Two senior IT leaders share their thoughts on how to get their IT teams into high gear

At the recent Midsize Enterprise Summit, two senior IT leaders of midmarket companies shared their thoughts on how to get their IT teams into high gear. The session touched off a debate among CIOs attending the conference as to best practices and techniques they use build teams when assuming new roles inheriting a team or bolstering existing teams. The speakers included John Regula, CIO of Woods and Nick Dell, a longtime senior IT leader. What follows is an interview with both individuals following the conference to dig a bit deeper into the topic. The interview was conducted over email by Robert DeMarzo, senior vice president, event content and strategy, The Channel Company which organizes MES.


Robert DeMarzo: It seems the issue of getting a team into high gear is especially important for midmarket IT leaders. Why is the issue of team work so important for midmarket IT organizations and companies?


John Regula: Members of a mid-market team tend to wear many hats. The teams tend to be smaller and, thus, there is limited opportunity for skill sets to be replicated among team members. This combination makes it difficult for a team to function well if each member is not in “high gear.” – There simply is not a deep enough bench to continually cover for the “weakest link.”


Nick Dell:  Midmarket leaders have smaller teams and if they are not firing on all cylinders it can limit the perception of how important IT is to the business moving forward into digital transformation.  We need to help lead the transformation and not just drag along with it.  


DeMarzo:  How have your views on team building and motivating teams changed as you have matured in your roles as senior IT leaders?


Regula: Early in my career (my first network manager job), I viewed strong team members in terms of their technical competence and motivation focused on salary.  Today, my view of team embodies many more skillsets – relationship building, execution, analytical, learner/teacher, and mentor. Likewise, today’s workforce (especially true, but not limited, to millennials), seek motivations beyond money. They would include flexible work hours/places; relaxed dress code; advancement potential, and an opportunity for skill development. Simply, to find (or retain) a team member they need to both the right technical and right character for your team.


Dell: Over the last few years, I have matured in learning that moving the whole team towards the overall goal of the department and the businesses success, does build a powerful tool for the company to use, instead of just one or two people in the department. IT becomes the go-to tool to get stuff done.


DeMarzo:  You have been part of teams in the past, now you are leading teams. Share some best practices and perhaps some missteps?


Regula: I will start with a misstep. As newly recruited team leader, I assumed, by nature of my “position”, that I was immediately respected by my team. I tried to leverage past accomplishments that were unknown to my new team. I did not take the time to develop relationships before passing out edicts from on high. Today, I recognize that a team needs 4 things (as adapted from Clifton Strengths-Finder) from its leader: trust, hope, compassion, and stability. Everything I say to my team is re-enforcing one of those principles.


Dell: I have worked for 9 different companies in my IT career, so I have learned a lot about what not to do and what to do. Two items to share, do not worry about how you are perceived, but make it about your team, when they look good you look good. Second is to make work fun and truly care about your people as they will return that enjoyment into their work.


DeMarzo: Given how often midmarket IT leaders change jobs, how important is it to win over the existing team vs. replacing it with people you have worked with in the past?


Regula: There could be immediate and comfort in bringing in familiar talent. CAUTION needs to be exercised. This move will (not may, it will) cause resentment from your new team.  A bigger challenge for a new team lead is firing.  Retaining staff just because they existed when you arrived, is NOT a way to build teams. In short, the correct answer is that as team leader you are called upon to create the right team (period).  That evaluation should be based on character and technical skills independent of length of service to the team or company.


Dell: Replacing a team can be easier, but a bumpy ride to everyone. There is no better feeling as a leader then taking an average or underperforming team and making them the best department in the company.


DeMarzo: Who was the best team builder and team leader you encountered in the past and why?


Regula: My best boss (and team leader) often used the phrase that he had his VPs on a long leash and every once in a while, tugged on it to see if we were still there.  He was able to set a vision and allow his team to carry it out. He knew the skills of each team member and how to leverage them to complete projects. I work hard to emulate his management style.


Dell: Steven Ratliff was the leader that I learned the most from in the short 18 months working with him. He showed me how to have fun while building teams of doers and inspire people with goals and objectives to be the best department.


DeMarzo: How tired are you of sports analogies when it comes to managing and motivating teams?


Regula: I am going to hit it out of the park with this answer because it’s a slam dunk to reply. My team needs to carry the ball, do the full court press, keep your eye on the ball, go the distance, come out swinging, and block and tackle so that we cannot drop the ball when we are down to the wire.  I’m throwing in the towel now and just answering – YES!


Dell: Since sports is a big part of American culture and mostly built on teams it works most of the time, as long as they are not over-the-top and in-your-face. Analogies are everywhere, and a good leader should look at their audience when using them.


DeMarzo: Some can argue that your team goes beyond direct reports into the partnerships with trusted advisors and vendors and employees in other departments. How does that impact your team building strategy?


Regula: This is a requirement of every member of my team; they (and my team) cannot be successful without each member building successful relationships with stakeholders.  During team sessions, we actively practice (e.g. active listening) to help build skills in this area.


Dell: I agree, that the team does extend outside of the department into every side of the business. Building relationships with every department is what I work on with my managers all the time, as we all support the goals of the business.


DeMarzo: What’s the greatest lesson you ever learned when it comes to team building outside of the business world?


Regula: I learned two leadership skills from my days as Scout Master. First, you cannot put an old head on young shoulders. People take time to acquire skills and mature in any position. The assignment given the new tenderfoot has to be commensurate with their current skill level today not the skills you hope they have 5 years into the future. Second, not every person responds to the same carrot or stick. Team building is more of an art than a science; it is definitely not a one-size fits all. One scout may change their maladaptive behavior to avoid the extra mile hike after dinner while another scout may think that hike was actually a reward. You have to fine tune your message to suit each person.


Dell: The one that currently has been influencing me is that you have to “try, try at everything you do!”. This came from my Dad being in hospice care that mainly spoke another language. The fact that everyone tried to do their best and we all worked together to make it a wonderfully peaceful experience.


DeMarzo: Let’s say you take a new job and inherit the former leader’s team. What do you say at the first team meeting?


Regula: Remember those four traits? Trust, Hope, Compassion and Stability. I would focus my words on each one of them. Trust is the hardest to earn in that meeting. Your words will not get the new team to trust you. I will start that process by highlighting something incredibly positive that I learned about them through the interview process. For hope: Management wants each of you to succeed. I also come with some political capital that we can leverage to get projects moving or to get issues that you may have lived with for a long time resolved.  For compassion: I would talk about an experience in my career of being faced with a new boss. For stability: I would say directly that I am not here to make changes today. I am here to build upon the amazing team that exists today and look forward to working with each of you.  And, most importantly, this first meeting time will be used building relationships. I need to get to know them as much as they need to know me. Time will certainly be allocated for that.


Dell: I reassure my team by telling them about me and my passion for transforming the business with technology and helping people understand the value of technology. Letting them know that I can handle the truth and I really want to know the truth.  Let’s go try and make peoples experience with technology awesome.