Tips for Fostering an Experimental Mindset in Learning and Development

The more mistakes a team makes, the more quickly they learn and more resilient they become… yet so many of the teams I work with are terrified of making a mistake! They have so much on their plates that they’re singularly focused on crossing things off their lists so the thought of experimenting with a new approach and having to redo it is soul-crushing. OR They’re operating within a prove-your-worth culture in which mistakes are attributed to personal failure and incompetence. OR There is no appetite for risk and the only acceptable way of working is to do things the way they’ve always been done. OR any number of other reasons top performers make themselves small instead of taking a risk that could be a win. This is bad for business. And for morale. When mistakes are seen as part of the process, teams feel safer taking risks, which leads to creative solutions and faster progress. Leaders need to focus on 3 things to encourage experimentation so their teams will risk making mistakes in pursuit of a win: 𝟭. 𝗙𝗼𝘀𝘁𝗲𝗿 𝘀𝗲𝗹𝗳 𝗮𝗻𝗱 𝗰𝗼𝗹𝗹𝗲𝗰𝘁𝗶𝘃𝗲-𝗰𝗼𝗺𝗽𝗮𝘀𝘀𝗶𝗼𝗻 When we meet failures with compassion, we soften the emotional blow and decouple it from identity. With compassion, the individual is not a failure (fixed mindset)… they’re an innovator who tried something that failed (growth mindset). ❇ Tip: Normalize mistakes and conversations about mistakes by conducting regular retros for missteps, large and small. Emphasize the key learnings and takeaways, not the flawed logic or approach. No blame, no ego threat, no identity crisis, no problem trying it again another way. 𝟮. 𝗖𝘂𝗹𝘁𝗶𝘃𝗮𝘁𝗲 𝗮 𝗹𝗲𝗮𝗿𝗻𝗶𝗻𝗴 𝗰𝘂𝗹𝘁𝘂𝗿𝗲 When learning is valued over perfection, teams are more willing to experiment, try new approaches, and push boundaries. ❇ Tip: Reinforce growth mindset as a core cultural tenet. Encourage team members to set personal development goals and allocate a budget to it. Even a small contribution can have symbolic & cultural value. Reward effort and improvement, not just outcomes and encourage voluntary share-outs or team-wide trackers. 𝟯. 𝗖𝗿𝗲𝗮𝘁𝗲 𝗮 𝘀𝘆𝘀𝘁𝗲𝗺 𝗳𝗼𝗿 𝗲𝘅𝗽𝗲𝗿𝗶𝗺𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 Experimentation increases both the absolute number of failures and the failure rate. AND Done with systems, strategy and intention, it also accelerates growth, discovery and successful solutions. Establishing a system for experimentation allows teams to test ideas in controlled, low-risk environments where failure is seen as a step toward success. ❇ Tip: Implement a process for innovation sprints in which team members are encouraged to suggest & test bold ideas with clear guidelines on how to analyze & iterate based on the outcomes. These shifts to culture and process can have a massive impact. Teams that are encouraged to make mistakes ✔ learn more quickly, ✔ are more resilient and ✔ are more likely to take smart risks that can lead to sustainable, step function success.

Memoirs of a Gully Boy Episode 44: Experimenting and Flirting with #Failure In the corporate world, growth often comes dressed as messy, unpredictable experiments. Yet, the fear of failure keeps many from venturing into the unknown. What if failure wasn’t the end of the road but a necessary step toward success? Mastering the art of experimentation, and accepting failure as part of the journey, can redefine your career. Failure is a Lab, Not a Cemetery Scientists don’t expect every experiment to succeed. Instead, even their failures provide valuable data. Corporate life works the same way. Experimentation drives progress, but it demands risk and resilience. In one of my pivotal projects, we implemented an automation system for a major client. Our initial rollout had setbacks—some workflows slowed instead of improving. It felt like a disaster in the making. But we analyzed the gaps, restructured the system, and eventually delivered a solution that became a benchmark. Each failure taught us something vital, pushing us closer to success. Failures don’t bury potential—they reveal opportunities to innovate. Daring to Fall, Learning to Soar Think of a trapeze artist trying a daring new move. Falling is part of the process, but without those falls, they’ll never achieve the perfect landing. Similarly, the willingness to risk failure separates innovators from those who stay in their comfort zones. Early in my career, I hesitated to pitch bold ideas. Fear of failure kept me quiet. But as I grew, I realized that even my “bad ideas” sparked valuable discussions and new directions. I learned that courage to try—and fail—often leads to breakthroughs. The Resilience of Experimentation Failure builds resilience, a quality crucial in today’s fast-evolving world. Here’s how to transform failure into a stepping stone: 1. Analyze Setbacks: Each mistake is a lesson. Break it down to uncover the root cause and learn. 2. Reframe Failure: Replace “I failed” with “I learned.” Mindset matters. 3. Celebrate Effort: Recognize the courage behind trying something new, regardless of the outcome. 4. Iterate Quickly: Adapt and pivot fast—progress favors momentum. Fostering a Culture of Experimentation As a leader, the way you respond to failure sets the tone. Celebrate team efforts, encourage bold ideas, and turn mistakes into learning moments. When people know failure isn’t final, innovation thrives. Velvet Glove Over Iron Fist Failures aren’t dead ends; they’re detours leading to discovery. Experimenting and flirting with failure isn’t reckless—it’s essential. History’s greatest successes were born from persistence through setbacks. So, take that leap, try that bold approach, and don’t fear the fall. Each stumble is a lesson, and every experiment pushes you closer to greatness. Failure isn’t the enemy—it’s the guide. To be continued... DC*

It isn't an experiment if it can't fail One of the warmup exercises I run for my workshops is to have people write down or draw what their biggest fear is with regards to running experiments in their organizations. Their responses often illustrate that far too few of us work in environments where it is safe to fail. "That we run out of patience with management" "It fails and my boss thinks I'm stupid" There is a big difference between Fail Safe and Safe to Fail in organizations. Fail Safe implies an organization that is designed to prevent failure and emphasize control. There are systems where this is applicable, often when both the problem and solution are known (and nothing changes). Safe to Fail on the other hand, acknowledges that a failure is inevitable and is designed to absorb these failures without significant impact. Here we identify and map the risk, then run experiments to address our riskiest assumptions. It is my belief that leaders are ultimately responsible for the environment of their organizations and I'm not convinced this fear of experimentation is intentional. There are several ways leaders can begin to create an environment of Safe to Fail inside their organizations:   👉 Promote an open dialogue where employees feel comfortable sharing ideas, asking questions, and expressing concerns without fear of retribution. 👉 Openly share stories of failures, lessons learned, and how these experiences contributed to growth. This helps demystify failure and frames it as a valuable learning opportunity. 👉 Recognize and reward not just successful outcomes but also the willingness to take calculated risks and experiment, even when the results are not as expected. 👉 Actively participate in experimentation, showcasing their commitment to a safe-to-fail environment. Leadership behavior sets the tone for the rest of the organization. 👉 Ensure that failures are met with constructive feedback rather than blame. This helps maintain morale and encourages ongoing risk-taking. 👉 Shift from traditional performance metrics that focus solely on success rates to metrics that value learning, experimentation volume, and adaptability. 👉 Share stories and data that highlight how experiments, even those that didn’t go as planned, contributed to the organization’s strategic goals. If you've made this shift in your organization, what has worked for you?

Success gets all the applause, but growth? That happens in the messier moments—the experiments that didn’t go as planned. And that's a difficult mindset to maintain in legacy organizations like Act!, where our organization's decades create long-standing SOPs, layers of approval, and budget accountability. But if your team doesn’t feel safe to fail, they won’t feel safe to innovate. It really is that simple. And a lack of innovation? That's like signing a death warrant for any SaaS company. Why? Because fear of failure stifles creativity, limits problem-solving, and keeps teams playing it safe. But when failure is embraced as part of the process, everything changes: → Lessons stick. The best solutions often come from ideas that didn’t work the first time. Humility makes those lessons unforgettable. → Creativity flourishes. Teams take smarter risks when they know mistakes won’t lead to blame. → Resilience grows. Every misstep strengthens the muscle to adapt and bounce back—and even failed ideas can spark brilliance later. So how do you create space for experimentation (and failure)? → Celebrate effort, not just outcomes. → Ask, “What did we learn?” instead of, “What went wrong?” whenever possible. → Lead with empathy — honestly this is the most important piece. → And, of course, always stay focused on what’s next. Because failure isn’t the opposite of success—it’s the foundation. And I think it's time more leaders embrace that mindset. #saas #leadership #innovation

Experimentation isn’t just A/B testing. It’s a mindset that never ends. 🧪 People think of A/B testing when they hear “experimentation”. But that’s only one tool. For me, true experimentation is about being open to change, trying new things, and learning fast. The way we work now? It might look different in a year (or even next month). That’s the point. What matters is being willing to test, adapt and build on what you learn. Here’s how we keep that spirit alive at Avlana: → Team setup: We built a group with different skills and backgrounds. No two people are the same. That mix means we move fast, trust each other, and give real ownership. (Trust is everything, right?) → Community feedback: We show early versions & mockups to users, gather feedback, and watch where they get stuck. Sometimes, it’s a small tweak that unlocks big value. E.g., for us: one small change but big unlock was introducing a smart table view next to our gallery view. → Non-stop learning: We try new models, features, and ideas as a team. AI is moving SO fast right now that if you blink, you're already behind. We make sure our tech lets us swap models in and out, test quickly, and measure what works. No guessing. In the end, experimentation is not a task. It’s a way of building, learning, and working together. every. single. day. What’s your take? How do you keep an experimentation mindset alive in your work? 👷🏼🧑💻🚀

If your company is uncomfortable with failure, show them this: True story: I recently met Erin Weigel, a former design leader for a $100B business that you’ve certainly heard of. I asked her how many experiments they run per week, and she said “a thousand.” “Per week?” I clarified, “A THOUSAND per WEEK?” “Yep.” “Wow. And how many of them are successful?” “Nine percent.” She didn’t hesitate. “Nine percent?” I repeated, stunned. "Yep.” 𝘛𝘩𝘢𝘵 𝘮𝘦𝘢𝘯𝘴 𝘰𝘯𝘦 𝘰𝘧 𝘵𝘩𝘦 𝘸𝘰𝘳𝘭𝘥’𝘴 𝘮𝘰𝘴𝘵 𝘴𝘶𝘤𝘤𝘦𝘴𝘴𝘧𝘶𝘭 𝘤𝘰𝘮𝘱𝘢𝘯𝘪𝘦𝘴 𝘪𝘴 𝘸𝘳𝘰𝘯𝘨 91% 𝘰𝘧 𝘵𝘩𝘦 𝘵𝘪𝘮𝘦. Look, nobody likes failing, and it’s no fun to discuss our failures. But if you’re not failing, you’re not learning. And if you stop learning, sooner or later, you’ll stop earning. What about a little startup? Maybe you can’t run 1,000 tests per week, but most startups I work with aren’t even running 10. And when they do experiment, they expect success rates that are wildly unrealistic. This expectation creates a paralysing fear of failure, so they run fewer experiments, take fewer risks, and miss critical learnings. How can you address such a deep cultural issue? Here’s my advice to leaders: 1. Talk about your own mistakes, every week. Start with the ones you’re still a little embarrassed about. You’ll be surprised what a bit of authentic vulnerability does for your team’s engagement.     2. Present your ideas as hypotheses and your decisions as experiments.     3. There are people in your team who aren’t afraid to challenge you. Find them. They’re your secret weapon against blind spots. This sounds scary. I get it. Maybe they’ll fire you. But a fixed-mindset company is a sinking ship, so they’re probably doing you a favor.

"Great leaders empower teams to learn, experiment, and adapt without fear of failure." This resonated deeply with me because it captures the essence of modern leadership. When teams feel safe to take calculated risks, innovation flourishes. I've seen this firsthand: The most successful projects often emerge from environments where 'failed experiments' are viewed as valuable learning opportunities rather than mistakes. Leaders who create this psychological safety don't just get better results—they build stronger, more resilient teams. Three key practices I've observed in leaders who do this well: 1️⃣. They share their own lessons from past failures openly 2️⃣ They celebrate the learning process, not just the outcomes 3️⃣ They ask "What did we learn?" instead of "What went wrong?" The paradox? Teams that feel safe to fail often fail less, because they're more likely to speak up early about potential issues and collaborate on solutions. What's your experience with creating a culture of psychological safety? How do you help your team embrace experimentation? #aileadership

I used to be THAT coach. The one who handed out homework like it was going out of style. It didn’t resonate with my clients: - Homework is about as fun as a root canal - It gets done with the enthusiasm of a teenager cleaning their room - It has the connotation of an after-hours burden In short, it's the fastest way to make your clients hate learning. But then I had an epiphany. What if we ditched the “homework” and reframed it altogether? I started pitching it as “experiments.” The result? It kind of blew my mind. Experiments: + Light a fire under your clients’ asses (in a good way) + Turn passive note-takers into active problem-solvers + Allow for real-world experiential learning, not just pen & paper. The moment I made this switch, resistance melted away like ice cream on a hot sidewalk . Suddenly, my clients were diving into their Experiments with the gusto of a kid in a candy store. Why? Because Experiments aren't chores. They're opportunities. They're not about ticking boxes. They're about exploring possibilities. Even as I type out this post, I’m experimenting. It’s fun. It’s invigorating. And if it works for myself and my clients, it might be worth running a little experiment of your own. ***** Words are tools. As leaders, we need to leverage them. “Homework” makes people want to bang their heads against a desk. “Experiments” make people want to tinker, catalyze, and grow.