How to handle your CEO’s new obsession with AI

If your CEO isn’t all in on AI, there’s a good chance they will be soon. Here’s how to assess and react to their fascination with AI.

👋Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

I like shiny new ideas – so much so that new team members are told to wait till I Slack them three times about the same idea before paying attention.

I got obsessed with AI last year for three reasons:

1. Two of my companies have been acquired because we rode a technology wave – e-commerce (when it was the thing) and mobile. So if AI is the next wave, I want to ride it and get acquired.

2. Section is a content company at its core – we create courses – and anything that generates content faster and cheaper is valuable for us.

3. Edtech is a competitive industry with few moats, so being early AI adopters could help us be different (at least for a while).

AI felt like an opportunity for finding growth, differentiation, and energy – we had gone through a rough year and I figured we could use a bit of a boost. But my team wasn’t as energized by it as I was. They were all overworked, understaffed, and not excited about the idea of extra credit homework.

It took me six months to break through their resistance. I think they wanted to make sure: 1) I was serious 2) AI was real. Now we are all in – and seeing some payoff from the last 12 months of AI investments. 

So here’s how you can assess and react if your own CEO is pushing AI (based on what I and my team learned in the process).

– Greg

Figure out where it’s coming from

CEOs are restless. They feel the burden to be looking ahead, making moves now that will pay dividends in 12+ months. They want to be “strategic”, with investments that could accelerate the business in some way – a new pricing model, an acquisition, a new market – or… AI!

 Their CEO friends are making AI moves, their board keeps asking about AI, and competitors have announced new AI features. There’s also a good chance your CEO has really thought it through, and has a point of view on how investing in AI can accomplish one or more of the following:

1. Lower costs: make the company more efficient and productive and therefore increase margins.

2. Generate revenue: via a new AI product or feature that existing customers will pay for.

3. Increase enterprise value: by adding the AI halo over your company, since AI = the future right now, and investors and acquirers want to buy the future, not the past.

Or maybe they just microdosed over the weekend and got a vision about how AI will transform your company. In any of these scenarios, how you react matters – here’s our playbook.

How to react in these moments

While a good CEO doesn’t want everyone on their team to blindly follow orders all the time (let’s be honest, sometimes they do), they also don’t want to work with someone who’s negative from the outset. 

It’s easy to get distracted by some of the big questions around AI – how will it impact job loss? Do we need copyright reform? How do we limit the spread of disinformation in elections? 

While these are important questions, don’t focus here first. Instead, get to understanding the potential application of AI to your business – and as a leader, you should form your own opinion.

Start by trying to determine which of the three goals above (lower costs, higher revenue, or higher enterprise value) AI could drive for your company. This will give you a better sense of what sparked your CEO’s obsession. Then, take these steps:

✖️Don’t be reactive. This means your response shouldn’t be immediate even if an AI pivot feels imminent. Listen, and take some time to do your research, use AI yourself, and build your own POV.

✔️Be the first to build the AI habit – If you’re not using AI several times a week, you’re not informed and you have not earned the right to be in the conversation – and you want to be in the conversation. If your company has rolled out an LLM, start using it today. If they haven’t, get your own ChatGPT or Claude account (our 2 favorite LLMs). Use it every day for 30 days, and report back. Find your own use cases for AI – even if they seem trivial.

✔️Participate in the discussions – make time for the AI lunch and learns or webinars. Turn up at the vendor demos or read-outs from AI hackathons. Be a consistent player as your team or company tries to figure this out.

✔️Nominate your team as a guinea pig – Pick out a few workflows that AI could augment on your team, and run a 30 day pilot. If your company is already running AI pilots, get yourself or your team in that pilot.   

⭐ Think about company-wide use cases – This is where people with leadership potential distinguish themselves. Go beyond your team and think about how AI could drive more meaningful value – again, through the lens of lower costs, higher revenue, or higher enterprise value. Build the case that your CEO has (or should have) built – then share it and pressure test it with your manager, leadership team – and the CEO, if you can get access. 

There will be potential challenges or risks of using AI, but let the higher ups focus on that. Your focus should be on gathering evidence for or against the on-the-ground business case.

Our advice

New obsessions are common among CEOs – before AI it was crypto, and AR/VR. And often, these don’t pay out – i.e. Zucks investing over $50B in the Metaverse with little to show for it (but that’s another post about shitty board governance).  

Your job is to accept the obsession, and then participate in a meaningful way – unless you are convinced the CEO will move on in a week or two. This year the obsession is AI – and CEOs (and CFOs) are not likely to give up on this one easily. 

So run this playbook: try expanding on their ideas and spotlighting what they might not see. Share the enthusiasm, but bring some reality. And most importantly, do this from a position of being informed – own that responsibility.

And if you do find yourself pushing back a little (or a lot), know that this will cause some tension and discomfort – but the people that do this are usually the ones good CEOs want to work with again in the future. 

To the next 10 years,

Greg & Taylor