At a recent discussion, a leader described what he wanted from a technology provider: someone willing to work through implementation with his team.
He was concerned about the opposite experience. A large commitment. An expensive license. A provider eager to move ahead at a pace the customer could not absorb.
It was the kind of comment that makes you think about every obligation hiding behind the word “implementation.”
Clean the data. Find the process owner. Reconcile conflicting policies. Persuade people to use the system. Explain why the promised launch date has moved again.
Somewhere, a sales deck says “partnership.” On the customer’s calendar, that partnership can look like a second job.
Legal leaders should pay close attention to that gap. The success of a technology purchase depends heavily on how the parties work together after the contract is signed.
Ask The Vendor To Sit Through The Mess
A polished demonstration tells you something about a product. Watching the provider work through an actual customer problem tells you something about the relationship.
Take a contract review workflow. The official process may look straightforward: Procurement uploads the agreement, the tool flags issues, and legal reviews the exceptions.
Then someone explains that the supplier sent three versions. The business owner negotiated a concession by email. The playbook covers the U.S. entity, while the agreement names a subsidiary elsewhere.
Now the useful conversation can begin.
Ask the provider how it would handle that situation. Which information must the customer supply? What can the product resolve? Where does a person need to intervene? Which limitations will remain?
Pay attention to whether the provider asks thoughtful questions and can describe those limits clearly. You will need that candor when a real problem arrives.
Partnership Needs Names And Calendars
“Customer will provide reasonable cooperation” sounds harmless until everyone discovers how much cooperation the project requires.
Who is preparing the data? Who is configuring the workflow? Who can approve changes? How much time will legal, procurement, security, and IT need to contribute?
A credible implementation plan identifies those people and gives them work they can realistically perform.
This deserves attention during diligence. Ask reference customers what their teams actually had to do. Find out whether the provider’s implementation staff remained involved, how problems were escalated, and whether the promised support survived the sales handoff.
Head count alone tells you little about the attention your account will receive.
Legal can help make the workload visible before the business commits to a timeline that depends on several imaginary full-time employees.
Put The Promised Outcome Into The Working Plan
The debate about a SaaS reset has pushed value into the center of the buying conversation. Buyers asking harder questions about recurring fees should also examine what the provider needs to deliver the promised benefit.
If the goal is faster contract review, establish the baseline and define acceptable quality. If the goal is fewer escalations, determine which escalations should disappear and which remain essential.
Those distinctions matter. A falling escalation rate could reflect better decisions, poor issue detection, or users abandoning the workflow.
Value pricing makes the measurement choices particularly consequential. The parties need a shared understanding of the result, the evidence, and their respective contributions.
The statement of work should connect that understanding to delivery milestones, acceptance criteria, and a practical process for fixing problems. Otherwise, the value promise and the implementation obligations can drift into separate conversations.
Leave Room For The First Unpleasant Discovery
Every implementation has the potential to reveal something nobody understood at the beginning.
Perhaps the source data is unreliable. Perhaps a workflow depends on an undocumented exception. Perhaps users need a capability the original scope never addressed.
Agree on how the parties will handle those discoveries. Identify who can approve scope changes, how costs will be assessed, and what warrants pausing the rollout.
Starting with a bounded use case can help both sides learn before expanding their commitments.
Clear allocation of responsibility matters here. Shared accountability works when each party knows what it controls, what it owes, and where to seek a decision. A general promise to collaborate leaves too much room for an issue to circulate indefinitely.
Legal Can Make Partnership Concrete
Legal leaders can help the business translate an appealing sales promise into a workable relationship.
Bring the people doing the work into the evaluation. Examine their capacity. Connect the commercial model to measurable outcomes. Make sure the agreement provides a usable way to resolve the problems everyone hopes to avoid.
Then ask one final question before signing: When the first serious implementation problem appears, who will join the call with the authority and resources to solve it?
That answer will tell you quite a lot about the partnership you are buying.
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics. She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.
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