My Wingman helps me spend my energy on valuable decisions
I describe my requirements in human language. Then I observe what my Wingman does.
I have built an AI Wingman.
It manages my calendar, does customer research and helps me work out the most valuable thing I can do next to move towards my goal. It knows what that goal is. Calendar administration and customer research are parts of running a business that I tend to postpone or find draining. Having help with them changes how I spend my day.
When people ask what I find most valuable about my Wingman, I keep coming back to the decisions I make.
I still have to decide what matters, which opportunities I want to pursue and what I am willing to put my name behind. But I spend less of my energy working out all the steps needed to get to those decisions. More of my attention goes to decisions that have value for the business and the life I want to build.
I started by helping it understand me
I have built my Wingman using Claude Code and ChatGPT Codex. Before giving them more work, I wanted to give them a better understanding of me.
I used Voice Mode in ChatGPT and asked it to interview me from the perspectives of different coaches and psychologists. I went for long walks and talked about my strengths, weaknesses, blind spots, interests and ways of working. What gives me energy? What drains it? What do I want more of, and what would I like to do less?
Those conversations became a working model of me that I could use in the collaboration.
I then connected the digital history I could collect: emails, documents, meeting transcripts, notes and earlier conversations. Together, that gives my Wingman information about both the work and the person doing it.
Knowing that administration drains me is useful when we decide how to divide the work. Knowing my goals matters when we consider what deserves attention.
The work around a decision
Calendar administration and customer research are two practical examples of work my Wingman has taken over.
Before a customer conversation, it can bring together the company research and the history of our relationship. I can review that preparation and use it in the conversation, without personally gathering every piece of information first.
The same principle applies to the calendar: having Wingman handle the practical administration removes work I would otherwise have to remember and carry around in my head.
It can also investigate a problem, build what is needed, help put it into use and keep it running. That ability to carry work through matters. It means we can do something about what we discover together.
I describe, observe and adjust
I draw on the experience I built through practical AI work in my company, Agentic First. That experience helps me describe what I want.
But the way I work with Claude Code and Codex is quite ordinary. I describe my requirements in human language. Then I observe what my Wingman does.
If the behaviour does not match what I intended, I explain what needs to change. Then I observe again and adjust again. Gradually, the way it works becomes closer to what I need.
That is how I build it while using it.
I also check and approve what is going to be sent or acted on. I am still the sender, and I remain responsible for what happens on my behalf. My review is part of the process.
The value I feel in my working day comes from having more room for valuable decisions. My Wingman knows enough about me and my work to take on more of the preparation and execution around them, while I keep the judgment and responsibility that are mine.