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title: "Field Notes: Who’s in your corner on AI?"
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The conversations leaders aren’t having at work ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­    ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏  ͏ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­  

| View in browser THIS MONTH'S FIELD SIGNAL The Conversations Leaders Aren’t Having  Lately, a lot of my conversations end up in the same place. We start with AI: the tools, the pilots, the pressure to show results. Somewhere along the way, the person I’m talking with says some version of this: I don’t really have anyone to think this through with. It shows up at every altitude. Senior executives describe peers who are just as stretched as they are, so there’s rarely time to work through anything together. Founders describe having no one inside the company they can confide in. Solo practitioners describe working without colleagues at all. I think this pattern is surfacing now because AI has changed what leaders are being asked to decide. They’re making calls about tools, governance, their workforce, and role design with very little precedent. Often they’re expected to sound more certain than they feel. And some of what they’re learning is hard to say inside their own building. It might be that AI is creating more work in the short term, not less. Or that they’re worried about where the next generation of experienced talent will come from if AI absorbs the entry-level work where people used to build judgment. The research reflects what I’m hearing. Gallup’s 2026 State of the Global Workplace research looked at leaders who manage other managers. They are more engaged and rate their lives more highly than individual contributors, yet they are simultaneously more likely to report feeling lonely for much of the previous day. Engaged leaders, though, were far less lonely than disengaged ones. That suggests this isn’t simply the price of seniority. It depends on conditions, and conditions can change. There’s a broader version of this too. Many people I talk with, at every level, describe work that’s faster and more productive and somehow thinner, with more time spent with tools and less with people. What they’re hungry for isn’t more information. It’s real conversation with people who understand what they’re dealing with. I go deeper on this in my new article, Who Do You Tell the Truth To?, including why peer groups matter so much right now and what makes them work. Read the article FROM THE FIELD Supported, but Not Understood A leader I’ve known for years recently made a big move. After a long tenure at a large company, she took a senior role at a much leaner organization. Her team is a fraction of the size of her old one, and so is her budget. She’s building something new, and she’s energized by it. Like nearly every leader I talk to, she’s also working out what AI means for her function at the same time. What she hadn’t fully anticipated was who she’d be building it alongside. For the first time, she reports to someone outside her discipline. Her boss is supportive and usually defers to her judgment. When they do disagree, though, she has to start by explaining the reasoning behind work her former peers would have understood without explanation. And most of those peers are back at her old company. When we talked, she said she’d been feeling isolated. What struck me is that she wasn’t describing a lack of support. She has that. What she was missing were people who could look at the same problem from her angle and push her thinking on it. I think a lot of leaders are in that position right now. A peer group doesn’t replace a good boss or a strong team. It adds something they can’t provide: people at a similar level, facing similar questions, who can take on your problem as if it were their own. QUESTIONS FROM THE TRAIL Ask Yourself Who outside your reporting line could you tell the truth to about how AI is actually going in your organization? When did you last talk with them? What’s a question about AI you’ve been carrying that you haven’t said out loud at work? What makes it hard to raise? If you lead other leaders: where do they get to learn from peers outside their own chain of command? Is that happening by design, or only by chance? TOOLS FROM THE TRAIL A Simple Format for Your Own Peer Roundtable You don’t need a formal program to start getting some of this value. If you want to pull together a few peers for a one-time or recurring conversation, Lean Coffee is a format worth borrowing.   Everyone proposes topics at the start. The group votes on what to discuss. Then you work through the topics in short timed rounds, and the group decides at the end of each round whether to keep going or move on. Because the agenda comes from the participants, the conversation stays on what people are actually wrestling with, not on what one organizer guessed they’d want. It works just as well virtually, with a shared online board.   A few things make it work better for leaders: Keep the group small. Invite people from non-competing organizations. Agree up front that what’s shared stays in the room. ONE SMALL STEP Navigating This Together If this issue resonated and you’d like a place to think out loud with peers working through the same questions, I’m building a peer cohort for senior leaders navigating AI and organizational change. If you’d like to take a small step, reply to this email or reach out, and I’ll tell you more about it. Learn more about the cohort Field Notes from the AI Trailhead is drawn from real conversations with leaders navigating AI adoption. Names and details are anonymized; patterns are not.   You’re receiving this email because we’ve connected at some point about AI, leadership, or communications/marketing, and I thought you might find these field notes useful. I’ll send this about once a month. If it’s not helpful, you can unsubscribe anytime using the link below—no hard feelings. Trailhead Communications, 7327 SW Barnes Rd #1014, Portland, OR Unsubscribe Manage preferences |
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