Good list. I recommend briefly capturing the answers aka creating a reusable doc, which helped me improve at delegating over time. And adding info like "this is best used for/when..." and "alternatives include..." can help delegatees become even more independent.
Pausing to ask the right questions before handing something off has saved me from a lot of rework. Delegation feels less scary when the thinking is done up front.
At Embarc, the account teams who wrote things down even when nobody asked always shipped less rework. Half of delegation is just making the ambiguity visible before someone else has to guess at it.
I spent 27 years on the NYSE floor interviewing seasoned CEOs on TV. I noticed some answered a different question. The question they wanted to answer, versus the one I asked. The audience usually knows.
When I coach senior women today, the failure isn't a confidence problem, it's usually a structural problem: She hasn't pre-built the three sentences.
A no without architecture around it reads as “Oh she’s being difficult” A no with architecture around it reads as graceful and still preserving the relationship.
The transfer of judgment is what I see most people underestimate. The hard question - the one that decides whether the delegation actually works - is how much context goes along with the task. I've seen this in EdTech too: the briefing that felt thorough rarely was.
Number 4 is the one I only learned through AI. I had a whole page of rules describing the tone I wanted and the drafts kept coming back dull. Then I pinned one message I'd already approved at the bottom of the rules and said match this one. Fixed it immediately, which was annoying after all those rules.
Would you adjust your questions to add a seventh. Or perhaps overarch it with ~ Have I built the culture where people feel safe to ask questions, challenge assumptions and make mistakes?
Good list. I recommend briefly capturing the answers aka creating a reusable doc, which helped me improve at delegating over time. And adding info like "this is best used for/when..." and "alternatives include..." can help delegatees become even more independent.
Pausing to ask the right questions before handing something off has saved me from a lot of rework. Delegation feels less scary when the thinking is done up front.
At Embarc, the account teams who wrote things down even when nobody asked always shipped less rework. Half of delegation is just making the ambiguity visible before someone else has to guess at it.
Super actionable post! I've turned it into a Claude Skill ;)
Thanks for pulling this together and sharing.
I spent 27 years on the NYSE floor interviewing seasoned CEOs on TV. I noticed some answered a different question. The question they wanted to answer, versus the one I asked. The audience usually knows.
When I coach senior women today, the failure isn't a confidence problem, it's usually a structural problem: She hasn't pre-built the three sentences.
A no without architecture around it reads as “Oh she’s being difficult” A no with architecture around it reads as graceful and still preserving the relationship.
I call it the “anatomy of a good no.”
The transfer of judgment is what I see most people underestimate. The hard question - the one that decides whether the delegation actually works - is how much context goes along with the task. I've seen this in EdTech too: the briefing that felt thorough rarely was.
Number 4 is the one I only learned through AI. I had a whole page of rules describing the tone I wanted and the drafts kept coming back dull. Then I pinned one message I'd already approved at the bottom of the rules and said match this one. Fixed it immediately, which was annoying after all those rules.
Would you adjust your questions to add a seventh. Or perhaps overarch it with ~ Have I built the culture where people feel safe to ask questions, challenge assumptions and make mistakes?