Winning Trust Through Modern Contracting

“We weren’t wrong. We just couldn’t prove we were right fast enough.” That’s what a GC told me after her team spent weeks negotiating an AI-enabled SaaS contract. The deal was strong. The tech was validated. The pricing aligned. But when the contract landed—with a sprawling, defensive AI addendum—it raised more red flags than it resolved. The buyer’s legal team got stuck in the weeds: data rights, indemnity gaps, model usage. What should have been a clean close spiraled into rounds of redlines and revision calls. By the time clarity arrived, the fiscal quarter had turned. The budget had moved. The deal didn’t die, but it never signed. That sentence—“we couldn’t prove we were right fast enough”—has stayed with me. Because it captures a growing challenge for modern legal teams: How do you defend your terms when the benchmarks don’t exist—or aren’t easy to access? In this month’s newsletter, I explore why AI clauses are creating new contracting frictions—and how the best in-house teams are adapting by trading instinct for insight. It’s a shift from defense to evidence. From redlines to readiness, not reactivity. You’ll find lessons in how AI benchmarking can accelerate trust by replacing guesswork with grounded comparisons. You’ll see how leading teams are categorizing contracts by real risk, training business units to spot slow-down clauses, and—most importantly—turning negotiation into a proof-driven dialogue. But this isn’t just about efficiency. Delays do more than eat time. They erode credibility. And in a world moving this fast, that’s a cost no one can afford. So I invite you to read, reflect, and rethink with me. If your contract terms aren’t benchmarked, they’ll be questioned. If they’re not clear, they’ll be delayed. And if your legal strategy is still reactive, you’ll be outpaced by teams who aren’t. Three questions I’m sitting with—maybe you are too: • What would it take to make your standard terms instantly trustworthy? • Are your AI clauses signaling confidence—or complexity? • And when someone asks why a deal hasn’t closed, can your answer begin with: “We can prove it”? Read the newsletter. Let’s build the next chapter of contracting—grounded in data, and designed for trust. -------- 🚀 Olga V. Mack 🔹 Building trust in commerce, contracts & products 🔹 Sales acceleration advocate 🔹 Keynote Speaker | AI & Business Strategist 📩 Let’s connect & collaborate 📰 Subscribe to Notes to My (Legal) Self

Over the years, I have negotiated a lot of commercial #contracts and one thing that’s clear is, negotiations are more straightforward when preceded by good relationships with the other party. Imagine this scenario, you send the same contract template to two different #suppliers, one comes back bleeding with redlines the other one only has a few minor edits/concerns. Folks will argue that this outcome is a reflection of the #risk appetite of the supplier but I’ll tell you this. Half the time, a supplier you have a good relationship with considers your relationship more protective than contract clauses. They trust your word and can live with minor edits in the contract. Post contract #negotiations, good relationships again play a crucial role in enforcing provisions in a contract. Again, think about this. Same type of contract, two different contractors. Imagine the #design of the project changes along the way, how the two #contractors respond will usually be different. I’ve seen some quickly submitting costly change orders, I have also had a contractor tell me, “look, we know the design has changed, just buy materials and we will install for you at no additional #labor cost since we already have staff on site”. The latter will usually also offer value #engineering by suggesting ways to deliver the project at low cost but with the same #quality, their interest is not unlocking their #remedies in the contract but protecting the relationship. I always argue that adding some “teeth” in contracts is great but that shouldn’t replace good personal relationships with #vendors, a contract anchored on good relationships is easy to manage, #accountability comes naturally and in most cases, it helps reduce overall spend and builds #trust.

Last quarter we walked away from a 200k+ RFP. With these 7 tactics we still won it. Most companies see an RFP and rush to respond. We looked at the requirements and said no. The list was long, rigid, and clearly not written with us in mind. So we opted out. Not because we couldn’t deliver. But because it made no sense to play a game we hadn’t helped shape. That triggered something unexpected: The project lead called us. “Why won’t you participate?” That question opened the door. We walked through it. We mapped must-haves vs. fluff. Got clear on what actually mattered. Shared what we could support and what we couldn’t. And showed up as a true partner, not just a bidder. Weeks later? We were the only vendor to reach contracting. A 3-year, multi-department deal built on trust. Here’s what it taught us: 1. Disqualify fast, even if the deal looks big 2. Challenge vague or generic requirements 3. Focus on real must-haves 4. Multi-thread early with decision-makers 5. Involve execs before the proposal stage 6. Let your “no” build trust 7. Requalify through conversation, not compliance Most importantly? Don’t waste anyone’s time, including your own. We turned that story into a 7-step playbook. It’s now live on GTM OS or via koenstam [dot] substack [dot] com. Curious how often your team dares to disqualify?