Setting organizational direction.

It took me two years as a manager to reach the “leadership is lonely” phase. Folks had warned me it would happen, and it did. The team was struggling to acclimatize after acquisition, and I felt like I was carrying the stress alone. I saw the problems, but didn’t know how to make progress on them. Two years later, I’d learned more about management, increasingly able to rely on experience over invention, and no longer lonely.

When I began managing managers, things shifted. I felt certain that I knew how to solve all the problems, but didn’t know how to rely on others to solve them, and often learned of problems long after they’d deteriorated. Delegation, metrics, meetings and process–practices that I’d considered obvious or unimportant–crept into my toolkit, and I started to regain my footing.

Over the past year, as I’ve transitioned into largely working with managers of managers, things shifted again. Let’s explore that a bit.

Scarce feedback, vague direction

For much of your early career, you’ll have folks who are routinely giving feedback on your work. As your span of responsibility grows, particularly if it’s somewhat specialized, increasingly no one will feel responsible for or able to provide that feedback. In a new function, at a small company, your team might be two people, and already you’re inhabiting this realm of muted feedback.

Where you used to get direct, actionable advice, now you’re listening for ghosts: grumbling on your team about too much technical debt, the rumor that two peers are engaged in some light feuding, agitation where there was previously calm.

As a functional leader you’ll be expected to set your own direction with little direction from others. When things in your area are going poorly, you’ll be swamped with more direction and input than you can readily absorb, but when things are going well, you’ll often be responsible for supplying your own direction and that for your team.

If you don’t supply it yourself, you’ll start to feel the pull of irrelevance: maybe no one really cares what we do? What would happen if I stopped showing up? Maybe I should be doing something different?

That initial instinct to leave after hitting a pocket of seeming irrelevance is a comforting one, but the wrong way to go. You can certainly avoid the current swells of ambivalence by switching jobs, but if you’re successful at another company then you’ll end up in the same situation.

This is a symptom of success. You have to learn the lesson it’s trying to teach you: setting your organization’s direction and your own.

Mining for direction

The first step to setting direction is to cast the widest possible net for ideas. Talk to folks at your company who have worked at different kinds of companies and ask what those companies did really well. Talk to your team, and see if there are ideas to draw out that they’ve been noodling on but haven’t yet volunteered. Read some new technical papers. Meet with peer companies and ask them what they’re focused on. Do the same with the Googles/Facebooks and the smallest, most interesting companies.

This first phase is discovery without judgement: take ideas from everywhere and generate a pile of ideas that folks are pursuing, even if you think they’re terrible.

Once your pile of ideas has gotten large enough, craft it into a strategy, and then start testing that strategy. Keep refining and exploring your strategy until you can figure out what the key decisions are, a kind of ad-hoc sensitivity analysis. Once you identify the key pivots in your strategy, you’re finally prepared to define a direction!

Make a clear decision on each of those pivots, write up a document explaining those decisions, and then see if you can get anyone to read it. They’ll disagree and be confused by a bunch of what you’ve written. Keep testing, and refine the confusion down to the smallest group of controversial problems possible.

Once you have those problems, return to your rounds of engaging with experienced leaders at other companies, and ask them how they’ve made those tradeoffs before. Ask them for their stories. Ask them for the context that made one path perfect early on, and why they changed their minds as they grew larger.

Incorporate everything you’ve learned into your strategy document, and you’re done.

Well, almost. The one remaining problem is that almost no one will have the time to soak the full detail of your overly-precise document, so the one final step is to distill it into something comprehensible without hours of close reading. I’m still working on the best way to do this, but I suspect it’s cutting all unnecessary and even most essential complexity to capture as much of the meaning as possible in three to four bullet points.