Delegation - An Inside Job


My executive coaching clients often struggle with delegation. Sometimes they find that they hand things off but then they bounce back; sometimes they just don’t feel like their staff is up to what is needed. They may have learned a ton of “tools and techniques” still nothing shifts. So what’s up with that?

Often it’s that there is important inner work to be done before the tools and techniques are worthwhile. My teacher and mentor Doug Silsbee was fond of talking about the “double helix” of the outer work (in this case, delegating more successfully) and the inner work. If we just address the outer work, we will at best get temporary fixes until the inner work is tackled.

A couple of months ago, I was talking with Federico (not his real name). Federico is a social entrepreneur in the education space. When he delegates to one of his passionate volunteers, things fall through the cracks. As we consider this challenge, he sees that he’s not having the uncomfortable conversation to be very clear and specific about his expectations. His basic desire to make everyone like him is at play. This is familiar territory for Federico. We’ve been coaching for several months and he’s developed a way to bring awareness to this aspect of himself more readily. That’s his inner work in this situation. As he does that, he can clearly see what’s missing in his delegation and can find the resources within himself to have those conversations. Only at that point is it useful to hone his techniques.

As we talk about the specifics of Federico’s situation with his volunteer, I outline three steps for delegating a “stretch assignment.”

  1. Lay out the overall desired outcome clearly, including the “why.”

  2. Identify a relatively small first piece of the work and assign just that piece. (Using delegation basics like setting clear parameters for success, etc.)

  3. Ask the volunteer how s/he plans to approach this task.

It’s step 3 that sets up success for the “stretch” part. Federico gets to see how his volunteer thinks about this task and assess his readiness for the task, while also providing coaching/input. The volunteer is more likely to both be successful with the task and grow into larger assignments. This is the outer work of successful delegation.

Without the inner work of mastering his relationship with the voice that wants everyone to like him, Federico can’t do this outer work wholeheartedly. That’s the double helix of the inner work and outer work.

Each person’s experience of frustration with delegation is different of course. And yet, this inner/outer dynamic is almost always at play. Identifying the inner challenges that block your ability to delegate and working on those side by side with learning new skills and techniques – that’s where the power is.