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Stop Playing With AI. Your Team Needs a Real Strategy Now.
Shopify just made AI mandatory. Here's what it means for every manager.

Read Time: 4 minutes.
One of the hardest challenges for leaders is deciding when something is a fundamental change that demands our full attention and when it a fad that could easily distract out team.
Fresh on the heels of cryptocurrency fad (that may in fact be a slow moving trend), it’s easy to forgive leaders for being initially skeptical of the hysteria around AI.
And please count me among this group.
I was curious when ChatGPT first came out and give it a spin.
It was magical: how could such simple instructions yield such impressive results?
It was also disappointing: that is Will Smith eating spaghetti, but not really, and not really of any use.
After a few experiment, I shelved it. The ROI just wasn’t good enough.
My one exception was Fireflies AI, which I used to record and transcribe all of my meetings. But I chalked this less up to improvements in AI and more my nostalgia for having every meeting recorded in my decade at Bridgewater.
The ability to “go back to the tape” was a huge asset and these tools make it economically accessible and technically simple. Huge win.
Of course, the dots I can now only connect in hindsight should have told me that this was the just the beginning a truly fundamental change.
And it’s a change I’m leaning into now.
I get help from Claude and MidJourney for social media posts.
I use Poe to experiment with a range of models for the price of 1.
I built drag-and-drop employee “dashboard” with Poppy for our next MGMT Accelerator.
BTW - If you want to get a preview of how this works, make sure to join one of our free workshops next week:
But as much as I’m now paying attention, Tobi Lutke’s memo to the Shopify team last week felt like one those moments we’ll look back on as pivotal.
So much of the AI focus has been on the models. OpenAI, Antrphic, xAI, Meta, etc. All updating their models seemingly weekly to outdo the last.
But this is a call to arms on the application of AI.
And it’s problem-solving that demands AI get the first look.
This is not some upstart startup suggesting AI will change the world. This is the leader of a 125 billion dollar company that does more than 10% of global ecommerce on their platform.
The highlights:
Everyone needs to grow as fast as the company just to keep up.
Everyone needs to exhaust solving problems with AI first.
Everyone needs to be hand-on with AI yesterday.
And while the whole memo is a worthwhile read, I wanted to call out a few items that I think should give every leader pause.
High Standards Are Accelerating
This framing describes a phenomenon I see all the time. When a company is growing, you have to grow at the same rate to keep up. And even faster to get promoted.

Read that again.
You must improve at the same rate of the company just to re-qualify. Not get promoted, but just to get invited back. Just to re-earn the spot you’re already in.
How many employees hold the standard this way?
How many leaders hold themselves to the same standard?
It is almost impossible to see how anyone will do this without technology. If for no other reason than someone else will do it with technology.
There Is No Distance Learning For AI

I tried to recount my experience with this above, but almost every person who has gotten into AI described the same cycle:
Let me give it a shot.
Oh wow, this is pretty cool!
Hey wait, this isn’t what I really need.
Iteration, Iteration, frustration, more iteration.
I can’t believe that I used to do this any other way!
You must suffer the iterations to truly understand the application.
Tip: It is the first tool you can use to teach you how to use it better. Ask it for directions on giving it directions. Ask it to ask you questions it needs to best assist you.
Going “meta” like this isn’t most people’s first instinct. But it’s wildly effective.
And something you’ll only learn by using it a lot.
AI is a Fundamental Expectation

We work with a huge range of leaders. And I’d say right now it’s 50/50 between those encouraging AI use and those that are preventing it.
I don’t believe you’ll lose tomorrow if you resist AI. But I do believe you’ll leave yourself far too large a gap to close if you start using it once you realize you’re losing.
Perseverance Is Rewarded

This one really hit home. I tried to get AI to give me some very simple writing leverage early in 2024. It produced the worst combination of mediocre management advice with a near Shakespearean tone I could imagine.
There were no edits - they required complete rewrites. Negative leverage.
By late last summer - a mere 8 months later - far less sophisticated prompts we’re producing drafts that I could edit into completion within an hour. 10x leverage.
The models are getting better. And I’m getting better at working with them.
The only way around is through.
Hiring is Now Bot-First

He may have saved the best for last. We talk about codifying your culture in magnetic terms that attract those who share them and repel those who don’t. This does that.
We talk about making implicit expectations explicit so that people know how you’re keeping score. And if you care about how they achieve them, you must be clear. This does that too.
And we talk about how you can do better with fewer. That small, agile teams armed with the best technology will outrun large teams in almost every circumstance. This drives that point home as well.
If you don’t know where to start, we can help.
But not matter what, please start.
Free Workshops: AI-Enhanced Leadership
The most common question in our last cohort of the MGMT Accelerator:
How should I be using AI to lead my team?
There is no right answer. Other than you just need to start. Let us help:
Manage Up Confidently: Use AI to Synthesize Top Insights
(April 29 @ 12 PM ET)
3 Easy Ways AI Can Make You a More Thoughtful People Leader
(May 1 @ 11 AM ET)
Anyone who signs up will get the recording even if you can’t attend live.
What You Missed This Week
Our Saturday AM posts:
📌 10 Bad Habits I Had To Unlearn To Lead (Dave)
📌 9 Lessons to Avoid Regret (Mar)
And here are our most popular posts last week:
📌 Did you miss last week’s MGMT Minute?
I shared how I use the Good Time Index to keep myself focused on the most important things. And how AI is helping me spot patterns and solutions I had overlooked.
Our goal is to build a community of 1 million thoughtful, curious leaders.
You can help us by sharing anything that resonates with you.
Thank you for reading. Appreciate you!
Dave & Mar
Ways To Work With Me
MGMT Accelerator- Join us May 13 - June 5, 11:00 am -12:30 pm ET. Perfect for leaders with 3-10 years of experience. This hands-on, live program builds the tailored systems that help leaders achieve more while doing less. And this time we’re supercharging it with AI. Enroll today!
1:1 Executive Coaching - I have new slot opening in May. My sweet spot is solving real problems to help leaders build their management OS. Email me to setup an intro call.
Customized Leadership Programs - Bring our MGMT Accelerator or MGMT Fundamentals in-house for a tailored, intensive workshop. Ideal for 15+ leaders.
Speaking - We’re now booking keynotes for Fall of 2025. Hit reply on this note, and we can set up a time to discuss topics and pricing.
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