Bright People with a Dream

There are three basic roles for leaders, and whether it’s just you and Frank in a garage or 1500 of you, it’s important that you understand this model so that you can tear it down. This is a descriptive, not prescriptive, model that is intended to explain how the different types of leadership evolve and stratify over time. It describes the high-level responsibilities of these different leaders, and how these different roles might (or might not) communicate with each other.

DISCLAIMER: As a means of easily explaining these roles, I’m going to express them hierarchically from an org-chart perspective. There are entrepreneurial folks out there who are going to shake their fingers vigorously in my general direction, saying, “Keep your orgs flat! Titles are toxic! Why are you forcing bureaucratic power trips on me?”

These folks haven’t seen shit. It’s a good thing—the lack of preconceived notions keeps them mentally and entrepreneurially limber—but they haven’t seen shit. They don’t understand how groups of people organize, nor have they ever attempted to build something with more than a handful of individuals. They have an intense belief in the power of the individual. This is their bias because this is who they are: a handful of bright people with a dream.

I deeply believe in the power of the individual, but I also believe that in order to build epic shit at scale, a colorful tapestry of talent and degrees of experience is essential. And when I say colorful, I mean people who often don’t get along precisely because of this diversity.

To you finger wavers, I helpfully suggest you just read to the end. Because I’m going to help you tear it down.

Three Leaders

There are three leaders. I’m going to describe these three archetypes in a hypothetical large company, but I believe aspects of them exist in all groups of people working together on a collective goal. These leaders are:

• The Lead

• The Lead of Leads

• The Director

The Leadis at the beginning of their career of not doing the work, but rather leading the work. These recently minted leaders are leaving the day-to-day job of being hands-on with the work and becoming hands-on with their team. The focus of The Lead is the team—this is their entire world.

In this role, The Lead is still intimately aware of how the work is done because they were very recently doing it. This knowledge makes them valuable mentors for their team as well as credible representatives of the team to the rest of the company. They can effectively describe the work to others, and they understand how to measure the work as this is their domain and the team is their people.

The Lead is tactical, but is showing the first glimmers of strategy. They are beginning to understand the power of delegation, and they are still wrestling with the idea that they have authority. What is familiar to them is the work and the types of people doing the work. When a situation arises relative to these areas, The Lead acts authoritatively and quickly because they understand deeply. However, they are also beginning to understand that there are different domains out there with different rules, and a new aspect of their role is interfacing with these foreign elements. The Lead begins to see there is a larger game board with additional pieces and new rules. One of these new pieces is. . .

The Lead of Leads’ obvious defining characteristic is that they are responsible for multiple leads, but it’s not the most important characteristic. In my experience, the Leads of Leads are running the company. I’ll explain.

As these folks are usually responsible for multiple teams, this role often means that the Lead of Leads no longer has any hands-on responsibility. They have true distance from the day-to-day work. This is fine, because they have a set of Leads who are credible and effective because they are intensely focused on their individual teams. With this effective relationship in place, the Lead of Leads can focus not on a single team, but rather on all of them. It sounds hard—it is hard—but it’s the Lead of Leads’ job.

If a Lead’s focus is downward on their team, a Lead of Leads’ focus is across the company. They worry about both the health of their teams as well as the health of other teams on which they have dependencies, or, perhaps, just an interest. Through this worry, they discover and build a profile of the health of the portions of the company they can see and they share it with their Leads, other Leads of Leads, and Directors. In doing this job well, they provide essential communications connective tissue by which information is discovered and acted on.

The Leads of Leads are switch hitters. Their day is equal parts tactics and strategy. While they have developed true distance from the day-to-day work, they still know how the work is done and can have an informed opinion about tactics relative to the work. They also have a more complete picture of the state of the company, which enables them to make better decisions and define better strategy. They see the complete game board. They see all the pieces, so they can be credible strategists. Sometimes.

The slightly obscured secret that you may not know is that the Leads of Leads are running the company. That’s right—all those fancy Directors running around looking important and emitting those pithy one-liners on productivity—they are dependent on the Leads of Leads to make sure the work actually gets done. This is not to suggest that the Director role isn’t essential, as we’ll see it is in a moment, but these Leads of Leads, these folks who are ridiculed for being “middle management,” they are the people and process machinery that keeps the machine running efficiently.

An unfortunate aside on middle management. This piece describes an idyllic leadership situation where everyone understands their role, communicates flawlessly and selflessly, and information moves smoothly around the organization. This situation has never existed in the history of ever. There’s a good chance you’re on a team or in a company where these roles landed long, long ago, and there’s an equally probable chance that you call the Lead of Leads folks “middle management” with a grimace on your face.

I know those folks. They are not leaders; they are the definition of shit management. You’re grimacing because they can’t lead—they’re too busy managing. They either lost touch with the Directors (and now lack essential strategic data) and/or with their Leads (and now lack essential tactical data), so they’ve become uninformed, inept, political buffoons who own teams, products, or processes not because they are qualified, but because someone long ago (and long gone) decided they should.

These managers are aware enough to understand that they are on their lonely island of political buffoonery, and they devote an inordinate amount of time to protecting this lonely, ineffective island. This is energy they should be spending building bridges to either the folks doing the work or the folks who have the vision. If you’re buying my thesis that the Leads of Leads are running the company then you’ll understand why a poor Lead of Leads has the ability to significantly damage the health of your company quietly and invisibly. Detecting and fixing this horrific management situation is the job of our last archetype: the Director.

The Director’s primary focus is outward. The Director’s job is to figure out how the company fits into and interacts with the rest of the world. Yes, the Director is often the face of the company, but, more important, they are the interface between the company and the world. They are the curator of the vision, because they understand the game board is really just one game board sitting in a world of infinite game boards. Ideally, they are purely strategic. It’s likely they are strong tactically, but they lead with compelling strategy, not efficient tactics. In my experience, Directors tend to be viewed as being a little nuts, and explaining why is one of the reasons I wanted to write this piece. See, pure strategy doesn’t look or feel anything like raw tactics.

Have you had this meeting? The Director (or CEO/SVP/VP—all the same, really) shows up for a meeting and gives an impressive 20-minute talk regarding the future. It feels good, the person in charge showing up and spending time with the team. It sounds good, the words are right and appropriately inspirational. They furiously and passionately wave their hands, but as you and your team stream back to your desks, you wonder “How does all the hand-waving apply to me? It sounded great, but, well, so what?”

There are a couple of potential scenarios here. Either your Director is giving you an impressive line of important-sounding bullshit, or perhaps they are speaking strategically and either can’t or won’t translate that strategy for your team. The bad news is that it’s really hard to tell the difference between crazy batshit insane and crazy batshit inspired.

The good news is that for crazy batshit inspired, on a healthy team there are qualified Leads of Leads capable of translating for the Director—remember that the Lead of Leads has a foot on both sides of the fence. They equally speak Lead and Director. These two archetypes need each other. Sure, it’d be great if your Director could descend out of her high-Earth orbit, but she’s great there—she thrives there just like this Lead of Leads thrives on translating her vision into action.

For crazy batshit insane, I have no good news.

Keep the Sub-Minions in Line

Let’s recap. There are these crazy Directors at the top, and they have the real power because they dictate all the strategy, mostly to these Lead of Leads types who are running the show but don’t want anyone to know it. These Leads of Leads don’t actually own anything; they just tell all the Leads and their minions what to do. The Leads, well, the Leads are just glorified minions who are mostly qualified to keep the sub-minions in line.

In reality, I’m saying none of that, but I’m pretty sure that some statement in the prior 2000 or so words about these three archetypes has pissed you off. Much of what you hate about my archetypes is likely a result of people abusing their roles at your expense. You’ve had a bad Lead who doesn’t communicate; you’ve suffered at the hands of crap middle management; or perhaps your CEO is legit batshit crazy insane. I’m sorry—that sucks—but there are humans who thrive beautifully as these different archetypes, and sometimes they do this naturally and with no experience.

There are humans who thrive in the Lead of Leads role. They have this stunning ability to gather and maintain a tremendous amount of state about a great many people and projects in their heads and they do this seemingly effortlessly. There are engineers who blossom as they step into a Lead position. Yes, we lost a full time coder, but he’s suddenly doing what he did as a coder with seven engineers. He’s a force multiplier as a Lead. It’s his goddamned mission in life.

There is no actual hierarchy in the roles I described. You might have applied one in your head because you think that is how business is structured. While it works for some companies, I’m increasingly coming to believe the way to build a healthy team in this millennium is as flat as possible, where flat doesn’t mean everyone is equal in ability, but rather that we value those interesting differences in ability and experience equally. In a time when we in the high tech industry are actively questioning the value of structured leadership, I enthusiastically say, “Bring it.” In my opinion, there is no more qualified demographic than engineers to measure the value of leadership structures and to consequently tear them down if they have no obvious value.

See, when I speak, when I ask “How many of you are leaders?” I want the whole room to raise their hands because I know leadership comes from everywhere.