For Douglas Robare, insurance has never been just about numbers or risk tables. It has always been about people — and the narratives that connect them. Having grown up in a small town in western Massachusetts, he finds it humbling that his work now spans insurance markets from Europe to Asia to the Americas. That perspective shapes his approach: “At the human level, we all want the same things — to be understood, to feel valued, to see our role in something bigger. That’s where bridge-building through narrative becomes paramount.”
Strategy as Shared Mission
That lesson became central to Robare’s leadership style. For nearly 30 years, he has led underwriting teams, advised boards, and guided organizations through M&A, governance reform, and innovation. He sees strategy not as a set of targets, but as a story in which people recognize themselves. “Telling something of yourself can bring you closer to someone and give individuals a vision where they can see themselves being part of it.” One example came during a transaction with an underwriting business. A CEO expressed enthusiasm for “the project,” but others had failed to show him how he fit into their growth plan. Robare succeeded by tapping into what motivated him and painting a vision of the future he could embrace. “Others had similar offerings, but they weren’t able to connect — and connection is everything.”
Humanizing a Data-Rich Business
That instinct for connection comes from his small-town roots. “When major industry left my town, you wouldn’t say the population decreased by 20%. You’d say the Fields family left, and the Brooks family too. That human context changes everything.” He believes the insurance industry has drifted from this mindset, relying too heavily on metric-heavy decks that create distance between stakeholders and mission. Numbers alone, he argues, can alienate the very people expected to act on them. Robare recalls being in London meetings where departments were closed, impacting more than 70 people. On the spreadsheet, it was labeled “cost optimization.” But when he delivered the message, he reframed it: expertise was being redirected into areas of growth like digital transformation. “That human context changed everything. The task should always be to translate figures into shared meaning and shared stakes.”
From Slide Decks to Stories
Most managers, he observes, rush from an executive meeting to a team briefing with a slide-by-slide replay. “It’s not what is said that’s important, it’s what is heard that’s important.” Take strategy communication. Instead of announcing: “We’re implementing a new underwriting platform to improve operational efficiency by 23%,” Robare reframes it: “Remember how frustrated you get when clients wait days for pricing decisions while competitors respond in hours? This system changes that game entirely — and the competitive edge comes from the expertise you’re building right now.” When employees can retell a strategy as a story — with a clear problem, a reason to act, and their role in the solution — alignment shifts from compliance to ownership.
AI as Augmentation, Humans as Connection
Robare is an AI enthusiast who has implemented machine-learning systems across three continents. But he sees where technology stops. “When AI flags a $100 million cyber exposure, that’s the easy part. The hard part is sitting across from a CEO who built their company over 30 years and explaining why legacy systems create vulnerability. That conversation requires understanding their story, not just the output.” This matters even more with younger buyers. “A 28-year-old choosing insurance wants to know you understand remote working, blockchain, and climate risk — not just whether you can beat a competitor’s quote by 10%.” For him, innovation without narrative becomes “just another transaction in an increasingly transactional world.”
The Playbook for Leaders
Robare distills his approach into four rules:
- Start with the problem — make it real before introducing the solution.
- Turn metrics into meaning — connect numbers to human impact.
- Keep AI in a supporting role — algorithms deliver answers, but people provide context.
- Test the story on the street — if it can’t be explained at the pub without PowerPoint, it’s not ready.
“When leaders weave technical capability into human narrative, you bring people in better,” Robare says. “It stays longer, and they commit harder.”
