Executive coaching from seasoned CIOs makes the difference

CIO legend Charlie Feld doesn’t hesitate when he says, “This is an outstanding time to be an IT leader.” And for good reason. In the digital era, IT leaders have more opportunities to spearhead innovation, orchestrate large transformation efforts, and drive business value.

But with the speed and complexity of business today, CIOs and IT leaders also face many new challenges, the stakes of which have never been higher. Having the ability to see around the corner and choose the right path is paramount. Here, the experience, perspective, and advice of someone who’s “been there, done that” can be critical.

I know hundreds of successful CIOs, and they all have mentors. In fact, many have a personal board of mentors from varied perspectives. Through these relationships, these great leaders are constantly learning and asking questions to gain new perspectives and any edge, no matter how seemingly small, to set up themselves, their team, and company for success.  

Many of these leaders also leverage executive coaches to maximize strengths, address blind spots, and anticipate potential landmines and unintended consequences. They engage their coach as sounding board and thought partner to work through real-world issues, expand their toolkit and playbook, and decide the best path to take.

My colleague Erica Hartnett, Ouellette & Associates’ director of IT workforce strategy and client initiatives, and I spoke with five former CIOs who have served as executive coaches to hundreds of technology leaders: Larry Bonfante started moonlighting as an executive coach during his successful CIO career, setting himself up for a thriving chapter two. Hall of Fame CIO Barbara Cooper is known for navigating multiple cultures as CIO of Toyota North America, while also leading Toyota University and founding the first women’s network. Julie Cullivan has written one of the great CIO-to-boardroom stories. In her last operational role, she held both the CTO and chief people officer roles. John Hill most recently served in a multidimensional CIO-plus role. Like all great leaders, he is a lifelong learner, having graduated from the US Air Force Academy and recently completing his doctorate degree while holding down a demanding day job. And Joel Jacobs, another longtime, award-winning CIO and CSO, positioned Mitre as one of the perennial “best places to work in IT.”

Here, these seasoned IT leaders turned executive coaches offer their viewpoints on the executive coaching experience, how it can benefit both your career and organization, and ways to ensure you get the most out of what can be a very valuable relationship.

How executive coaching can benefit IT leaders

As a leader, it’s not easy to find the space to think, test out ideas, and get clarity around complex issues. Yet that’s exactly what’s needed today. Executive coaching gives IT leaders the opportunity to explore specific challenges and receive unbiased feedback and support to refine their decision-making and leadership approaches.

When you’re working with an executive coach who’s walked in your shoes, you get more than just a neutral sounding board. As Bonfante puts it, you get to take advantage of a hard-earned “PhD from the school of hard knocks.”

“There’s enormous value in working with someone who has actually lived your reality,” he says. “Someone who’s not giving you theoretical or academic advice but advice based upon real-world experience and success. When I’m talking to you, I’m talking to you from a place of knowing your world because I’ve lived your world.”

Jacobs adds that clients also gain the benefits of the coach’s perspective in having faced similar challenges but in different venues. “As a result, the executive can learn what’s worked and what hasn’t in other environments,” he says. “Coaching also gives them the opportunity to test ideas and gain perspective based on what the coach has been through, and the coach can then tailor the direction of the engagement in ways that allow the participant to explore these ideas in a safe environment.”

A great coach will also help an IT leader recognize potential blind spots that could sabotage their success. Because IT leadership is so difficult, coaching is critical to help leaders develop their executive presence, find their voice, and build and execute a successful playbook so they can lead big initiatives and navigate the sometimes-thorny political dynamics.

Cullivan herself has benefitted greatly as a recipient of coaching over the course of her career. “There was one I worked with for many years, and it was a nice blend of marrying some very specific coaching around my core values and who I am as a person and what drives me. She was able to help me understand that, because of these core values, it was actually getting in the way of me being able to be more strategic,” she says.

Working with the coach, Cullivan found ways to stay true to herself and become the leader she wanted to be. She sees similar breakthroughs with leaders she works in her role as coach. “Sometimes coaching leads you to realize, hey, this thing that I’m trying to get to isn’t really for me. It opens up people’s minds to think about, what are the other ways for me to leverage what I’m great at and leverage what I enjoy and grow in a different way,” she says.

As Jacobs points out, the specific benefits of coaching ultimately come down to the individual’s goals and aspirations. “Some of the people I’ve coached over the years have gone on to significant advancement, promotions, and new assignments,” he says. “Others have found different perspective in the roles that they were already engaged in and, as a result, greater enrichment in their current roles.”

Bonfante adds that the day-to-day benefits can be just as powerful. “I always refer to it as helping you build your strategic competencies while improving your tactical realities,” he says. “Instead of discussing things in some generic and abstract way, let’s use your existing relationships, projects, and challenges as grist for the mill, so that while you’re building your capabilities for the future, you’re also being more effective in the here and now.”

How the organization benefits

Organizations can also benefit from their executives’ coaching experiences. Hill points to three outcomes he’s observed: “It helps organizations drive innovation and change. If the executive shares that they have a coach, it encourages continuous learning in the organization. And most important, it will improve the organization’s operational performance.”

Cooper has also seen benefits in the organizational context. “Clients gain perspective not only about themselves but about those in their work orbit. Above all, they adapt better to their corporate culture and learn how to navigate the politics of the organization much more effectively. And with a more motivated and focused individual who now has more enhanced competencies, well, the organization is the beneficiary of that,” he says.

One of the hallmarks of top IT leaders is that they’re continual learners and teachers. Executive coaching facilitates a leader’s personal learning, and it sets them up to be stronger teachers, coaches, and mentors themselves. Many CIOs also choose to enroll their direct reports into executive coaching programs to help them take their leadership games to the next level as well.

Maximizing the coaching experience

While executive coaching is highly individualized, some best practices will help a leader maximize their time with their coach. For Hill, it’s all about ownership and accountability.

“Successful participants will set clear goals, they’ll be open and transparent, and they’ll be committed to owning the experience and maintaining a continuous learning mindset,” he says. “It is only by being vulnerable and then owning the journey that participants will be able maximize the value of the executive coach relationship.”

Bonfante agrees, emphasizing it’s important to pinpoint what you want to get out of the coaching engagement from the outset: “The first thing you have to have is clarity on what you’re trying to accomplish. What are your goals? What does success look like to you? A year from now, when we’re celebrating the engagement, what’s different than when we started together?”

Of course, you’ll also have to be introspective, open, and honest, both about your areas of development and your strengths. “I can’t help you if I don’t know what’s really going on in your world,” Bonfante points out.

Additionally, it’s up to the IT leader to make sure their coach understands what they want to work on and achieve. “Depending on the level at which the person is and what their career aspirations are — are they aspiring to get up to C-level, for example — that changes some of the conversations and some of the focus of the coaching,” Cullivan says.

Before each session, Cooper suggests spending time identifying current challenges you want to talk about and the skills and competencies you want to improve. Maybe you want to work on refining your communication skills or how you handle difficult conversations. Take the time to think this through in advance, she says, and make a point to stick to the schedule.

“Obviously things happen that are unplanned, especially in IT. But try to book sessions at a day and time when you’re most likely not to have to reschedule,” Cooper says. “When I have a client who’s the CIO of a Fortune 5 company and can go 12 sessions without one reschedule, and another CIO who can miss 8 out of 12, you can easily see the difference in how priorities work.”

Considering how busy IT leaders are, it can be tempting to think you don’t have time to do this kind of work, but there’s a reason top technology executives make — and protect — the time for coaching. That’s because working with someone who’s been through what you’re going through can be a valuable resource in helping you meet the continually evolving demands and complexities of leading an IT organization.

Get in touch if you’re interested in learning more about executive coaching for yourself and/or your direct reports.