If you have a co-worker who’s risk-averse, telling them to “just think positive” or just trust you”  rarely works. Risk-avoidant folks aren’t irrational; they are often reacting to well-earned caution, fear of failure, perfectionism or deeply held beliefs about accountability.

Instead of lecturing about the potential rewards, you can use your emotional intelligence (EI) to help them approach risk in a more thoughtful, sustainable way. Here’s a practical, people-first approach:

Build Emotional Safety

Change is hard when people feel threatened or judged. Start by showing you see and respect their caution. Risk aversion often has roots in past experiences or perfectionism. Psychological safety isn’t a buzzword—it’s the bedrock of real change.

Example: “You’ve been thorough for a reason. That caution has value. Considering this risk  isn’t about being reckless—it’s about giving ourselves more options.”

Are there situations in the past in which you proposed risks and failed? If so, is this proposition any different and how?  How did you learn from that prior experience so as not to repeat that mistake?

Point out the pros and cons on paper or in some graphic form to help your colleague process what you’re asking. If risk-taking or decision-making is particularly difficult for them, the emotional tension could make it hard to hold all the factors in their head at once.

Further reading:

• Amy Edmondson on Psychological Safety (HBR)
• Why Leaders Need to Make It Safe to Speak Up (McKinsey)

Explore Their Emotional Narrative

People don’t just avoid risk because of data—they’re responding to the story they tell themselves about it. Get curious instead of persuasive. When telling their story out loud they may see the flaws in their argument and reconsider.

Ask them questions like:

• “What outcome worries you most?”
• “Has something in your past shaped how you see this?”

This kind of reflective listening helps them unpack assumptions.

Further reading:

• Daniel Goleman on Emotional Self-Awareness

Reframe Risk as Leadership

Many see risk-taking as recklessness. Without minimizing our denying their fears, help them see it instead as a leadership responsibility: demonstrating courage and modeling adaptability.

You can say:

“If you’re feeling uneasy, that’s a sign you’re trying something new. It doesn’t mean it’s the wrong decision.” Instead, help them accept that discomfort is part of growth.

“Give the team a chance to see how you handle uncertainty.”

• The Discomfort Zone (Harvard Business Review)

It’s not about gambling—it’s about leading the team through the unknown fully aware of the possibility of encountering bumps in the road as we move forward.

Further reading:

• Brené Brown on Leadership and Vulnerability
• Leading in Uncertainty (MIT Sloan)

Make It a Small, Safe Experiment

You’re not asking them to bet the farm. Co-design a low-stakes trial:

• “What’s one small way we could test this?”
• “How can we make this feel safer to try?”

This approach mirrors complexity leadership’s “safe-to-fail” experiments, making risk manageable instead of overwhelming.

Further reading:

• Safe-to-Fail Experiments (Harvard Business Review)
• Dave Snowden on Complexity and Safe-to-Fail

Further reading:

• Building Resilience at Work (APA)

Anchor to Meaning

Help them connect risk-taking to purpose or legacy:

• “What decision would you be proud of when you look back?”
• “What example do you want to set for your team?”

Meaning turns fear into motivation.

Further reading:

• Simon Sinek’s “Start With Why”
• The Power of Purpose in Business (McKinsey)

A Note on Listening

None of this works without truly listening. Helping someone work through risk-aversion requires patience, empathy, and the skill of making them feel heard.

If you want to go deeper on how to listen in a way that creates trust and change, my book The Zen of Listening: Mindful Communication in the Age of Distraction offers practical, time-tested guidance.

Summary

Emotional intelligence isn’t just a leadership add-on. It’s what turns discomfort into growth. By listening, validating, reframing, and co-creating safe experiments, you can help even the most risk-averse colleagues take thoughtful, strategic risks.

Reflect on this question: What kind of risk-taking culture do I want to create? Write down 2–3 ways you can encourage healthy, strategic risk-taking in your team this quarter. Share it with your co-founders or leadership team.

Need help with these difficult conversations? Reach out to me at Rebecca@MindfulCommunication.com. Visit www.MindfulCommunication.com