A few months ago, I started calling Taylor (my COO) about AI every day.
I’m a classic type six Enneagram – a worst-case thinker who processes my anxiety by immersing myself in research. I had done this on AI, and the implications were clear to me: AI was going to change the world and especially change the way we create and process content. As a business that sells content, we needed to start using it immediately.
But first I needed to convince everyone else. First of my vision, and second that they needed to de-prioritize other things on their (very long) to-do lists.
If you’re a leader and you believe in AI, you’re probably facing the same challenge. You might be hearing what I heard: “Greg, we get that AI is the cool new thing, but we have 4,000 other things to do, and this is a distraction.”
Don’t beat your COO into submission with 11 PM phone calls – there’s a better way. Here are 10 lessons I learned about bringing the team along.
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10 ways to get your team to move faster on AI
1. Develop a wall of conviction. Your team’s pushback will be strong, so your conviction has to be stronger. AI cannot be a “nice to have” feature for the product roadmap. It has to be the difference between winning your category (or maintaining your winning position) and losing to a disruptor. Research the impact of AI on your category, know how your competitors are using it, and use Claude or GPT every single day so you have use cases to point to.
2. Make the outcome clear. The biggest pushback I got was, “It feels like we’re doing AI just to do it.” No – we’re building the AI class of working professionals. Get clear on your outcome and then never shut up about it.
3. Pick 2-3 people to be the tip of the spear. You can’t convert everyone at once. Pick 2-3 people with some enthusiasm and influence, and ask them to lead the AI scouting mission. When they make progress, make it highly visible to the company. Show other people that progress on AI results in ownership, promotion, and praise.
4. Pay for GPT. This one’s easy – reimburse people for ChatGPT Plus. They need to use it to understand it. It’s $20/month well spent.
5. Talk about the fear (and the failures). Don’t be a delusional techbro optimist. Talk about your team’s fears around AI. Acknowledge when it doesn’t work (which it often doesn’t right now). But don’t let people wallow in cynicism. It feels good to be cynical, but it’s more often lazy and cowardly than productive.
6. Appeal to people’s self interest. Don’t go on and on about how great AI will be for the company. Most people don’t care that much about the company. Tell them it’s great for them (which it is). It’s easy to be in the top 10% of AI business users now – it won’t be in 5 years. People who start using GPT today will have better opportunities by 2025.
7. Share your use cases early and often. Don’t wait until you have a huge AI product launch to celebrate. If you develop an email template with AI, that’s a win. If you use AI to plan your next meeting, that’s a win. Share your use cases as you come across them – it will benefit your team and keep AI top of mind in their work.
8. Install a “shoutout to AI” at the company meeting. Every week at Section, we do a shoutout to AI as part of All Hands. It’s another good way to share people’s successes and to give visibility to the people who are joining “the AI class.”
9. Make your leadership team use it. You can throw your weight around a little bit here. No one will use AI if the leadership team isn’t using it. Make it an expectation of your C-suite.
10. Say thank you / great job. Not “I told you so.”
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Use code AIFIRST to get 25% off a seat to the workshop: Building an AI-First Organization.
