Awhile back I was working with an Executive Team who shared that one of their biggest strengths was how much they empowered their direct reports. Now, as part of the assignment working with this Executive Team, we agreed that I would undertake a series of “skip meetings”. A skip meeting, for those who may not be familiar with the term, is a one-on-one conversation with an employee who works a level or two down from the Executive Team. These meetings capture insights to improve performance and decision making largely because the information gathered is raw and unfiltered.
In this assignment, I interviewed several people at the Director level, reporting to AVPs and VPs. And I’ll never forget my last interview. It was with a person who’d worked in the organization for 12 years. I asked, “How empowered do you feel to take action and make decisions in your role?" Up until this point in our interview she was rather shy and I had the feeling she was holding back. But when I asked that question, she swivelled her chair to face me directly, locking eyes with me. She said, “I can’t make any decisions here. Every day, I feel her breath (the VP she reported to) on my neck.” Imagine being 12 years on the job and being treated like every day is your first day.
When was the last time you empowered someone on your team to make a made a decision without checking with you first?
For many leaders, that question lands with unease. Some say their team needs to check in because the work is complex. Others say they prefer to stay close because standards matter. A few will admit, if they sit with it long enough, that the checking in has become a pattern neither side knows how to break. The team waits. The leader steps in. Everyone stays busy, and yet something essential stays stuck. Empowerment is a practice both sides build together, over time. That is where most conversations about delegation miss the point entirely.
When the System Works Against Everyone
The breakdown I see most often is structural rather than personal. Leaders stay too close to the work out of habit, reviewing outputs that have already been handled well, stepping into conversations their team could navigate alone, absorbing decisions that belong further down the chain. Slowly, without anyone choosing it, the team stops exercising judgment and the leader stops doing the strategic thinking their role requires.
The cost runs deeper than efficiency. Leaders get evaluated on how much their people have grown, not on how much they have been absolved others from making decisions. It’s often in these feedback moments that leaders question their own leadership and whether they are building people capable of delivering results without them. That is a different kind of accountability, and it catches many leaders off guard.
There is a second layer worth naming. Leaders with years of experience carry a strong instinct about the right way to approach a problem. That instinct is genuinely valuable. When applied without flexibility, though, it becomes a ceiling. A team member who tries a different approach and gets redirected back to the familiar path learns something important from that moment. They learn that initiative carries risk. Over time they stop generating ideas and start waiting for direction. Waiting becomes the culture, and the leader wonders why things are moving so slowly and why engagement has gone flat.
Leaders want to instill agency in their teams, creating the conditions for new processes to be tried, new ways to see problems and inspiring team members to take calculated risks within their roles that stimulates performance. Successful organizations thrive when team members are trusted to bring full capability to the work you were hired to do. When agency is present, people move with confidence. When it is absent, they move with caution.
Three Practices to Build Real Empowerment
Tool One: For the Leader — Make Authority Explicit
Most leaders believe they have made the boundaries of delegation clear. Their team members, in the same conversation, will describe a very different picture. Self-determination is one of four core conditions people require to feel genuinely empowered at work. But that self-determination becomes accessible only when authority, guardrails and boundaries are stated plainly rather than implied. Before delegating a project or responsibility, have a direct conversation. What can this person decide on their own? When do they check in? When leaders make this explicit, hesitation gives way to momentum.
Ask yourself: Have I made it genuinely clear what this person is empowered to decide on their own?
Tool Two: For the Team Member — Say Where You Need Support
Empowerment asks something of both sides. Successful leaders know that team members are motivation at work and perform at higher levels when three core needs are met: autonomy, competence, and relatedness. Research shows that when people feel unsupported in building competence, motivation erodes regardless of how much freedom they are technically being offered. A team member who stays silent about a skill gap, hoping no one notices, is quietly withdrawing from the very relationship that could help them grow. Naming the gap is an act of ownership. Asking for support is how agency gets built.
Ask yourself: Where am I quietly struggling, and who needs to know?
Tool Three: The Shared Monthly Check-In
Edgar Schein spent a career studying the quality of questions leaders ask. His central insight was that most leaders ask questions designed to confirm what they already believe, rather than questions genuinely open to a new answer. The monthly check-in is built on the latter. Fifteen minutes. Three questions.
· Where do you feel most confident right now?
· Where do you need more room or more support?
· And what is one thing I could do differently that would help you do your best work?
Over time this simple ritual closes the distance between what a leader believes they are offering and what a team member is living. Relationships built on that kind of honesty make real empowerment possible.
The Real Return
And here’s the most important thing about empower that is often overlooked. When empowerment takes hold, it allows leaders to step back from the details and into strategy, where they belong. Teams stop waiting for permission and start contributing with conviction. The culture that emerges reflects that shift in ways that performance reviews rarely capture but everyone in the room can feel. The leader who once felt buried in the work discovers something worth holding onto. Their team was ready. They were the ones who needed to let go.
Ask yourself: Where in your leadership are you holding on to work that someone on your team is ready to own?
Continue the Conversation
This reflection is the third in a seven-part series exploring the Seven Interlocking Practices at the heart of The Compassion Advantage. Each practice builds on the one before it. If this one resonated, I invite you to share your reflections in the comments, particularly where empowerment has felt most difficult in your own experience. Leadership grows best when it grows in dialogue.