The Crumblestones Of Acquisition: Contracting Culture (Part 2)

Serialized from Contracting for Rapid Acquisition: A Practical and Personal Guide to Disrupting the Status Quo for a More Responsive Future by Lorna E. Tedder

Contracting Culture: The Most Invisible Anchor That Can Sink Any Strategy

When I launched this series, I described six persistent weak points that show up in acquisition organizations again and again. I call them Crumblestones instead of cornerstones because they often start with hairline cracks, barely noticeable at first, but can compromise the entire structure of your mission. Of all the Crumblestones I’ve seen in the field, none runs deeper or resists change more stubbornly than Contracting Culture. Like the pillars holding up a five-sided building, if the one in the center, Culture, is solid, the structure can stand.  Precariously perhaps, but it’s possible.   If the center pillar crumbles—the culture of the organization is horrible—but all the outer pillars are strong, the integrity of the structure will eventually fail because the center of it isn’t supported.

Let me start with a story.

The last time I briefed these structural issues in person, I arrived early to prep my slides while attendees were still at lunch. I’d paused on a slide that simply said CULTURE when one young attendee entered the room and saw it as she found her chair. Her eyes widened. She looked anxious. Moments later, she bounced up out of her seat, crossed the room, and asked me gently but urgently what kind of “culture” I planned to talk about.

We were both immersed in our own definitions. I was thinking about risk aversion, bureaucratic norms, and the decision paralysis I’ve seen stall contracts for months. She was thinking about heritage, identity, and inclusivity. Neither of us was wrong, but we were definitely talking about different things. That moment became a lesson not only in cultural nuance, but also in communication—the next Crumblestone we’ll explore.

For now, let’s talk about the kind of culture that quietly erodes our ability to move fast and think clearly in acquisition: the deeply ingrained contracting culture that shapes our sense of what’s possible.

The Way We’ve Always Done It

Ask someone why they do something a certain way, and you’ll often hear, “Because that’s how we’ve always done it.” It’s not laziness: it’s identity. That process, that approach, that level of caution? It’s part of what makes people feel competent, safe, and relevant in a system that rarely rewards risk.

And that’s part of the problem. We’ve grown an entire generation of professionals who aren’t comfortable saying yes because the system has trained them not to be. No matter how many times you tell them to think “Yes, if” rather than “No, but.”

I’ve worked with GS-15 equivalents and colonels who had never once used innovative contracting tools, not because they were resistant but because they didn’t want to look foolish. Their inexperience-based fear evolved into even more inexperience.  They weren’t going to try something new to them if they might make a public mistake or have to ask for help privately, so the new tool became even scarier.  How do you provide top cover to your team if you’ve never seen these tools work firsthand? It’s a Catch-22: If leaders aren’t comfortable with innovation, they can’t defend it. If they can’t defend it, innovation dies on the vine.

The Innovation Gap

Many of our most senior leaders haven’t attended the new tool or technique courses they send their teams to. They got their certifications decades ago—and unless it’s a mandatory leadership seminar, they haven’t stepped into a classroom since. Meanwhile, newer staff are told to “be bold” while watching every initiative get slow-walked through outdated review chains and unnecessary approvals.

I’ve seen the shift firsthand. As a GS-12 in the late ‘80s and early ‘90s, fresh with a new warrant, I had more latitude to try new approaches than I did decades later as an NH-4. I’ve lost track of how many GS-15 equivalents and even SES leaders have told me they can no longer do the kinds of things they once could when they were junior. Rules that didn’t exist back then have tied today’s leaders down, or worse, beaten the willingness to try out of them. It still amazes me that I had so many encouragers when I was “the kid with the new warrant,” and I’m both grateful for the freedom and positivity I was given then and the understanding now of how important it is not to stifle the next generations’ ability to step up. 

If you’re junior, you may not realize that much of the bureaucratic oppression comes from the discomfort of individual leaders who may be very good at what they know and unwilling to fight for what they don’t know. One of my last contracts before leaving DoD in 2018 should have been a breeze—a $1M effort under SBIR Phase III. I wrote my first SBIR Phase III contract in1995 and had written many since. I was everybody’s go-to person to understand how to use them. 

To my shock, it stalled because the competition advocate, unfamiliar with the Phase III flexibilities, insisted I write a Justification and Approval document under FAR Part 6, which wasn’t required and which she doubted she would approve. My contract package hadn’t even gone to her for review.  She was aware of it only because she overheard a conversation in the hallway and made it her business since it was sole source. Her discomfort with the unfamiliar killed momentum. The only way it got through all these unnecessary wickets was that I had literally decades more experience with SBIRs and had the confidence to argue my case whereas a less experienced Contracting Officer would have been more deferential to a competition advocate’s position. 

That’s not about contracting policy. That’s about contracting culture.

Over time, we’ve unintentionally grown an entire generation of acquisition professionals who aren’t just cautious—they’re uncomfortable saying yes at all. Not because they lack ideas, but because they’ve learned through example that the safer career move is always “No, but” instead of “Yes, if.” It’s a risk-averse culture that’s been carefully passed down, often without anyone even realizing it.

This disconnect highlights an even bigger danger: if we don’t deliberately teach young acquisition professionals how to be innovative early in their careers, they’ll be trained out of it by the time they reach leadership roles. Conservative approvers, whether from personal fear or outdated systems, become gatekeepers who smother the very initiative we claim to want. And the cycle repeats.

The Isolation Trap

Contracting culture discourages cross-pollination. Some government offices—doing unclassified work—still prohibit employees from using LinkedIn, a platform that has become a thriving ecosystem for acquisition tools, peer insights, and real-world lessons learned. If you’re not seeing how other agencies solve problems, you may think your way is the only way. If you’ve spent your entire career in one location, how would you know what you’re missing?  You don’t know what you don’t know.

This isn’t about social media access: it’s about professional curiosity. Culture encourages people to stay in their lane, keep their head down, and avoid rocking the boat. And that comes at a cost.

Breaking the Habit of Familiarity

Changing contracting culture is like changing the way you were raised to eat dinner.  Or in my case, supper.

The culture I was born into back home told me I couldn’t eat all of Grandma’s sweet potato casserole with the marshmallows and home-grown pecans on top and then move on to the fried squash chips and then to the fried chicken and then to the dressing with mushroom gravy and cranberry sauce. Nope, 100% sequential eating was forbidden. I had to take a bite of the garden peas and another bite of the lime-green cottage cheese salad in the fancy mold before I could circle back to the other foods on my plate.

Since I was 8 years old, I’ve been eating my meals as a variety in either every spoonful or every other spoonful. When I would complain about the “pea juice” touching my fried chicken leg—ewwwww!—Daddy would tell me it was gonna get mixed up in my stomach anyway, and I needed to grow up and “eat right” if I didn’t want to get “what for.”

Eventually I “matured” and even learned to love casseroles, the ultimate variety in the dishes I grew up eating.

Out of the blue, my biohacking experiments took a turn for the better when I turned my culture of origin on its head.

That’s right: I did the unthinkable and ate my food separately and sequentially.

Why ever would I do such a bizarre thing? Purely as an experiment. As a biohacker, I wanted to improve my blood sugar, so the experiment—flying in the face of my food culture—was to eat all my green veggies first, before touching my proteins, and leaving anything sweet or starchy for last. I tried it for 3 days with meals I normally ate, but in a different order.

It felt weird, eating this way, but the numbers (think lead times) surprised me. No glucose spikes. Lower overall blood sugar for the entire meal by at least 20%. Same foods, same macros, same calories. Just a little different method to my consumption. And a much better outcome.

I’m sure plenty of people back home will tell me I’m “doing it wrong” because it’s different from what they know and have always known. But you know what? I’ll take that better outcome, thank you kindly.

Contracting is the same way. Sometimes, changing the sequence or the mindset yields better results. The system says, That’s not how we do it. Even when how we do it no longer works.

So we dress up the old systems with new language. We issue memos about being “agile” while forcing agile teams through ten-layer approval cycles. We pretend we’re doing something new when we’re still clinging to the comfort of the casserole we know.

Diagnosing Your Hidden Culture

Changing culture is often discussed as if a new leader’s brief tenure will create some kind of utopia overnight, but it can take years—an entire generation even—for real change to occur without aggressive attempts to cultivate something different. Few people account for just how hard it can be because culture is ingrained and comfortable, or at least comfortable in a “devil you know” sort of way. 

It’s usually the generational differences and technology that change contracting culture over time.  Think of the difference in how Gen-X and Gen-Z approach work-life balance, for example.   Think of how newer technologies, like AI, might change market research and proposal evaluation in the future:  automatically scouring contractor websites or government databases for commercial products’ pricing and availability, evaluating videos of demos instantaneously, spitting out a contract.  

Did that last sentence excite you?  Make your stomach twist? That’s how changing culture can feel.

A big part of shifting contracting culture isn’t just being open to change. Instead, it’s building systems that support change. That’s why real agile acquisition approaches matter. It’s why Other Transaction Authority (OTA) agreements, rapid prototyping contracts, and commercial solution openings (CSOs) are so critical when used correctly. They aren’t just faster. They represent a mindset shift: moving away from simply cutting-and-pasting FAR templates toward actually thinking about how to solve problems differently. Too often, we say we want to innovate but then stuff new authorities into the same old processes, bogging everything down again. True agility means embracing flexibility from the start, not just adopting new tools but learning to think differently about risk and opportunity.

What if you don’t have a whole generation of time to wait to improve culture?  What if you’re not even sure what cultural issues you’re struggling with because you’re down in the muck with them and can’t see them objectively? 

Here’s a handy technique to use to figure out where you can make initial changes:

Look at your organization’s awards program, if you have one. Don’t have a formal program?  Chances are, you have some sort of recognition program, whether it results in trophies, cash, raises, or a pat on the back in front of the employee’s coworkers.  

Next, think about what you reward employees for.   Think about the nominations you write for them to compete in an awards program or to justify a financial bonus.   What are you praising them for?  This is the key to what’s important to your organization’s view of success, regardless of its stated goals.  Maybe that success looks like negotiating an agreement that saved 25% funding.  Maybe it looks like awarding the same contract at the expected price but in a week instead of a year.  Maybe it looks like establishing a healthy partnership with another organization or company that previously had trust issues.  Maybe it looks like a creative agreement for Intellectual Property that will set the standard for all future IP valuation. Or maybe it’s being a good little employee and complying with everything the boss says and has more to do with loyalty to the boss versus his adversary.

Whatever success looks like should show up, especially if you look back over how employees have been rewarded for the last few years under your organization’s current or previous leadership.  But the cool part of this technique to figuring out where the problems are? Look specifically at awards write-ups, nominations, or justifications that include how an employee found a way around the organization’s policies or structure.

Yes, employees actually can be and are rewarded for getting the job done in spite of what they are normally supposed to do!  And that’s a problem.  It’s a red flag waving under your nose to tell you where to start trying to fix the culture you have, as well as other Crumblestones.  

For example, if the Contracting Officer of the Year won because she got waivers for all your restrictive policies and local processes that would have taken her a year of running that gauntlet instead of three months to award the contract before funding expired, then those policies and processes are a good place to begin changing the culture of the organization by pruning those restrictions and also by looking at why those restrictions are there at all and whether they are worthwhile or even applicable anymore. 

Looking at why employees are rewarded may seem like an administrative task, but it can be enlightening. If it’s a formal awards program, start with the winners in all categories, then review the nominees who didn’t win.  You’ll still get a flavor for what actions are considered “above and beyond” and where the true barriers are for all employees to achieve the same level of success.  

Not enough time to try this technique? Or plenty of time, but still too deep in the trenches to be objective? Run the write-ups through your organization’s approved AI tool and prompt it to tell you what your organization values, how your organization defines success (speed, savings, innovation, etc.), what barriers employees are facing, and maybe a pie chart or two if you’re a visual learner.

Changing the System

Here’s the hard truth that’s rarely said out loud: you can’t truly change contracting culture if you don’t change the underlying system that created it. For decades, we’ve been putting Band-Aids on acquisition problems—new policies, pilot programs, innovation labs—without fundamentally rethinking the old structures they’re built on. I’ve spent most of my career inside that system, trying to push it forward with the tools available, and while there have been bright spots, real transformation is rare.

I once heard a speaker say, “We don’t change big systems from the inside.” It struck me because that’s exactly what we keep trying to do in acquisition: patching the same tired framework instead of building something genuinely different. Sometimes, the only way to change culture is to stop rebuilding the devil we know and start imagining a system that’s designed for the outcomes we want, not just compliance with the systems we inherited.

Laying a New Foundation

Building a healthier contracting culture doesn’t mean tearing everything down overnight. It means recognizing that the biggest obstacle isn’t always the regulation—it’s the reluctance to imagine a better way.

When you’re ready to rebuild, start with mindset. Then add the tools. Then invest in the relationships. Designing and implementing a better culture often means taking the Trifecta of Effectiveness out of order because so much of culture starts with how we think.

Next up: Communication Gaps—where misunderstanding between teams can stall even the best-intentioned effort.