How do we enable (and measure) that which does matter?

A reader prompted me to write a little more after the “Infinite goods, finite measurements” post.

“follow up from this thought and talk about how we should enable (and measure?) that which in fact does matter. We’re talking company culture change here that is difficult to get the CFO’s of the world to understand.”

-Clearly an avid reader

So many thoughts, chief of which is that no CFO has ever listened to me on this subject and I don’t think it’d go that well…

  1. Enabling is easier than measuring. When humans connect the effort they put in to results they achieved, via recognition from their leaders, there is joy. When the efforts and results are disconnected, we call it bureaucracy. (E.g. “she works so hard” is rewarded over the person who dutifully didn’t spend $400k authorized budget by finding a better way).
  2. Measure the rhythm and the results. A great quasi-boss once told me that he was keeping me on a project I botched because he knew that someone who makes 9 out of 10 decisions as really great ones is exactly the person to entrust with the 1 screw up—the next decision on it will be a great one, and better than any outsider. Rhythm is a momentum feeling of repeated success over time—it requires setting desired objectives, rewarding human factors like commitment and achievement and adaptation, and burning midnight oil or taking a foot off the gas depending on the results—a true professional often avoids sprinting by planning ahead on a big objective, so they never break a sweat (but get better results!).
  3. Use OKRs. That’s why I’ve adopted the Objective and Key Result format over and over again on teams, releasing software engineers, QA, and designers from time tracking and capacity measurements to gaining their commitment towards long-term objectives then following up with weekly reports where they take pride in their own work as they bend reality to ensure the objectives happen.

But that would require leaders to know and articulate what they want, and listen to their team on what’s possible.

Which is built on good hiring.

Which is built on great instincts.

Which come from great mentorship and a life of choosing to live openly (“with a good eye”).

Which is never a conversion experience or revelation.

Which is why I like hiring young, unjaded people and entrusting them with 2-3x their weight class of tasks, and outperforming established teams counting the beans.

But I am epically awful at convincing any execs, until after being entrusted for 3-6 months to prove the results.


More Posts

Make Startup Bets *Quickly*

Imagine you’re at a roulette table with 100 chips. You’ve heard of this happening before but never imagined it would happen to you… the dealer

Focus on outcomes

Another post for “emergent tech professionals” on this list. Executives often express inputs as their desire. Inputs like “make an app,” or “do this,” and

Scroll to Top