Updated: Jul 17, 2019
In Which I Fail to Take Good Advice
The VP Engineering sat in front of me. I had screwed up a project: late, poor quality, unhappy people. Definitely a miss. He was a few years older than me, and, I thought, kind of burned out (we were both somewhere around thirty at the time).
He leaned back, looked out the window. “Well”, he said, “nobody bats a thousand” and did a kind of “meh” shrug of the shoulders.
I was horrified. “I bat a thousand”, I thought. “I totally bat a thousand! What's the point of doing this if you don’t bat a thousand!?”.
I was fooling myself, of course. I hadn’t been perfect up to that point. But I’d managed projects for over five years, all in startups, and most of them had turned out well — volatile teams, lots of moving parts, good to great products delivered close enough to on time and on budget.
No real misses, until this one. So I thought, “batting a thousand!! That’s what I do. Mr VP is a burned out wreck, and I’ll file this one under Stupid Advice from the Wrong People”.
And it came to pass, a year or so later, he took off for a bigger job, and I became VP.
In Which I Painfully Learned My Limits
For a while, being VP was like being a manager: I put structure in place — dates, goals, processes, roles — managed the details and helped trouble-shoot when things went off the rails. There was more to track, and the added stresses of exec staff and board meetings, but it was more or less the same job, just bigger.
And then it wasn’t.
Somewhere around sixty or seventy engineers, heading quickly to a hundred, it felt (to me) like things got out of control — or, rather, uncontrollable. We had a quality panic — a major customer threatened to drop the product — fixed, but a nasty scramble. We had a critical engineer threaten to leave. We acquired a remote team with a different culture. Every month brought something that I couldn’t just fit into a structure and then diligently track.
“Batting a thousand” became a distant memory, and I missed it, terribly.
In Which I (Slowly) Came to Terms With Ambiguity
A new CEO came in and I watched, with astonishment, then irritation, and then admiration, how comfortable he was with not knowing, with not trying to force reality into boxes of his creation. When it wasn’t clear if our financials were accurate, he was able to say “well, we don’t know. We will, but we don’t now”. When there was a bad miss in product, his response was “yeah, that’s a bad miss. Fix it next time, will ya?” (he did talk like that). He could wait, live with uncertainty until the organization came into the right alignment with it and we could move.
He wasn’t casual about the need get things done, and get them done right. He was just much more aware of what he (and we, as an exec team) could control, and what we couldn’t. It was like seeing a higher definition view of reality, with more space, more room to move.
To my amazement, the company worked better when we weren’t trying to force reality to explain itself.
So I learned, slowly, to see the organization less as a machine which could be perfected, and more as an organism, who’s behavior could be adjusted and trained, with perfection in some of its parts, but never in the whole.
Nobody Bats A Thousand: From Control to Guidance
A great baseball manager wins a little over 50% of their games, and wins the World Series a couple of times (picking one more or less at random: Tony LaRussa, win percentage .536, three World Series titles). It’s a good metaphor. No senior manager gets everything right. Somewhere in the organization there are always mistakes, screwups. The skill is in accepting uncertainty and becoming masterful in understanding where to intervene — where structure will work.
The transition from early manager to exec is, at a fundamental level, coming to terms with the fact that you can guide a group of people to overall success (and, in fact, that’s your job), but you can’t control a group of people to perfection.
Early Management: Clarity, Structure and Control
This evolution, from control to guidance is a recurring journey, which shows up frequently in my coaching clients — always different in specifics, but very similar in outline.
When we first take on a management job, the skills we need most are the ability to clearly see the work, structure it in some way, and then control the structure.
Our job is to get three, or five, or ten, people from A to B, and the best way to do that is to:
understand exactly what A and B are
break down the steps from A to B
carefully track the steps
The skills we need are analytical, and we need to be uncomfortable with ambiguity. Clear goals and clear reasoning are our friends.
Director to VP: Getting Comfortable With Ambiguity
A Director or VP runs an organization of teams. Communication to the people actually doing the work is indirect, and it’s impossible to understand exactly what each person in the organization is doing, let alone directly control it.
Thinking analytically is necessary, but not sufficient. A purely analytical view of the work of fifty or a hundred (or more) people won’t capture the nuance of all the thousands of decisions that are being made daily in the organization.
The skillful judgement becomes not “I need to break this work down and control it” but “I need to set clear goals and boundaries and then give the organization what it needs to do the work”. And bear in mind “what the organization needs” may include timely, strong decisions, direct feedback and some serious motivation — not just free food and a nice office.
The Dance of Structure and Ambiguity
Organizations exist to create structure out of ambiguity. We take a set of ideas (a market, a product, customers) and put them together into something that feels tangible, solid. Management is the craft of building those structures in the face of a constantly changing and essentially unknowable reality.
Above first-level management, a tolerance and respect for ambiguity becomes a fundamental skill as we start to understand that our structures are never permanent and our organizations exist in a sea of complexity and change.
Ambiguity is not our friend. But we get to dance with it, so we might as well get comfortable.