Does your exec struggle to delegate effectively?

It seems we all know that effective leaders delegate well. What if your executive doesn’t delegate well to you or his or her staff? There are tons of articles on HOW to delegate more effectively. But, as with so much change, if it were a simple matter of knowing how, wouldn’t your exec already be doing it? Here are some questions you can ask your exec that will help explore WHY he or she doesn’t delegate more:

  • Ask your exec about a specific example. “I’m wondering why you didn’t just hand that personnel matter to the CHRO instead of handling it yourself. Can you help me understand your thinking there?”  A lot of people skip the very important step of asking, because they don’t know how to ask without putting the exec on the defensive. I argue that even if the question does lead to a defensive response, it’s still worth asking because the answer can be so revealing.
  • Probe your exec’s motivation by asking some deeper questions about a specific task or project: “What’s the benefit to you of holding on to <X project>?” “What does it cost you to hold on to it?” “What are the benefits and costs to <staff leader> if you hand it off or if you hold on to it?”
  • As you uncover some of your exec’s hidden motivators, think of strategies for mitigating those. Maybe your exec’s tending to micromanage because he or she doesn’t want to look bad in front of the board. You can circumvent that by suggesting he hand off to someone else but check in at intervals along the way or have a dry run before the board meeting where everyone can ask questions and get on the same page.If it’s about control, help your exec find a solution that still helps him or her feel some control. Or, maybe the leader that your executive is not handing off to dropped the ball before, and there’s a trust issue. You can suggest that your exec needs to address that trust issue, whether by giving the offending leader the space to try again and learn from the past mistake or by providing additional supports that weren’t present when the ball was dropped.

In my book, I name Coaching as one of the universal competencies for chiefs of staff that I identified in my research. Coaches create the space for an exec to explore, and they ask big, provocative questions that expand the exec’s thinking. So, to the extent that you can,  coach your exec. Be a part of helping your boss learn new ways of doing things (hint: it helps if you model continuous learning in your work, too).


Do you need help coaching your exec or otherwise “managing up?” This is the kind of topic we discuss in our Chief of Staff Mastermind Cohorts, a year-long learning experience with 12-20 chiefs of staff that combine the power of peer advisory, group and 1:1 coaching, and CoS-specific training. Learn more and register here:

I also occasionally open up 1:1 coaching slots if you’d prefer to work solo. When you’re ready to move to the next level, find a 30 minute slot for us to talk about availability and next steps here.

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