Beyond Buzzwords: Rethinking Leadership and Strategy with Ben of Strategy Teaming
I’ve been known to roll my eyes at the word strategy (especially in the marketing world, where it’s often used to mean… well, everything and nothing). But that’s exactly why I wanted to interview Ben of Strategy Teaming, a master of strategy who doesn’t just talk about alignment, leadership, and systems; he redefines them in his signature grounded, curious, and human way.
Ben works with senior leaders inside big, complex organizations … and yet he shows up without the fake corporate gloss. No buzzwords unless they serve a purpose. Just clear thinking, intentional language, and an unshakable sense of curiosity that challenges people to think differently.
I went into this conversation skeptical about strategy as a concept. I came out of it interested in a new reframing of what strategic discussion could mean for organizations. If you've ever felt like strategic work is too abstract or inaccessible, Ben’s perspective might surprise you - in the best way.
Q: One of the reasons I enjoyed speaking with you so much is that you don’t get stuck in the “corporate” vernacular—you show up as grounded, authentic, and kind. I noticed you mention in your marketing that you’re focused on “unorthodox ways to intentionally think, know, and do.” Can you tell us more about what that means to you?
Ben:
I try to avoid corporate jargon because it’s sometimes difficult to tell whether someone’s using a buzzword to be more precise in what they’re saying, or if it’s just a way to self-soothe when feeling scrutinized by other people. Buzzwords are pocket sand!
To be fair, jargon can be useful between experts in the same area of work; it helps them have super dense conversations without covering the same ground over and over. But I’m often helping senior folks from different parts of the business try and work together. Speaking plainly when working across boundaries is just a good place to start in my work, at least until they find their own language.
And part of the reason that I talk the way that I do is also because it contrasts so heavily with the frustrating ways of speaking that many folks endure in their workplaces. Let’s double click on that and circle back on synergy on our glide path blah blah blah, etc.
Okay, so I admit there’s a sort of irony, then, in using a $10 word like “unorthodox” to describe what I do. I guess the best I can do is own it by unpacking it a little.
If something’s orthodox, then it’s normal and expected. It seems reasonable to say there are plenty of well-established ways of “thinking, knowing, and doing.” They seem to work for many. But what do you do if those ways aren’t working for you? From what I see, what people share, and what I’ve experienced myself, I get the impression that these well-established ways are failing us far more often than we’re comfortable admitting.
So that makes unorthodox options interesting. They’re strange, different, unexpected! That’s where I play. One of my favorites is a project I co-authored with my business partner, David Holl [pronounced “hall”], published by the UK-based Pip Decks. It’s called Strategy Tactics.
We saw that the dominant “strategy” tools and techniques weren’t working for many people who we knew were extremely capable, so we wrote 50-some recipes for strategic thinking, to provide them with an alternative.
And on the topic of jargon, because communication is so important in strategy, there’s a card in Strategy Tactics for dealing with buzzwords. It’s called Buzzword Breakup, and it helps you build a glossary of terms with a group by acknowledging all the different ways people use any given buzzword. Then, you can decide together what to do about it, from defining a buzzword it when you use it, to even banning it altogether. Harsh but sometimes helpful if you want to find new words!
Q: What is the current state of their business usually like when your ideal clients find you? What are they going through that leads them to you?
Ben:
We’re hired by senior leaders in large organizations that are building infrastructure important to our future. Think science, food, education. Not speculative AI ventures or consumer profiteering.
Usually, there’s too much work happening at once, and even though there may be lots of people involved, nothing feels like it’s getting done. It’s a stressful, uncoordinated environment. The small drama of everyday happenings and interpersonal issues is more compelling than the reason everyone is there in the first place. Leaders are also worried about saying the wrong thing, so they say very little. But then they might also micromanage the issues that do reach them and feel guilty about it afterwards. They wonder, “Is there something wrong with me, or wrong with the team?”
That’s their situation. From there, we do something that almost no consultants do. We promise outcomes. For instance, for our alignment work, we build a contract around salaries spent on-target or off-target. If we can help a leader create clarity that improves how aligned the work is to the strategy by 10 or 15%, that helps them twice: first off-target work stops throwing away people’s time and energy, and second, now that it’s on-target, you're more likely to get more of the results you actually want, whether it’s more revenue or more patients getting treatment, and so on.
Q: As you know, I tend to avoid the word “strategy”—it can mean so many things to so many people. But you mentioned that you’ve been exploring definitions of strategy that treat it as simultaneous planning and execution. Can you tell me more about that?
Ben:
On the meaning of words: I completely relate. I used to obsess about words and their definitions. (“Dammit, define your terms!!”)
And then I learned about Wittgenstein’s language games. (For example: Water. Water! WATER!! Water? Water!?? Five (probably more) different meanings and games to play with just one word!)
After language games, I gave up on defining the word and just focused on what the person was doing with it. I found that version of things less stressful, and it also made me less abrasive.
But now I’m back to defining words, albeit as playful proposals rather than perfect declarations. I retain the chill, but still get to make things meaningful.
On strategy: I am on fire about a version of strategy that wraps strategy and execution together as an ongoing, alive process.
For contrast, consider what we usually see: a strategy document, written in great detail over the course of many months, placed on the shelf, immediately made obsolete by current events, followed by weeping and gnashing of teeth about how the org is failing to execute, etc. (So far, I like my version better).
This “alive” process has been proven over hundreds of years (some parts of it over thousands), and it’s still in use today.
It all starts with having some way of appreciating the situation. Seeing it for what it is. Knowing how it likely works. You can use your favorite framework here. For me, it’s Wardley Mapping.
Once you have a grasp of the situation, then you must decide what’s wrong. What isn’t working? After all, if everything were fine, you wouldn’t need to do anything. Why bother with strategy?
Once you know what’s wrong, then you can decide what must be done. This part can get messy, but I like the Ideal Present approach by Dr. Jabe Bloom. You select a move that opens up new moves, or at least preserves as many future moves as possible. This becomes our “intent” — what to accomplish and why.
This is where the strategy / execution breakdown usually occurs. So instead of yelling at people now to do the thing we want, we start a process of ongoing feedback, making the process come alive.
First, is it clear what must be done? To test, we share the intent with people who we’d normally expect to carry it out. We ask them to repeat back what they heard, in their own words. Unsurprisingly, we will hear things we did not expect. Perhaps we got a key assumption wrong. Or maybe we shared our intent in a confusing way. Either way, we learn from that quickly and can adjust. We repeat this process until it’s clear that what we said is what they heard and understood.
Next, will we get the action we want? We ask the same people how they intend to act, now that they know what we want to do and why. They will likely share surprising intentions of their own. We have to sense whether their intended actions are likely to take us in the right direction, even if it’s not the way we’d do it ourselves. As you can imagine, we sometimes learn that we must add some important guidance. We repeat this process until it’s clear to all what must be done and why, and that they have their own intentions for how to go about it.
What we’ve created in doing things this way are the conditions for initiative. As soon as things fall apart (and they will), the people doing the work will adapt and still achieve the intent. They already understand how to overcome. They think like leaders.
You might not realize it but, what we’ve described so far is modernized command and control (with a few extra elements). It’s the way NATO performs joint operations, and what Stephen Bungay translates for civilian organizations in his book, The Art of Action.
I don’t know about you, but I aspire to go beyond just command and control. I think modern leadership is best viewed as a function of facilitation. In the view of Mary Parker Follett, to help the group see the situation for themselves and decide what must be done, without one person having to give orders.
This approach is far from chaos. It happens every day in places you’d least expect. People engaging in power-with rather than power-over (another Follett reference) to make things better, together.
We call this non-authoritarian version of living strategy, “Strategy Teaming,” taking inspiration from the likes of Amy Edmondson, Woody Zuill, and others. In short, we believe strategy ought to be a team activity.
Q: One of the things many of my clients struggle with is being so close to their business that they can’t see the bigger picture. What are some ways you help leaders or business owners get out of that tunnel vision and start thinking more strategically?
Ben:
Every person is different, and groups work very differently than individuals. So when it’s just one person, like a VP or CEO, I tend to do a lot of listening. I cannot go around beating people over the head because I want them to change. They have to want to change, and they have to change the way they want to.
For me, it’s a lot of open questions. “What’s happening?” “Can you tell me more about that?” “What do you think about that?” “What’s behind that?”
Occasionally, I get to be more confrontational and ask them harder questions. “Why does that matter?” “How do you want things to be instead?” It can feel like sparring at times. But that can only happen when there’s care, trust, and mutual respect.
If push comes to shove, I can always ask what will happen by default if nothing changes. “Do you like the future you’re likely to get, given what we’ve talked about so far?”
If someone can’t see the bigger picture, my instinct is to provide them with an experience. Something that lingers in the back of their mind. But in general, I’m not inclined to do interventions. The people I want to work with already want to see the big picture. They just aren’t sure exactly how to do it. I’m not in the business of convincing anyone to be more strategic!
Q: What do people often get wrong about having strategic conversations inside their organizations?
Ben:
A few big things come to mind:
Not having a process, just wandering through it and hoping for the best.
Letting vibes rule the day, with decisions based on what feels good.
Theorizing, for far too long without taking any sort of action to prove/disprove the theory.
Avoiding feedback and challenge, and needing to be right. (You gotta be wrong in order to learn, sometimes.)
Q: How can people connect with you or find out more?
Ben:
You can sign up for our newsletter at StrategyTeaming.com.
So, what do you think?
Talking to Ben opened me to the idea that strategy doesn’t have to be vague or inaccessible. It can be alive. Responsive. Grounded in listening and built on trust. It can be a plan that actually gets implemented. It’s not about having the right buzzwords or the “perfect” plan, but instead, it’s about learning to see clearly, act intentionally, and adapt as you go.
Ben’s work lives in that rare overlap between intellectual rigor and genuine care. His approach invites people to think bigger and get more honest with themselves, their teams, and the systems they’re trying to shape. In a world full of performative leadership and jargon-filled decks, Ben’s voice is the one I want in the room!
If you're curious about what real strategic work looks like—or if your organization feels stuck and you're not sure why—go get on his newsletter at StrategyTeaming.com.
