Change is hard, but change is good.
This simple truth sits at the heart of every digital transformation I've seen in our industry and others I've been in. Technology is on the minds of all business leaders. Legacy systems can feel like an anchor, holding a business back, while modern systems are like a jet engine, propelling it forward.
With cloud-based platforms, AI-powered workflows, and integrated ecosystems replacing legacy systems, the biggest challenge isn't the technology itself. It's leading people through the journey. It's about being okay to get out of the comfort zone and operate in the learning zone.
For example, implementing a new CRM might take weeks, but getting sales teams to adopt new workflows and see the value of automated lead scoring can take months of consistent communication.
Successful change starts with leaders who can see and articulate the future clearly as well as communicate with authenticity and honesty about WHY the change is necessary. The transition period is the hardest, but the pain is worth the gain.
The Chief Repeat Officer: Communication communication communication
Great leaders and change champions communicate the future state with positive energy and conviction. They paint a vivid picture of what success looks like and help everyone reimagine how things will work plus what the benefits and outcomes will be.
They don't communicate this vision once. They become what I call a "Chief Repeat Officer," sharing and cascading the message 100 times in 100 different ways. One week it's a team meeting explaining how new systems will streamline workflows. The next week it's a story about a team member who saved three hours per day after mastering new tools. The week after that, it's a demonstration of how automation can reduce errors and increase efficiency.
This repetition is reinforcement. People need to hear the same message multiple times before it sinks in, and they need to hear it in different contexts to understand how it applies to their specific roles and what's in it for them. It's a bit like learning to drive. Instructors (or parents) repeat "check your mirrors" or "indicate before turning" until these habits become second nature.
Consider a health insurance company rolling out a new claims processing system. Using the Chief Repeat Officer approach, the core message of 'faster, more accurate claims' is reinforced across multiple channels: monthly newsletters highlighting speed improvements, interactive dashboards showing real-time metrics, and celebration emails when teams hit efficiency milestones. Each format delivers the same message in a fresh way.
Authentic leadership: Acknowledging the reality
The most effective leaders I've observed are authentic. They acknowledge that the transition period is challenging and explain the why behind the change. They don't pretend that learning new systems is easy or that there won't be frustrations along the way. They openly discuss the problems with current systems and processes, helping the team understand why change is necessary and what improvements the new approach will bring.
"Yes, the first few weeks with new processes will feel different from your known day-to-day routines," they might say. "But here's why we're making this shift: soon you'll spend less time chasing information in three different places, you'll cut down the back-and-forth emails, and you'll be able to find what you need in seconds instead of minutes. That means fewer late nights, fewer mistakes, and more time for the parts of the job you actually enjoy."
An authentic approach builds trust. When leaders are honest about the bumps in the road and connect the change to everyday wins, people feel heard, understood, and more willing to come on the journey.
Tools like Microsoft Teams can support communication with real-time chat, Q&A sessions, dedicated channels for the change initiative, and live meetings that can be recorded for later viewing.
Realistic optimism: The vision with a path
Having a realistic optimism about the future vision is what separates true leaders from cheerleaders. They don't just say "things will be better", they map out how to get there. They break the transformation down into manageable phases, celebrate small wins, and provide clear milestones along the way.
I've seen this approach work across many industries. Take something as simple as an office move. Instead of saying "the new office will be great," effective leaders outline the journey: support for packing, clear timelines, maps of the new layout, and a first day welcome tour. People know what's coming and when. Each phase, from communication to training to setting expectations, builds confidence and shows progress before adding more complexity.
Project management and workflow tools like Asana can visually track these phases, automatically sending updates that show how completed milestones move the team closer to the envisioned future. Seeing 'Week 3: Packing crates delivered ✓' and 'Week 4: Layout maps shared ✓' on a shared dashboard turns the project into something tangible.
Finding and nurturing change champions
The most successful transformations identify change champions throughout the organisation - often they're naturally curious team members who embrace new technology and enjoy helping their colleagues.
These champions become informal leaders in the change process. They're the ones answering questions on the floor, sharing tips and tricks, and demonstrating that the new tools make work easier, not harder. When you see a colleague easily navigating a new platform and genuinely liking the capabilities it provides, adoption accelerates naturally.
Internal platforms like Microsoft Teams or Slack amplify champions' voices, letting them share quick video tutorials, celebrate wins, and build informal learning communities. When Sarah from accounting drops a 30-second clip showing how the new expense system saved her 20 minutes, it resonates more than any training manual.
The change journey never really ends
Digital transformation isn't a destination, it's a mindset. Change is a constant, especially in the insurance industry, and modern leaders need to develop the skills to guide your teams through it effectively. Whether it's innovations that step change a business or incremental improvements, the change journey never really ends.
Change is hard, but change is good. The leaders who master this contradiction don't sugarcoat the difficulty, and they help people see the value on the other side.
Great leaders communicate the future state with positive energy and conviction. They paint clear, compelling pictures of what success looks like and why it's worth the effort to get there. Importantly, they believe it too!
They're authentic about the journey. They acknowledge that the transition period will be challenging while explaining why the change matters. No false promises, just honest communication about both the struggle and the payoff.
The best leaders also pre-empt the questions their people are already asking themselves but might not voice out loud - Will my role still exist? How will this affect my workload? By addressing these concerns head-on, leaders remove unnecessary stress and fear, creating space for people to focus on adapting to the change rather than worrying about their role.
They maintain realistic optimism. They're guides who show people the specific steps to get from here to there, celebrating progress along the way.
Most importantly, they become Chief Repeat Officers. They understand that saying something once means it wasn't heard, saying it ten times means it might be remembered, and saying it 100 different ways means it will stick.
Every organisation's journey will be different, but these principles remain constant. When you combine them consistently, and are supported with the right tools, something powerful happens - teams start to embrace change and even start to drive it.
Leaders can master both the human side of change and the technical side of innovation. When these come together, transformation stops being something that happens to your organisation and becomes something it does naturally.
When leading change, remember that stepping out of our comfort zone and into the learning zone is where transformation actually happens. It's uncomfortable, but that's where the growth lives.
