A few weeks back, we brought together a group of learning leaders for a Champagne Round Table at the CLO Exchange in Boston to explore one big question: How can we make a culture of experimentation a true competitive advantage?

And, yes, a champagne round table is basically a workshop where everyone drinks champagne. Highly recommend. But, I digress…

The conversation was a rich, candid exchange about what it takes to foster experimentation across individuals, teams, and organizations. And how learning teams can facilitate that culture.

This note captures the shared insights, practices, and provocations that emerged from our roundtable, as well as what we’ve learned from over a decade of leading innovation with companies of all structures and industries. It’s a co-created guide, shaped by the experience and insights of those leading this work every day.

But, before the tips, let’s take a step back.

What is a culture of experimentation?

It’s what it sounds like: a culture where people feel safe to experiment, try new things without the guarantee of success, and move forward with ambiguity.

What happens if we don’t have it?

When things feel uncertain, as they do in nearly every organization right now, the instinct is to freeze. To play it safe. To stick to the status quo. To wait it out. In times of rapid change, though, waiting it out may not actually be a safe option. With that approach, you risk falling behind or missing a crucial window of opportunity. Now is the time to get more curious, not less. To learn faster. To adapt as you go.

What does it unlock for a team or organization?

A culture of experimentation helps teams stay sharp, adjust quickly, and continue to improve, even when the ground beneath them isn’t standing still. Make experimentation a habit, and the future feels a bit more like a sandbox on a playground than a pit of quicksand.

So, how do we foster a culture of experimentation?

Let’s get into it.

5 Ways to Build a Culture of Experimentation (Without Waiting for Permission)

1. Make It Safe to Try (and Fail)

This is about emotional permission. If people don’t feel safe to take a risk, ask a question, or share a half-baked idea, they won’t experiment, no matter how much you tell them to.

That’s why psychological safety is the foundation of a culture of experimentation. And a big part of that is what leaders model. When people see their leaders trying new things, owning mistakes, and learning out loud, they believe it’s safe to do the same.

Ask yourself: Do people on your team feel safe to try something new, even if it flops?

Try this: Go first. Share a story about a time you tried something that didn’t work, and what you learned from it. Then invite others to do the same. Bonus points if your HiPPO (highest-paid person’s opinion) shares theirs, too.

“This permission to try, fail, or learn is encouraged by specific leaders who themselves are not risk-averse.” — Public Sector Learning Leader

2. Start Small, Learn Fast

Experiments don’t have to be big or risky. Small, scrappy tests reduce fear and build momentum.

Ask yourself: Are we encouraging small tests as a normal way to work and learn?

Try this:

• Embrace the “Sh*tty First Draft”: Ask your team to share early ideas or half-baked prototypes and give one another feedback.

• Pick one team meeting each month to reimagine. Try a new format, tool, or approach.
  

3. Experiment Like a Scientist

In the rush to get the momentum going, don’t forget your why. Too often, we see teams launch pilots or tests without getting clear on what they’re actually trying to learn. (As Enneagram 7s, Sara and I are guilty of this ourselves.) An experiment needs a clear purpose and a way to measure what matters.

“A tactic we use is being clear on the measurement strategy upfront. Was the experiment driven to reduce development time, improve knowledge transfer, or just a better learning experience? That drives what we measure and whether we continue.” — Learning Leader, Multinational Professional Services Firm

Ask yourself: What are we testing? Why? And how will we know if it worked?

Try this: Before launching any new idea, take five minutes to align on these three questions:

1. What’s our hypothesis?

2. What can we measure that will indicate success?

3. What decision will we make based on what we learn?

4. Remove the Barriers

If you want the culture of experimentation to thrive, you need to proactively remove the friction that hinders it. If you are a team leader, this is a place where you can have a significant impact.

Ask yourself:

• What’s getting in the way of more experimentation on your team?

• What approval, policy, or assumption could you challenge this week?
  

Try this:

• Do a “barrier audit” with your team. What’s slowing us down? What’s unclear, assumed, or unspoken? What orthodoxies exist that are in our way?

• Reframe constraints as design prompts: What’s possible within this boundary?

• Offer a micro-grant ($500–$1,000) to fund experiments—no approvals required.

“In my current workplace environment in state government, I always ask my team: If regulation or legislation weren’t a factor, how could we change this? It opens the door to creative thinking. Once we have possibilities on the table, we can calibrate to what’s real.” — Public Sector Learning Leader

5. Celebrate the Learning Loop (Not Just the Results)

This is about recognition and reinforcement. If your team only gets high-fives for polished, successful outcomes, they’ll hold back ideas until they’re perfect or not share them at all.

But if you recognize thoughtful effort, good questions, and honest lessons learned, you create space for real innovation to take root.

Ask yourself: Are we celebrating the trying, not just the winning?

Try this:

• Shine a light on a “brave try” in your next team meeting

• Create a Slack channel or end-of-week roundup for small experiments and what was learned

Bring It All Together

A culture of experimentation doesn’t emerge by accident. It’s shaped by what gets talked about, repeated, and shared. Teams need to hear, “This is who we are: we try, we learn, we evolve,” and “This is a place where learning happens out loud.”

You don’t need a full playbook, or anyone’s permission, to get started. Pick one question or try one tip from this list. You might be surprised by the ripple effects.

And if you’ve tried something that helped your team experiment more boldly, we’d love to hear about it. Seriously. Drop us a note.