AI as an accountability partner.
The Setup
Three weeks ago, I leveraged Claude to help me with a 12-month plan to build an advisory/consulting business while also keeping my eye open for the right executive operating role. As a team, Claude and I laid out a foolproof plan, inclusive of specific daily activities, weekly reviews, call lists, outbound communications, etc.
Three days ago, I did a review with Claude covering the work I'd done against that plan and told me I was three weeks behind…and I could feel the disappointment.
The Details
I've spent 25 years in restaurants and the technology that runs them. Last month I stepped out to build my own practice, advisory/consulting work for private equity, solution providers and operators. While I have a broad skillset, I’m sharpening my AI capabilities to help organizations deliver results and get things done.
The plan is detailed. I broke Year 1 into monthly milestones, a weekly review cadence, and ten moves in the first thirty days. I wrote it out in markdown files (Claude uses .md files for artifacts and support docs) in a single folder. The discipline is supposed to be that on Fridays I fill out a one-page review against the plan, and on Mondays I pick the three highest-leverage things for the week.
I have written plans like this before. I know how they go.
By Week Three, you're behind on the review. By Week Four, you're behind on the review and the outreach. By Month Two, you remember the plan was a good idea and start over.
AI Stopped the Pattern
I'm using Claude as a planning and accountability partner. It reads the same files I do. It knows the plan. It knows the cadence. It knows what I committed to and when.
The reason this works is not because the AI is intelligent. It's because the AI has no feelings and doesn’t want to hear my excuses.
I asked it, "How am I doing?"
It gave me back: “zero of three weekly reviews filed, zero of two outreach batches sent, target list still in draft state eleven days past deadline, no evidence in the folder that the two sell sheets I'd committed to writing existed.”
Imagine getting that feedback from your human boss!
Then it said: "You haven't failed the plan, you've stalled on it. Three weeks of zero logged revenue activity is a calendar-discipline signal, not a strategy problem."
A good coach would have said the same thing. A good coach would have charged me a significant hourly fee and scheduled the conversation for Tuesday. I asked Claude at 8pm on a Monday night from my daughter’s swim practice, and the answer was in front of me in 8 seconds.
I’m not discounting the Career Coach. AI will not replace their expertise or value. But, AI can help with accountability.
What I’ve Learned
Treat the files as the system, not the chat. The most common mistake I see senior operators make with AI is treating it as a conversation tool. It is a conversation tool. But the real leverage is when the AI has access to your actual documents: the plan, the pipeline, the financial model. It can reason against them, not against your description of them. My Year 1 Plan is a markdown file or .md. The AI reads it. When it tells me I'm behind, it isn't guessing. It's checking, and it knows.
Write the plan as if a stranger needs to execute it. I had to write My Year 1 Plan with enough specificity that an AI with no context could tell me what was due this week. That same specificity makes it easier for me to execute. Vague plans are easier to write and harder to follow. Specific plans are the opposite.
Make the AI ask the hard questions. The questions I rely on most are not the ones the AI volunteers. They're the ones I've told it to ask me. What did I commit to last week that I haven't done? What is on the calendar this week that fails the gatekeeper test? Where in the pipeline am I overstating progress? What am I avoiding? I wrote those questions into my own plan as a discipline. I am much better at honoring them when something else is asking.
Use it for the work you'd normally avoid. The weekly review is the highest-leverage forty-five minutes of my week. It is also the easiest thing to skip, because nothing breaks if I do. The AI doesn't let me skip it without comment. That alone has changed my behavior more than the plan itself did.
Final Thoughts
Most of the conversation about AI in senior leadership circles right now is about deployment. How to roll it out across the organization, where it creates productivity gains or what governance looks like. Those conversations matter. I do that work for a living.
But there is a separate conversation that I think is being missed.
The most useful thing AI has done for me in the last twenty-two days is not automate a task. It has held me accountable to a plan I wrote for myself. That is not a productivity gain. It is a leadership force multiplier and the people who most need it are the ones who have nobody senior enough above them to provide it.
If you're running something, the loneliest part of the job is the part where nobody is going to push back on whether your calendar matches your priorities. Boards don't do it at the granularity that matters. Coaches do it at an hourly cost. Spouses didn't sign up for it. Peers can't see the data.
The AI can. Not because it is smart. Because it is unsentimental, and it knows the plan.
I am 22 days into a 365-day plan. I am, as established, three weeks behind. This is not a victory lap, quite the opposite. I need to get my a** in gear and AI is not listening to my excuses. It’s looking for progress against goals.
The gap between where I am and where I should be has been measured, named, and turned into next actions. Three weeks ago, that gap would have been a low-grade anxiety I carried around. Today it is four specific things to finish before I stop working for the day.
That, on its own, is the case for an accountability partner. The fact that this one cost twenty dollars a month and is available at 8pm on a Monday at swim practice is a separate, smaller miracle.
I'll write more about this as Year 1 unfolds. What's working, what isn't, what I'd change. If you're building something of your own, or running something that feels lonelier than it should, some of this may be useful.
If you have an accountability partner or coach, great! If you don’t, get yourself an AI one.
