Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Diana Steinhoff, president and CEO of Renaissance Life and Health Insurance Company of America, to examine one of the hardest tensions in scaling: how do you grow fast without losing the human connection that makes your product worth having? Diana joined Renaissance in 2023 to lead a digital reset at a company serving more than 13 million members across dental, vision, life, and disability benefits. Under her leadership, Renaissance launched the proprietary Renaissance Operating System, acquired Ansel Health to deliver AI-powered claims experiences, and launched the 5X Scaling initiative, a company-wide commitment to scaling at five times the current rate without burning out the people doing the work. Her answer to the empathy-versus-efficiency tension is not a compromise. It is a framework.
This episode is for CEOs navigating a digital transformation who want to move faster without stripping the human judgment and empathy out of the customer experience.
Key Takeaways
- The 5X Scaling initiative at Renaissance sets a concrete growth target while explicitly protecting the team from burnout, because scale without sustainability is not scale.
- Automate what no one should be doing manually. Diana’s rule: if a process is routine and a customer should never feel it, technology belongs there, not a person.
- “Ask the what, not the why.” Why questions create defensiveness. What questions create psychological safety and produce more honest, actionable information from your team.
- A CEO who stays at the 50,000-foot level, monitors performance data, and asks questions of empowered leaders scales their own output without getting buried in operations.
- Mid-size companies scale faster with strategic partners than by building every function in-house. Fewer full-time resources forces smarter decisions about where to own capability and where to borrow it.
Digital Transformation Demands a Human in Every Loop
The hardest part of leading a digital transformation, Diana Steinhoff says, is not choosing the right technology. It is deciding where humans stay in the process and where they do not. Her framework at Renaissance is precise: identify every manual intervention and every bottleneck that an external customer will feel, then apply technology to make those processes invisible. What remains for people is everything that requires judgment, communication, and empathy.
“We want to review, and we do it regularly within Renaissance, we do often process reviews where we see where all the manual interventions are and the bottlenecks that the external user is gonna feel. And if we can somehow layer technology onto those processes to make that simple, to explain the process and then to make those processes a bit simpler within our organization, we’re gonna do that.”
The goal is twofold. Technology simplifies the process for the customer. It also frees the employee from doing routine work they should not be doing and puts them in front of more complex problems that actually require them. “It helps the constituent that’s receiving the service. We make the process simpler, but it also helps our employees manage more complex problems for us and not routine things that they shouldn’t be doing to begin with.”
This is the operating model behind Renaissance’s 5X Scaling initiative. The target is ambitious. The constraint is explicit: grow at five times the current rate without burning people out. That constraint forces discipline about which processes get automated first: back-office functions that carry no customer-facing risk. Customer-facing processes get technology only after the back office is proven.
Customers Feel Bottlenecks Before They Can Name Them
One of the most important shifts in Diana’s leadership philosophy is thinking about process friction from the customer’s emotional experience, not just the operational flowchart. Insurance is a product people use during hard times: a health event, a disability, a loss. If the claims process is confusing or slow, customers feel that friction on top of everything else they are already dealing with.
Diana draws a direct line from her clinical background to this perspective. Her years reviewing behavioral health claims and working in case management taught her that when a customer does not understand the policy language at the moment of claim, friction becomes a trust problem. “People think, well, it’s you all make it so difficult to even get the claim. It’s our job to explain that to individuals. And it’s unfortunate that it’s at time of claim when they’re going through a hard time and what they should be focusing on is their recovery, not necessarily a document that tells them how the benefit is administered.”
Her answer at Renaissance is plain language, everywhere. Every customer-facing publication is written in plain English. The ambition: a customer reads it once and understands it completely. That standard is hard to hit in an industry built on legal and actuarial language, but it is the measure Diana holds the organization to.
CEOs Who Ask “What” Instead of “Why” Get Honest Answers
When Diana talks about how she scales her own personal output as a CEO, she returns to a single discipline: stay at the 50,000-foot level, monitor performance data closely, and ask the right questions of the leaders you have empowered to run operations. The question that changed the most for her was the shift from “why” to “what.”
“One of the most important lessons that I learned from a leader that I worked under is to ask the what, not the why. And I still catch myself asking why questions. And when I do, I cringe a little bit. But what questions are so important because you’re kind of creating that psychological safety as you’re coaching and monitoring what your team is doing through those type of what questions. So what exactly do we know about the problem? What have we done about it? Right. Instead of like why is it happening? Because it sounds more antagonistic, if you will.”
Glenn Gow frames the same distinction as the difference between a defensive CEO and a curious one. Why questions signal judgment. What questions signal curiosity. Teams answer what questions more honestly because they do not feel they are being evaluated on whether their reasoning was correct. They are being asked what they know and what they have tried.
Diana’s rule for staying at the right altitude: monitor the data obsessively, ask what questions of empowered leaders, and use the answers to identify barriers she can remove. “Our role is to reduce, just remove barriers. And so that helps us understand, okay, that is a barrier. So then now I can work on that and figure out how to remove that so that the team can move forward.”
Mid-Size Companies Scale by Partnering Smarter, Not Hiring More
The move from Aflac, a household-name enterprise, to Renaissance, a mid-size carrier, taught Diana something about how smaller companies scale that large ones often miss. You do not build every capability in-house. You find partners who are better at specific functions than you are, engage them when you need them, and move faster than an enterprise would because you are not carrying the bureaucracy.
“We’re not gonna be because we’re not a huge organization, we may not need that full time. We just may need partners to go out and recruit contractors or whatever it may be to help us with those functions. So it opens us up more for partnerships across different domains, which is really good. Because then you learn more from instead of kind of growing that talent internally, you’re learning from your partners and what innovations they have in place.”
What makes this work is flexibility in the team itself. At a mid-size company, employees have to flex across business areas in a way that large enterprise employees rarely do. The people who thrive in that environment are not specialists who need a narrow lane. They are generalists with strong judgment who can move where the work is.
The competitive advantage is speed. Fewer internal approvals, fewer fixed structures, and a bias toward external expertise where it is better than internal talent produces an organization that can move and adapt faster than a larger competitor can authorize.
Scaling Principles Produce the Following Framework
| Principle | What it means in practice | Named evidence from this interview |
| 5X Scaling requires an explicit anti-burnout constraint | A growth target without a protection mechanism will consume the team that is supposed to hit it; the constraint forces smarter automation decisions | Renaissance’s 5X Scaling initiative pairs the growth rate target with a direct commitment to protect employees from burnout, driving the discipline to automate back-office processes first |
| Automate what customers should never feel | Routine processes that create friction for customers without requiring human judgment belong to technology, not people | Renaissance conducts regular process reviews to identify manual interventions and bottlenecks that external users experience, then layers technology to eliminate them |
| Ask “what,” not “why” | Why questions produce defensive answers; what questions produce honest ones and reveal the barriers a CEO can actually remove | Steinhoff learned this discipline from a mentor, applies it in every leadership conversation, and still catches herself defaulting to why questions when under pressure |
| Stay at 50,000 feet and monitor data | A CEO who drops into operations loses the altitude needed to see across the business; data and empowered leaders replace direct involvement | Steinhoff relies on performance analytics to identify red flags and asks structured what questions of her leadership team rather than running the work herself |
| Partner for capability rather than hire for it | Mid-size companies move faster by engaging expert partners for non-core functions than by building full-time capacity they do not have the scale to justify | The move from Aflac to Renaissance forced Steinhoff to replace enterprise infrastructure with strategic partnerships, which she describes as faster and less bureaucratic |
Quotes from This Episode
- “One of the most important lessons that I learned from a leader that I worked under is to ask the what, not the why. What questions are so important because you’re kind of creating that psychological safety as you’re coaching and monitoring what your team is doing through those type of what questions.” — Diana Steinhoff, President and CEO, Renaissance Life and Health Insurance Company of America
- “We want to ensure that when they come through our process, they get what they need right away. And they shouldn’t have to experience any of our deficiencies in process because we’re trying to fit it into a round peg in a square box.” — Diana Steinhoff, President and CEO, Renaissance Life and Health Insurance Company of America
- “It helps the constituent that’s receiving the service. We make the process simpler, but it also helps our employees manage more complex problems for us and not routine things that they shouldn’t be doing to begin with.” — Diana Steinhoff, President and CEO, Renaissance Life and Health Insurance Company of America
- “We’ve launched an initiative that we call 5X Scaling, which means we want to scale at a 5X rate without burning our people out. And that means that we have to scale intelligently.” — Diana Steinhoff, President and CEO, Renaissance Life and Health Insurance Company of America
- “Our role is to reduce, just remove barriers. And so that helps us understand, okay, that is a barrier. So then now I can work on that and figure out how to remove that so that the team can move forward.” — Diana Steinhoff, President and CEO, Renaissance Life and Health Insurance Company of America
Frequently Asked Questions
How do you scale a company fast without burning out your team?
Diana Steinhoff, CEO of Renaissance Life and Health Insurance Company of America, addresses this directly through the company’s 5X Scaling initiative, which sets an aggressive growth target while explicitly protecting employees from burnout. Her approach: automate routine back-office processes first, before touching anything customer-facing, so that people are freed from work technology should handle and redirected toward the complex, judgment-intensive work that actually requires them. The constraint is built into the target, not added afterward.
How does a CEO scale their own output without getting buried in the details?
Diana Steinhoff uses three disciplines to stay at the right altitude as CEO. First, she monitors performance data closely to identify red flags without needing to be inside every operation. Second, she asks “what” questions of her empowered leaders rather than “why” questions, which create psychological safety and produce more honest answers about where barriers exist. Third, she treats her role as removing those barriers, not managing the work directly. Staying at the 50,000-foot level is a discipline she describes as learned, not natural.
How should a CEO balance digital transformation with maintaining a human customer experience?
Diana Steinhoff at Renaissance draws a clear line: technology belongs on processes that customers should never feel, and people belong on interactions that require empathy, judgment, and communication. Renaissance conducts regular process reviews to identify bottlenecks that external users experience, then applies technology to make those invisible. What remains for employees is explaining complex situations to customers going through difficult moments, which Steinhoff says is the work people should be doing and the work technology cannot replace.
Executives Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, there are two ways to go further: Apply for Executive Coaching | Apply to Be a Guest on The Scaling Executive Podcast
