The 7 Dark Elements of Pioneering Leadership
Everything casts a shadow—even the lantern of pioneering leadership
Do you have ‘The Pioneer’s Curse’?
‘Pioneering’ is a term I am beginning to see crop up about the place. This is probably due to the fact that How to Lead a Quest is ‘a handbook for pioneering leaders’, with ‘pioneering’ being a concept I thoroughly romanced throughout the book. I may have a bias.
But, now that I’m seeing other folk get misty-eyed about pioneering, I’m inclined to point out it’s shadow side—The Pioneer’s Curse.
It’s a rather frustrating habit I relish in.* Give me conviction, certainty or any tightly-held beliefs, and I’ll happily season them with a fresh dose of doubt. This is not done with any malice or spite, but rather: to keep people open to possibility; to alternative pathways, perspectives and ways of seeing. It's probably annoying.
* Like speaking in paradox.
So, to the motivational leadership speaker who confidently shares their ‘formula for success’*—as though there exists a single hidden universal formula to follow—I say: ‘really?’. But likewise, when confronted with a friend who believes—with conviction—that they are ‘trapped’ with a limited range of choices, and stuck upon a narrow, default path—I say:‘is that really so?’.°
* My favourite straw man.
° The same could be said of any executive—you have more options than you think.
The world is never black and white. It’s never quite that simple: though it may be comforting to think so. The world is grey,* and full of contradiction and paradox.
* And ROYGBV. And then, do colours even exist?
Ahoy the fine art of self-contradiction
If you have read both of my books, you'll have noticed I contradicted myself quite significantly. In The Game Changer I waxed lyrical about the virtues of The Progress Principle—fascinating research by Professor Teresa Amabile and her partner Professor Steven Kramer. In a nutshell: our efforts gravitate to the things that provide the richest sense of progress. It's the #1 fulfilment factor at work. Want your staff, your customers, or yourself to be more motivated to do something? Reduce the latency between effort and feedback, and create clear visibility of progress.
This—when combined with principles of game design and behavioural psychology—makes for an incredibly effective way to shape your personal and collective work culture. Rather than try to change people, or motivate them with extrinsic rewards, you can change the game itself, and make work inherently motivating.
And thus: visibility of progress (paired with other elements of motivation design) became the main thesis of the book.
But then, in the year or so that followed the release of The Game Changer, I began to notice a trend amongst the senior leadership teams I was working with: a tendency for strategy to only default to things that provided a clear sense of progress. This is potentially fine for operational leadership—but if you’re pioneering, it’s potentially devastating.
To quote Amazon’s CEO Jeff Bezos:
"Some companies have more of a conqueror mentality. If you look at their annual strategic plan, it starts with their three top enemies, who they’re going to crush this year… We have an explorer mentality, so we like to go pioneering. We like to find dark alleyways and wander down them and see if they open up into broad avenues, and sometimes they do. That pioneering, explorer mentality is really what drives us."
Over time, I became so frustrated with executive teams seeking myopic quick fixes to conquer familiar goals on the default path in order to obtain incremental one-ups on competitors. Such things are all very reasonable. And such things are easy to set targets to, which makes it easy to craft accountability and viability of progress—the cognitive burden is minimal.
But such things detract from the bigger opportunity to pioneer—to explore new paths, to unlock new value and new ways of working.
And so, in How to Lead a Quest, I contradicted myself somewhat. I introduced the concept of The Progress Delusion—a scenario in which the things that provide us with a clear sense of progress are the well established default ways of working. Those routine things we’ve done before, that require minimal cognitive effort to achieve, and which provide a rich and immediate sense of progress.
The Progress Delusion is what sees us seek greater efficiencies within known paradigms, rather than explore new ones. And it is usually defended by familiar statements like 'what gets measured is what gets done.' It’s the thing that sees us clearing our inbox, organising another meeting, ticking off KPIs and filing yet another report—all at the expense of working on the activities most conducive to meaningful progress. It’s the thing that sees us cling to the security of certainty, rather than pioneer into an uncertain future.
I'm quite comfortable contradicting myself. Like Jeff Bezos, I don't believe consistency of thought is particularly useful trait—especially amongst leaders.
Rather, it's better to approach things like a scientist—to hold beliefs lightly, to challenge them constantly, and to update them frequently in light of new evidence.
Why am I telling you this?
I’m telling you all of this as a precursor to my unpacking of The Pioneer’s Curse. In my book, I discuss The Curse of Efficiency—the very thing that leads to Default Thinking and The Delusion of Progress. It seems only fair that I explore the dark side of pioneering.
I daresay this won’t affect many people. Most leaders just want to chase more revenue for their organisation (and their bonuses); and most workers just want to be paid well, achieve set priorities, and periodically receive an increase to their salary.
Most—but not all. If you’re reading this, you may well be different. Blessed, and cursed with a pioneering spirit.
The 7 Dark Elements of Pioneering Leadership
Pioneering leadership brings about many wonderful things—the key of which is enduring relevance. You can read more on that in my book.
Not in my book, though, are my thoughts on the shadow side of pioneering leadership. Because everything has it’s shadow side.
Let's see how blessedly cursed you are.
1. You frequently experience discontent
Most of us are familiar with the phenomenon of ‘constructive discontent’. If you’ve ever set a goal, you’ll have created a form of constructive discontent—a discrepancy between your current state and a desired future state. Your attempts to reduce the discrepancy between these two states is what gives rise to progress. And progress is glorious.
But unlike simply achieving goals, hitting targets or making incremental improvements upon previous performance, if you’re cursed with a pioneering spirit there is no victory. There’s always more that can be done, new things to learn, and better paths to discover. Success is fleeting—progress: infinite.
This can be incredibly fatiguing. After all, constructive discontent is still a form of discontent. You are still comparing the present state against a more ideal future, and comparison is a fantastic way to catalyse unhappiness. Left unchecked, it can wear away your wanderlust—the very thing that sparks the urge to explore and pioneer.
Mindfulness mitigates this.
The m-word. I still have a heap of work to do for myself in this area*. I find Rohan Gunatillake’s approach to be very useful, particularly for those seeking mindfulness within a digital world. He’s the creator of the Buddhify app and the author of This Is Happening. Many have also recommended that I read Tara Brach’s Radical Acceptance. Stoicism is also a thoroughly useful philosophy to explore. Oliver Burkeman’s The Antidote: happiness for people who can’t stand positive thinking is a useful primer, as is this very deep post from Tim Ferriss. And of course, there is a stack of science to support a daily ritual of gratitudes—the ability to appreciate the relationships you have, the lessons you have learned, and the progress you’ve made.
* Oh bless, constructive discontent again.
2. You don't (often) make quick decisions
Others might see you as indecisive, but really, you like to think thoroughly: to mitigate cognitive bias and maintain optionality—the ability to avoid being locked into any singular course of action, so that you may adapt your plans as you obtain new information.
To pioneer is to explore—to keep all options on the table, and to avoid collapsing possibility into a singular defined path.
Of course, decisions must be made, as choosing to not choose is still a choice. Pioneers just might take a little longer to decide, rather than rush in blindly, or default to the familiar.
Transparency mitigates this.
The more frequently and openly you share your thinking, the more others can appreciate the implications of the choices you need to make. Rather than keeping it all within your head, keep an active and open journal, or share your updated thoughts via an internal comms platform (like slack). When you do make decisions, frame them as experiments. You don't need to wait for clarity or certainty—this will allow you to proceed without conviction (and make meaningful progress without robbing your ability to pivot or adapt when needed).
3. You struggle to ‘dumb things down’
But why would anyone want to? Nothing is simple. And nothing is right or wrong, black and white—everything is multicoloured grey. Shit’s complex.
But unless they’re with you on the journey, it can be hard for people to keep up with you—to grasp the complexity as you do. And to be fair, the curse of knowledge is a known cognitive bias.
People want simplicity; to be reassured of their own world view—but you struggle to provide this reassurance. Rather than placating them with platitudes, you seek to provoke new and better thinking. You hold yourself and others to a higher standard of thinking: one that ruthlessly questions assumptions and biases, and one that sees people see more.
Thought leadership mitigates this.
If you’re pioneering, your job is to shine a light on the path for others. You’re the vanguard—nay: the avant garde. Matt Church (the founder of Thought Leaders Business School) recently wrote an article on the inside job of thought leadership—which is particularly apt for any pioneer. It was Matt that helped me learn how to ‘smarten ideas down’, rather than dumbing them down.
4. You constantly feel like an imposter
Any moment now, someone will call you out. They'll point to this heretical new thinking of yours, and denounce you as the fraud you are. You'll then be escorted from the building.
This imposter syndrome is not a bad thing—in fact, it’s quite common. And self-doubt can be a good thing.
But it’s still a thing.
As Oliver Burkeman writes: the more you rise and develop as a leader, the more likely you are to have other successful colleagues to compare yourself to. Of course, you’re comparing your internal thoughts with their external front. You can’t see their insecurity, and as such, your insecurity is amplified. If you’ve got the Pioneer’s Curse—if you’re inclined to lead through uncertainty, with no map to rely on—then this will only be amplified hugely.
Vulnerability mitigates this.
Naturally, you’re familiar with Brené Brown’s work. A good pioneering leader doesn’t pretend to have all the answers. Rather, you take a more antifragile approach—you're comfortable being 'found out', because it enriches your thinking. You know it is better to be caught having pioneering thoughts, than to be caught having no new thinking at all.
5. You're incredibly unproductive
You struggle to pursue tasks that only perpetuate the status-quo. And then, when busyness hits you, you're bad at it. You don't 'thrive' under external pressure, and you aren't anywhere near as efficient as you could be.
You are at your best when you're doing deep work—but this can appear lazy to others. Deep work, as Cal Newport puts it, is cognitively demanding work that requires you to focus (without distraction) and apply skills that are hard to replicate. It's deep work that produces the things that matter most in this world.
Delegation mitigates this.
You need to play to your strengths. Not everyone can pioneer all the time. In fact, for the vast majority of work, we need people who are efficient—otherwise nothing would get done. We need people who are operationally magnificent—otherwise we'd burn too much energy in un-leveraged effort. Play to your strengths, and work to the strengths of those on your team. If you don't have a team, outsource the things you suck at. If you can't do that, batch-process busywork so that you have uninterrupted make-time.
6. You're the black sheep in the boardroom
It’s a tough gig being a pioneer. You're the one challenging the status-quo, and it's making everyone uncomfortable.
Good! Comfort breeds complacency, which catalyses our collective decline into irrelevance. Pity the fools who think otherwise. We need to be uncomfortable. But that doesn't mean people are going to like it.
You want to be progressive and make clever happen, but everyone else just wants to be productive, and make shit happen. What's more, they resent your crazy new thinking, because it just means more work and change for them.
Diversity mitigates this.
Why is it just you who is the black sheep? Are you on an all male panel, perchance? Can we bring some other perspectives into the mix? Not more black sheep no. And certainly no more white sheep. But why not a purple sheep? Or a tangerine sheep? Let's get a rainbow flock happening. Because if you care about quality thinking, you care about diversity. To do otherwise is an anathema to meaningful progress.
7. Everything takes longer
If you have the Pioneer's Curse, you cannot fathom doing something that doesn't contribute meaningful progress. You're not so good at replicating, recycling or reproducing stuff that has been done before. Everything has a touch of the bespoke, because the context is always shifting, and your thinking is always evolving.
This is partly due to the curse of curiosity. I sometimes envy those folks who can become bored (not really; not at all). How simple their world must be. But if you're afflicted with curiosity, it can be insatiable.
As Nicholas Nassim Taleb says: “Curiosity is antifragile, like an addiction, and is magnified by attempts to satisfy it.” There are so many wonderful tangents to explore, so many opportunities to widen the keyhole perspective we have in life. And so, if you're cursed with a pioneering spirit, everything takes longer.*
Constraints mitigate this.
You need to play this like a progressionist, not a perfectionist. This means actively seeking constraints.° Future-pace possibilities, and work out the critical path for your missions and projects—remembering that the further into the future we go, the fuzzier things become.
* It's probably thanks to a combination of curiosity, constructive discontent and an incredibly healthy relationship with self-doubt (elements 1–5 above) that makes these museletters so long.
° I tend to treat deadlines as amusing hypotheses begging to be disproved—but I've learnt to dial up the pressure they provide.
And then, get comfortable releasing versions of your work, rather than waiting to ship a perfect, final piece. Everything is a draft. Combine this with a trio of the other mitigators mentioned above—thought leadership, transparency and vulnerability—and you'll be able to make meaningful progress (even if it's not perfect).