Now, of course, "never" in this case is a clear exaggeration since I have done work for this person and, of course, fulfilled all aspects of the assignment with accuracy, vigor, and panache.
Hyperbole notwithstanding....why has he had this dearth of successful delegation? If it was only with one or two people, you could say - well, it must be them. But if legions of workerbees have failed him...is it him? Maybe. Or is it both parties? Maybe.
Stephen Covey has a whole system of delegation, with various steps leading up to stewardship delegation. And he argues that one should not attempt a higher level of delegation than the relationship supports. In other words, if you are dealing with a shoes-and-socks person (that's my term for the type of person who, when told to put their shoes and sock on, ends up with the socks on the outside...because, hey, that's what you said!)....if you're dealing with that kind of person, you can't really assign a nebulous outcome and hope for the best.
But let's assume that the delegatees are quality individuals, creative-minded, and ready to attack a problem. Why are there still so may times when what we get is not what we wanted?
I've assigned my share of tasks and been underwhelmed by the results.
I've also, as a freelancer, submitted a deliverable filled with pride and anticipation (like a kid presenting a stunning macaroni and glitter necklace on Mother's Day), only to be gut-checked by the silent, awkward pause that means "wow, how in God's name did you end up with this?"
This is a classic lose-lose situation. The person who assigned the task is thrown into a tailspin because the critical path has stalled (or even moved backward). The person who did the work feels a melange of emotions from unappreciated to misunderstood to incompetent. And the work, the thing, is still un-done.
I propose there are five things that could avoid or reduce these situations.
Recognize that you have your own lingo and shorthand and the person you're talking to may not understand it. I've found only about 5% of the population will risk looking stupid to ask you to clarify something you say. Everyone else nods wisely, then goes back to their office or cubicle or whatever and thinks, "what the heck did she mean by "breadcrumbs on the PowerPoint"? Make it OK to ask for clarification -- one great way to do that is for YOU to risk looking stupid to ask the delegatee to explain his or her langauge. Make it safe to ask, and you cut down re-work caused by lack of clarity down the road.
If you have something in mind, take out a sheet of paper or a napkin and sketch what you see in your head. There's nothing more frustrating than bringing 5 or 6 ideas for review --- kneeling before the delegator like a supplicant with one idea after another --- and getting the "eh, not quite" response. If you know what you want, don't keep it to yourself.
Even if you don't have an exact answer in mind, you need to give the delegatee a clue as to how their solution will be used. If you ask a graphic artists to "create a compelling graphic" you've really not given her anything to work with. On the other hand, if you say -- "I don't have a specific solution in mind, but I need a graphic element that we can use all year, that will work on a handout or a billboard, that is consistent with the brand, and that suggests movement through the process" -- you've provided context for the scale, the level of detail, the color scheme, and the style. Let's face it, we often delegate because we want results beyond what we would have thought of ourselves, but there are also parameters that must be met. Don't leave out the context.
You're already nodding...sure, sure, everyone knows this one. But do you do it? Do you take the time to ask your delegatee to explain the assignment back to you in his own language? Or do you practice drive-by-management, flinging assignments over your shoulder (or worse across your Blackberry) as you rush out the door for the airport? Three minutes...that's about the investment to get the double-handshake that means your delegatee understood you....if you don't get the echo... 30 minutes, 300 minutes? How long will it take to re-do?
If you work with someone frequently, consider co-creating a scale that defines the type of assignment. For example, sometimes you need someone do to exactly what you want -- not terribly rewarding for the delegatee, but vital to hitting a deadline. So have a code for that: "this is a verbatim assignment." In that case, the delegatee knows to listen careful and execute exactly; this is not the time to spitball alternatives. On the other end of the spectrum, sometimes you have a wild idea that may not even be possible, but you want someone to think about it and spend a little time on it: "this is a percolator assignment, put about 5 hours into it and let's see if it has any legs." (it is important to tell the person how much time to invest on this kind of thing and where it falls against other priorities). Obviously, the type of scale has to make sense for your situation...but think about a way to shorthand the types of tasks.
None of this is easy to do in the rush of an average day --- but it issimple. If you are not happy with an end result, revisit the moment of assignment. The seed of the solution is likely there.