First Principles

What Entrepreneurs Can Learn from Contracting Officers

The habits that make a good contracting officer, structure, risk-pricing, documentation, are the same ones I wish every new entrepreneur had on day one.

By Joary Khairudin-Casey, Founder · Principal Consultant · September 7, 2026 · Long Read · 5 min

Most people picture a contracting officer (CO) as the person who slows things down. The one who asks inconvenient questions, points out risks nobody wants to hear about, and insists on documentation when everyone else is ready to move. I used to hear that caricature in classrooms and hallways for years. Here is the part nobody says out loud: the very habits that frustrate program staff are the same habits I wish every first-year entrepreneur had from day one.

I have spent most of my career inside the federal acquisition system, teaching it, advising on it, and watching the best COs work. Now that I run my own business, I keep reaching for the same mental models they use. Not because I want NovaLux™ to feel bureaucratic, but because COs are, at their core, rigorous risk managers who make decisions with other people's money under real consequences. That is also what entrepreneurship is, even when it is described in nicer language.

Here is what I have learned worth borrowing.

Treat Every Commitment Like It Has a Clause

A good CO reads the contract before they read the email about the contract. They understand that every promise is part of a structure, and the structure is what protects both sides when the relationship gets tested. Entrepreneurs tend to do the opposite. We make verbal commitments over coffee, send a one-line confirmation, and then wonder six weeks later why the scope has quietly doubled.

I have started treating every client conversation like I am drafting a mini statement of work in my head. What is the deliverable? What is the timeline? What is in scope and, just as importantly, what is not? When I send the follow-up email, I write it the way a CO would write a modification: specific, dated, and unambiguous. It is not about being rigid. It is about protecting the relationship from the fuzziness that creeps in when two busy people assume they heard the same thing. That discipline has already saved me from one scope creep situation this quarter, and I am only a few weeks into building this business.

Price the Risk, Not Just the Work

The best COs I have worked with understand something most entrepreneurs do not: price reflects risk, not just labor. When they evaluate a proposal, they are not just asking whether the number is reasonable for the hours. They are asking what happens if the contractor underperforms, what the government's exposure looks like if assumptions change, and whether the price includes enough cushion to absorb the inevitable surprises.

Early-stage entrepreneurs, myself included, tend to price based on what feels fair or what competitors charge. That is the wrong baseline. The right question is the CO question: what could go wrong here, and does my price account for it? When I took on my first training development project through NovaLux™, I initially quoted based on the hours I thought it would take. Then I stopped, thought like a CO, and asked what happens if the client changes direction mid-build, if the subject matter turns out to be deeper than the kickoff suggested, or if the review cycles go from two to five. The price I landed on was meaningfully higher, and it was the right number. That is not greed. That is risk-adjusted pricing, and it is how sustainable businesses stay sustainable.

Document the Decision, Not Just the Outcome

COs are trained to build a defensible record. Every significant decision has a memo, a rationale, and a record that explains not just what was chosen but why it was chosen over the alternatives. It looks like overhead until something goes wrong, and then it looks like the smartest thing anyone did all year.

Entrepreneurs rarely document their decisions. We remember the outcome, forget the logic, and then repeat the same mistake eighteen months later because we cannot reconstruct what we were actually weighing at the time. I now keep a simple decision log for NovaLux™. When I say yes or no to an opportunity, I write down the alternatives I considered, the assumptions I was making, and what would need to be true for the decision to look right in six months. It takes five minutes. It has already changed how I evaluate my next bid, because I can see, in my own handwriting, what I got wrong and what I got right the last time I faced a similar call.

The Discipline Is the Advantage

Here is what pulls all of this together. Entrepreneurs celebrate speed, agility, and intuition. Those are real strengths. But without the CO's discipline underneath, speed becomes carelessness, agility becomes instability, and intuition becomes wishful thinking called strategy.

The contracting officers I admire are not slow. They are deliberate. They are not risk-averse. They are risk-aware. They do not kill deals. They structure deals so the good ones hold up in practice. That is exactly the posture I want to bring into NovaLux™, and it is the posture I would recommend to any independent professional who is trying to build something that lasts longer than a good quarter.

The next time someone at a networking event rolls their eyes about a picky CO they worked with, ask them what the CO was actually trying to protect. Nine times out of ten, it was the same thing you are trying to protect in your own business. You just have not built that habit yet.