It’s funny how much we techies like to talk about data. Data, data, data. Big data will feed into AI systems to solve youth homelessness, make a dent in world hunger, fix climate change, and make everyone richer, to name but a few of the banners being waved.
…Except there’s also extreme bias issues, the possibility of a Minority Report-like pre-criminalization, and could result in the sudden end of our species, even without the malice of the robots a la Westworld.
But hey, at least we’ve got Dall-e.

Okay, got it: we love data.
Yet chatter and mantras around “data-driven” are often mere data drivel. That’d be a good post someday soon, actually, so let’s hold that thought for now.
One of the ways that we’re so pennywise with data is in the way we ignore the hundred some-odd pounds of data standing next to us at the coffee pot in the break room. You know, Keisha. Or Matt. Or Dominic. The person you work with, your coworker, your direct report.
While we can’t put Mixpanel on top of them to build out some funnels or watch a Fullstory recap of their days, we can ask them about how things are going.
We can schedule 1-1’s that we don’t cancel and take seriously, part of which is devoted not to tactical portions of the work, the so-called hard skills, but the person in actual possession of those skills.
There is a mountain of data that you can get in a < 5 minute conversation.1
The Secret to Success
One of the best tools for this I learnt from a former (and favorite) CTO I worked for. (Thanks, Nic!).
Admittedly, I don’t remember his exact prompt, but here’s what I’m using several years later: “What's your score?”
On the first pass they’ll likely ask what you mean. This will give you a chance for some orientation and contextualization. How are you feeling overall? What’s your happiness quotient? Satisfaction level? Frame it in whichever way makes sense for them, the scale being 1-10.
You’ll likely get an uncertain answer: “I don’t know, a 4?”
Congrats! Now you have context to work with.
People always have feelings. What they rarely have, though, is a good sense of their own feelings, a clarity to the internal realities they’re walking around with.
The storm is raging inside, but they don’t have a good Doppler system to measure or track it. And while it’s a fool’s errand to try to actually be precise about such things, we can create a place-in-time model that allows us to partner with them in tracking what’s going on and working towards some new, presumably better state.2
So now, with a number in hand, we get to ask some follow-up questions:
What’s something we could take off your plate to help bring that number up?
What’s the biggest negative contributor currently to your score?
What’s something we could work towards in the next few weeks that you think would bring that score up?
Have you subscribed CTORly yet or are you actively avoiding ever reaching a full 10?
You get the idea. (And that last one is realllllly important.)
But seriously, that’s the long and short of it. It’s simple, sure, but by god is it effective.
Just recently I was able to stop asking someone their score because we’d dragged it out of a 2 into a consistent 7-8 over the course of about 6-8 weeks. I created a Slack reminder for every Friday morning to make sure I’d get the new data point at the end of each week and then follow up with my “Why” and “What now?” type of questions. Today, instead of finding a way to escape what was becoming a miserable situation, we’ve found a renewed excitement for what’s ahead and are in a healthy steady-state. Huzzah!
Do Ask, Do Tell
“Ye have not for ye ask not” applies to a huge swath of leadership shortcomings. If we would just learn to ask some simple questions instead of contriving overwrought predictions and thoroughly complex guesswork we would be blown away by how easy it’d become to get deep, thoughtful, and actionable data.
Go get some data this week and drive meaningful improvements with your people, then we can all get back to talking about being data-driven to our heart’s content.
What’s This?
Every Thursday’ish I send out a new article related to who knows what, though usually centered around leadership, communication, and management within product engineering teams and startups.
Opinions are my own and they’re usually damned good, so make sure to subscribe!
The hard part is getting to the point where those 5 minutes are rich with information because that requires trust, and trust takes time, patience, and a lot of work. “Trust is built in drops and lost in buckets.”
‘Better’ is, of course, contextual in nature and ultimately defined by the person on the other side of the conversation.