How We’re Getting Our Team to Actually Use AI

Hey everyone, hope you’re having a great week!

It’s been a while since my last email, and a ton has happened. Today, I wanted to talk about something that I think every single business owner needs to be thinking about right now… which is getting your team to actually use AI.

This has been my biggest focus over the past few weeks, and I wanted to break down exactly what we’re doing.

The Problem

So here’s the thing. We’ve had AI tools available to our team for a while now. We have a Claude Team plan that everyone has access to. But when I actually looked at the usage, it was pretty bad.

A lot of people were barely touching it. Maybe using it once a week to write a quick email or something. That’s like buying a Ferrari and only driving it to the mailbox.

And I realized this is probably happening at most companies right now. You give your team the tools, you tell them, “Hey, use AI,” and then nothing really changes. The output stays the same. The hours stay the same.

It’s super frustrating because I know how much of a multiplier AI can be when you actually use it well.

What We’re Doing About It

So about 6 months ago, I brought on an AI implementer. Someone whose entire job is to get every single person on the team comfortable and productive with AI.

Here’s what that looks like:

1. One-on-one calls with every team member

This has been huge. Our AI implementer is hopping on individual calls with everyone on the team. Actual one-on-one sessions where they sit down, look at what that person does every day, and show them exactly how AI can make their specific job faster and better.

A video editor’s workflow is totally different from a recruiter’s workflow, right? So the training needs to be specific.

2. Getting everyone on Claude Co-Work and Claude Code

We’re pushing hard to get everyone using Claude’s newer tools beyond the basic chat interface.

Claude Co-Work is pretty wild for non-technical team members. It lets them work alongside Claude on real tasks in a more hands-on way.

And for our dev team, Claude Code has been a game changer. We’re seeing people write code and build things way faster than before.

3. Building custom skills and agents

This is where it gets really fun. We’re building out a ton of custom skills and agents specifically for our workflows.

Think of these as specialized AI assistants that know exactly how we do things at our company. We have agents for content research, recruiting workflows at Paired, and channel management at Academy.

Stuff that used to take hours now takes minutes. We’re building these out constantly and adding new ones every week.

4. The internal dashboard (this is the big one)

Here’s what I’m most excited about. We built an internal dashboard where we track everyone’s AI usage. And yes, there are leaderboards.

I think the accountability piece is super important. You can tell people to use AI all day long, but if you’re not measuring it, it’s just a suggestion.

So now we can see who’s actually using the tools, how often, and what they’re using them for. And the leaderboard gamifies the whole thing. People are naturally competitive, and nobody wants to be at the bottom.

The Goals

Here’s what I’m expecting in terms of output:

• 30% increase in output within the next few weeks

• 50% increase after that

• 100% increase, meaning doubling output, as people get more comfortable

• Long-term goal: 3x to 5x output per person

Is that aggressive? Maybe.

But honestly, when I look at how much time people spend on tasks that AI can do in seconds, I think it’s very realistic. The people who are already using it well are already seeing those kinds of gains.

Why Every Company Should Be Doing This

Look, I know hiring an AI implementer sounds like an extra expense.

But think about it this way. If you have a team of 20 people and you can get even a 50% productivity increase across the board, that’s like adding 10 people to your team without the payroll. The ROI on this is absolutely insane.

The biggest mistake I see companies making is treating AI adoption as optional or self-serve.

People need guidance. They need accountability. They need someone showing them exactly what to do with these tools in their specific role.

The one-on-one calls, the usage tracking, the leaderboards, all of that matters way more than just giving everyone a login.

If you’re running a business right now and you’re not actively pushing AI adoption across your team, you’re going to fall behind. It’s a matter of when, not if.

Start now, invest the time, and the returns will be massive. My company Paired Recruiting can help you guys find an AI implementor, just book a call with us here.

Hope this gives you some ideas for your own team!

Have a great rest of your week!

- Charlie

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I just dropped this one and it ties perfectly into what I talked about above. I go over the 5 AI tools that I think are non-negotiable for business owners right now and show you exactly how we're using them.

Shopify CEO Tobi Lutke's AI memo on X

If you haven't seen this yet, go find it. Tobi posted an internal memo to his team saying that AI usage is now a "baseline expectation" at Shopify and that teams need to prove why AI can't do a job before requesting more headcount. He also made AI proficiency part of performance reviews. This is the direction every company is heading. The line that stuck with me... he basically said opting out of learning AI isn't a viable path forward. Agree 100%. If you're a business owner, this memo is worth reading in full.