I heard from a middle manager who struggles with his manager’s unclear delegation and occasional absence of direction. His senior manager constantly shifts assignments, switching up what’s urgent today and what’s important tomorrow with virtually no notice — and does this so consistently that it almost feels as if the confusion is intentional.

Middle likes to do well, wants to be a team player, and cares about managing his own schedule in a measured, non-frantic way, so he emails Senior frequently to ask which tasks have immediate urgency or high priority.

The situation is pretty nerve-wracking for Middle because when Senior doesn’t communicate, and Middle does not guess correctly, he winds up not completing all the tasks that Senior expects. In fact, sometimes Middle completes tasks that either turn out to be unnecessary or that Senior also does, duplicating efforts and irking Senior further.

The situation upsets both parties and leads to embarrassment — as well as a developing sense of hopelessness about being able to succeed and thrive in the job — for Middle.

More often than not, Senior doesn’t even answer Middle’s questions, leaving Middle to fret that he’s supposed to have both ESP and unlimited availability.

Two intelligent people are frustrated, significant amounts of time are wasted, the work is often a mess, and the relationship is deteriorating.

Middle’s current approach has now been tested enough to be proved ineffective.

Finding a New Approach

If you’re having a similar problem, try to find a new method of communicating and a different emotional stance, instead of getting indignant (the most natural immediate reaction) or resentful and despairing (the natural long-term reaction).

As the subordinate, instead of continuing to bang your head against an unyielding wall, consider that your “checking in” is somehow not working for your Senior, no matter what your intent and how strong your willingness to help shoulder the workload.

In this particular case, Senior may wonder why Middle is so annoying, always asking what’s next. She may feel that Middle is actually supposed to know and is somehow bucking the culture or being self-protective.

If your Senior were a reasonable, moderately structured, judicious decision-maker, it might be enough to shift the offer of help slightly: “I have some time to work on Task X this week. If you let me know by Date 1, I can finish it by Date 2.”

Getting Expectations Out of the Middle

But if your Senior is as distracted and frenzied as this one, it’s the relationship that needs to be addressed, not the specifics of completion dates. It’s worth asking for a meeting to discuss “how I can support you better” or “how we could get more accomplished” and engage your Senior in an actual dialogue.

The conversation could also include something like: “I’m concerned that I haven’t communicated clearly how much I want to be helpful and stay on top of the many things coming in. Is there a different way you’d like me to handle it when I check in about assignments? What will work best for your schedule? Would it be helpful if we sat together to plan the week? Or do you just want to send me an email once you see how the week is working?”

Expressing curiosity may help. Ask about the best way to work together — “I was wondering how you like to go through these assignments” — or the relationship — “I was thinking that I could be more helpful if I understood the rhythm of the work better, as well as which jobs you feel are the most crucial. Would you mind spending a little time explaining it to me?”

An in-person meeting is by far the best option, so you can read your Senior’s responses and see when to probe or when to pull back. Phone is next best because your Senior’s tone of voice can give you clues about how to proceed. Email is the last resort, and if it’s your only option, get some positioning advice from colleagues who have worked successfully with your Senior in the past.

The more stressed and/or disorganized your Senior is, the more crucial it could be to help her only in the way that she is comfortable accepting help — your way of helping may not meet her needs, and could actually become an irritant to her. If you’re a frustrated Middle and you want to reduce the stress of your relationship — and your schedule — first figure out what will work for your Senior, and then see if you can make it work for you.