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Overcoming Resistance: Strategies for Quick Wins
When you’re leading change, especially around AI adoption, resistance is part of the process it's not personal. It’s human nature. People don’t resist change as much as they resist uncertainty and loss of control. That’s why one of the fastest ways we help teams shift from hesitation to momentum is by focusing on quick wins. Quick wins create immediate, tangible proof that change is worth it. They lower defenses, build confidence, and open the door for bigger conversations. When we teach teams how to integrate AI into their daily workflows, we don’t start with the most complex strategies. We start with something small but valuable, like saving 15 minutes on a repetitive task or building your first custom GPT. Once people experience that first win, something clicks. They see the ROI, not just in theory, but in real time, and that creates a snowball effect. The more small wins they stack, the faster the momentum builds. Curiosity turns into capability. Capability turns into confidence, and confidence makes resistance fade. Start small. Win fast. Build from there.
Overcoming Resistance: Strategies for Quick Wins
Awesome quick read
This article from Forbes outlines five practical shifts that can help bridge that gap and drive meaningful results. https://www.forbes.com/sites/nadyazhexembayeva/2025/06/27/ai-isnt-paying-off-yet-5-fast-fixes-to-finally-see-results/
Adopting AI is about more than just tools — it’s about mindset.
I had the opportunity to attend the EO One Canada conference this past week and saw an incredible talk by Zack Kass, Former Head of Go To Market at OpenAI. He shared a simple but powerful lens for what’s needed to thrive in the age of AI: ✨ Adaptability✨ Curiosity✨ Empathy✨ Courage✨ Wisdom These resonated deeply with me because AI is moving so fast, and success isn’t just about knowing which tools to use. It’s about how you approach change on a human level. I’d also add a few more qualities that feel essential on this journey: ✨ Flexibility — things will keep evolving; stay open and fluid. ✨ Discernment — not all AI applications will serve your mission; choose wisely. ✨ Playfulness — experimentation leads to learning; don’t be afraid to play. ✨ Collaboration — AI is not a solo sport; share, learn, and build together. The leaders and teams who cultivate these qualities will navigate this wave with far more ease (and joy). Curious — what would you add to this list? What qualities have served you as you explore AI in your work and life?
Creating Safe Spaces for Experimentation
One thing I’ve learned again and again, especially in the age of AI—is that innovation doesn’t happen without safety. If your team doesn’t feel safe to try, test, mess up, and learn, they’ll wait for permission instead of taking initiative. And here’s the thing: most people aren’t resisting AI because they’re lazy or behind—they’re afraid. Afraid of getting it wrong. Of looking unqualified. Of wasting time. That’s where we, as leaders, have to shift the culture. Here’s how I’ve approached creating safe spaces for experimentation on our team: 🔹 Celebrate process, not just outcomes. When someone tries something new, even if it flops—we talk about what they learned. Not every AI test will be a win. But every attempt is a step toward clarity, insight, or progress. Make that visible. 🔹 Model imperfection. I try to regularly share something I’m experimenting with—especially the messy parts. Whether it's a prompt that completely missed the mark or a tool I still don’t fully understand, naming my own learning curve helps others feel more comfortable in theirs. 🔹 Create structure for low-risk testing. We carve out space for low-stakes trial and error. Maybe it’s 20 minutes on a Friday where a teammate shares something they tested with ChatGPT, or a simple "Experiment of the Week" highlight in Slack. The goal is to normalize the trying, not just the winning. 🔹 Acknowledge courage. Trying something new takes guts. I make a point to thank people for stepping up and being curious. That kind of effort needs to be seen, especially early on, when momentum is still building. A few questions to bring to your team this week: - What’s one thing you’d love to try—even if you’re not sure it’ll work? - Where do you feel pressure to “get it right” instead of just starting? - How can we create more room for trial, error, and shared learning? Safe spaces aren’t soft, they’re strong. They’re what allow teams to stretch, explore, and grow together. Let’s build that kind of culture one small experiment at a time.
90min Challenge: Experimentation
I’ve been reflecting a lot on something Salim Ismail shared recently that really stuck with me: “Most leaders still think success comes from making fewer mistakes. But the real secret to exponential growth? Making more of them—faster.” This couldn’t be more true, especially as we step into the age of AI. If we want our teams and businesses to stay relevant, we have to create environments where learning moves faster than planning. That starts with psychological safety—not just to succeed, but to try. In our own team, we’ve seen the biggest growth when we shifted our mindset from “get it right” to “get it moving.” This could mean running small, time-boxed experiments—trying tools, prompts, workflows—even if we’re unsure what the outcome will be. And the most important part? Giving people permission to fail, share, and try again without fear of judgment. That’s where the breakthroughs live. Here’s my challenge to you this week: Block off 90 minutes and call it “Experiment Time.”Design one small test. Try one new tool. Test one new idea. You don’t need it to be perfect—just in motion. Because in this next chapter of business, the teams that learn fastest win.
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