I think all managers are told they must delegate to succeed and/or survive. Seems obvious, a manager can’t do it all, nor should they. So why don’t more managers delegate successfully?
The first reason is that often they were promoted from within the team they manage, and doing stuff is their comfort zone, plus they are usually very very good at doing stuff – it’s a big reason they got promoted. This is one place where the next level manager can make a big difference, force them to step back – even if stuff fails in the short term – until they get a new comfort zone.
The second reason is that when you delegate, you’re handing off the task, not the accountability. If a ship runs aground, it’s the Captains fault, even if he had delegated to a highly trained and trusted deck officer. Delegating sounds good until someone lets you down, and you get to suffer the consequences. Have it happen a few times and even the best manager starts to hold tasks back, preferring to work longer than suffer the consequences of handing off to someone else.
That’s the path to the dark side. The fix, though painful too, is to teach employees (and contractors) to be accountable. For me, it means that if I hand off a task, large or small, the employee owns doing the task and for making sure I know if things are off track. That doesn’t mean telling me the day before the due date, it means telling me as soon as they see a problem. A good manager checks on stuff, but not every day – they don’t have time and you don’t want them asking every day either.
For me it starts with little tasks and little lessons, and first I find out who is trustworthy and who is not. It’s more than whether I’d let them hold my wallet, are they willing to tell the truth when the truth is going to be painful? Will they recognize that I need to know? Those become the intial set of go-to people, and then I start on the ones that aren’t quite there. A lot of it setting expectations – here is the task(s), here is the target date, and here is the expected level of communication. Then you wait to see if they do it. As soon as they miss a checkpoint, you intervene, quietly but forcefully. Have to make it clear from the beginning that while it’s ok for things to go wrong, it’s never ok to not communicate when things go wrong.
Trust and delegation go together. Want room to work and not be micro-managed? Show the boss that you will communicate clearly and often, the rest just happens. Let a couple things slide, don’t expect a lot of freedom.
If you find your boss asking “where are we at on…” at anything besides a planned meeting, odds are you’re not where you need to be.