We're All Managers Now: My Journey Into AI-Assisted Development | Matt McCormick

We’re All Managers Now: My Journey Into AI-Assisted Development

Matt McCormick

2026/07/05

What does the future of software engineering look like? Everybody is trying to figure out the answer to that question right now. This article shares the journey I’ve been on for the past couple of months toward discovering that answer for myself.

Exploration and Discovery

A few months ago I left my job as an engineering manager (EM) at a FinTech company (Chime) to take a sabbatical to have more time and energy to work on my own projects, ideas and interests. In retrospect, another reason was that I could see myself falling out of date with respect to the AI tooling that is available now and I wanted to have time to explore that more. Having been a manager for the past four years, I could tell that I was in danger of becoming out of touch and being one of those managers that people don’t take seriously because they are still referring to how things were done 10 or 20 years ago.

A bit of context about me. While I work in tech and have been a software engineer for many years before becoming a manager, I wouldn’t consider myself an Innovator on the Innovation Adoption Curve. When cell phones originally came out, I was the last person in my friend group to get one. The same thing happened when Facebook revolutionized social communication when I was in university - again I was one of the last people in my social group to sign up. I tend to choose boring, stable programming languages and tools for my work and side projects. I’m pretty much one of the people that needs to be dragged into trying out new things.

Figure 1 Innovation Adoption Curve - I likely fall into one of the Majority categories when it comes to adoption among other tech-peers

My journey with AI programming has followed a similar path. Over the Christmas break in 2024, I had some time and started playing around with using AI for programming on my personal projects. While I was initially skeptical, I was pretty impressed. I started with some simple tasks and got to the point of asking it to build a very specific setup using some niche libraries. Before prompting it, I thought there was no way it could pull this off, since there was likely very little knowledge available about these libraries. So I was stunned when it did complete the ask and that’s the point when the light bulb went off for me. In June 2025 I was using it enough that I started paying for the basic Claude Code plan. That then increased to the Claude 5x Max plan in March 2026.

After leaving my job at the end of March, I’ve been working on a startup idea and using Claude on a full-time basis. I started by just emulating how I previously worked as a software engineer. I used it to refine my idea, build a plan, and help with software development. I was always the one providing the input, though. So the cycle was a continuous Prompt -> Process -> Response cycle.

flowchart TD<br>subgraph User["👤 User Actions"]<br>Prompt["📝 Provide prompt(question or request)"]<br>Review["👀 Review response(evaluate output)"]<br>end

subgraph Claude["🤖 Claude Actions"]<br>Wait["⏳ Process & analyze(understand context)"]<br>Generate["🧠 Generate response(write code/text)"]<br>Return["✅ Return result(deliver response)"]<br>end

Prompt -->|send| Wait<br>Wait --> Generate<br>Generate --> Return<br>Return -->|receive| Review<br>Review -->|refine| Prompt<br>Review -->|accept| Done["✓ Complete"]

style User fill:#e3f2fd,stroke:#1976d2,stroke-width:3px,color:#000<br>style Claude fill:#f3e5f5,stroke:#7b1fa2,stroke-width:3px,color:#000<br>style Prompt fill:#bbdefb,stroke:#1565c0,stroke-width:2px,color:#000<br>style Review fill:#bbdefb,stroke:#1565c0,stroke-width:2px,color:#000<br>style Wait fill:#e1bee7,stroke:#6a1b9a,stroke-width:2px,color:#000<br>style Generate fill:#e1bee7,stroke:#6a1b9a,stroke-width:2px,color:#000<br>style Return fill:#e1bee7,stroke:#6a1b9a,stroke-width:2px,color:#000<br>style Done fill:#c8e6c9,stroke:#388e3c,stroke-width:2px,color:#000

Figure 2 Prompt -> Process -> Response cycle when pairing with AI<br>During this time Claude was pretty much writing all the code and I was reviewing it all. I thought I should do this as part of being a software engineer: to understand the system, and to help influence the setup and best practices early on. I also didn&rsquo;t really have enough trust yet in AI development.

Originally, I was also following Claude&rsquo;s output in real-time as it went through processing. This was useful to understand the steps it was taking. Sometimes I would be able to catch issues early if it was going off in the wrong direction because I hadn&rsquo;t explained something well enough. Eventually, though, I felt I didn&rsquo;t need to do this anymore as I started to trust Claude more.

So this led to me mainly reviewing the output after it was generated — providing feedback, or merging the code if it looked good...