Trust and Technology in the Age of Intelligent Contracting

A recent interview by McKinsey with Wikipedia’s founder offers valuable insights to a question challenging many commercial teams and business negotiators: how do we build trust in an age where technology increasingly mediates our relationships?

Jimmy Wales observed that trust is declining almost everywhere, whether in politics, journalism, or institutions. This erosion of confidence makes it harder to agree on even the simplest facts – yet the Wikipedia model continues to function. It’s grounded in two simple principles: assume good faith and make integrity easy to verify. These principles have deep relevance for today’s commercial and contracting professionals.

Deliberate Vulnerability

Wales once wrote on his user page, “Yes, you can edit this page. I trust you.”

That willingness to extend trust as a core principle became part of Wikipedia’s culture. The community allows anyone to edit, but with the safety net of instant reversion and transparent oversight.

Commercial teams could learn from that mindset. Too often, contracts are written as if every counterpart is an adversary waiting to exploit a loophole. We legislate against bad faith instead of designing for good faith. Yet successful partnerships typically begin with an act of measured vulnerability -sharing data, explaining assumptions, or exposing real cost structures. When it is paired with sensible guardrails, acts of trust invite reciprocity.

Trust by Design

Wikipedia assumes good faith, but not blindly. As Wales puts it, “Assume good faith is not a suicide pact.” Trust is supported by a well-structured system: transparent edits, public records, clear rules, and the ability to revert or block bad actors.

In business relationships, trust must likewise be designed, not declared. Governance frameworks, data accuracy, and digital records serve the same purpose as Wikipedia’s edit history. They allow for correction without accusation. In the era of AI and digital contracting, this means traceable data flows, version control, and transparent performance dashboards. Technology becomes the architecture that sustains integrity.

Reputation as the New Currency

Wikipedia relies on “pseudo-anonymity” – consistent identity and behavior over time. Reputation counts – and builds over time.

That lesson translates directly into contracting. Buyers and suppliers alike build credibility through consistency of conduct: fairness in negotiation, honesty in communication, reliability in delivery. As digital ecosystems expand, formal and informal reputation systems will increasingly determine who is trusted, who gets opportunities, and who is left out.

Shared Understanding of the Facts

Wales warns that democracy fails when people no longer share a common reality. The same is true of commerce. Negotiations and contract management collapse when each party operates on different data or conflicting interpretations of performance.

AI and analytics can help, but only if they reinforce a shared factual baseline. Joint dashboards, open data repositories, and agreed definitions of success turn technology into a trust amplifier. Without that alignment, technology simply speeds up misunderstanding.

The Simplicity of Integrity

“Tell the truth. Give the facts. Don’t be biased.” Wales calls it the “kindergarten test.” These values have never been more relevant. As algorithms begin to draft contracts, monitor delivery, and even recommend negotiation tactics, we must embed these ethical principles into the systems we build and use. Transparency, explainability, and fairness should be the cornerstones of any AI-enabled contracting environment.

Scaling Trust

Wikipedia’s community thrives because it combines individual integrity with systemic accountability. That’s precisely what modern commercial ecosystems require. Trust grows through one relationship at a time, but it scales only when systems reinforce the same values.

Adaptive contracts, shared data, and relational governance are the business equivalents of Wikipedia’s edit logs and community norms. They make trust not an act of faith but a design feature.

Technology Cannot Replace Trust: It Can Encode It

Wikipedia’s success is not about technology; it’s about the values the technology supports.

The same choice confronts commercial and contracting professionals. As AI enters the negotiation room and digital platforms manage our obligations, we face a defining question: Will we use technology to control people or interactions, or to empower trust between them?

Trust remains the invisible capital of commerce. It is what turns data into decisions, contracts into relationships, and promises into performance. The tools may be new, but the lessons remain the same.

Tell the truth. Give the facts. Don’t be biased.