Why Jackson CIO Mike Hicks had to flip the script on his proven 100-day plan

With two major initiatives in flight, and a budget deadline looming, the new CIO of the Michigan-based retirement income business had to rethink his long-established approach. Here, Martha Heller, CEO of Heller Search Associates, finds out how such a fundamental shift played out.

What has your 100-day plan looked like historically?

It’s evolved over my 25 years as a CIO, but in general my approach has been a “listen-plan-act” model. The first 30 days are about listening more than speaking, engaging my business stakeholders and IT team, and identifying people who will be trusted advisors on our transformational journey. During that time, I also learn the dynamics of the business and evaluate our overall technology capabilities. These initial 30 days are really level-setting.

In the next 30 days, I start working on vision and roadmap, and begin assessing team capabilities. I also prioritize quick-win projects, which are usually about solving a prickly issue that nags at people, like system stability or a recurring customer complaint. If you hear about a problem from a handful of people, you know you have an opportunity to fix what matters to people.

The next 40 days are when I take action. I might reorganize the team for execution, if necessary, but I don’t believe you always need to reorganize just to reshuffle the deck chairs. I also implement a business value scorecard to showcase progress during those 40 days, seek feedback from trusted advisors I identified upfront, and adjust course as needed. That’s been my typical game plan, probably not much different from most CIOs.

But when you joined Jackson, you had to throw out that traditional 100-day plan. Why?

I joined at the end of last April when we had multiple converging forces at play. The company was in the final stages of refreshing our business strategy; in September 2021, we spun off from Prudential plc to become an independent public company. Our strategy was to accelerate our core competencies to position ourselves and our brand in the market.

As a part of this strategy, we were in the final two months of a multi-year platform modernization initiative that was consuming a lot of time and resources, and was considered a high impact project.

And in terms of broadening our portfolio of offerings, we were also in the final six weeks of a significant product launch: an updated version of our registered index-linked annuity.

Finally, we were two months away from submitting this year’s budget, which is always a challenge because of the legwork that goes into a budget cycle. At the same time, generative AI became the hottest global technology topic in my lifetime, and everyone was asking what we’ll do with it.

So, I didn’t have the luxury of following a formulaic approach to establish myself. I had to jump right in. I didn’t want to be the person who listened for 30 days but failed to deliver on two of our largest ever initiatives. But I also needed to focus on strategy to make sure we had capacity in the budget for new initiatives.

So how did you change your approach?

I pivoted from listen-plan-act to listen-act-plan. I did listen, but at the same time, I jumped right into action, and I put formal planning on hold.

In hindsight, what I liked about the shift to acting before planning was that the execution work gave me time to put aside my biases before planning a vision for the future. When you join a new company, if you don’t give yourself time to balance your own experience of what has worked for you in the past, with what will work in this new culture and with this new team, then your own bias can overpower your strategy.

By jumping right in and delivering on the modernization and product initiatives, and getting through the budgeting cycle, I had a chance to see my team in action, and then focus on our IT strategy with some experience under my belt. This has been different than the traditional top-down approach. What helped was having a strong IT team with a track record of delivery excellence; this wasn’t a turnaround situation.

When you plan before you act, you often find out a year later that you need to completely redo your strategy, because you’ve learned what’s really happening within the company. So I’ve shifted from top-down to more of a bottom-up and lateral approach, where I can observe firsthand the team’s dynamics during an entire implementation process. I wouldn’t give that up for anything.

What is the strategy you eventually developed?

As a company, Jackson is a hybrid of financial services and insurance focused on the retirement income market. We recognize that in five years, our industry is going to look different than it does today. With digital disruption, our customer experience is no longer being compared to other insurance companies, but to our customer’s last experience on Amazon or TikTok. This means customer experience is now a critical part of our product, so our strategy is centered around amplifying digital and data to power our transformation.

From a digital perspective, we’re making CRM an enterprise capability and reimagining our website as part of our larger omnichannel strategy. Additionally, from a data perspective, we’re mobilizing our advanced analytics teams to leverage the latest AI capabilities. However, it’s the convergence of these digital and data capabilities that’s truly transformative.

What advice do you have for CIOs driving digital transformation?

First, get out of the tug-of-war between technical debt and modernization. CIOs will say they have technical debt and modernization programs, but all of that is just short-term noise. CIOs need to embrace technology lifecycle management as a long-term approach to ensure all technology is current, resilient, and secure. That’s a fundamental shift in thinking. Technology lifecycle management should be a core capability.

Second, recognize the role of the CIO has changed significantly. For example, with cloud, our infrastructure has been demystified and we can no longer hide behind acronyms and request tens of millions of dollars for infrastructure renewal and then use that capital to fund CIO side projects. The technology knowledge playing field has been leveled with everyone from internal stakeholders to new customers who are digitally savvy, so you better be on your toes.

Finally, recognize that the CIO role is no longer just about technology leadership. It’s about value creation. If you’re not creating value in today’s world — and you’re relying on your old playbook — you won’t be in the seat for very long.