Change Starts at the Top: Why Executive Involvement Makes or Breaks Technology Initiatives

Why Executive Involvement Matters

One of the most successful implementations I’ve been part of involved a large association where the CIO and Director of IT were deeply involved. That executive engagement made a measurable difference in both momentum and outcomes.

Two things stood out immediately.

First, communication was consistent and multi-level. Executives spoke directly to department heads, who then briefed their teams. At the same time, the IT team shared formal updates across the organization. This created clarity, minimized confusion, and gave senior leaders a true sense of ownership. Buy-in followed naturally.

Second, escalations actually worked. When product issues stalled, executives escalated directly to their peers at the vendor. Problems that had lingered for weeks began moving quickly once leadership became involved.

How Executives Can Support a Technology Initiative

If an Executive Director asked me how to support a major technology project like an AMS implementation, here is what I would recommend.

1. Be aware of the risks. If no one is bringing risks forward, ask. There are always risks. Naming them early builds trust and prepares the organization to respond.

2. Make space for your team. Most leaders underestimate how much staff time implementations require. Help your team protect the time your consulting partner recommends.

3. Be ready to escalate. When the project team hits a wall, your voice can unlock solutions they simply cannot access.

4. Champion communication. Especially when things get hectic, executive messages reinforce timelines, expectations, and progress.

   
   

Knowing When to Step In and When to Step Back

Executive involvement does not mean living in the weeds. One of the most powerful things a leader can do during a major technology project is clear the path without walking it for the team.

When leaders stay too close to day-to-day execution, teams become hesitant to make decisions, project managers lose authority, implementation partners receive mixed signals, and progress slows because everything requires approval.

When leaders play the right role, they step in when roadblocks arise, reinforce priorities and timelines, celebrate milestones, motivate the team, and trust their people to do the work.

In my experience, teams do not need executives to solve every issue. They need leaders who back them up.

What Leadership Involvement Actually Looks Like

Leaders sometimes say, “I’m not a tech person.” That is fine. You do not need to know how to write code, but you do need to show up.

I have worked on projects where leadership was absent. Decisions stalled, staff were pulled in multiple directions, timelines slipped, and eventually an executive appeared frustrated and looking for someone to blame. The common signal was a stressed and overworked project team with no clear direction.

By contrast, the strongest projects had leaders who were present. Even when things went off plan, the tone remained calm and solution-oriented. Executives helped clear roadblocks so teams could focus on the work.

Real involvement looks like this:

• Showing up for key meetings, not just the kickoff

• Asking questions about impact on members and staff

• Backing your team when tough tradeoffs are required

• Championing the change internally, not just approving budget

• Modeling accountability, curiosity, and trust

  
  

Your team takes cues from you. If technology is strategic to you, it will be strategic to them too.