The Evolution of Super-Doers

Life is full of transitions. One that seems to be particularly common in the technology realm is that of super-doer to super-manager. Unless you were born with a super-rich daddy, most of us started our careers with a whole lot of heavy lifting. Our success was measured by the quality and quantity of work we could individually produce. Sure, we were part of teams but the team stars were those whose Herculean feats were greater than the others. But a strange thing started to happen. Those Herculean feats of strength became a calling card, and as your success grew so too did the number of people seeking your advice and support when they were up against a challenge. One moment you were the student and the next you were the teacher.

For each of us that make the transition from doer to leader, there is a point time when you realize the task(s) at hand exceeds your Herculean strength. It is no longer about what you can do, but rather what the team can do. It is a concept that you read about and study but until it actually happens, it is all rather academic. And so it is that the transition can be a little intimidating. The super-doer likely grew up always knowing that when push came to shove, they could simply overcome whatever challenge lay in their way through pure grit and dogged determination. Suddenly you are a manager, and your success is no longer in your own two hands. You cannot just pick up the ball and carry it across the goal line. Somebody else has to do it, and if you are any sort of leader, they are looking to you for how to do it. Most people think of managers as having more power and control, but for a super-doer it can feel quite the opposite. Control of their destiny has been dispersed among a broader group of people. It isn’t more control, it’s less and frankly it is a scary transition. Not everyone makes it, or should even try.

Entrepreneurs are by their very nature super-doers and they take justified pride in being the chief cook and bottle washer of their start up enterprises. In the early days, everything depends upon them. But over time with some success and luck, the team grows from one to many, and the business becomes more than any one person can handle. Suddenly the business no longer needs a Herculean do-it-all entrepreneur, but rather a super-leader entrepreneur. It is a scary time for everyone involved with the company. In the best-case scenario, the entrepreneur makes the transition to super-leader. In the second best-case scenario, the entrepreneur realizes their limits and hands the reins to a new leader. And in the worst-case scenario, the entrepreneur fights the transition and drives the business into failure. Unfortunately, the third scenario is the most common. It is as if the same pure grit and dogged determination that created their early success becomes their Achilles’ Heel.

Cowboys, Bureaucrats & Pirates

One of the biggest challenges of any startup is dealing with the cultural battles that arise when a company starts to implement structure and process into its operations. Communication and coordination are easy when the entire company can sit around a single lunch table, but once you have a lunchroom life becomes a little more complicated. Increased size and scope of business operations drive the necessity for formality and process. I have always thought of organizations as having two archetypes: the cowboy and the bureaucrat. The cowboy is the lone wolf nomad who operates best with total freedom away from the formalities of society. The cowboy’s credo is just get’er done. That is a great credo until customers start having an opinion on how things should be done (e.g., in accordance with ISO registration), or God forbid they want two of their products to be the same. That’s when the nomadic cowboy shows his limits. Once the ‘wild west’ [phase of your business] has been won, the cowboy’s role must be complimented with somebody with an eye for structure and repeatability. Enter the bureaucrat - the kind of person that understands the power and necessity of administration and process. To a bureaucrat, true beauty lies in efficiency and effectiveness, and so the bureaucrat is driven to tame the wild and bring order to things by building structures.

Unfortunately, cowboys and bureaucrats hate each other with a passion. The cowboy sees the bureaucrat as wanting to stifle innovation and creativity, and the bureaucrat sees the cowboy as a petulant child that cannot do anything without leaving a mess for somebody else to cleanup. It is an all-out cultural war that constantly shifts as the ratio of cowboys to bureaucrats changes along with the maturity of the company.

The truth is that companies need both cowboys and bureaucrats. The normal management strategy is to keep the warring parties apart, and just hope their cages (i.e., cubicle walls) are enough to keep them from fighting. I have come to think however that there is a third archetype out there – somebody that can cowboy when it is necessary but also build organizational capability along the way. It needs to be somebody that understands the value of process and infrastructure, but not in a dogmatic way. I struggled with the appropriate name and description for this archetype until my friend Ken Cook suggested the notion of the Pirate.

Pirates are masters of their craft. Yes, they are driven by the quest for the bounty, but more fundamentally they are sailors – great damn sailors. Sailing is one of those activities where coordination is an absolute necessity and each crewmember must master their role to perfection. Mastery in any field is achieved through discipline. It is this combination of superb skill and discipline that makes them masters. Seeking challenge (i.e., great bounties) in their work often places them in the role of pirates.

Most masters have a simultaneous distain and understanding of the need for rules and process. Their own personal discipline means that they do not need process or rules - control comes from within. Masters are given the tough jobs (i.e., sent into "no mans land") so they often run into situations where everyday rules, processes and standing orders are not relevant to the situation at hand, and stand in the way of getting the job done. At the same time, the master knows where his mastery starts and ends, and realizes that where there is not mastery, one needs processes or rules to follow to prevent harm to themselves or others.

The cowboy and the bureaucrat share a common attribute in that they are not masters nor do they understand mastery. The bureaucrat values blind adherence to procedure without insight or skill in a subject, and the cowboy values his personal insight and skill without appreciating the power of procedure. The bureaucrat will smother peak performance in the name of consistency. The cowboy will have occasional moments of glory punctuated by spectacular failures that take forever to clean up.

So, small startups can tolerate the cowboy because the organization needs their brilliance, and are nimble enough to contain the inevitable failures. However the small startup, when successful, quickly outgrows its ability to tolerate the downside of the cowboy. It usually takes a long time before the organization is large enough to tolerate the inflexibility of bureaucrats, but once they take root they tend to be a force to be reckoned with.

Overcoming the inevitable cultural battles that arise by trying to maintain some sort of détente between cowboys and bureaucrats is a losing proposition. Neither has the right answer and they will never agree to a ‘reasonable balance’ between their views. But there is a way forward: the relentless quest for mastery and the associated discipline it entails. Strive to build an organization whose culture values mastery toward the corporate mission above all else. Like the pirate sailor, set sail for blue oceans, endeavor to be a master of your crew position (be it captain or seaman), respect and coordinate your actions with the other crewmembers, and never lose sight of the bounty. It's the perfect cultural archetype and many thanks must go to Ken. The pirate culture - bounty-obsessed sailors with a healthy disrespect for the law.

To Build or Grow?

Seed capital. Incubate. Grow. Harvest. The innovation and entrepreneurism industry is full of farming and gardening analogies. The implied concept is that success is about finding a single idea (seed) that has the potential to grow into a profitable business (crop) that we can then harvest. As farmers, our strategy is to provide resources (sunshine, water, fertilizer) to a seed that already has the DNA of success. We are not adding to the DNA of the seed, but rather promoting and facilitating its germination and growth.

It is an interesting analogy, but I can think of no examples where it actually worked that way. In business, I have never seen a single idea go from seed to magnificent oak. Companies are not grown. Businesses are built piece by piece, brick by brick, idea by idea, and employee by employee. And each addition brings its own DNA which it turn changes the very fabric of the whole. That novel new ‘seed’ idea may be the cornerstone of a new business concept, but ultimately it is only one piece of the puzzle.

Our task as designers and builders of businesses is much like the child building a lego figure. Something sparks an idea (often a new lego piece that we imagine will allow us to build something totally new) and we develop an image in our mind of what we want to build and how we might play with it once built. We usually go right from idea to the building process by laying out all the lego pieces in front of us, searching for the necessary blocks to build. We pick out the first pieces and then starting building. We pick more pieces and build a little more. Inevitably we get to a point where the piece we really want isn’t there or it doesn’t quite work, and so we disassemble things a bit and try again. Eventually we get to a point where we have a figure. It looks kinda like what we imagined but never exactly.

Building businesses follow a similar pattern. It always starts with a ‘fuzzy’ idea about a product or a business, and we image how the product or business might create value. We think about what pieces we would need to put it together: technologies, channels, partners, expertise, financing, etc. Which pieces do we have, which can we develop ourselves, and which pieces can we acquire or partner for? And then, assuming we have most of the foundational pieces in our grasp, we begin the building process. As we start to build, we inevitably discover the pieces don’t fit together quite like we imagined and so we step back a bit and rejig the design accordingly. Eventually we get to a point where we have a product and a business. It looks kinda like what we imagined but never exactly.

Hypothesis Testing

NEWS FLASH: Every business plan is wrong. Not to worry. As Dwight Eisenhower once said, “plans are useless but planning is essential.” This is certainly true for business plans. The actual documents aren’t worth the paper they are written on but the process of creating them … priceless.

The value of a company is inversely proportional to the uncertainty surrounding the assumptions that make up its business plan. We must therefore systematically and iteratively drive out the uncertainty in our business plans. Here’s the shocker: the place do this is not the boardroom, but rather the marketplace.

It is all too easy to treat assumptions as knowns. The danger is that we lose sight of the uncertainty of the assumptions as we build a complicated spreadsheet business model around those assumptions. Never forget that no matter how fancy your model, it is worthless if the underlying assumptions are not true. That is why I no longer use assumptions in my planning. They are just too dangerous. They tend to lie hidden in the details and then blow up at the most inopportune times. Instead of assumptions, I insist our business models are built around a set of hypotheses. It is a subtle but important difference because it emphasizes the ‘unknowns’ in the business model. The business priority therefore becomes validation (or testing) of the hypothesis rather than building upon it as you would do with an assumption. If the hypothesis is validated, the uncertainty is reduced and it is far easier justify investing into the next stage. If the hypothesis turns out to be wrong (something that happens quite a bit), we’ve hopefully learned early enough in the process to try a different approach.

Director of Opinions

Please be advised that I’ll no longer be accepting applications for the role of Director of Opinions. I wish to thank all the pundits, armchair quarterbacks, and self-proclaimed experts out there that have shared their opinions about how we can all do better. Your energy and passion for finding flaws in others is really quite something. However, after much contemplation I have decided to go in a different direction. Henceforth, I will be exclusively seeking solution-oriented people to work with.

I appreciate that this decision will be controversial and that I will no doubt be accused of not being open to diverse opinions. I actually think that I am pretty open to differing approaches. It’s just that I have found that 20-20 hindsight and efforts to assign blame after the fact are … well … not all that helpful. I am not debating your superior intelligence or that you would have done way better had you tried. It would have been great had you applied your greatness to making things better. But you didn’t and so I have decided it preferable to work with those that try to solve problems rather than those that just pontificate about them. I know. I know. I am being overly pragmatic and too narrow-minded.

Thanks again for your interest in the role of Director of Opinions. I am sure that there is an organization out there somewhere (perhaps a consulting firm or an opposition party) that will value your passion for pointing out the flaws in those trying to accomplish something.

Best of luck,

Passion and Perseverance Trumps Experience

Carl Jung once said that in the first chapter of a man’s life, he foolishly tries to change the world to suit his purposes. And in the second chapter, he comes to realize that that the world is not about to change for the likes of him and so he comes to terms with his limitations. Jung concluded that the people that actually change the world are those that live in the first chapter.

Experience is great when we learn from it but not so good when we are jaded by it. I think the secret to success is having the determination and perseverance to never give up on the goal, combined with an ability to learn from and adapt to the challenges along the way. It is somewhat of a paradox in that you have to be steadfast in where you are going, but flexible about how you get there. The trouble with experience is that it can lull us into thinking we already know the ‘how’ part of the equation. And just as so many military generals have gone down to defeat by just reusing the plans of a previous war (e.g., Maginot Line), experienced managers tend to rely too heavily on past strategies.

When I consider what I value in leaders and team members, I realize that experience is not always at the top of the list. I like people from Jung’s first chapter – competent and determined folks that embody a willingness to try and learn. And yes, sometimes that means trying things that didn’t work before or won’t work this time. But failure is the price of progress, and so it is that we need leaders that are not terrified of failure.

To Hell with Chicken Littles

While we justly celebrate creativity and intelligence, I am strong believer that perseverance is the base ingredient of success. The world is not nearly as friendly or fair as we imagine in our Peter Pan dreams. The reality is that business, like life itself, is a contact sport - brutally hard, bumpy and exhausting. We fight and struggle to overcome challenges only to find new ones quickly replace them. We certainly need ingenuity to solve any given problem, but before that we must have the tenacity and intestinal fortitude to rise each morning emboldened enough to fight the good fight for another day. As Walter Eliot once said, “Perseverance is not a long race; it is many short races one after another.”

We must have our eyes wide open to the challenges that stand in our way, but the moment we become overwhelmed the game is up. Perseverance is not about being oblivious to the challenges, but rather being able to see the goal beyond them. And like any other skill, the ability to persevere is something that must be constantly practiced, honed and perfected. As leaders, perseverance is absolutely essential because regardless of our genius or planning, shit happens. For me personally, it is not the next problem that I fear as much as my old nemesis - the Chicken Little. I get that people get down, tired and frustrated. It happens to us all, but the Chicken Little is different. The Chicken Little is not content to simply lose faith and rant a bit. No, the Chicken Little must drag down and frustrate everyone around them with their proclamations that the sky is falling and that the end is near. As a team tries to muster the energy for the next fight, the Chicken Little will arrive on the scene to highlight and exaggerate every challenge and every failing. It is exhausting and demoralizing.

We all know the Chicken Littles of the world. They are hideous and horrible beasts, but alas I suppose they are part life. Indeed they are just one of the many hurdles we must overcome along the way to success. Rationally I get it, but damn I wish the Chicken Littles would just go to hell so we can get on with taking the next hill.