Dirt Road, Gravel Road, and Paved Road Managers

Sometime back in 2010, while hanging around Google Ventures one day, I had a brief conversation with a entrepreneur where I picked up maybe the most useful metaphor I’ve ever come across in assessing leaders for tech companies. It tears me up that I can’t remember who this entrepreneur was to give him credit for it, though he actually was quoting a conversation he once had with Umang Gupta, one of the first 20 employees at Oracle and the current CEO of Keynote Systems. So – blanket statement – this idea did not originate with me, it’s third hand so it’s probably inaccurate and in this day and age everyone is making shit up all over the internet and not giving credit anyway so who cares.

This entrepreneur told me that back in the day he had interviewed with Mr. Gupta. “Before we go any further,” Gupta asked, “I need to know what type of manager you are: a Dirt Road manager, a Gravel Road manager, or a Paved Road manager?” I thought this was an awesomely simple way to frame one of the hardest candidate assessment problems in technology recruiting: can someone from a bigger company succeed at a startup? And vice versa?

I’ve never met Mr. Gupta, but this is how I’ve translated this idea. And Umang if you’re reading this, hit me up on LinkedIn, I’d love to hear it from the source.

Dirt Road Manager: When driving in the wilderness, there are no places to stop and ask for directions, no other cars to follow. The goal is to keep moving forward without breaking down or getting lost and this is accomplished by making lots of adjustments very quickly. A Dirt Road manager thrives in an environment where there is no guidance and everything is hard because it’s being done for the first time – a situation often found at an angel phase startup or in starting a new line of business.

This independence requires a certain fearlessness, with a healthy dose of hardheadedness and recklessness. There are few startup enterprises worth talking about that didn’t begin with some decisions that flew in the face of common sense or what everyone else was thinking. I equate this to the person driving a car down a dirt road with – let’s be honest – no idea where they’re going, but it just feels right and they’re going to figure it out. In the workplace, all the “you can’t”, “that won’t work”, “show me the data”, “someone else already tried that” just gets steamrolled by the Dirt Road manager. They’re on a mission.

On the down side, this can also be the type of person who rails against going down the road well traveled when there is adventure to be had. This person can seek out unpredictability and uncertainty over repetition and consistency. The absence of direction beyond their internal compass is a thrill. These ones live off the land and are typically found off the reservation. In a professional environment with an established culture, Dirt Road managers can call to mind one of those sandstormed Jeeps coursing the Bay Bridge, coming back from Black Rock City on Labor Day. Props for being a revolutionary, time to clean it up is kind of how that one plays out.

Gravel Road Manager: The transition from driving on a dirt road to a gravel road — when all of a sudden there is traction and things smooth out a bit and start moving faster – is palpable. That idea translates well to a startup that finds some success in the early going and also at a new venture within a larger company that gets the next level of funding or resourcing. The Gravel Road manager has a feel for when to stay on this newer road that has more momentum and velocity, but also won’t hesitate to go offroad if there is a giant tree in the way or suddenly a new dirt road emerges as a possible shortcut. In Silicon Valley, there are a ton of people in this category – the ones who’ve left the Googles and Facebooks to go to smaller startups, but that also did not want to go all the way to the beginning to start their own company on their own. They’re probably not as strong as a Dirt Road manager in a pure startup or as a Paved Road manager in an established company (see below), but they know how to use the tools required in both environments.

Gravel road managers deftly balance driving to innovate with sticking to a strategy that is showing success. They speak both languages (though sometimes it’s at the “I took Spanish in high school” level of fluency). At a growing startup, they can knowingly empathize with the early stage founding group who rail against the first signs of “process”, “frameworks”, and “best practices” as signs that “we are becoming a big company”, while also giving the newly hired exec (read: adult) some confidence that at least someone is capable of thinking constructively past three months from now. Flipping that around, in a bigger company, Gravel Road managers are also the ones who can balance taking the time to get the right people supportive of a new idea with the impatience of “nothing ever changes around here” to push people to make some things happen.

While this flexibility is a core strength of the Gravel Road manager, sometimes the situation requires the extreme; in a truly innovative environment or in a company where the gameplan is clear, the Gravel Road manager will probably be secondary to those whose strengths are better suited to the proximate challenge. They augment the efforts by adding breadth but they won’t likely match the Dirt Road manager in a state of creative chaos or the Paved Road manager in a clear structure.

Paved Road Manager: I’m not sure I would have internalized this concept if I hadn’t partnered with several execs at Google managing global business across 100s of people. A Paved Road manager understands that they can absolutely haul ass down the highway if they fully resist the temptation to turn off at every exit to look for a faster way. Like when driving on the highway system, they end up staying on the main road just because of inertia and habit and that’s not necessarily bad.

At a startup, one thing that is paradoxically liberating and debilitating at the same time is how easy it is to convince everyone to try out a new idea. While innovating and failing fast is imperative to survival early on, the risk to the Dirt Road manager is that when the company’s offering starts to catch on, there is this trap of wanting to constantly keep redefining a new opportunity as even bigger than the initial opportunity before the company has fully succeeded with the product that is just starting to take hold. Paved Road managers understand that, especially in a larger environment, there are millions of ideas worth exploring and that a team can lose an advantage by constantly trying something new instead of capitalizing on what is working. Paved Road managers don’t push to constantly redo the strategy and they actually don’t care to even debate it because they see it as a waste of energy that could be spent executing on a approach that is showing signs of winning already. They just go make it happen and then they keep doing the same thing. They take a bird in hand over two in the bush every time.

On the flip side, however, this is also why a Paved Road manager can fail in a startup or avoid a similar creative challenge altogether: without a clear direction or strategy to follow, their lack of improvisational skills or inability to act when surrounded with chaos or ambiguity can be paralyzing. Paved Road managers are great at accelerating a product or service that already has considerable forward progress – like going from 60 to 80 on the highway. On a dirt or gravel road, where the goal is just to go in a relatively straight line let alone get up into third or fourth gear, this skill set might go totally unrealized.


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