Clarify, Coach, and Get out of the Way: Empowering IT Teams to Perform Independently

One of my biggest revelations about effective IT leadership came early in my career. It wasn’t the result of a big success but from a realization of the limitations of my leadership style to that point.

"Your team isn’t successful,” a mentor told me, “Because they have to come to you for everything.” I was unintentionally stifling our potential by centralizing decision-making. My approach to leading was creating one big bottleneck: me.

Self-awareness is a never-ending journey, and that comment was a wake-up call. So, I shifted my role from gatekeeper to facilitator, focusing on empowering my team to make decisions, innovate, and run their projects. 

This change was about more than just letting go. It required building a culture where each teammate could take ownership of their work. The result was a much more adaptable technology team capable of managing challenges independently and driving meaningful change.

This is even more essential in 2024 than it was then. The IT function is responsible and accountable for much more than technology order-taking, support, and maintenance. The business relies on us to keep production environments stable, secure our environment and data, deliver technology-driven business outcomes, and run IT like a business. 

First, Address the Fundamentals

In today’s world, technology leaders must move beyond managing every detail. Empowering teams to learn — and even embrace mistakes—requires creating an environment in which teammate potential and innovation can be unleashed.

In my experience, there are a number of actions IT leaders can take to accomplish this:

• Align IT’s day-to-day with the business objectives. Building an empowered tech team starts with a deep understanding of the business in which you work. Tech leaders can get caught up in the minutiae of switches, routers, and code, losing sight of the broader business strategy. IT leaders must be deliberate about bridging the gap between technical expertise and business acumen, ensuring their teams are technically proficient and strategically aligned. Once IT leaders understand their business and how it operates, their technology teams can more effectively contribute to positive business outcomes. Then, the technology function evolves from a service provider to a strategic partner.
  
  
• Be clear on what’s urgent versus important. When we as leaders mistake important items for urgent, our teams suffer. A significant outage or major issue being exploited would be urgent for our team, whereas a risk that has existed for years, while possibly important, is likely not urgent. If you can’t articulate why something is urgent, rethink the priority. This helps the team stay focused, avoid burnout from chasing every task, and concentrate on what moves the needle. It also prevents them from feeling as if  priorities are always changing. Clearly understanding the business (as described above) and building deep relationships with our business partners has helped us differentiate between the important and the urgent and prioritize needs.
  
  
• Establish a strong technology subculture. Culture is the backbone of any technology team. It fosters a sense of belonging, purpose, and a shared commitment to the organization’s success. Even the most skilled teams with cutting-edge technology will struggle if they don’t understand or embrace the business culture and the tech team's unique subculture. We’ve developed a formal technology subculture within our organization—what we call “Techniculture,” where technology, business and culture collide. From town halls to annual live events, our goal is to create a “one team” message across our highly decentralized organization.
  
  
• Plug into the power of “we.” A core aspect of the culture here at Brown & Brown is a “we, not me” mentality. Everything we do ties into that. We don’t have employees; we have teammates. We don’t have managers; we have leaders. We hire talented individuals, invest in teaching them the business “why,” and connect that to their “how.” This supports the “we” mindset and encourages curiosity, out-of-the-box thinking, and critical decision-making. The result is a team that’s engaged and empowered to take initiative.
  
  
• Foster accountability. Winning as a team requires accountability. Some 60% of our teammates own a stake in the company, which gives them more skin in the game to push us to new heights. We also encourage team members to share ideas and take risks while holding them responsible for their contributions. When tech teams understand the vision, embrace their roles, and commit to delivering results, they drive collective success. They’re more likely to accept accountability not just for getting stuff done but challenging the status quo in a positive and productive way. 

Hire for Cultural Fit, Not Tech Know-How

Recruiting the right people goes beyond matching skills and experience. Ultimately, the question is whether the candidate can deliver in the way our culture needs them to. The technology itself is the easy part; getting teams across the globe to adopt new ways of working is the real challenge. Scaling a technology team effectively means adding the right people who fit and fuel the team’s dynamic, not just increasing headcount.

At Brown & Brown, we look for curious, resourceful, and entrepreneurial individuals. We want more than just tech specialists; we want people who are excited to contribute to something bigger than themselves.

When we interview, our focus isn’t on technical capability. It’s about curiosity, cultural fit, and even culture add — what the new teammate can bring to Brown & Brown and vice versa. I spend the first part of interviews talking about personal topics: my family, why I’m at Brown & Brown, and what it’s like to work here. This isn’t just small talk; it’s a subtle test to see if candidates can pick up on our values and reflect them back in conversation. If they can connect with these ideas, it’s a good sign.

Teach Your Team to Look Around Corners

Hiring talented people is just the beginning. The bigger challenge is how you support them once they’re on board. An IT leader needs to trust their team to make decisions, empower them to take risks, celebrate their successes, and stand by them through failures.

When you take on a CIO role, what got you into the position isn’t what will keep you here. To be an effective leader, I need to dedicate more than half of my time to coaching, mentoring, and guiding my team.

For example, at Brown & Brown, we have a real “get stuff done” mentality. As a result, sometimes a team will want to move into the solutions phase before they’ve identified a future-proof path forward. My feedback to the team is always the same: “How much time did we spend planning versus jumping straight into execution?” Stepping back and anticipating potential pitfalls can help address and avoid challenges. So, I have to prioritize instilling this perspective in our tech teams.

Some best practices I’ve learned for coaching and mentoring include:

• Holding meaningful one-on-ones. Make coaching, not just mentoring, a consistent part of your routine with teammates. It’s about solving today’s problems and preparing your team for tomorrow’s challenges. Make sure your one-on-ones are more than just task updates. Use this time to discuss career growth, strategic thinking, and long-term aspirations.
  
  
• Developing multiple three-to-five-year roadmaps. Each division or business vertical will have a clear roadmap outlining where they are, where they want to go, and the business outcomes they aim to achieve. Our business-aligned IT teams are focused on addressing the challenges those divisions and verticals face in moving the needle every day —whether that means creating efficiencies in workflows to free resources up for higher value work or leaning into innovation to better support our customers.
  
  
• Resisting the urge to provide all the answers. When someone on the team comes to you with a problem, encourage them to explore other perspectives, consult with peers, and bring in some proposed solutions (versus just the challenge). This builds problem-solving skills and fosters independent thinking. 

The ultimate goal is to develop your team’s ability to think strategically, anticipate challenges, and look around corners rather than feeling like they need to rely on you for every decision.

Your People Will Drive the Business Forward

Creating an environment where individuals are more likely to thrive, hiring for cultural fit rather than tech skills, and coaching the team to anticipate or avoid pitfalls takes significant effort. But it’s essential to build the kind of innovative, resilient, and self-propelled team that not only meets the business’s needs but drives it forward.