Allstate

I’m a little over a year into my current role as chief digital transformation officer at Allstate. It’s been a great opportunity for me to re-center on what transformation means, and re-baseline what impact requires. I like to begin with a playful story of my mandate, which is to “Accelerate Digital Transformation.” As part of the interview process, I asked “What does this mean for Allstate?” And the reply was something like “Well, we were hoping you could tell us.” An exciting proposition for one of the nation’s largest insurers, but one with a lot of leeway for how to proceed!

As I got going, I could have anchored on “new and flashy”. I could have started by incubating bleeding edge technologies or applying Generative AI to the max. But instead, I started at the beginning. I started with the outcomes we were trying to achieve and the pragmatic steps to drive these outcomes. This is because real transformation requires a real re-think based on what creates value – starting at the beginning. I framed it around the why, the what, and the how; and I think it’s an ever-green and instructive way to think about digital transformation.

The “why” for digital transformation generally boils down to two things: protecting the core—revenue, expense, control, risk, customer and employee experience, and disrupting—new business models, new products and services, new markets, entrenching with ecosystem partners. Protect and disrupt. These should directly flow from the enterprise strategy. Often, you have to earn the right to disrupt by protecting first, but you need at least a bit of both. It’s no secret that P&C insurance is getting hit hard by inflation and loss costs – so improving margin is our protect focus. But, we are also investing in new technology, products, and services that will disrupt.

  ​Real transformation requires a real re-think based on what creates value – starting at the beginning. I framed it around the why, the what, and the how; and I think it’s an ever-green and instructive way to think about digital transformation    

The “what” should follow squarely from the “why”. “What” is the portfolio of digital initiatives that will deliver on the intended protect and disrupt outcomes? I used a few techniques to ensure that we were pursuing the right things. First, I incorporated both right brain (i.e., creative, design, experience) and left brain (i.e., structure, process, organization) thinking to generate a broad set of potential initiatives. Second, I evaluated and narrowed this set by leveraging the powerful viability-desirability[1] feasibility framework. This ensures that we’re prioritizing the right initiatives that create value for the business (viability), truly delight our customers and users (desirability), and are achievable in a reasonable amount of time (feasibility). It also ensures that the right voices from across the enterprise are represented including the business and product ownership (viability), CX/UX (desirability), and technology and data analytics (feasibility). Third, I took a portfolio view—just like an investor would—to ensure that we’re balancing some near-term sure things with some longer-term bigger bets. Fourth, overtime we are measuring and rebalancing to ensure, that our “what” portfolio is still delivering against the “why” outcomes. With these techniques, I’ve created a portfolio that balances process optimization and automation with digital experience with long-term digital innovation, all underpinned by consistent tools.

The “how” must support the “why” and the “what”. Digital isn’t just the technology delivered; it’s the new way of working as well. It’s being digital to deliver digital. It is of course the underlying technical capabilities that enable flexible engineering: modern platforms fit for purpose, service-based architecture, integrated data, consistent and powerful tooling. In addition, there is a heavy people component that I’ve invested in. Getting talent right is a must, including refreshing external talent, crisp role definition, and ongoing skill development. Loads have been written on this topic. New ways of working is another critical one to get right. Agile is the easy buzzword, but it really comes down to an operating model where folks are focused on outcomes, against a prioritized backlog, collaborating efficiently as one accountable team, with no roadblocks, and the resources they need to deliver. It looks a little different in each organization, but these five things are always true. Finally, a digital-first culture wraps all of the “how” together. Aspects like customer centricity, empowerment, a sense of urgency, transparency, and external orientation are often critical aspects.

Three words I’ve been using a lot to represent this cultural change that we’re making are outcomes, vulnerability, and grace. Outcomes like margin and customer experience that form our “why”, guide our “what”, and inspire our “how”. Vulnerability to admit when we’re wrong, or don’t know (and go fix it or learn the answer), and bring partners into the co[1]creation process. And, grace for others as we’re moving fast and transforming and need to assume the best of others.

We’ve made a lot of progress leveraging this simple why, what, and how framework. If you lack this same level of rigor, give it a try to structure your path for digital transformation!.