Each chapter is made up of essays whose titles complete the following:
Under no circumstances should you...

Do you know what kind of leader you are? Are you sure you want to answer that question? For all my conflicts with him as a CEO, I did learn a pretty succinct way of categorizing managers from Doug Erwin during his time at the helm of RLX. According to him, there are “generals,” who lead from the front, and there are “sergeants,” who have to push from the rear to get people to go where they need to go.

The “sergeant,” as used by Doug, was meant as a derisive epithet. He was talking about me. In his world, the sergeant is the guy who is responsible for taking a hill, and will do so no matter what the cost. In this way, he will not engender positive will with his team, and many of them will in fact have a negative set of feelings associated with their sergeant. As such, according to Doug, the sergeant is in the rear, quite literally pushing his men up the hill because they don’t want to follow him. He was letting me know he didn’t think too much of me as a leader. I disagree (of course), but debasing this claim is not the point of this essay. Illustrating that leadership persona is, and sergeants have their place inside of companies.

Sergeants can be useful when you really need to get the job done, and aren’t worried about team morale or the leadership path of the sergeant with that team. Sometimes it is absolutely necessary to have this person who is going to force people up the hill. If done right, he will get more productivity and performance out of the team than even they thought possible. Some members of the team will reach the top of the hill and want to quit. Others will be much stronger for the process. Clearly you want a disproportionate of the latter than the former when all is said and done. The risk with being a hard-nosed sergeant is that you will burn through your staff, and, worse, gain a reputation as someone who burns through headcount, making hiring much harder in the future.

I actually have some issues with this bimodal classification of leaders, and would prefer to expand on it just a bit. I think there are three types of leaders. The “general” Doug referred to is more like a “lieutenant.” A lieutenant is much more likely to be leading from the front, and they will know the name and responsibility of each and every person on their team. When you are thinking about a startup, this is your leader/founder. Ideally, they exude confidence and leadership, and always have an answer, even if it ultimately is the wrong one. A lieutenant never says “I don’t know” to his troops. They will know when to ask for help, and will do so from their trusted advisors, but never letting on to those down the chain of command that they are not in control of the situation. A lieutenant can make the transition from small company to large by way of checking their ego at the door; essentially becoming a middle manager.

The “generals” to which Doug was referring do in fact exist, but they lead from off the battlefield, and have a very broad view of it. Not everyone who is following them will necessarily have even met them, but know that they must follow their directions. Think of a general as a construct appropriate for a larger company. The risk with a general in a startup is that they are likely to be too separated from the work, and instead choose to lead the team(s) by management sound bites and motivational stories. These can be a bit tiresome on a small team, especially when the members of the team feel like they are doing all the work.

Knowing what kind of leader is going to gate what kind of results you are likely to see, and what kind of situations you are most well suited to take on. As a general, you generally (no pun intended) can’t have a very depth oriented view of the details. You know what the overall goals are, but you are no longer a front line soldier worried about the minutia of the tasks to get it done. This will actually prevent you from making some of the harder real time decisions, for no other reason than you lack context (or data). These generals will need strong downstream leaders who are closer to the action to make those decisions.

Generals are also less likely to be willing to roll up their sleeves and do “real” work. They’ve done plenty of it in the careers, but having reached this point in their leadership career, they are more apt to seek opportunities where they have a team of doers, so that they can be a planner and strategizer. As I stated earlier, this type of leader is a hard sell for any new venture, and you have to know if this is the type of person you are before you get involved in a startup or smaller company.

When we first invested in RLX, the management team was thought to be full of rock stars (remember what we talked about with regarding rock stars) from Compaq. The CEO had literally built the server market from scratch. That was a long time ago, and he was quite removed from the day to day requirements of creating business from the ground up, and certainly quite a bit removed from the resource constrained environment that is a startup. Because he was of this leader type, and the fact that his entire senior leadership team had a similar mind set, the company had some problems relating to conserving cash, building customer pipelines, having small teams, and building product cheaply. Not understanding that the stage of the company necessitated a different type of leadership was a failing on the part of the investors, and, to his credit, it wasn’t until Doug showed up as CEO that things really started to turn around from a sales and product development standpoint.

As a leader, Doug had just come out of a startup environment, with a very successful exit. He had spent many of his formative years at IBM. I bring this up because it’s important to note that just because you have a substantial amount of big company experience doesn’t mean that you can’t take the lead role in a smaller company and be successful. You just have to be willing to roll up your sleeves and do actual work, and ensure that your management team has a similar view on their responsibilities.

The moral? Know what kind of leader you are, and whether or not it is appropriate for the environment into which you are stepping. If you are the wrong leader for the given scenario, you risk alienating your team, and potentially burning through headcount by way of disenfranchised employees.