How to Get Answers From Your Boss... Without Asking Questions

Have you ever not known what to do next at work?

That's a question I ask often when I'm addressing groups of workers and managers. The answer is always a sort of mixed unanimity: a little vehement nodding and smiling alongside a larger amount of subtle, nearly imperceptible nodding and scowling.

"Don't be embarrassed," I continue. "That's why they hired you. Our work is complex and dynamic. Across industries and geographies, many, many professionals find that their first task is to figure out what their next task should be. There's certainly no shame in being confused."

"So" -- this next part is delivered with a bit of a devilish grin -- "how many of you solve that problem by asking: "Hey, Boss, what should I do?'"

In every crowd, a few nod proudly and affirmatively. I'm glad. If they're telling the truth, it indicates the kind of open, communicative superior/subordinate relationship that leads to useful output at minimal stress.

Everyone else, of course, looks mortified. For most, the idea of sitting down with "Boss" and asking what to do is downright frightening. Outside of a few specific circumstances -- being new to the job, facing some sort of unusual calamity, etc. -- this feels like nothing short of an admission of incompetence. Confusion can be scary.

It also feels like, if you go this route, Boss is likely to answer with reproach: "Someone at your level should already know." Tsk, tsk.

You may think I'm about to encourage you to ask anyway. It would be just like a guy like me to tell you that a good boss will appreciate your candor and respond positively and helpfully, right? Oh, sure. And then, unicorns will dance and we'll all sing songs of happiness together.

Well, okay, it's not so far-fetched. As I said, in some cases Boss may respond well. And I do think you should raise the issue somehow. But if I were you, unless I were certain it would work, I wouldn't bluntly ask Boss what you should do. I think, with that approach, you're at least as likely to get the "tsk, tsk" response as anything else -- even if your particular Boss is pretty good.

Questioning, you see, is verbally aggressive. Asking a question forces the conversation onto the topic you've defined -- questioning subtly seizes conversational control. In this case, you're demanding that Boss provide you with specifics about what you should do.

The thing is, Boss doesn't know. Boss probably doesn't even know his or her own next step, much less yours. Boss probably isn't too sure of exactly what you're doing. And yet, Boss feels pressure to know. Our media and popular culture tell us that leaders and managers are strong, forceful go-to people with all the answers; that good ones are decisive, quick-witted, and abrupt. Communication in this context is a quick back-and-forth of questions and answers. Good bosses don't tolerate incompetence, and don't hesitate to chastise when they detect it.

So, our culture and your question conspire to put Boss on the spot. Boss should know the answer. In fact, Boss feels a little embarrassed at not knowing it. Boss doesn't want to look clueless or weak. Also, Boss doesn't want to demoralize you by suggesting that your work isn't important. Your work is crucial -- if you don't perform, Boss's reputation is on the line! Herein lies another problem with asking your question that way: It suggests that you might not be terribly competent. That's a big red flag for Boss.

Is it really any surprise that, faced with your question, Boss bites back?

"How can someone at your level not know what to do?" bellows Boss. That's return fire. It's strong, it seems leader-like, and it avoids admission of cluelessness on Boss's part. It lends an air of importance to your work, and delivers a not-too-subtle "get with the program" message. It's exciting, it's dramatic, it feels like leadership, and it would make for great television.

Unfortunately, it's not effective information exchange. You leave chastised, your boss leaves embarrassed, you both leave worried, and nobody has any new insights or information - just battle scars.

What to do instead? Here's the good news: You don't have to change your boss, your job, or your personality -- only your approach.

Lead with statements, not questions. Start with about a 90-second summary of what you're working on. Don't talk much about the processes you're following -- things like meetings and travel. Instead, articulate the useful output you're working to deliver -- things like project completion, sales numbers, or documents created. (Here's a video that will help.)

Be careful, though. Don't do it in a sort of Rambo-esque, "here's what I'm doing and you'd better be on board" kind of way. Instead, explain that you'd like for Boss to edit your list, please, as he or she sees fit.

That's right - say "please." And mean it. Stay open to Boss's edits.

This approach turns confusion into opportunity. First, you teach Boss what you're working on, eliminating his or her embarrassment at not knowing already, and at the same time subtly advertising your value. Second, you teach Boss that you figuratively and literally know what you're doing, eliminating any worry over your competence. Third, you make it clear that Boss is in charge, eliminating any discomfort stemming from perceived role pressure. Fourth, you create an opportunity to bring your work into alignment with Boss's expectations, eliminating any surprises down the road, and building trust.

Let's pause for a moment on the point of trust, because it's pretty important. This conversation enables you to make commitments and then meet them. By articulating what you're working on now, then coming back later with that work completed, you create a reputation as someone who follows through. This is a fundamental building block of trust: a promise paired with its fulfillment. Here, you'll make several promises that you're pretty likely to deliver upon, because they represent work you're already doing.

But perhaps best of all, this approach creates a safe context for you to discuss your confusion. "Let's return for a moment to item 2 on my list," you might say. "I'd like to talk with you briefly about how to proceed in that area, because I'm unsure of my next step." By turning your confusion into an opportunity to strengthen your relationship with your boss, and to communicate your value, you're much more likely to get it resolved.

Give it a try. Even though it's not dramatic or loud, even though it's not exciting to watch, and even though it would make terrible television, it works.

Or, on second thought, maybe that's why it works