Jeff asks three questions before he builds another AI agent

The story

Jeff asks three questions before he builds another AI agent

A note from Jeff.

Once you learn how to build an AI agent, you start seeing work for one everywhere. My inbox. Weekly reports. Meeting notes. Expense receipts. Follow-up emails. An agent for each. If that has not happened to you yet, it will, and it is genuinely fun.

Then one afternoon I caught myself wondering whether an agent could handle a hard conversation I had been putting off for a month.

I am not the only one building these. On Microsoft's July earnings call, Satya Nadella told investors that Agent 365 had "nearly 40 million agents registered across tens of thousands of companies" two months after launch. Registered is not the same as working, and Microsoft wants that number to sound large. Even so, it tells you how many people are now doing what I did.

I do not worry much about AI replacing leaders. I worry about leaders quietly handing AI the things that make them worth following.

Paul told the Ephesians to live "not as unwise but as wise, making the most of every opportunity". AI can help you make the most of your time. It can also fill every open minute with more output. Then you spend your week managing the agents you built instead of doing the work only you can do.

So before I build another one, I ask three questions, in this order.

Keep is casting vision, having hard conversations, making consequential decisions, and encouraging someone who is struggling. An agent could write the words for any of those. In every one of them, the person on the other end needs to be hearing from me.

Delegate is scheduling, research summaries, routine reports, and basic follow-ups. That is good work for an agent. Hand off anything that keeps you from the work in your Keep column, and do not feel guilty about it.

Collaborate is where working with AI beats working alone: brainstorming, challenging assumptions, testing a message before you send it. Ask it to argue with you. Have it poke holes in your plan before your board does. Tell it to play your toughest customer. AI brings speed and a second angle. You bring judgment, values, and responsibility for the result.

More this week

Leaders want to hear what another leader got wrong

Last week Jason Malec and I called our Base Camp members one at a time and asked what they wanted more of. They want to hear how other leaders are actually using AI in their own work and their own companies. Most of all, they want to hear what those leaders learned the hard way.

Information about AI is easy to come by. Any paid AI plan (Claude, ChatGPT or Gemini) will explain any tool you ask it about. What they asked for is harder to get: an account of which attempt failed, what it cost, and what the leader would do differently.

CEOs put the difficulty in the same place. IBM surveyed 2,000 CEOs and equivalent senior leaders across 33 geographies this spring and reported that 83 percent of them say AI success depends more on people's adoption than on the technology. Those same CEOs estimated that only 25 percent of their workforce uses AI regularly. Reading more about AI does not move either number.

So this week, pick one leader you respect and ask two questions. How are you using AI right now? What is one thing you learned the hard way? Then mostly listen.

The practice

Sort one week into Keep, Delegate and Collaborate, then do it with your team

Jeff again.

Draw three columns on a sheet of paper, head them Keep, Delegate and Collaborate, and sort the work that fills your week into them. Do not build anything yet. Just think.

Then bring the same three columns to your next staff meeting and have everyone sort their own week. Compare Keep columns first. You will learn what each person believes only they can do. You will probably find something one person is holding closely that someone else would gladly take today. And the conversation about AI will start from what your team values rather than from whatever tool launched this week.

Higher ground

The Keep column is hard to write by yourself. Left alone with it, most of us either guard work we should have handed over years ago, or give away something we miss only once it is gone. Proverbs puts the sharpening between two people, which is why the second half of this week's exercise happens with your team.

Do the twenty minutes alone. Then read your Keep column out loud to your team, and to one leader outside your organization who will tell you plainly where you have it wrong.

The next step

Base Camp is one ninety-minute session a month with founders and executives, plus the written briefing every week. Members bring the work they built, and the room takes on one hard question together.

See what Base Camp is →

Then hit reply and tell us what you put in your Keep column. We read every one.

Climbing with you,
Jeff and Jason