Your Team Has 15 People Now. Here's How AI Helps You Lead Them All
Twice the people. Same broken toolkit.
2025 was not kind to managers. The end of the Zero Interest Rate Period (ZIPR) and the rise of Large Language Models both hit management hard. You had to put your career on hold when hiring freezes went into effect. Then, you had to keep your team motivated when layoffs started. And your reward for plowing through these challenges? Leadership wants you to manage twice as many people, with no promotion or raise. It’s just the new baseline.
Management was hard enough as it is.
Luckily, there’s a silver lining. Too many leaders focus on how AI helps engineering. Not enough explore how AI can help managers.
I was in a conversation with a Manager OS graduate recently. He shared how he used some of the AI tools we built in the course. It completely transformed his approach to 1:1s and the levels of trust that he could build with his team.
AI is a transformational technology for leadership.
In this new series, I’ll share exactly how to use these tools. Even if you watched my talk from early 2025, this series has new tools.
Stop missing the signals
When I started teaching engineering managers in 2022, I used a radar metaphor. New managers have a common failure pattern: they are blind. So much information about their team is out there, just waiting for them to notice.
The often chatty engineer is now reserved
The quiet engineer spoke up with a great idea in the team meeting.
Terrance and Felippe have been avoiding each other for weeks now.
The head of engineering shared a change in the organization’s priorities.
The product manager ignored the tech-lead and talked with Megan instead.
A foundational leadership skill is listening. Not just with your ears but with all of your senses. It’s noticing what’s being said and how it’s being said. Even more important is noticing what’s not being said. The negative space.
So, open your leadership radar. Pay attention. Don’t forget the “Care Bear Frequency” and notice how awesome your team is; how else can you give positive feedback and reinforce great behavior?
This advice is no less true in 2025/6 than it was in 2022. You just have a new tool at your disposal. With LLMs, you can now build your human leadership radar.
LLMs are great at connecting the dots. In fact, this is the transformational breakthrough in transformers, the attention mechanism.
There are many ways to build this AI leadership radar. The easiest to get up and running, at the expense of some usability, is to create one project for each of your directs. The AI persona here is to be their private coach. The key AI context is the user persona document. Before every 1:1, throw the latest meeting transcripts and other artifacts into a new query and ask the AI to refine the persona document and share what the AI learned about them.
As an example, here is a snippet of a persona for one of the course participants (I dog food what I teach):
### Communication Style
- **Thoughtful & reflective** - Asks clarifying questions, seeks understanding
- **Candid about uncertainty** - Comfortable saying “I don’t know if that’s the right strategy”
- **Collaborative learner** - Engages with peer feedback and course discussions
- **Integrative thinker** - Connects concepts quickly (”this is not different from tech lead to manager transition”)
Now that the AI understands the people on your team, you can ask it a series of questions to help you notice. Each question is like a different frequency on your leadership radar.
What was their latest accomplishment relative to their personal goals?
Was there an opportunity they missed to pursue a personal goal?
Did anything change in their behavior?
With this tool, you’ll notice more opportunities to praise, coach, and support the humans in your org.
Before moving on to the next tool, a word of caution. Using an AI leadership radar in 2025/6 is a lot like driving with adaptive cruise control. You just can’t rely on these tools if you lose the skill to notice things yourself. There are a lot of signals that AI just doesn’t have access to, such as tone of voice. Subtle bugs, like context window saturation, can reduce the quality of the feedback.
For 2025/6, use this AI leadership radar as feedback for yourself. The goal is not for it to catch everything. Rather, it’s for it to help you build your own human radar.
What next?
So what do you actually do?
Hack away at your first AI leadership radar. Create a Claude/ChatGPT/Gemini project for the person you have a 1:1 with next. Ask it to act as their coach and drop in your last three 1:1 notes and to interview you to create the initial persona document. You can get it up and running in fifteen minutes.
Using it for a 15+ person team will require manual work, so tie it to a recurring anchor, like your 1:1s. Once you figure out how you like to use the tool, invest a couple of hours to scale and automate it.
If you do, you’ll have an AI tool that won’t just help you manage better. It will help you become a better listener and a better leader.
