Boston CIO of the Year winners share 5 lessons on tough talent challenges

Award-winning CIOs discuss their approaches to hiring and IT talent development
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If you think hiring and retaining tech talent is difficult in your region, just try being a CIO in the Boston area, where tech represents one-third of the jobs in the state. We caught up with five CIOs who recently won the 2018 Boston CIO of the Year ORBIE Awards to find out how they’re approaching hiring and talent development. The awards were presented by the Boston CIO Leadership Association, a professional community that annually recognizes CIOs for their excellence in technology leadership.

Among the common themes we heard from these award-winning CIOs: Promote a culture of continuous learning, encourage internal collaboration, and to be careful not to ignore the power of strong individual contributors. Naturally, each leader has some of their own personal tactics for IT talent success as well. Read on to learn some of their approaches. 

1. Help blend work/life and emphasize continuous learning

Nonprofit Boston CIO of the Year

Joel Jacobs, Vice President, CIO and CSO, The MITRE Corporation: For us, it starts with mission. We offer our IT workers a challenging, rewarding environment that lets them turn their ideas into tangible results for an inspiring mission. Additionally, employees benefit from a company committed to work/life balance through flexible work arrangements, which leverage technology and virtual collaboration tools and include telecommuting, part-time, and flexible schedules. We have robust online collaboration tools so that "getting to work" is easy, regardless of location.

[ With digital technology blurring the lines between our personal and professional lives, learn a new approach. Read: Work-life blending. ]

MITRE also values continuous learning, with options to build knowledge both through internal and external resources. Our internal MITRE Institute offers courses, e-books, and training videos. We also offer opportunities for employees to continue their education outside our walls through our Educational Assistance program, which offers tuition reimbursement and an Accelerated Graduate Degree Program. And we cover costs for certification programs.

We have robust online collaboration tools so that "getting to work" is easy, regardless of location.

We also put a great deal of effort into rounding out staff experience – shifting promising leaders from area to area. For example, we recently selected an individual contributor for a senior management role. Previously, he moved among technical roles and, frankly, had avoided ‘managing people’ for years. Yet, in this new role he has been terrific, and he has realized that he really likes the job. 

2. Sometimes you need to be the recruiter

Corporate Boston CIO of the Year

Bob Barrett, Vice President of IT, Rochester Electronics: Building a strong, respected IT team is the most important thing I can do. As such, I take the hiring process very seriously. Although I rely on internal and external recruiters, most of my top positions come through people and connections that I have maintained myself over a long career in IT in the Boston area. I keep tabs on former employees, co-workers, teammates, and peers in IT from other organizations, enabling me to personally recruit most of my direct reports. On several occasions, I've even found and recruited talent for other departments.

I also encourage all my people to continue to learn and develop their talents. I tell my team that I might not always be able to guarantee them employment, but we should both work to make sure they always maintain employable skills. The opportunity to always grow and learn is appealing to technical talent, and often gives them reason to stay. 

I keep tabs on former employees, co-workers, teammates, and peers in IT from other organizations ...

It’s also important to recognize the true strengths of your talent and make sure you’re matching them with roles where they have an opportunity to be successful. Not only does it benefit the organization, but it also helps morale. As an example, at a previous company, I had a manager who led both operations and the helpdesk. While his technical skills were tremendous, he was severely overworked and he was not as strong on customer service aspects. Although he meant well, this had an impact on the reputation of the entire IT organization. I decided to split his responsibilities, focusing him on infrastructure and replacing him on the service desk. While he was initially disappointed, a year later he thanked me for helping put him into a position where he could succeed as a highly-respected contributor. The move benefited the organization and likely kept us from losing a talented technical resource in our IT organization.

3. Be proactive with training


lobal Boston CIO of the Year

George Marootian, Executive Vice President and Head of Technology, Natixis Investment Managers: The technology market is constantly evolving, which creates a challenging environment for maintaining skills. It’s critical to ensure your IT talent is continuing to progress its technical knowledge and skills development. My leadership team and I have been able to help my teams navigate the evolving technology landscape by supporting them with courses and practical skills that will allow them to evolve with the technology market.

[ Is your IT leadership playbook outdated? Read our new report from HBR Analytic Services: Transformation Masters: The New Rules of CIO Leadership. ]

As the suppliers of technology solutions to the business, we’ve been focused on building a flexible IT infrastructure to better support the business and create agility. For example, my team and I migrated our legacy data warehouse team from the role of hardware managers to a team that manages a virtualized data warehouse in AWS. The team was able to progress their technical skills while helping to implement a major technology transformation for the firm.

Many technical employees do not want to manage people, but that doesn’t mean they can’t lead in other ways.

Certainly, leadership opportunities play a key role in retaining great IT talent, but leadership is not always indicative of managing staff. Many technical employees do not want to manage people, but that doesn’t mean they can’t lead in other ways. We work on the development of technology leaders (managers) and believe it’s also important to develop technical leaders within our software engineering department. We have a number of leaders who are highly regarded for their strong individual contributions but who do not manage people. Having this balance of technical and staff leaders continues to be the foundation for a strong and agile IT organization that drives results for the organization. 

4. Blend technical and emotional intelligence

Healthcare Boston CIO of the Year

Lee Anne Howe, Chief Information Officer, Lantheus Medical Imaging: Building a collaborative culture, with shared values, is a personal passion of mine and core to our success. I believe developing a great team is accomplished through consistent, fair, and engaged leadership. It is developed by being clear and following through with my team and treating each individual fairly and with compassion. 

I hire with technical skills equally balanced with interpersonal skills. Emotional intelligence is as important as technical ability when serving multiple stakeholders in a dynamic environment. Additionally, I look to ensure diversity of all types in my teams because diversity of thought brings more creative and stronger results. 

I believe developing a great team is accomplished through consistent, fair, and engaged leadership.

Building a collaborative culture has also helped us build our talent pipeline. By engaging with employees outside of IT, we've brought high-potential employees into the IT organization. We also believe in promoting high-potential employees into senior level roles, allowing them to learn new skills, mentor new employees, and engage in special assignments. For example, we recently promoted a senior developer, and he is now mentoring a recent college graduate to take over his application support responsibilities. It’s a win-win for everyone involved. 

5. Don't rush the hiring process


nterprise Boston CIO of the Year

Kevin McCahill, Senior Vice President and CIO, Connection: When interviewing a candidate, the most important aspects I am looking for are a positive attitude and drive, or eagerness to be successful. Technical skills can be learned, but the right attitude and willingness to put in the effort to be successful are the traits I try to find in a new hire.

Delegation is also key, as is giving high-potential employees stretch assignments.

It’s important to be patient and take the time to hire the right person with the right attitude. Once you hire that talented individual, let them do what they were hired to do; no micro-managing them! Delegation is also key, as is giving high-potential employees stretch assignments. On the flip side, it’s important to take swift action on under-performers; put them on a performance improvement plan first, but don't drag it out if there's no improvement in a couple of months.

I'm also a big proponent of mentoring high-potential team members, not just in IT but in other areas of the company as well. There is so much a mentor can offer in terms of how to act in certain situations, exhibiting professionalism, responding to challenges, etc. I find it very rewarding to be a mentor and see those being mentored succeed. 

[ Which of today's IT roles are vanishing? Read our related article, 4 dying IT jobs. ]

Ginny Holden is an independent consultant who brings the practice of IT to life through memorable storytelling.