Pre-S: A quick note to start today’s edition. Ryan Jasperson and I have been collaborating so closely on this work that he's basically a co-author of this piece. Ryan has been steeped in research and writing on the topic of discontinuity, so much of what you’ll hear today, while penned by me, is the result of his efforts. You’ll get to know him more in the coming weeks, promise!

I spent last week at the Transform conference in Vegas. Three days of back-to-back sessions, hallway conversations, dinners, and parties with people who are thinking hard, swapping insights, and trying to make sense of potential futures of work.

While there, I had a primary mission: to be attuned to if and how the theme of discontinuity was showing up in the people space. And it certainly presented itself.

One moment in the plenary session stood out. In a room of 500+, Inna Landman, CHRO at Procore Technologies, was asked what it's been like to navigate her role amid such change. She responded: "I've had to be okay with being behind. And that's really hard for a high achiever who feels like they have to have all the answers."

The room got quiet. Because she wasn't describing a personal failing. She was describing the actual condition of leading right now, and being honest about it in a way most executives aren't. And I found myself thinking: why is that so hard? Not personally, but structurally.

What is it about how we've built leadership, developed it, and rewarded it, that makes "being behind" feel like failure rather than just a condition?

This week, I want to explore that question by offering the three traps of leading in a discontinuous environment that Ryan’s identified. We’re calling them “traps” because they're not obvious mistakes. They're things that used to work. That's what makes them particularly perilous.

1: The Expertise Trap

The most successful organizations are often the most vulnerable.

All that accumulated knowledge—the proven playbooks, the hard-won pattern recognition—becomes a cognitive architecture that filters out signals of fundamental change. Your expertise is literally preventing you from seeing what's in front of you.

During a panel entitled "C-Suite Succession in the Age of Disruption," Ana White from Walmart said: "Leadership attributes of today are very different from the past. One of the biggest is learning agility combined with a growth mindset. You need leaders who can learn, relearn, unlearn, and learn again."

What she’s advocating for is the knower-to-learner shift. However, we’ll take it a step further to say that what we do with that learning is critical. Does it simply continue to reaffirm our previously held beliefs? Or, does it contribute to collective intelligence, which asks the group to see what none of them could see alone? Shifting to a learner’s mindset is not a coaching platitude; it's a structural response to the expertise trap. The more you've succeeded, the harder it is to recognize when the environment that rewarded your success no longer exists.

2: The Predictability Illusion

Most organizations are still investing heavily in planning tools designed for a different kind of world.

Roadmaps. Dashboards. Annual strategy cycles. These assume stable underlying dynamics that, if you think carefully enough, you can anticipate what's coming. In a discontinuous environment, that's a trap. You end up with beautifully constructed plans built in environments that no longer exist for worlds that will never come to fruition.

Every January at Experience Institute, we kick off the year with a team strategy retreat. We used to focus our time together heavily on creating a 3-year plan with a 1-year strategy that laddered up to it, quarterly goals aligned with meticulous KPIs to measure our progress. Now? We’ve ditched the 3-year plan, and focus way more on small experiments and pilots that test our hypotheses about what we think our partners will want and need for the year.

The uncomfortable version: your annual planning process may be optimizing your organization for the wrong future.

3: The Individual Heroism Fallacy

This one is the hardest to name because it's so embedded in how we think about leadership.

We built the entire executive development model on the belief that "better" individuals—more skilled, more experienced, more emotionally intelligent—can solve any problem. And for a long time, that was close enough to true.

But at Transform, I kept hearing a different signal underneath the AI conversations. In a session on aligning people and technology, Melanie Naranjo, CPO at Ethena, put it plainly: "Too many C-suite leaders try to solve problems by themselves instead of leveraging the collective brain power of their employees." Her point wasn't about being more collaborative in some warm, cultural sense. It was more pointed than that: leaders operating at altitude, disconnected from the day-to-day, miss the intelligence already within their organizations. The answer isn't a better leader at the top. It's going to the ground to ask what's working, what isn't, and what hasn't even been explored yet, and then actually enabling people to solve problems from there.

The shift isn't cultural. It's architectural.

Come think with us

Ryan and I are hosting a live session on April 15, Discontinuity: When Experience Becomes the Problem, geared toward senior people leaders and HR executives, where we're going to do more than name these. We're going to give you a direct experience of the alternative.

True to Ei fashion, this won't be a lecture, but an exercise in collective intelligence, so the concept lands as something you've lived rather than just heard.

You can register here.

I hope you'll join us. And as always, if any of this is landing (or not, for that matter!), let's connect.