What working with me looks like

I listen first

In the first few conversations I’m mostly listening, to the CEO, to the engineers, to sales and to a couple of customers if I can get them. After about twenty-five minutes with one founder, everything she was dealing with came down to one sentence: “We just keep missing dates or building the wrong thing.” That’s where we started.

What does it really need to be? I want an answer before anyone starts building, and I get there by comparing what leadership thinks is happening with what the team is actually doing.

I look at the whole system

Most of the stuck projects I get called into turn out to be as much about the people as the code, so I map the code, the data, the vendors and the people together, and I take note of where work slows down, gets deprioritized, breaks down or disappears into a void. Then I ask the question I’ve borrowed from Gary Keller for years: which one thing, done well, makes everything else easier or unnecessary?

I challenge, then I trust

My loop is simple: listen and observe, challenge and trust, support and hold accountable, examine and iterate. I push hard on the plan and the assumptions behind it, and then I trust the people carrying it out. Picking at people’s flaws mostly makes them defensive, and I need them telling me the truth.

Often the most useful thing a leader can do is get out of the way, put the team in touch with the people they’re serving, and hold them responsible for serving them well. How they do it is the team’s call, and I hold them to the result.

I architect the business and the technology together

I’ve spent most of my career in the gap between what a company is trying to do and what its technology can actually do. At BRC and Ideagility I learned how our customers made money and turned it into software that ran their ad campaigns with a fraction of the manual work. At Primo Chalk the company was mine, so I know what it feels like when a plan meets payroll. At Hideaway Report and Shep I ran engineering, and the work that mattered most was connecting it to what members and customers would pay for.

That’s what forward-deployed means to me. I sit inside your company, close enough to you and your customers to understand what has to change, and close enough to the code and the data to design how it gets built: the architecture, the data model, where AI belongs and where a deterministic system is safer, which vendors to trust and who to hire. Then I lead the people building it, more and more alongside AI agents that do a lot of the typing, and I check the work against real data and real customers before anyone calls it done.

From the start I’ll tell you which parts I’ll own and which belong to your team.

I’ve sat in your chair

I’ve founded and run companies, with the payroll and the hard calls that come with them. I’ve sold companies, and I’ve had my butt handed to me. So every technology plan I hand a CEO accounts for cash, people and timing.

I stay close to revenue

Every system I’ve built has had to earn its keep. At Ideagility that meant growing AgileBid to a million dollars a year in recurring revenue, at Hideaway Report it meant members, and at Shep it meant enterprise security reviews and pilots. I want to be in the room for those conversations, because they tell you what the technology actually has to do.

I plan to leave

The goal is a team that runs the system without me. I hire the people who will take over, make sure how everything works is written down, and step back once they’ve got it.