Moving the finish line.

When I was a young boy, a cousin gifted me a copy of Steely Dan’s greatest hits. In that era of CDs and 56k baud modems, I didn’t have much new music to play, and over the summer I listened to that CD enough that bits and pieces come back to me despite not knowingly listening to a Steely Dan song in at least 25 years. One song in particular, Black Cow, has a lyric that occasionally comes to mind, “You should know / How all the pros play the game / You change your name.”

The lyric comes across similarly to a joke that I sometimes tell managers moving into manager-of-manager roles: “Do you know why VPs never miss their goals? They move the finish line!” The joke isn’t funny at all, but I tell it because it captures something important that many new managers struggle to appreciate: executives are evaluated based on their perceived outcomes rather than their actual outcomes.

To give a concrete example, I worked at a company whose engineering teams were struggling to plan work. The head of engineering mandated that we move to scrum. To prepare, they told a manager to document scrum on the engineering wiki page. After the wiki was updated, the head of engineering declared that we’d moved to scrums successfully. None of the teams actually started using scrum. Planning didn’t change, let alone improve, but the head of engineering was proud of accomplishing their goal. Afterwards, the entire migration to scrum was never mentioned again. If you haven’t worked in the industry for very long, this might sound like a lie, but it absolutely happened, and it’s not particularly unusual.

Well-run companies don’t tolerate perception straying too far from reality, so their executives are generally accountable to their real outcomes. Poorly run companies often punish executives who are too familiar with reality, and consequently operate in a realm of shared delusion. If you’ve worked in a large company, you will be familiar with many techniques for editing reality: frequent reorgs that make it hard to attribute accountability, new leaders who’re quickly fired for failing to resolve a pre-existing problem, literal changes to quarterly goal targets, redefinition of general launches into targeted launches, transmutation of targeted launches into alpha tests, and so on.

The follow up lesson to my joke is that it’s pretty hard to force a poorly run company to become better run. It’s easy to make local improvements on your team. It’s a bit harder to allow your local improvements to spread organically, but doable. It’s very tricky to go further: small companies sometimes do weird things due to lack of experience with their current problems, but large companies behave strangely due to deliberate choices they’ve made. You really need to be in an executive role or have an engaged executive sponsor.

If you do find an engaged executive sponsor (if you’re not sure if they’re engaged, ask them to do something–literally anything–to help, and see if they do it), then you can move towards being well-run by running something along the lines of business review meetings and ensuring executives show up to push on the content. Are folks caught in the trap of blaming misses on insufficient headcount? Do their goals correspond with something that genuinely matters? Do presenters exit each review with a clear understanding of how leadership is evaluating their work?

It won’t change things overnight, but it’ll gradually become harder to move the finish line, and reality will slowly reassert itself on how the company operates.