“The CIO’s job is not just to run the technology group. Their job is to be thinking how technology is going to further the business—and that includes bringing in new possibilities.”
– Dave Condren, (retired) CIO Bond & Specialty Insurance, Travelers Insurance
With every major change, CIOs risk their jobs and their reputations. But if you don’t introduce change, you risk robbing your organization of unrealized value. That’s why strategic communication has become such a critical tool for today’s technology leaders. We need to make our ideas heard, our asks firm, and, most importantly, build the organizational consensus we need to keep things progressing smoothly.
Dave Condren is a veteran technology leader who spent most of the last 13+ years of his leadership career as CIO at Travelers Insurance. He’s deeply familiar with the challenges that come with getting things done, especially in an industry where existing legacy systems can be a definite drag on innovation.
In the dawn of his recent retirement, Dave sat down with us to talk with us about his experience selling ideas through to the business, cultivating consensus across stakeholder groups, and leading successful IT projects. The conversation yielded some powerful insights for fellow leaders looking to bring possibilities into their own companies and build the kind of relationships you’ll need to turn possibilities into reality.
Tip #1: Get to the point
When selling someone an idea, many of us are trained to go heavy on the build-up before we get to the big ask. This isn’t always the best tactic, especially with C-level folks. Dave relates a learning moment when he had to talk to some senior executives about funding for a strategic project he was leading:
“Like a typical IT person, I kind of laid out the whole history of how we got here and then what we were going to do,” he recalls. “My boss at the time reviewed the material I was going to present and gave me some great advice: ‘Everything before today—nobody wants to relive. So just take all of that out and talk about what we’re doing going forward.’”
Turns out most executives don’t want to relive pain or rehash history, and they typically have pretty short attention spans. If you can’t get to your point quickly, you’re less likely to be heard.
This is an idea that’s embedded in the Minto Pyramid Principle, which Dave says helped him hone his communication skills further. Developed by former McKinsey consultant, Barbara Minto, the pyramid offers a framework for better communicating ideas. Basically, it states that you should get to your point (in a CIO’s case, the ask) right away and then show how you got there—even if people react initially. “They’ll react because you’re basically taking traditional storytelling and turning it on its head,” explains Dave. “You still have to do all your prep work, but put the ask first and then back it up with all the stuff to justify it.”
Tip #2: Understand the business
In the B2C world, “customer empathy” is the holy grail: Knowing your audience so well that you can speak directly to their needs. In the world of IT leaders, this translates to “understanding the business”: Knowing the business needs so well that you can align your goals with the goals of executives on all sides of the table.
A lot of IT people can get caught up in technology and forget about the reasons that technology exists in the first place. “Forget about tech companies for a second,” suggests Dave, “In any other company, the only reason the IT organization exists is to make that company successful.” Understanding what success means for that business is table stakes for proposing a project that will impact any part of it. “If I don’t understand their business as a CIO, how do I know what to bring to them to show them what’s possible to make their business better?”
CIOs—especially new ones—should also be sensitive to the history, current processes, and implications of altering the existing technology, particularly when you’re dealing with legacy applications. “You want to start running, but you’ve got this big ball called ‘legacy applications’ you’re dragging around with you,” he empathizes. “The new stuff is great, but we’re not going to rebuild all our admin systems in the cloud overnight, stuff that took 40 or 50 years to create.”
In these situations, “understanding the business” also means exercising patience.
Tip #3: Talk the talk
As technology enthusiasts, we may be inclined to overshare the technical details to whoever’s listening. That’s the exciting stuff in our minds—and the more we can demonstrate our expertise, the better, right?
Don’t mistake glazed-over looks for rapt attention.
As a CIO, understanding the business also means understanding what business people want to hear, in addition to how they want to hear it. A lot of projects run into problems because business and IT groups are talking over each other. (Which is why agile teams can often succeed faster: you have smaller, more cross-functional teams).
When it comes to communicating effectively across the business/IT divide, Dave believes IT leaders should be the ones to carry the weight. “The onus, in my opinion, is on IT people to talk in business-speak, not the business people to talk in IT-speak,” he says. The main concern for business people is always going to be why they should spend money on an idea. “It’s our job to make that clear to them.”
Tip #4: Plant seeds
One of the biggest things that can secure success for any CIO is bringing other people to the table to support their initiatives. There’s an art to this—one not unlike cultivating plants.
Dave gives the example of launching a multi-million dollar, multi-year CRM project that would not only benefit his own department but the entire enterprise. There was a business person who had a lot of passion on the topic and could see the possibilities. “I partnered with that person and we started planting seeds: bringing a few vendors in to demo products with select senior business people. This helped us determine who was skeptical about it and who could really see the value. Next, we began to identify leaders within the business who would support the vision, who wouldn’t make it just about tech spend, but about building up business capabilities.”
It took a couple of years, but once Dave’s team had a few key advocates on board, they were able to produce a proof of concept and bring more business leaders over to the idea. What started out as a division project, turned into an endeavor that the company was excited about at an enterprise level.
Even though it can take some time and require careful management over time, the fruits of this “planting seeds” approach can yield huge value for the business, and the CIO leading it. “If you believe in it, don’t take the ‘no’s,” Dave advises. “Keep working at it until you get either a seriously hard ‘no’ or you start to build some momentum.”
Tip #5: Manage, don’t manipulate
Even with a seriously hard “yes,” it can sometimes be tough to keep the momentum going on evolving how the organization operates. There are a number of reasons that things get stuck: Business priorities shift, people start to resist, resources run out, or unforeseen roadblocks emerge right in your line of vision. That’s where the savvy CIO finds ways to protect business-critical projects and push them to the point of proving value—the kind that people can actually see. In certain cases, making business leaders see the possibilities is less about telling and more about showing.
Dave gives the example of the transition to the agile model. Agile was new to the organization and Dave and his team believed it would have a huge benefit long term. It was also clear that his team needed coaches to help them with a successful transition to Agile. Instead of risking a long debate or a hard “no,” with a request to add coaches, he found ways to work within his budget to get the coaching help he and his team needed. At the same time, he and his team embarked on educating division executives on agile principles. Once the broader organization could see the value of having these coaches, the spend would be justified—and in the meantime, he managed to meet his overall budget each month.
It’s not about acting unethically or avoiding transparency, Dave insists. It’s about managing relationships and feeling empowered within your role, all in service of building that critical consensus to keep things moving. “You want transparency, but that doesn’t mean you’re walking around the office with no clothes on. Sometimes you need to hold certain things or make decisions within your management purview, even if that means stretching the boundaries a little bit.” As a leader, sometimes you want to have a mindset of “asking for forgiveness” versus “asking for permission.”
Tip #6: Know when to pull the plug
Every CIO wants to be successful, but if you let your ego or bias get in the way, your attachment to success can become your downfall in the long run.
“Bad news, unlike wine, doesn’t age well,” advises Dave. “So, I think, as a CIO, you need to be ready to talk about bad news sooner rather than later.” Openly addressing failures or roadblocks fast enough can save the project: you can rally your teams to turn lemons into lemonade. But there’s always that point of no return where you’re just going to end up with lemons—and a lot of seriously unhappy stakeholders.
You can apply this principle with people as well. A big reason projects can go awry is that you simply don’t have the right people staffed. Admit that, and admit it early on. It’s fine to trust your team to have autonomy, but it’s important to know them enough to know what they’re capable of—and not “promote them to a level of incompetence” as the Peter Principle predicts.
Dave offers two pieces of advice on the people front:
- Know when somebody is no longer the right person for the effort, and you need to make that decision to pull them.
- If you’re going into new technology that your team doesn’t know, you need to get outside help from people who know it.
All of these tactics come back around to helping other people see the possibilities and keeping those possibilities front-and-center throughout the life of a project. As a CIO, it’s your job to build consensus, but also to train others to have your back. Be a mentor to others and enforce high standards of communication; teach your IT team how to communicate value clearly. That’s how successful CIOs end up leading major transformations that generate huge value for the enterprise and boost their reputations.
About the Author:
Dave Condren, (retired) CIO Bond & Specialty Insurance,
Prior to retiring in 2020, Dave was Vice President Strategy, Planning, Execution and Innovation Lead for the Bond & Specialty Insurance segment of Travelers Insurance. Prior to that, Dave was the divisional CIO for Bond & Specialty Insurance at Travelers, in addition to being the innovation lead and e-Business lead for the segment. Before joining Travelers in 2007, Dave held a variety of roles including CIO for Executive Risk and Divisional CIO for Chubb, as well as technology roles at The Hartford and Lincoln Financial Group.