If one thing is certain these days, it’s that uncertainty is top of mind for many leaders. In this episode of the Leading Learning Podcast, number 453, co-hosts Jeff Cobb and Celisa Steele discuss four habitsets that can help learning businesses navigate uncertain times: informed agility, strategic foresight, stakeholder intimacy, and portfolio thinking.
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Celisa Steele: [00:00:03] If you want to grow the reach, revenue, and impact of your learning business, you’re in the right place. I’m Celisa Steele.
Jeff Cobb: [00:00:10] I’m Jeff Cobb, and this is the Leading Learning Podcast.
Jeff Cobb: [00:00:17] There’s one topic that we can say with confidence is top of mind for a lot of learning business leaders these days, and that topic is uncertainty. More specifically, how to navigate your learning business in uncertain times.
Celisa Steele: [00:00:30] And so navigating uncertainty is what we’ll talk about in this episode, number 453, and in our next. Our two-part conversation is going to draw heavily on a keynote that you gave recently, Jeff, to a group of standards development organizations, but the ideas that you shared apply not just to SDOs but more broadly across all types of learning businesses.
Jeff Cobb: [00:00:54] Definitely. Whether you’re with an association, a higher ed continuing education unit, a for-profit training firm, or any market-facing learning business, we’re all operating in a much more uncertain, fast-moving environment than we were even a few years ago. That’s what I addressed in that keynote, and that’s what we’re going to dive into here today.
Celisa Steele: [00:01:16] You started your talk—good comp lit major that you are—with a Zen parable.
Jeff Cobb: [00:01:22] Yes, it’s always a good policy to start with a Zen parable. This is an old one I remember reading to the kids when they were younger. There’s a farmer whose horse runs away one day, and the neighbors say, “Oh, that’s very bad luck. You’re not going to be able to farm your land now.” And this farmer says, “Hmm, maybe.” A day later, his horse comes back and brings six wild horses with it, and the neighbors say, “Oh, that’s very lucky. Now you’re very rich.” And the farmer says, “Hmm, maybe.” A few days later, the farmer’s son decides to try and tame one of the wild horses, gets thrown off, and breaks his leg. The neighbors, of course, show up once again, and they say, “Oh, that’s really bad luck.” The farmer, of course, says, “Maybe.” And then the next week, soldiers come to draft young men into the army to fight in a brutal war, and the farmer’s son is spared because of the broken leg. “How lucky,” the neighbors say. And, of course, the farmer says, “Maybe.” That’s where the parable ends.
Celisa Steele: [00:02:30] Not to be too reductive, but the point of the parable is that what looks good or bad in the moment may not stay that way, and so a mindset of thoughtful uncertainty—a maybe mindset—can actually offer valuable perspective.
Jeff Cobb: [00:02:47] That kind of mindset leads to the question “How do learning businesses operate in a world where the outcomes aren’t always clear, and the variables keep shifting?”
Two Types of Disruption: New and Continuing
Celisa Steele: [00:02:59] You outlined two major types of uncertainty in your talk, Jeff: new disruptions and continuing disruptions.
Jeff Cobb: [00:03:07] That’s right. We’re facing some really intense new disruptions, and, by new, I mean the last year to six months or so. These newer disruptions include things like economic uncertainty with inflation, tighter budgets, slower decision cycles, those sorts of things. There are also political dynamics—both national and international—with elections, funding shifts, and geopolitical tension all affecting how people plan and prioritize learning.
Celisa Steele: [00:03:37] There are also continuing disruptions—things that have been reshaping our work and our lives over the past decade or so. Those disruptions aren’t going away. One of those is the evolution of the workforce.
Jeff Cobb: [00:03:51] Absolutely. The rise of non-traditional career paths, the emphasis we now see on upskilling and reskilling, new forms of credentialing—those have been growing for years, but now they feel like they’re accelerating. Learners expect more flexibility. They expect relevant, personalized experiences. And employers want proof of competence, not just participation.
Celisa Steele: [00:04:16] Then there’s ongoing disruption coming from the realm of technology, particularly artificial intelligence.
Jeff Cobb: [00:04:23] Yes, AI is obviously the big one right now. It’s reshaping how we develop content, assess learning, and even how we think about expertise. But it’s also the latest step in a longer trend of tech-driven change—massive open online courses, the evolution of LMSes, microlearning, mobile-first design. All of it’s pushing us to rethink how we deliver and sustain learning over time.
Celisa Steele: [00:04:53] With all of that swirling, a natural instinct can be to retreat or hunker down—to try to avoid risk by not doing anything. But you argue for a different response. You talked about antifragility in that speech that you gave.
Jeff Cobb: [00:05:12] Yes, it’s a concept that I really like. It comes from Nassim Taleb, who’s a philosopher who came out of risk management of all things, the financial world, and was informed by his work there in developing some of his theories. But the way he views it, a fragile system breaks under pressure. On the other hand, a resilient system resists pressure, and it survives. But an antifragile system actually grows stronger because of pressure. That’s really what we want in a learning business or any business—a structure and culture that not only can weather uncertainty and the disruptions that come with it but learns from that, adapts, and improves. It’s probably helpful to have some examples around this to get at what Taleb is talking about.
Jeff Cobb: [00:06:04] In the human body, for example, the muscular system I would describe as antifragile. If you’ve ever spent some time at the gym and had anybody instruct you on how to do things right, you know you have to work your muscles to the point of failure, to the point where you actually get little tears in your muscles for them to then grow and for you to develop that muscle mass. So that human muscular system is antifragile. In Greek mythology—this is often one of the examples that’s given for antifragility—the hydra would be an antifragile being. If you chop off one of the heads of the hydra, two are going to grow back. It’s always going to get stronger if you keep hacking at it. But let’s talk about something from the learning world, specifically from the association world.
Jeff Cobb: [00:06:50] A few years ago when COVID happened, Ralph Johnson, who, at that time, was the CEO of the Veterinary Medicine Association Executives (VMAE)—which is like the association for the heads of veterinary medical associations—saw what was happening with COVID. They had, I think, their own annual conference planned, and he was thinking, “We’re not going to be able to have this thing. It’s going to have to go virtual. As a matter of fact, that’s going to be true for all of my members. All of their meetings are going to have to go virtual as well.” Instead of holding the usual face-to-face meeting, he held a virtual conference about how to hold a virtual conference for his members, for the leaders of his membership organizations. He took that opportunity, that disruption, to do something that created tremendous value for his members, both right there in the moment, and, I’m sure, increased their perception of VMAE as a source of value over the longer term.
Celisa Steele: [00:07:50] Those examples are helpful. And bonus points for pulling in Greek mythology to go along with your Zen parable earlier. Well done there.
Jeff Cobb: [00:07:57] Spanning the globe here, yes.
Celisa Steele: [00:07:59] This idea of antifragility brings to mind for me that old saw, “Never waste a crisis.” Ralph Johnson was not wasting a crisis. He could have said, “Oh, no, we can’t have our annual meeting.” But instead of panicking or even just pivoting for his organization alone, he saw an opportunity. That was very powerful. That was definitely not wasting a crisis there. Now, when you talked about building antifragility, you were talking about some habitsets that we can cultivate to help us with that antifragility. “Habitset” is a term that you borrow from Kevin Eikenberry, who’s been on the podcast before.
Jeff Cobb: [00:08:42] Yes, even just recently. We often talk about skillsets and mindsets. I think everybody knows those terms. But what Kevin emphasizes—and what I found very powerful—is the idea of habitsets. They’re not just what you know or believe but what you consistently do. Habitsets are embedded ways of acting that help you navigate change effectively.
Habitset: Informed Agility
Celisa Steele: [00:09:07] You outlined four habitsets in your keynote: informed agility, strategic foresight, stakeholder intimacy, and portfolio thinking. Let’s talk through each of those four habitsets, and let’s start with informed agility.
Jeff Cobb: [00:09:23] Informed agility means moving quickly but not recklessly. It’s about testing early, learning fast, and adjusting in real time. A lot of organizations equate strategy with very long and deliberate planning. You do want to be careful, to be deliberate, when you’re putting together a strategy. But, in uncertain times, strategy has to be more fluid. It’s not about predicting and locking in a plan; it’s about sensing, responding, and iterating. It’s exactly what Ralph Johnson did at VMAE. That was informed agility there. He learned quickly what the whole virtual conference thing was about, and then he used that.
Celisa Steele: [00:10:05] You gave an example of organizations that experimented with new (new to them anyway) delivery formats during the pandemic—maybe launching virtual events, as was the case with Ralph and VMAE, or new on-demand learning resources—and not waiting for perfection but saying, “We’re going to go ahead and put this out there, and we’re going to learn based on how our audience responds to this.”
Jeff Cobb: [00:10:30] Right. They weren’t waiting for all the answers. They tried something, listened to feedback, refined the offer. That’s informed agility. It’s not just about speed; it’s also about insight. You need mechanisms to gather data and hear from your audience as you go, not at some arbitrary timeline of every three years or five years when it’s “time” to conduct your annual needs assessment again.
Habitset: Strategic Foresight
Celisa Steele: [00:10:53] That was a look at informed agility. Let’s move to the second habitset: strategic foresight, which ties very nicely to what you were just talking about, Jeff, about listening as part of what you’re piloting or trying out. Strategic foresight is about scanning the horizon.
Jeff Cobb: [00:11:13] Yes, strategic foresight is not about trying to predict the future with any real accuracy; it’s about watching for signals, seeing patterns that are emerging, and asking, “What might this mean for us?” And, more importantly, “What would we do if this trend accelerated?”
Celisa Steele: [00:11:33] We’ve had Rohit Bhargava on the podcast before (four times), and he talks about the non-obvious—that you’re looking for non-obvious trends; you’re looking for the stuff that’s out there, but nobody else is quite paying attention to it yet, but you can begin to get an idea of where it’s going to go and what that might mean. And, if you can do that, if you can pay attention to it and see what it might mean, boy, that’s a real leg up in terms of being able to respond to what your audience needs.
Jeff Cobb: [00:12:03] Rohit talks about that sort of thing. And Jeff De Cagna, who we’ve also had on the podcast multiple times (another four-timer), is really big on strategic foresight, so it’s appropriate to mention his name here too. He describes strategic foresight as an intentional process of learning with the future.
Celisa Steele: [00:12:21] I like that “learning with the future.” Some of those trends that you might be looking for, when you have your strategic foresight habitset going, are things like generative AI, remote-first workplaces, how certification and licensure requirements are shifting. None of those should be total surprises now. They don’t even qualify as non-obvious. But there may be some non-obvious trends that relate to those.
Jeff Cobb: [00:12:51] The signs have been there, and you need to carve out space in your planning and conversations to explore these things—before they become urgent. Strategic foresight isn’t extra; it’s essential as an ongoing habitset.
Celisa Steele: [00:13:05] It’s also important to note too that it’s not necessarily a solo activity. If you are going to be engaged in strategic foresight, yes, it’s probably about you carving out some time on your own to observe and reflect, but you could also involve others. You suggest forming foresight groups—even informal ones—inside a learning business.
Jeff Cobb: [00:13:26] It can be as simple as getting three to five colleagues together once a month to discuss, “What are we seeing out there? What’s on the edge that might move to the center?” That small investment can yield a huge payoff in organizational readiness.
Habitset: Stakeholder Intimacy
Celisa Steele: [00:13:43] We’ve talked about two of the four habitsets: informed agility and strategic foresight. Let’s move on to habitset number three: stakeholder intimacy. I really appreciate the way you phrase this one, as intimacy gets at the idea of this being a relationship. It makes it clear that this goes beyond customer service or even customer journey. This is about real people, not personas.
Jeff Cobb: [00:14:10] It’s about depth. Stakeholder intimacy means you know your learners, your members, your customers—not just in terms of their titles or roles but their motivations, their contexts, their struggles. And you know not just the most vocal ones and the ones that come to your annual meeting and sign up for your courses, but the ones who don’t. The ones who are reluctant for whatever reason to respond to your surveys. They’re the ones who maybe never even open the e-mail asking them to respond to your survey.
Celisa Steele: [00:14:41] And that intimacy can’t come from a one-time survey anyway. It takes ongoing, intentional engagement. It is a relationship, and relationships are organic and living, and they evolve and change.
Jeff Cobb: [00:14:55] You listen actively. You conduct interviews. You ask open-ended questions. You test things early and see how people respond. It’s about forming, again, genuine relationships with the people you serve. And the payoff is that you can design offerings that actually meet real needs—not just what you assume the needs are.
Habitset: Portfolio Thinking
Celisa Steele: [00:15:16] That was a look at stakeholder intimacy. And that brings us to our fourth and final habitset: portfolio thinking. This is about how you design and structure what you offer.
Jeff Cobb: [00:15:29] Exactly. We’ve been big on this for a long time. Too many organizations rely on a single-point revenue source, like an annual conference or one major course or credential. That’s risky. Portfolio thinking means developing a range of offerings—different formats, different price points, different entry points into your catalog of options.
Celisa Steele: [00:15:54] Then you’re not selling just one course. You might be building pathways. You might be offering microlearning, deep dives, and bundled subscriptions. You might have place-based learning. You might be offering ongoing support. There could be a whole range of things that might be part of your portfolio.
Jeff Cobb: [00:16:12] Ideally, these offerings reinforce each other. They’re telling that logical story that fits together. A Webinar leads to a short course. A short course leads to a credential. A credential leads to participating in cohort-based communities. So you move from isolated transactions to sustained engagement.
Celisa Steele: [00:16:31] You made the point that portfolio thinking isn’t about doing more—it’s about being more coherent and designing with intention. I think you were just pointing to that with that idea that your offerings hopefully reinforce one another.
Jeff Cobb: [00:16:46] That’s the core of any sort of strategy. It’s certainly the core of portfolio strategy—being coherent and designing with intention. You don’t want 37 unrelated offerings. You want a set of offerings that may be much smaller but that work together to serve the learner and support your strategy.
Recap, Some Homework, and a Preview of What’s to Come
Jeff Cobb: [00:17:10] We’ll recap the habitsets and preview what’s to come in the second part of our look at navigating uncertainty, so stick around to the end.
Jeff Cobb: [00:17:26] If you enjoy the Leading Learning Podcast, we’d be grateful if you’d mention it to one colleague or co-worker you feel would get value from it.
Celisa Steele: [00:17:35] To recap, we talked about four habitsets. First, informed agility—this is about moving quickly but with insight. You want to be piloting, testing, and then adjusting in real time.
Jeff Cobb: [00:17:47] Second, we talked about strategic foresight. Regularly scan for weak signals out in your marketplace, and explore possible futures.
Celisa Steele: [00:17:58] The third habitset, stakeholder intimacy—this is about staying really close to your learners, your members, your customers, really getting to know them deeply. And then the final habitset we talked about was portfolio thinking—this is about designing an integrated suite of offerings that help you spread risk and also reinforce value.
Jeff Cobb: [00:18:21] Cultivating these habitsets gives you a foundation for navigating uncertainty—not just reacting to it but learning from it and growing stronger.
Celisa Steele: [00:18:31] In our next episode, we’re going to turn to five practice levers that help you activate these habitsets, that help you move from ideas to action.
Jeff Cobb: [00:18:41] In the meantime, here’s a little homework, something to help with reflection and application. Think about a challenge you’re navigating right now—one that you attribute specifically to the uncertainty we’re experiencing, one where the ambiguity, volatility, or complexity of the current environment is making the solution difficult to see or act on. Pause here, and really think about that. Don’t go abstract—get specific.
Celisa Steele: [00:19:11] Maybe your challenge is a drop in enrollment or registration for an event. Maybe it’s a stalled product development issue. Maybe it’s a board that’s hesitant to invest. Whatever it is, identify that specifically, and then ask, “How is uncertainty shaping this challenge? And what opportunities might that uncertainty open up?”
Jeff Cobb: [00:19:34] Sometimes uncertainty isn’t just an obstacle; it’s a spotlight. It highlights the fragilities in your system. It forces decisions that were, frankly, long overdue. It creates space for new approaches.
Celisa Steele: [00:19:47] Once you have that specific challenge in mind, ask, “Which habitset, of the four that we talked about, could help you address that challenge more effectively?” Is it time to be more agile? Is it time to be more attuned to your stakeholders? To be more forward-looking? Or to be more intentional in how your offerings work together?
Jeff Cobb: [00:20:09] Again, this isn’t a rhetorical question. We mean this as something for you to truly try to answer. And these questions aren’t just for you as an individual leader—they’re great prompts for a team conversation.
Celisa Steele: [00:20:21] Thanks again, and see you next time on the Leading Learning Podcast.
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