What’s your approach to helping direct reports within the IT department develop their leadership skills?

In my opinion, the IT skills most at risk of being overshadowed by AI are the routine, repetitive ones, things like basic troubleshooting, simple scripting, and straightforward system monitoring. AI is getting very good at handling those tasks fast and accurately. But I’m less worried about widespread skill loss and more concerned about teams becoming too dependent on automation without understanding what’s happening under the hood. The real danger is letting foundational knowledge fade. That’s why it’s so important for IT teams to stay hands-on, keep learning, and treat AI as a tool that enhances their capabilities, not replaces their thinking.

My approach to helping direct reports in IT develop their leadership skills starts with giving them real ownership, not just tasks. I like to assign small but meaningful decision-making responsibilities, encourage them to lead initiatives or cross-functional discussions, and create a safe space where they can ask questions, make mistakes, and grow. Pairing that with consistent feedback, mentorship, and exposure to strategic conversations helps them see beyond the technical work and understand the bigger picture. Leadership isn’t built in a classroom; it’s built through guided experience, so I focus on creating those opportunities and supporting them every step of the way.

I take a hands-on, developmental approach rooted in empowerment and trust. Within IT, I pair each team member with stretch projects that push them slightly beyond their comfort zone, while I coach through regular one-on-ones focused on reflection and problem-solving. I emphasize situational leadership—adapting style to maturity and context—so emerging leaders learn to balance technical mastery with emotional intelligence and communication. Leadership grows when people feel both accountable and supported; my role is to provide that balance and clear visibility on how their growth connects to our strategic goals.

Teach and trust. I've been fortunate to (mostly) have people leaders that are eager to do a good job and grow their skill sets. Coach them when it's warranted, give guidance. Let them then exercise those skills and recognize that mistakes will happen and how to learn from those. There is also different skill sets required when you are leader of individual contributors or a leader of leaders. When people make a transition up thru those different levels, they have to be coached differently and educated on what their role is at the different levels. It's often difficult for people to let go of their old role, which is comfortable and embrace their new role. Put them in situations that will allow them to display their leadership skills both within and outside the department.

My learning over the years: Everyone is not aspiring to be a leader, some are happy staying in their comfort zone or happy with their operational roles. So 2 parts to the development plan:

For those who want to grow and on the fence, my approach has been to have frequent conversations and provide feedback on behavioral aspects which impact their growth as a leader. Put them in the front of conversations with customers and partners while guiding them through the journey. After a few such interactions leave them on their own. Some get through and others may struggle, but their real life situations give them lessons that will stay with them. Of course, encourage them to undergo assessments which highlight their strengths and areas that need development. Help them build a plan to improve with a defined timeline. Repeat again.

And for those who are reluctant, my message has always been quoting from Marshall Goldsmith: What got you here won't get you there. If you are not willing to change, probably as your role diminishes, we may not need anyone in that role. So you decide your future.