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How to Fill a Leadership Void With Your Own Agenda

The truth about politics at work.

I mean this post for young senior executives.

If you are a young executive, chances are you are being overruled, being shouted down, losing at politics or being quietly discounted. You’re young — don’t be too hard on yourself.

But if you want to get past this step — below are five realizations that help a lot.

Politics are not always Machiavellian

My first serious management role was as VP of Engineering at Odeo (the too-early podcast startup that just happened to birth Twitter). When I joined, the board and advisors were rightfully concerned about my lack of experience so they set me up with a series of meetings with potential mentors.

I met former Dot Com 1.0 engineering executives from Netscape and Infoseek and a few others.

And I went into these meetings with tons of management questions about hiring, performance reviews, project tracking, and estimation.

They all said essentially the same thing: none of that really matters. They thought any approach I chose for those goals would be adequate.

What they said instead was: “You need to pick the metrics you’re going to report to the board immediately so that you can control your own story. If you don’t do this, the board will try to micro-manage you.”

I remember thinking at the time that this advice was incredibly political. They also said, “It doesn’t matter what metrics you pick, just that you pick something and present it forcefully.”

See? Doesn’t that sound crazy?

Because I was a total rookie, I only had one view of company politics, which was that politics were 100% motivated by the selfish goals of individual executives.

This selfishness does happen. But now that I’m a little more worldly, I want to present the other side, what feels like politics is often the result of people behaving constructively.

Keep that in mind if you feel that you are losing at politics.— it might not be that people want your job. They might be trying to help or to be demonstrating what you should have been doing or to just keep the company’s momentum.

Leadership does not have clear boundaries

A general explanation of leadership is to think of a company as filled with voids.

These voids represent problems or opportunities that don’t yet have a solution or plan.

The vast majority of workers will not fill these voids. Instead they will persist in doing the defined tasks that are explicitly part of their jobs. This behavior isn’t laziness mind you — school and most parenting trains us to do what we’re told.

Think of leadership is an unnatural act. It’s part skill. But more than skill, it’s a deviation from the norm.

Spotting and filling voids is both a skill and a mindset. The people who rise through the management ladder learn this skill and eventually come to employ it as second nature.

So, you’re invariably going to run into people that are rushing into leadership opportunities at different speeds. If you and someone else share a boundary, then they might rush to solve a problem that you were thinking you were going to solve.

Important note: Spotting and merely complaining about a void isn’t leadership.

Your strength is now your weakness

Because nobody trains individual contributors for leadership, the ones who fall into it are often being rewarded for a personality characteristic that approximates good leadership.

The two most common healthy characteristics are improvisation or extreme fastidiousness. The most common unhealthy characteristic is extreme hubris (which I’ll ignore in this post, but which I covered here).

I’ll use improvisational leaders as a starting point and then give a fastidious example later.

Imagine a team that runs into an unforeseen problem. The problem turns into a disaster and the whole company can see it.

One person on the team is calm though. They aren’t flustered — they just start talking constructively about the options. And they lead a solution.

This person is going to get promoted into leadership for their improvisational skills. They saved the day and everyone saw it.

Unfortunately, this person is then going to run into problems after the promotion.

The most common pattern in leadership careers: your strength eventually becomes your weakness.

The great improviser is going to inherent a team of people who are demanding that she form a plan and offer it to them. That’s the opposite of improvisation.

At some fundamental level, this new leader will resist planning because she’s so proud of her improvisational strength. After all, that’s what got her the promotion.

This resistance is also easily rationalized by the universal truth that no plan ever survived contact with the enemy (i.e. reality). So, improvisers like to go in loose and adjust on the fly.

That lack-of-planning invites the well-meaning void-filling of neighboring leaders.

This pattern is nearly universal. You have so much pride in your rapid promotion that it’s impossible for you to see that the skills you’re proud of are no longer meaningful. This blindness will hold you back for awhile.

If you don’t fill the leadership voids, someone else will

Here’s an example of a well-meaning leader who stepped all over my territory when I was a newbie improvisational leader.

This is a continuation of the Odeo story where I was VP of Engineering. My plan when I was hired, if you’d call it that, was to change very little at first, see what was working and what was broken, and then fix what needed to be fixed.

In other words, if you asked me what my plan was I’d say “wait and see.”

About two weeks after I joined, a much more experienced person joined to be my counterpart as VP of Product, Tim. (He went on to help FitBit get to IPO).

Tim took me out to lunch on day one and then asked me what my plan was. Again, I had no plan. He was really nice about that — didn’t criticize me at all.

Instead, he came to me the next day with a “suggestion” that we implement an engineering management system called Scrum. From his perspective, this system would make his job much easier. Scrum comes with a clear system for filling out a product backlog (which would be his job) and a system for estimating future launches (also good for his job).

There’s nothing bad about what he did. He was kind. Scrum did turn the engineering team into something predictable. Pace of development, product planning, and transparency all improved.

But I felt bad, and still do. I think that’s okay to say. Lots of junior executives feel bad when this happens to them. It’s the leaders version of emasculation. Shouldn’t it have been my job to suggest Scrum?

But Tim was in the right. He was constructive and practical. And effective. He definitely wasn’t being political in my then naive understanding of politics as some form of empire building. From his perspective, what’s he supposed to do? Wait for me to mature (years)? Suggest I be fired? Tell me I’m bad at my job? Let the company struggle?

The point here is that if you don’t fill the leadership void, someone else will. And that person is not a bad person. Rather, the bad feeling you’re feeling is the indication that you weren’t filling a crucial void.

Aside: ironically, the main value of Scrum was that it gave the CEO a sense of stability which allowed him to think bigger instead of being bogged down in operational anxieties. Given that opportunity, the CEO decided we were working on the wrong thing. That’s one facet of how Odeo became Twitter.

People need to know you have a plan

I’ve seen this five times now as a coach. (I’m not fastidious — so I have no personal experience.)

A fastidious person makes tons of plans, the trains always run on time, the details are taken care of.

Their extreme competence means that they get promoted into leadership just because they’re so rock solid.

Then, for some reason, they start developing a reputation as not strategic. We live in such a genius worshiping culture that this feels like a put down. If you’re not strategic then you must not be very smart.

Here’s what’s happening. There’s a deep pragmatism underneath the fastidious mindset.

That pragmatism leads to a simple belief: there’s no point making big plans that you can’t execute. So this type of leader is waiting on announcing any long term strategies until their own team is running at top speed.

During this waiting period, the company will develop a hierarchy of strategic thinkers. This hierarchy is not based on quality of strategy — it’s based on speed of announcing a strategy.

The hubristic leader will announce first. They are all talk and these big strategic plans are what defines them. The improvisational leader will announce as soon as they perceive a major company problem (which is pretty often). The fastidious leader will never announce because they’re always too late. That’s why no one thinks they’re strategic.

So the problem is speed. To guard against this the fastidious leader should announce early what their big plan is. Here’s a hyperbolic way of doing that while also staying true to your pragmatic sequencing of work:

“I believe that my team can eventually make X impact in the company,” where X is some ridiculously grandiose plan. “Unfortunately, we are currently not fully meeting our most basic responsibilities. Expect me to spend two months shoring those problems up and then I will move on to X. The results of X will be so grand. You won’t believe how grand X is going to be.”

That strategy ends with a #trumpism — the fastidious leader would benefit from adding a little bit more hyperbole to their statements. The reason is simple — you are the most competent people in the company and you want to make sure you have a chance to execute.

If you don’t advertise that you have a plan, someone will take the opportunity away from you.

Yes, you always need a plan.

Yes, pragmatically, you always need to have a plan and communicate that plan.

Even if your plan is “it’s too early for a plan” you need to be saying instead, “Because structured process is premature in teams of less 15, I’m holding off on implementing <placeholder plan> until we reach that size.”

Otherwise, you’re going to have people meddling in your business when they should rightfully be trying to solve some other problem in the company.

And, this might be the most important part, you need to let people know you have a plan. Because new executives tend to think in terms of assigned responsibilities, they often don’t tell people about their plans.