New ways to understand and measure team happiness in AI-reflexive orgs

I think it was Tobi at Shopify that coined the term, “AI-reflexive” but it could have been someone before them, who knows, I don’t really want to go down a rabbit hole. But at least for me, I heard about it first from Tobi, and it really had an impact on me and my team in a very positive way.

If you haven’t read Tobi’s tweet yet, read it: https://x.com/tobi/status/1909251946235437514

Like most frameworks, I think AI reflexive means different things to different orgs, and is uniquely different within departments in an org. For me, as a founder, I think about this a lot, especially since we moved fast in early 2025 to adopt ai workflows across our company.

I think of AI reflexive as a great efficiency unlock if done correctly, but it also has some sharp edges that I think we’ve done a great job of learning and working through, but that have also made me think more about something that might get lost for a lot of companies at a time like this.

First, I will say that if it’s November of 2026, and you haven’t pushed your org to be AI-reflexive yet, you are likely falling behind. But don’t let people shame you into immediately changing. You’re with a big group that are also behind, and I do believe everyone is going to catch up quickly.

This is one of the reasons why I wanted to write this post and Tobi’s tweet, to hopefully give a little extra nudge to anyone that needs it…but I also want to share an important thing about moving to AI-reflexive across an org that I think is so important.

The focus, as an org moves to AI-reflexive very quickly shifts to - increased efficiency. And you see all kinds of measures of it. In engineering, leaders talk about how many more PRs they’re getting done, in sales talks about increase in outbound emails, customer success looks at how many more tickets they’re resolving, marketing shows how much more content they’re getting out.

And usually, that’s step one for an org that shifts to AI-reflexive. Then comes the more important question though, okay so more PRs, more outbound, more tickets closed, more content, but how does that translate into actual code that impacts customer experience, increased sales, happier customers, and content that drives more pipeline?

Then things get stressful. I’ve seen a lot of orgs overload teams, they’ve already been pushed to “do more faster” with AI, now they’re being pushed to show why this is leading to better results.

The entire time, I think the most important thing gets overlooked, which for me as a founder, is what matters the most to me - how happy is your team? And are they enjoying things more or less with these changes?

As founders we have a great responsibility, and this applies to venture-backed and bootstrapped founders alike. We have a vision for the future, build a company with great people, and together we build great products that hopefully people love. The hiring and retaining great people part is what I would say is our biggest and hardest task as founders. It is what has kept me up at night the most over the years, and where I’ve also learned some of the hardest and most painful lessons, and had some of the greatest moments of incredible pride.

With the shift to AI-reflexive orgs, and AI-native workflows, I think it can be all too easy to focus on squeezing out more efficiency, to keep up, and show your investors, your clients, etc. that you’re using AI to move faster, but at the expense of team happiness, and I don’t think it has to be this way.

When I first read Tobi’s article, I put together a presentation based on what he wrote, and how I thought we could apply it to our company. Then I talked about it with our team, got their feedback, gave them the tools, and then, rather than pushing for more efficiency, faster, right away. I decided to just let them be creative, learn, and dive in.

For me, being AI-reflexive also meant using these same tools to understand how my team was leaning, or not leaning into this new way to work. Some people adapted quickly, others didn’t. I could have told the people who were falling behind, “hey you’re falling behind, you need to do x, y, and z,” but instead, I thought more about how to help other teammates inspire them instead.

It happened in a pretty beautiful way. People who were faster at adopting and becoming truly AI-reflexive started sharing more with their team and with the company, this inspired others, and they started to do the same. Not to sound overly dramatic but in my mind it was the difference between what I think really felt magical to people vs. forced.

Which brings me to the title of this post, how to understand happiness in AI-reflexive orgs. Happiness is not measured by engineers that feel like they need to pump out more PRs faster, or customer success teams that feel like they have to decrease time to response on tickets by 20%, it’s about teams who feel like they get to do more creative and interesting work now vs. before.

I often talk to my team about freeing up their time to be more creative. And at the core, this is where I think happiness comes from in many ways. And I think, done correctly, moving to a fully AI-reflexive org, in many of the ways that Tobi described back in April of last year, is how people can remove some of the more mundane, less-creative work off of their plate, and do the truly fun, inspiring creative stuff.

But I don’t think this is measured with traditional KPIs. Instead, what I’ve just learned through watching my team, is that it is measured by the increase in the number of new, creative things team members create. Customer success creates a new custom dashboard, an engineer builds a fascinating new QA gate visualization, marketing is running Figma through an MCP and generating new ideas faster.

In many ways, I see a shift away from me as a leader saying to my team, show me how you’re doing “20% more of X” and instead, letting them show me, and each other, how they truly are AI-reflexive, which means agents are now doing the mundane stuff, and they are doing the creative stuff. And in my mind, at least right now, that is how we can get happier teams.

Of course, in the end, we still have to look at metrics, and yes, I like any leader want to see teams being more efficient and moving faster, but not at the expense of happiness. And I think there is a path where you can win across both vectors, but you have to put happiness first.