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Pioneers in Hell: How to Stop Killing Their Potential

Last year, a Pioneer—let's call him Jack—was being lauded by his company for boldly departing from convention and leading his business unit to new heights of innovation. Shortly thereafter, Jack got a new boss. Before their first in-person meeting, his boss asked him to put together a plan for the upcoming year. And populate a detailed template. In a spreadsheet. With multiple pivot tables and complex macros.

Jack, a consummate Pioneer, put off completing it as long as he could; he didn't have a particular aversion to numbers, but he felt they missed the bigger point of his ideas. Not to mention how his eyes would cross and his mind would wander every time he looked at row upon row of inputs and outputs and compounding variables. If he could have used a tool to visualize the data that would have helped. He finally got it done just in time for the meeting, but the process sucked the life out of him.

On the day of the meeting, Jack entered his boss's office relieved to have the whole spreadsheet ordeal behind him and ready to brainstorm possibilities for the year. But he barely began to wax enthusiastically when his boss shut him down with the words, “Let's just walk through the template, shall we?” And they did. Line by line. Cell. By. Cell. And at every stop his boss would question the numbers, the assumptions, the formatting. Every time Jack would ask her to “imagine this” or “picture that” she would simply sit there with a grim expression, whereas she positively lit up when she found a rounding error!

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That meeting was just the start of a series of agonizing “interrogations,” as Jack called them, where the intent seemed to be to have him confess to the crime of impracticality with intent to harm. Jack had always thrived under laissez-faire leaders who liked him precisely because he was a bold thinker who didn't let today's reality get in the way of tomorrow's opportunities. He kept trying to bring up some of his ideas in different ways. Maybe if she could just visualize it she would see the potential? Or maybe if he came up with more novel options for her to consider she would become interested? But the bigger and bolder he got, the more his boss tightened in on the questioning. His new boss's scrutiny impacted him like kryptonite. He felt like he couldn't flex his creative muscles, while at the same time he was being tortured with a forced march through granular details.

After a few months, came the final straw. HR implemented MEMO #104: REGARDING THE MATTER OF WORKING ARRANGEMENTS AND OFFICE UTILIZATION , requiring leadership, including Jack, to be present in their assigned offices during business hours. Up until that point, he'd had the freedom to more or less work where he wanted, when he wanted. His favorite spot was a bistro table outside the local coffee shop, but he also loved the main conference room with the giant whiteboard, and of course some of his best ideas often came to him during his afternoon run. His euphemistically named “office”, in contrast, was a cramped closet with white file cabinets (never used), white walls (poorly lit), and NO whiteboards. After pacing restlessly in his office cage for a week, Jack gave his notice.

Last we heard, he was trekking in the Himalayas, spending some of the signing bonus he got from joining a venture-backed start-up as their “chief disruptor in residence.”

Let's Talk About it

Remember we said in Chapter 2 that we were going to share some of our conversations with you? We're going to do so here and in the next three chapters. It might help to remember as you go along that Kim is a Pioneer-Driver (specifically a Scientist) and Suzanne is a Guardian-Integrator (specifically a Dreamer).

img KIM: This story highlights a classic conflict we see all the time: Opposite types clashing because they approach things from completely different perspectives. In this case it's our Pioneer Jack interacting with his new boss, who is likely at the more extreme end of the Guardian spectrum.

There's an expression that constraint breeds creativity but that's definitely not the case here. Here you have a guy brimming with ideas who is constrained at every turn—first in how he's asked to think about his ideas, then in how he has to communicate his ideas, and finally in where he needs to work. He has no outlet in which to express his creativity and vision—the things he's best at—and instead he is tortured doing things that clearly are not strengths for him. It's like watching a race horse get harnessed to a plow. The thing is, for Pioneers, being held back from exploring possibilities can indeed feel like a physical restraint that weighs on them. Pioneers are high-energy types, but that energy feeds on the rapid generation of concepts and what if's . If you take that away, or worse, like in Jack's case, go further and force them to do something completely contrary to their nature, it depletes them.

img SUZANNE: One of the unfortunate things about this story is that, while Jack seems to experience his Guardian boss as a bit of a wicked step-monster, she's probably not really trying to ruin his life. She's simply getting the work done in the style that's most comfortable for her. She either hasn't made the effort to get to know Jack and how he's different from her, or she gets that part, but not how she might need to adjust her approach in order to get the best from him. We often see this when people report to someone that's their opposite type, regardless of which party is which type. In this case it cost the organization an enthusiastic and imaginative leader who had been thriving under his previous boss. That's really a shame.

img KIM: You're right, it's unlikely his boss is trying to be malicious, but people who are “the boss” often have an expectation (consciously or not) that others should bend to them. After all, they're the ones in charge. And perhaps they believe they owe their leadership positions in large part to the success of their particular approaches and thus are unwilling, or unaware, that they should modify them. For Jack, it sounds like his previous leader was more similar in style to him, or at least explicitly valued his contributions, so the contrast with this role change is even starker.

img SUZANNE: I think the “I'm the boss so we'll do it my way” approach is pretty typical, regardless of the boss's type, and if you're the boss, then maybe you do feel it's your prerogative. The thing is, it doesn't usually bring out the best in your people (at least those who are different from you), because it can mean their needs are unmet. So it's often counterproductive.

img KIM: Yes, counterproductive but common. And there are common mistakes people tend to make in response. A mistake Jack makes in this situation is one we see with all types—when he's not successful in making a connection, he doubles down on what's made him successful in the past, and what he feels he's great at. He gives his boss more, even grander possibilities—exactly not what she's looking for. And although this doubling down is a normal reaction for all types, it's amplified in a sense for Jack because, as a Pioneer, he's naturally optimistic. His assumption is going to be that of course she will ultimately come around; he just needs to keep trying. He's looking for that classic, validating yes, and… response from her, and all he's getting is a series of buts and nos .

img SUZANNE: I think that's a great point to keep in mind when working with a Pioneer—even if you can't say yes , can you avoid saying no , especially right away? Because nothing dampens a Pioneer's enthusiasm faster than the word “no .” I'm not suggesting anyone go ahead and do everything a Pioneer suggests (actually I'd pretty strongly recommend you don't do that!), just that you demonstrate you have an open mind and are eager to hear and consider the Pioneer's creative ideas. We'll make some suggestions in the next chapter for how Guardians might do this, because they're often seen as most likely to burst bubbles, but these strategies work for any type. One of these suggestions is to try something more like, “How might we?” or “I like/I wish,” as in “How might we test your idea in a low-risk way?” or “I like the vision of the future you're painting. I wish I had a clearer idea about how we'd overcome the barriers that exist.”

img KIM: At the risk of piling on here, the word no is more than just a buzzkill for a Pioneer (though it is that). For a Pioneer, your no is like a neon sign over your head flashing “closed for business.” Because Pioneers love the contributions of others in the brainstorming process—it fuels their thinking—so if you're not even open to discussing possibilities, in a Pioneer's mind, you might as well have your lights off with no one home.

Now, I get it, some Pioneer ideas are a little out there, maybe just plain…well, bad. And it can be hard to say nice things about ideas that you believe are obviously terrible. So if you can't in good faith say something like, “I really like the way you're thinking,” try a question instead. Not “Why the heck did you think that was a good idea?” Rather something like, “Have you ever seen something like that before?” “How do you think our customers would react if we did that?” or the old but good standard, “What would [insert respected name here] do in this situation?”

img SUZANNE: Another idea for making a situation like this work a little better is to explicitly acknowledge the differences in perspective and the flexing on both sides that will likely be needed to make it work. This can be helpful in any opposite-type pair, but in this case Jack's boss might admit that she is less likely to latch on to big, grand ideas right away, and ask for Jack's help in getting her there by providing her what she needs—answers to her specific questions. Then she might promise that in return she'll try hard to be a problem-solving thought-partner, rather than a party-pooping killjoy.

img KIM: If they're comfortable having that type of conversation it could help, but it seems even harder here because this is a new relationship. Jack's boss might be willing to give him a little more latitude if they had a strong foundation of trust, but trust takes time to build, particularly for a Guardian. You and I have worked together for years and I think one of the reasons you tolerate some of my crazy ideas and quick decisions is that you know that ultimately I will come through and not leave you hanging. That knowledge is based on a long history of interactions, so you're basing your trust on evidence, not wishful thinking.

img SUZANNE: True. I've had lots of opportunities over time to see, not only that you won't leave me hanging, but also that your crazy ideas are a much needed balance for my sometimes overly practical ones (not that there's anything wrong with practicality in the right dosage).

img KIM: But unlike you and I, Jack's boss probably doesn't know much about Jack other than that he's got a reputation for doing things outside of the norm (which doesn't necessarily sound like a good thing to a Guardian). But is he a man who keeps his word? Who follows through? Who brings something more substantial than flash in-the-pan ideas? She's essentially putting Jack through his paces until he proves himself to her. And yes, there are ways she can make that process more palatable to him, as you point out. But Jack could also have been less miserable, I suspect, if he used one of the Pioneer super powers of looking at things from a whole new perspective. Instead of seeing the situation as a worthless set of interrogations he could have changed the lens for himself, and approached it as a chance for him to build trust and rapport.

img SUZANNE: Speaking of trust, I'd like to bring us back to Memo #104: Regarding the matter of working arrangements and office utilization. Kim, you hinted before that constraints rankle Pioneers particularly, and this memo (and the policy behind it) is such a good example of how to create the exact opposite of an engaging work environment for a Pioneer. Not only does it force everyone to work in a physical setting that sounds quite uninspiring, but just the idea that people are being told what they have to do is likely to set teeth on edge. And a Pioneer's teeth are likely to be extra sensitive to such a thing.

Instead of just announcing a (quite unimaginative) solution to a perceived problem, a better way to handle such a situation, especially if you've got some Pioneers hanging around, might be to present people with the problem itself. Suppose the issue is that people have been complaining they don't ever know where to find anyone when they need to get in touch. Go ahead and pose that problem to a Pioneer or two. Not only are you likely to end up with some much more creative solutions to the problem, but they are likely to be solutions that engage, rather than offend your Pioneers—and probably others too!

img KIM: I love the idea of getting others involved in addressing the perceived issue versus putting out solutions that are unlikely to suit anyone. That approach is particularly appealing to the Pioneers as they love creative problem solving. Unfortunately because Jack didn't feel he could truly contribute to his full potential, he solved that problem by leaving the company.

It's important to note that, as a Pioneer, Jack probably didn't agonize over the decision to leave. He probably didn't review and question everything he did and reflect on whether he could have done things differently. Chances are he didn't even consider for a moment that maybe the problem was with him. He might have felt it was unfortunate that he couldn't continue his work, and streak of success, but the point is he didn't take it personally. He decided the overall environment didn't suit him, and so he moved on to the next thing. This means that this is much more of a loss for the company than it is for Jack.

img SUZANNE: Given that a Pioneer probably won't agonize over the decision to leave, it seems even more important for leaders to focus on creating environments that make them want to stay. And not just stay, but bring that typical Pioneer passion to bear on whatever the goals of the organization are. One powerful way to do that is to make sure Pioneers are well positioned to do what they most want to do—tackle tough problems by innovating. Now this doesn't mean you should let Pioneers totally off the hook when it comes to doing some of the more mundane tasks that we all need to do—that wouldn't be fair to others. (I'm speaking as a Guardian here, since we're the ones who tend to end up with all that mundane stuff if Pioneers get the impression they don't have to do any of it.)

img KIM: This is a fine line, because I know that many Pioneers (myself at the head of that chaotic throng), would leap at any opportunity to avoid what we think of as day-to-day drudgery. So while I do think it's important to give Pioneers things they love, it can help to follow a little Mary Poppins advice: “A spoonful of sugar helps the medicine go down.” Break up the unpalatable tasks into more bite-sized chunks, interspersed amongst more Pioneer-friendly activities.

img SUZANNE: And it's not just about giving them “fun” things to do. We know Pioneers are the most likely type to say they thrive when they have opportunities to learn and try new things. We know that they aspire, not only to lead, but also to innovate, and that making a difference is important to them. So to keep a Pioneer engaged for the long term (or probably even the short term) it's critical that some good percentage of a Pioneer's time can be dedicated to doing what they're great at or what they're excited about. After all, we all want that! And the organization benefits when people are able to play to their strengths.

img KIM: I would take that a step further and say that organizations benefit not only when people can exercise their unique strengths, but also when they are put in environments that actually give them strength. So for our Pioneers, don't just give them an assignment to innovate something. Also provide sources of inspiration—place them on cross-disciplinary working groups, send them on research field trips, encourage them to spend time in a public co-working space on days they don't need to be in the office. Environment is not just a physical reality, although that plays a role. Rather it's a mix of factors that contribute to an overall experience.

Creating optimal environments can be a tall order for leaders, because it isn't a single thing and it's different for each of the types. And of course you can't cater to everyone all the time. That being said, many leaders overestimate the amount of effort it takes to flex, and underestimate the degree of positive impact. Like a chef in a kitchen who takes the time to sear the meat and steam the vegetables versus throwing everything in a pot of boiling water, the leader who understands what is required for different people and proceeds accordingly will get much better results.

img SUZANNE: Boiled meat. Yuck. But it's true—meeting everyone's needs at the same time can seem tough, especially when people's needs sometimes conflict. And that's why providing options works so well. A Driver might think field trips feel like a waste of time. A Guardian would possibly think a public co-working space was even worse than an uninspiring office. The idea is not to make everyone do the same things, but to give everyone the same level of opportunity to choose what they do (or at least where they do it).

I think this is more important than ever when people need to do some of those tasks that are particularly hard for them. So for example, most of us have to do some level of required stuff related to performance management, security, technology, and such things. These kinds of tasks might be particularly painful for a Pioneer—so couldn't we at least give them some freedom in when, where, or how they get it done?

img KIM: I'd vote for that. The question for leaders though becomes: How do you give them some freedom while keeping guardrails in place to mitigate risk? Because, perhaps not coincidentally, some of the things that Pioneers hate to do are usually required to manage risk in some way.

Your problem as a leader here is two fold. First, Pioneers likely do not want to follow the process you've put in place to deal with the risk (please, no more three-hour instructional videos on employee policies). Second, they tend to downplay or even dismiss the risk itself, saying things like “Come on, is it really that big a deal? What's the worst that can happen?” or “How likely is this anyway?” For these situations you need to paint a picture of the threat. Bring it to life for them in a visceral way that lets them envision the grim possibilities. And then maybe you can get them more onboard with a process (hopefully tailored to better suit the ways they engage).

img SUZANNE: I have this picture in mind of a devastated and desolate landscape, and it's quite depressing! Another likelihood is that Pioneers might say (or at least think) something along the lines of “All truly great innovations have been realized because someone ignored the potential risks that others feared,” or “Only great risks bring great rewards.” But that's actually not the case, and you can engage in a bit of myth-busting by sharing some pretty compelling evidence to help Pioneers (and others) see this. Both Malcolm Gladwell1 and Adam Grant2 have written about very interesting research exploring our (faulty) associations of risk taking with entrepreneurship. One of the key points they highlight is that, generally speaking, entrepreneurs do tend to take lots of risks, but also, generally-speaking, entrepreneurs tend to fail. Further more, the reasons for these failures often revolve around poor or even absent analysis, a lack of foresight, and a failure to properly prepare (all things Pioneers are accused of). The entrepreneurs who succeed, far from chasing blindly after a dream, tend to hedge their bets in several different ways, by keeping their day jobs even after launching a successful start-up, for example.

Taking great risks can sometimes lead to great things, but share with your Pioneers the idea that such risks should be engaged in as you would a well-balanced stock portfolio; you protect yourself with some relatively safe investments so you can make some risky ones too. In this case, the safe investments are all those policy-related processes, and it's adhering to these closely and thoroughly that enables us to go ahead and take some of those other risks.

img KIM: Spoken like a true Guardian—but I get your point. There's another aspect here that's important to address, particularly for Pioneers but really for all types, and that's overconfidence bias. There's been lots of research showing that people tend to overestimate their degree of certainty, and probability of success, even in the face of tempering data.3 The classic example I've seen quite a bit living in the Silicon Valley is the entrepreneur who is convinced that their venture will be successful, even though the success rate in general is abysmal. But enough ventures do succeed that the myth persists, largely due to base-rate fallacy, essentially the concept that people will put more weight on specific examples than general information.4 These biases are part of being human and thus plague all types, but I suspect that Pioneers might be particularly at risk because of their optimism and inherent confidence (arrogance?), which is not helped of course by their overall tendency to trust their gut over statistics and probabilities.

That's a Wrap

We just shared a whole lot of tips for how to create an environment where Pioneers excel, and we thought a summary of those points might be helpful. While focusing on the needs of Pioneers, you'll want to watch out for turning off the other types. After all, you want everyone to excel, not just Pioneers. So we've added to our summary some ideas for how to keep things palatable for Guardians, the Pioneer's opposite.

To meet the needs of Pioneers To make it palatable for Guardians
Allow time for free-flowing discussion and idea generation. Timebox discussion so it doesn't carry on too long.
Brainstorm and whiteboard on the spot. When possible provide an option to prepare in advance, or at least take a few moments for quiet idea-generation before opening the floor.
Keep an open mind. Even if you can't say yes, try to avoid saying no. Let Guardians know there will be a time for critique, it just isn't now. Coach them on less soul-crushing ways to share concerns, such as saying “I like/I wish” and similar techniques.
Provide options for where, when, and how to work. Guardians likely want these options too!
Position them to do what they love and explain how more mundane tasks enable them to do so. Don't let Pioneers off the hook on some of the more mundane tasks.

© 2018. Deloitte Touche Tohmatsu Limited

Stick with it

Einstein famously once said, “It's not that I'm so smart. It's that I stay with problems longer.” Executing on a visionary idea, and seeing it through to fruition, takes a certain amount of stick-to-it-ness. Visions don't typically become reality all on their own. And while Pioneers are often thought of as visionaries, people sometimes complain that they struggle to stick with an idea long enough to make it a reality. And there's research suggesting that when the going gets tough—like when a problem gets really difficult to solve—Extroverts give up more quickly than Introverts do.5 And as we know, most Pioneers probably lean more toward extroversion than introversion. One of the reasons for this lack of follow-through is that Pioneers, more than any other type, like to tackle what's new. That's great, except for the fact that what feels bright and shiny new now will eventually feel old and a bit tarnished, and that often happens before something is actually finished.

If you're a Pioneer, try breaking your idea into smaller execution chunks and celebrate the achievement of each one (Pioneers love a good party) before launching into the next “new” phase. In addition to keeping up the enthusiasm, this also gives you a way to evolve your plan as you go (let's face it, you know you will), while still getting things done!

Make the New Seem Old

In the early 1800s, the first automobiles were often referred to as horseless carriages. Why? Because people understood what that meant. They were used to carriages pulled by horses, so it wasn't a very big leap to imagine a carriage without a horse. Calling an automobile a horseless carriage made it seem familiar. While it may seem counterintuitive to novelty-embracing Pioneers, when trying to sell something quite revolutionary to ordinary people, the familiar can be a good thing.

It's important for you to remember, Pioneers, that your love of novelty isn't equally shared by everyone. Indeed, some people are quite suspicious of ideas that seem totally new or foreign. Instead, they're more comfortable with what's familiar. They respond more positively to change that's incremental rather than disruptive. So when you're hoping to get people on board with your innovative idea, emphasizing just how new and different it is may be the wrong move. To reach these people, emphasize what's not new. This will likely feel counterintuitive to you, but it can get people comfortable with your idea more quickly.

Say it Again… and Again…

You may be a brilliant visionary who can paint a picture of a new future that will make people swoon. You may be such a great communicator that communication experts ask for your advice. But chances are, you're still under-communicating about your ideas. Because here's the thing: As we suggested earlier, for many people, the more familiar they are with something, the better. This is called the exposure effect .6 So even when your idea is quite new, if people keep hearing about it over and over, it will start to seem familiar. Management guru John Kotter has suggested that most change agents under-communicate their vision by a power of 10, so just an extra mention or two isn't likely to do it.7 If you really want to get others behind your idea, be ready to tell them about it repeatedly, and preferably in multiple ways. It's also best to leave a bit of time in between when you first present an idea and when you ask people to tell you what they think about it. Pioneers tend to process things quickly and go with their gut, but many others don't work this way. For the best response, give the idea time to marinate.

Take a Breather

Yes, Pioneers (and anyone wanting their ideas to stick) should overcommunicate their vision. But that doesn't mean they should be the only ones communicating. A common complaint about Pioneers is that their high-energy, put-it-all-out-there, talk-to-think style can be overwhelming, and can crowd out other voices. Pioneers often aren't even aware of their verbal steamrolling, so simply making a conscious effort to let others get a word in edgewise can help. But Pioneers, don't include others in the conversation just to be nice (although it never hurts to have good manners). You should include others because they might have something to say that would make your idea even better, help it see the light of day, or spark another idea.

If you're a Pioneer, amp up your inquiry. When you get on a roll, pause occasionally to ask a question—and not just the rhetorical kind. Give people a chance to share their thoughts and when they do, actually listen. You never know where that can lead.

Seek First to Understand

Pioneers often describe themselves as uninterested in details and process. At least that's how they say it when they're being polite. Sometimes Pioneers even use the phrase “unnecessary details,” which to a Guardian sounds like an oxymoron. If you're one of those Pioneers, think twice before you ignore the details or process, or before you “improve” something by stripping everything away. Take a moment to find out why the detail or process is important to others. Ask: “Why does this matter? What would be the consequence of skipping this step, ignoring, this detail, etc.?” If you think you have a better way to do something, that's awesome! But proposing a better way without thoroughly understanding why things are the way they currently are will not only annoy others, it might also result in your messing things up. Start by getting a lay of the land. Once you've done that, you'll be better positioned to offer ideas that might actually be helpful.

Red Flag: Cages, Clipped Wings, and Coal Mines

As we've said before, Pioneers tend to be very adaptable, which means in theory they can make themselves comfortable in most work situations—particularly since many of their core characteristics map so well with established leadership stereotypes. That said, if Pioneers are constantly being caged in and not given room to roam and grow, or they are consistently kept from letting their ideas take flight, chances are they won't be very happy. And if you're an unhappy Pioneer, you're also unlikely to stay that way for long. Pioneers rate loyalty lower on the scale of importance than other types and will be off to other opportunities. So in other words if you're a Pioneer, most of the time you'll probably know when it's time to go.

We think the bigger red flags to look out for, as Pioneers, are not those obvious threats but the more insidious ones. There's been an interesting discussion in the business literature about the role of so-called deviants.8 9 10 These are people willing to step outside the box and question the status quo—often a natural role for Pioneers. Deviants are invaluable to organizations because they help them evolve and break new ground. But they also shoulder personal risk in so doing. After all, if the train is chugging along fine and you're the lone voice who insists on taking a different track, you might expect some upset people if the train then derails.

In an organization with strong leadership support, this may not be a big problem, but some organizations use their deviants like canaries in the coal mines. They send them out into uncharted, risky environments. If the canary chirps away and shows it's safe, they come charging in to mine the riches. But if the canary stops chirping because it's not safe, they figure they can always get another canary. Such fair-weather organizations might seem like they're giving you great opportunities, but make sure you know what you're signing up for. And if you get the sense that they're out for their own success at the expense of yours, you might want to flex those wings and fly to more welcoming climes.

References

  1. 1. Gladwell, Malcolm. “The Sure Thing.” The New Yorker , January 18, 2010.
  2. 2. Grant, Adam M. Originals: How Non-Conformists Move the World . New York: Viking, 2016.
  3. 3. Kahneman, Daniel. Thinking, Fast and Slow . New York: Farrar, Straus and Giroux, 2015.
  4. 4. Ibid.
  5. 5. Howard, Rick, and Maeve Mckillen. “Extraversion and Performance in the Perceptual Maze Test.” Personality and Individual Differences 11, no. 4 (1990): 391-96. doi:10.1016/0191-8869(90)90221-c.
  6. 6. Zajonc, Robert B. “Attitudinal Effects of Mere Exposure.” Journal of Personality and Social Psychology , 9 (2, Pt.2 (1968): 1-27.
  7. 7. Kotter, John P. Leading Change . Boston, MA: Harvard Business Review Press, 2012.
  8. 8. Gino, Francesca. “Let Your Workers Rebel.” Harvard Business Review . June 08, 2017. https://hbr.org/cover-story/2016/10/let-your-workers-rebel .
  9. 9. Pascale, Richard, Jerry Sternin, and Monique Sternin. The Power of Positive Deviance: How Unlikely Innovators Solve the World's Toughest Problems . Brighton, MA: Harvard Business Review Press, 2010.
  10. 10. Vadera, Abhijeet K., Michael G. Pratt, and Pooja Mishra. “Constructive Deviance in Organizations.” Journal of Management 39, no. 5 (February 26, 2013): 1221-276.