Shopify’s AI memo was bold, but one-dimensional
What it got right, what it missed, and what you can do differently
A couple of weeks ago, Shopify’s CEO, Tobi Lütke, published a memo declaring that AI is now a “baseline expectation” for every employee. The language throughout the memo was direct and unflinching: “Frankly, I don’t think it’s feasible to opt out of learning the skill of applying AI in your craft… If you’re not climbing, you’re sliding.”
It’s the kind of message that spreads fast on the internet - and it did. You can read the full memo here.
It was first shared with me on a WhatsApp group with a couple of ex-colleagues (and now close friends). Whilst their response was “urgh” and “disappointing”, my first reaction was intrigue and in some way, admiration. I think it’s smart to set expectations around AI usage. It will reshape how we work, and there’s something powerful about a founder taking a bold stance.
So, in many ways, I’m not against what Tobi is trying to do. But the more I read it, the more it felt one-dimensional. The memo was clear, but it was missing a lot of nuance. And for something (AI) that is going to fundamentally shift our world, that absence of nuance feels significant.
The memo didn’t ask deeper questions about personal values, ethics, or what kind of society we want to live in 10 years from now. It didn’t acknowledge the emotional reality of change - the fact that even good change can be hard, and that not everyone responds to change in the same way. It didn’t call out where human creativity can and should be chosen, even if AI is faster in those situations.
I don’t think this is just about Shopify. It reflects a broader pattern I’m seeing in leadership right now around AI. It feels like there’s a rush to take a stance, and with this comes a desire (or a pressure) to sound decisive, futuristic, and strong. There’s a fear about being seen as a Luddite or being left behind.
Who does the memo leave out?
The memo presents a binary: you’re in, or you’re out.
I found myself wondering—who does that bring in, and who does it leave out? I read a brilliant post recently, AI and the Human Condition, by my friend Evgeny, where he explores how people’s attitudes to AI often mirror their broader outlook on life. It made me think that the people who instinctively love Tobi’s memo tend to be the blind optimists, while those with more caution or concern about the future may feel shut out.
And, more cynically, it’s often those who stand to benefit most from this new AI-powered world - investors, CEOs - who are cheering the loudest. The ones who feel disoriented, displaced, or even a little scared about what this shift means for them are the ones I see pushing back. A quick scroll through Reddit shows how many software engineers had a very different reaction.
Surely, we need a balance of perspectives. It feels overly simplistic to say, “The future is AI” - no questions asked. Questions should be asked. And leaders should be the ones inviting them.
You can set a bold direction and leave space for emotion
Change is hard - even when it’s the right move. And too often, leaders expect their teams to adapt without acknowledging the internal friction. I’ve seen major internal backlash over things far less consequential than this. At Intercom, when we lost the privilege of poached eggs at breakfast, it dominated the All Hands Q&A for weeks. I never quite understood why the poached eggs mattered so much to people, but the lesson wasn’t about food - it was about emotion, control, and how change feels, even when it makes perfect sense on paper.
That’s the part I wish more leaders would speak to. You can set a bold direction and still make space for emotion. You can move fast and still honour the questions. You can declare that AI matters and still invite people to engage with it creatively, not just compliantly.
What the memo could have said
What if this memo had said: “Here’s where we believe the world is heading - and we want you to shape that future with us”? What if it had opened space for showcasing great use cases, hosting friendly challenges, or sparking discussion around the deeper ‘why’?
That’s the kind of leadership I believe in. Not because it’s softer, but because it’s stronger. It asks more of people and it invites them to think, not just execute and keep their heads down. It trusts them to hold complexity, which is what this new phase of working in tech requires.
We’re in a moment where AI will transform how we work. I feel pretty confident in that. But that doesn’t mean we should let it decide what we value, the role of original thought and creativity, and what we protect. I keep thinking about this excellent piece on gradual disempowerment, which explores how small, subtle shifts in responsibility can quietly erode our sense of agency. That’s what’s at stake - not just how we use AI, but whether we still feel like we have a voice in how it’s shaping our work.
What’s on your memo?
Brilliant leadership isn’t just about setting direction - it’s about being clear on why it matters, and giving your team the tools and space to get behind it. It means inviting original thinking, not just compliance. And knowing that real progress comes from people who feel ownership, not just obligation.
What did you think about the memo? What message will you be sending to your teams?
If you’re a founder or executive looking for deeper coaching on strategy, leadership, and personal growth, I’d love to chat. Just reply to this email, and we can explore whether it’s a good fit.
As always, thanks for being here!
Flora
