Hello!
I’ve been getting questions lately about how I got into this AI space. And honestly, the answer keeps looping back to something I struggled with for years in my operator roles.
More on that below. It’s that time of year for reflecting, right?
~ Harry
I spent five years as a Chief of Staff. And for most of that time, I couldn’t really explain what I did.
Not because I wasn’t doing anything. I was everywhere. Strategy meetings, cross-functional projects, putting out fires, connecting dots, and having a blast being somewhat of a rogue generalist. I was, as many operators describe themselves, “the glue.”
But explaining that to someone new or outside the company, no matter the context (interview, resume, networking), sucked.
Glazed eyes for days.
“I improved cross-functional alignment.” And?
“I streamlined our quarterly planning process.” Okay, but what does that mean?
“I was the person who made things work.” Sure. But what did you actually *do*?
Too vague, and I sounded like a corporate training manual. Too casual, and I tended to devalue what I was doing. Unless you knew what a Chief of Staff was... good luck.
I didn’t have a good answer. None of the operators in related communities did. The value was real, but the proof was... words. Just words about work that was nearly impossible to demonstrate.
“You had to be there.”
The Invisibility Problem
Operators have always had this curse.
Our best work doesn’t photograph well. It’s the meeting that didn’t blow up in our faces. The project finished on time. The cross-functional political battles and nonsensical riffs that somehow turned into alignment because of your you. It’s preventing problems, not solving visible ones.
This is genuinely valuable work. Companies run on it. But it shows up in micro-moments rather than KPIs. It’s felt more than measured. And when it comes time to prove your worth (in a performance review, a job search, a conversation about your next role), you’re left with descriptions.
“I was strategic.” “I drove initiatives.” “I wore many hats.”
These are just, again, words. Fancy (and cringey) ways of saying “trust me, I was useful.” The corporate poetry (h/t Shaina Anderson) that somehow becomes second nature.
I’ve been on both sides of this now. Struggling to articulate my own value as a CoS, and then coaching other operators through the same conversation.
Honestly, there are only so many ways to say it without sounding like everyone else applying for the same type of career paths.
And for a long time, that was just the reality of being an operator. You accepted that your work was invisible. You hoped the right people noticed. You got good at telling stories.
But something’s changing.
The Follow-Up Question
I’ve been talking to founders and people hiring for ops roles lately. And there’s a question I keep hearing that I don’t remember from a few years ago.
It comes after the standard stuff. After “tell me about your experience” and “how do you approach ambiguity.” After you’ve explained your ability to figure things out, handle complexity, operate in different environments.
The follow-up: ”What have you actually built?”
Not “what did you work on?” Not “what were you responsible for?” What did you build?
Pre-AI, this would have been a tough standard to meet. Some might consider it unfair. Operators don’t build things - engineers build things. We design, we scope, we coordinate, we manage. The actual making was always someone else’s job.
But the question makes sense when you realize what it’s really asking: Can you produce something tangible? Can you show me, not just tell me? How did you turn an idea into something that impacted growth?
And until recently, most operators couldn’t.
What Changed
They couldn’t because the requirements to do so meant becoming engineers, learning to code, or - on a deeper level - stepping away from their generalist and operator roots that made them valuable in the first place.
But now those requirements are not as far to reach. And combined with the business sense of an operator, you can learn to architect real, ROI-driving solutions with tools that didn’t exist five years ago.
Custom GPTs that solve real problems. Automated workflows that actually run in production. Internal end-to-end applications that teams use every day. Real artifacts.
Think about how designers have always worked. They don’t just talk about their aesthetic sense. They show you a portfolio. “Here’s what I made. Here’s the impact it had.”
Operators can have that now. Except instead of mockups, it’s workflows and tools that actually run.
“Here’s the automated process I built that saves my team 10 hours a week.”
“Here’s the Custom GPT my sales team uses to prep for calls.”
“Here’s the system I deployed that tracks X and alerts us when Y.”
That’s a different kind of proof. It’s about demonstrating.
The Threshold Is Higher Than You Think
I want to be clear about something, though. The bar isn’t “I can prompt.”
Everyone can prompt now. That’s literacy. Knowing how to use ChatGPT doesn’t set you apart any more than knowing how to use Excel did in 2010 while on Wall St.
The real threshold is production. Things that:
Actually work reliably
Teams adopt and use daily
Solve real problems that tie to real goals, OKRs, and EBITDA
Artifacts that prove you can produce from start to finish (and may even show up on a GitHub contribution graph).
This is harder than it sounds. Most operators I talk to have tried AI in some form. They’ve used ChatGPT, followed a tutorial or two, maybe even started building something. But they don’t have much to show for it. Their experiment hit a wall. The workflow they tried got ~70% of the way there. Their teams don’t really use what was built.
Now, this doesn’t mean you need to be vibe coding SaaS applications left and right. But from what I’ve seen in the market today, there is still a gap between where operators are today and where the opportunity lives.
What This Means
I want to be careful here. I’m not saying the invisible work doesn’t matter anymore. Coordination, synthesis, and making things run smoothly are still essential. Companies still need people who can do that (and perhaps more than ever, given how fast some of these seed-scaling companies are growing).
What I’m saying is there’s now an additional dimension for people to consider.
And the operators who can support themselves with real artifacts will have a different kind of perspective to share.
It compounds, too. Every solution you build adds to your portfolio. Every working system becomes a reference point. There is more proof in the promise.
What I’m Doing About It
This thinking is what led me to build a course launching in January.
Not another course about understanding AI or promising an outdated PDF of prompts that AI generated in the first place. Trust me, we have plenty (too many?) of those.
My focus is on helping others build. It’s about leaving with artifacts you can point to instead of knowledge you can absorb anywhere else.
The idea is simple: operators who want to answer “what have you actually built?” should have a real answer by the end. Something deployed. Something that works. Something that proves you can produce.
If that sounds like what you need, the first cohort starts January 12th, and you can use ‘AI4OPS’ for a nice lil discount.
I also ran a lightning lesson last week on some of the initial topics for that course - free to check out, and may be helpful if you’re specifically thinking through the CustomGPT vs Workflow vs Agent decision-making process.
The Bigger Picture
But beyond any course, I think this shift is worth paying attention to.
The question “what have you built?” is going to keep getting asked. By founders, by hiring managers, by the people deciding your next role or your next raise. And operators who can only provide descriptions of activities or hopes will be at a disadvantage compared to those who can show their work.
As I said earlier, some challenges can’t be solved by building. And there’s a reason operators are the ones who solve those. They have solutions and ideas that others don’t possess. But now, even more of your ideas can be prototyped faster and don’t need as much support from others; the potential value you bring is greater than ever.
I’m still figuring out what most of this means for future organizational design. But I know it starts with being able to answer the question.
What have you actually built? And what will you build next?