Tips for Managing Change in the AI Era

I asked the smartest people I know about AI... I’ve been reading everything I can get my hands on. Talking to AI founders, skeptics, operators, and dreamers. And having some very real conversations with people who’ve looked me in the eye and said: “This isn’t just a tool shift. It’s a leadership reckoning.” Oh boy. Another one eh? Alright. I get it. My job isn’t just to understand disruption. It’s to humanize it. Translate it. And make sure my teams are ready to grow through it and not get left behind. So I asked one of my most fav CEOs, turned investor - a sharp, no-BS mentor what he would do if he were running a company today. He didn’t flinch. He gave me a crisp, practical, people-centered roadmap. “Here’s how I’d lead AI transformation. Not someday. Now.” I’ve taken his words, built on them, and I’m sharing my approach here, not as a finished product, but as a living, evolving plan I’m adopting and sharing openly to refine with others. This plan I believe builds capability, confidence, and real business value: 1A. Educate the Top. Relentlessly. Every senior leader must go through an intensive AI bootcamp. No one gets to opt out. We can’t lead what we don’t understand. 1B. Catalog the problems worth solving. While leaders are learning, our best thinkers start documenting real challenges across the business. No shiny object chasing, just a working list of problems we need better answers for. 2. Find the right use cases. Map AI tools to real problems. Look for ways to increase efficiency, unlock growth, or reduce cost. And most importantly: communicate with optimism. AI isn’t replacing people, it’s teammate technology. Say that. Show that. 3. Build an AI Helpdesk. Recruit internal power users and curious learners to be your “AI Coaches.” Not just IT support - change agents. Make it peer-led and momentum-driven. 4. Choose projects with intention. We need quick wins to build energy and belief. But you need bigger bets that push the org forward. Balance short-term sprints with long-term missions. 5. Vet your tools like strategic hires. The AI landscape is noisy. Don’t just chase features. Choose partners who will evolve with you. Look for flexibility, reliability, and strong values alignment. 6. Build the ethics framework early. AI must come with governance. Be transparent. Be intentional. Put people at the center of every decision. 7. Reward experimentation. This is the messy middle. People will break things. Celebrate the ones who try. Make failing forward part of your culture DNA. 8. Scale with purpose. Don’t just track usage. Track value. Where are you saving time? Where is productivity up? Where is human potential being unlocked? This is not another one-and-done checklist. Its my AI compass. Because AI transformation isn’t just about tech adoption. It’s about trust, learning, transparency, and bringing your people with you. Help me make this plan better? What else should I be thinking about?

I'm knee deep this week putting the finishing touches on my new Udemy course on "AI for People Managers: Lead with confidence in an AI-enabled workplace". After working with hundreds of managers cautiously navigating AI integration, here's what I've learned: the future belongs to leaders who can thoughtfully blend AI capabilities with genuine human wisdom, connection, and compassion. Your people don't need you to be the AI expert in the room; they need you to be authentic, caring, and completely committed to their success. No technology can replicate that. And no technology SHOULD. The managers who are absolutely thriving aren't necessarily the most tech-savvy ones. They're the leaders who understand how to use AI strategically to amplify their existing strengths while keeping clear boundaries around what must stay authentically human: building trust, navigating emotions, making tough ethical calls, having meaningful conversations, and inspiring people to bring their best work. Here's the most important takeaway: as AI handles more routine tasks, your human leadership skills become MORE valuable, not less. The economic value of emotional intelligence, empathy, and relationship building skyrockets when machines take over the mundane stuff. Here are 7 principles for leading humans in an AI-enabled world: 1. Use AI to create more space for real human connection, not to avoid it 2. Don't let AI handle sensitive emotions, ethical decisions, or trust-building moments 3. Be transparent about your AI experiments while emphasizing that human judgment (that's you, my friend) drives your decisions 4. Help your people develop uniquely human skills that complement rather than compete with technology. (Let me know how I can help. This is my jam.) 5. Own your strategic decisions completely. Don't hide behind AI recommendations when things get tough 6. Build psychological safety so people feel supported through technological change, not threatened by it 7. Remember your core job hasn't changed. You're still in charge of helping people do their best work and grow in their careers AI is just a powerful new tool to help you do that job better, and to help your people do theirs better. Make sure it's the REAL you showing up as the leader you are. #AI #coaching #managers

With all the posts on "vibe-coding", "AI-prototyping", and "look at how I use Cursor as a PM" it can feel like you're behind. But most folks are just getting started. The people posting who appear to be experts? They only got started months ago ◡̈. Take it from my 63 year old father. He's a seasoned executive - WAY smarter than I am (he'll beat AI at virtually any math problem). We've been meeting regularly so I can teach him AI. This video is from our 1st session and it proved to me just how early we are on the AI adoption curve. I've learned several key lessons about AI adoption from my dad and from trying to spearhead adoption at work: 1️⃣ Change is really hard, even more so in enterprise organizations. There are two keys to combating change: 1) You have to show folks why/how AI makes their job better. The best way to do that is to find a champion in each org who can serve as an advocate and build use cases tailored to that orgs specific role. 2) Create programming to build the habit! Consider challenges, 30/60/90 day plans, and even incentives like leaderboards and gamification. 2️⃣ There's a lot of red tape for the more advanced AI usages. Connect GPT to company email? Lengthy IT/Security approval process. Zapier agent? Every connected app requires API access. The only way to make this less cumbersome is to get the entire leadership team to prioritize AI adoption, so that Legal and IT teams are bought in and aligned. 3️⃣ Start with what you can control. While you're waiting for those enterprise approvals, focus on the AI tools you already have access to. Use ChatGPT, Gemini, or Claude for critiques on your first drafts, analyzing competitor messaging, and just plain ideating (use voice mode!). Download spreadsheets / CSVs and then upload them and ask for insights. These wins build your confidence AND give you concrete examples to share when you're ready to propose bigger changes. 4️⃣ Document what works (and what doesn't). Keep a running list of prompts that actually save you time e.g. the ones you find yourself using again and again. If you aren't happy with the output, tweak the prompt, not the output. These prompts become your internal products. Once you nail a prompt for a specific need save it and make it easily reusable via a custom GPT, Gemini Gem, or project. Share these "AI recipes" with your team. You'll quickly become the person others turn to for AI advice. 5️⃣ [More advanced] Think about your company's tribal knowledge. What are the areas where something is blocked or unanswered until a very specific role or person takes a look at it? For ex: RFP gap analysis, FAQs that come up about your product (is this supported or not?). These can be streamlined via a project, custom GPT, etc, freeing up that person for higher order thinking. The gap between AI beginners and experts is smaller than it appears. Most of us are just figuring it out as we go! Start where you are, with what you have access to, and build from there ◡̈.

🎯 The CIO's Organizational Playbook for the AI Era... I recently spoke with a CIO friend about how IT teams are changing. Our discussion made me think about what sets apart IT teams that succeed with AI from those that don’t. I looked over my research and reviewed my interviews with other leaders. This information is too valuable not to share: ✓ Build AI-Ready Capabilities 🟢 Establish continuous learning programs focused on practical AI applications 🟢 Implement cross-functional training to bridge technical/business gaps 🟢 Prioritize hands-on AI workshops over theoretical certifications ✓ Master AI Risk Management 🟢 Develop processes to identify and mitigate technical failures early 🟢 Create a strategic AI roadmap with clear risk contingency protocols 🟢 Align all AI initiatives with broader business objectives ✓ Drive Stakeholder Engagement 🟢 Build a cross-functional AI coalition (executives, HR, business units) 🟢 Communicate AI initiatives with transparency to reduce resistance 🟢 Document tangible benefits to secure continued buy-in ✓ Implement with Agility 🟢 Replace waterfall approaches with iterative AI development 🟢 Focus on quick prototyping and real-world testing 🟢 Ensure infrastructure scalability supports AI growth ✓ Lead with AI Ethics 🟢 Train teams on bias identification and mitigation techniques 🟢 Establish clear governance frameworks with accountability 🟢 Make responsible AI deployment non-negotiable ✓ Transform Your Talent Strategy 🟢 Enhance IT roles to integrate AI responsibilities 🟢 Create peer mentoring programs pairing AI experts with domain specialists 🟢 Cultivate an AI-positive culture through early wins ✓ Measure What Matters 🟢 Set specific AI KPIs that link directly to business outcomes 🟢 Implement continuous feedback loops for ongoing refinement 🟢 Track both technical metrics and organizational adoption rates The organizations mastering these elements aren't just surviving the AI transition—they're thriving because of it. #digitaltransformation #changemanagement #leadership #CIO