forward as much as the next person. Ambiguity isn’t a flaw in the process; it’s a skill to develop. Acknowledge that it’s uncomfortable but remind your team that this is how they grow. Over time, they’ll build confidence in navigating the unknown.

Ambiguity is a skill, not a barrier.

The goal isn’t to make your team comfortable with ambiguity. It’s to help them develop the tools to work through it effectively. When you shift from “forcing” people into uncertainty to coaching them through it, you’ll see your team becoming more self-managed over time.

Want to work with me? Here are 2 ways I can help you:

1. Upgrade to a paid membership: You’ll get VIP access to monthly deep dives on newsletter topics shared on Tuesdays, as well as the archive of all free Tuesday posts. This includes scripts and templates you can put to use immediately.

2. Enroll in my Management Fundamentals course:

   • Prefer to learn at your own pace? Check out my self-paced course, where you’ll gain the tools to identify and coach team members, manage conflict, and give effective feedback on your schedule.

   • Looking for live interaction? Join one of my live cohort sessions for personalized guidance, group discussions, and Q&A.