Winning Over Stakeholders Who Hate Change
Posted on October 23, 2025
Here’s something that might surprise you: stakeholders love improvements. They just hate change. Sounds contradictory? It’s not. Even people who claim they love change will struggle to do something as simple as wearing their watch or bracelet on the opposite wrist for a day. (Don’t believe me? Try it!) Now, imagine asking someone to change things when they have received positive performance evaluations for many years, using the processes they are currently familiar with.
Many stakeholders spend their days making critical business decisions. They’ve developed habits and workflows that let them operate efficiently under pressure. When you come in with a project that disrupts those carefully honed routines, you’re essentially asking them to relearn their job while still performing at peak effectiveness. So, there are valid reasons for their reluctance! Here are ways to overcome that reluctance.
• Embrace tiny, provable changes. Don’t start with a massive system overhaul. Begin with minor improvements that clearly demonstrate value without disrupting critical workflows. Build trust through quick wins before tackling bigger transformations.
• Invest heavily in the “how.” Stakeholders need to understand not just what you’re changing, but exactly how it will improve business outcomes. High-level discussions about improving efficiency won’t suffice. Show specific scenarios where your project prevents errors, saves time and money, or creates different opportunities for success.
• Plan for the 66-day rule. – Research shows it takes about 66 days to form new habits. The first 22 days are hard, the next 22 are messy, and the final 22 become natural. Your project timeline needs to account for this transition activity, not just the technical implementation. Schedule checkpoints to assess stakeholder actions and results. Extra training sessions and recognition for those who adopt the new processes and drive success are just a couple of things that help stakeholders navigate the 66 days.
• Avoid implementing a “black box.” New technology, especially AI systems, can be perceived as threatening to professionals who pride themselves on exercising critical judgment. That threat often comes from stakeholders feeling that technology is a “black box.” Things go in, and come out altered, but how or why those alterations took place isn’t understood. Acknowledge these concerns and provide extensive training on how new tools handle data and processes. Ideally, they can be demonstrated as providing improved decision support, versus a decision replacement.