Question Authority: A Workplace Imperative

08/14/2014 12:01 pm ET | Updated Oct 14, 2014

Question authority. Go ahead, ask me anything.

This remains one of my all-time favorite bumper stickers. Someday I'll put one on my own car, for comedic value. I'd also like to hand out boxes of these stickers to executives in my large corporate clients, to post on their office walls.

In that case, my goal isn't to get a laugh.

I recently wrote about how an email typo from an executive created huge waste within his organization, as his employees scrambled to respond to a request he didn't intend to make. The story nicely illustrates the total downstream costs of requests made by executives and upper management. All leaders and managers must take extra care in what requests they give and commands they make, or risk wasting the resources they're chartered to direct. It's an important reminder for all of us at any level of leadership, and it only gets more important when face to face communication is replaced with more error-prone virtual methods.

But there's an equally important second part to that story. The employee involved was expecting an email from his leader with either a clear approval, or a request for more information. But what came across the wires was neither; it was a brief, vague statement that seemed to express disapproval without a clear indication of why.

Much of the work the email engendered, as a result, consisted of a team effort to figure out what the executive really meant. What wasn't good enough? What more was needed? How could they best present it? Second-guessing this leader's intentions and influencing him accordingly became much of the team's agenda. Doing the work took a distant back seat to guessing what the work actually was.

The error here was two-sided. The executive's poorly crafted email was half of the story, but the employee's response was the other half. Upon receipt of an unclear directive, an employee's first responsibility is to stop everything and say, "I don't understand what you mean."

Of course, taking such action is much easier said than done. Being placed in a relationship that makes someone the source of our livelihood -- like a boss, or a client -- creates a predictable dynamic for any of us. We become focused on fulfilling the person's requests, and loathe to display anything that might seem like the inability to do so. With very few exceptions, we want to be -- and to be perceived as -- fully capable. Statements like "I don't know what you mean," and "I can't do what you want," become terribly uncomfortable.

Of course, as I often remind participants in my classes, those statements are not nearly as uncomfortable as "I didn't understand what you meant," and "I didn't do what you wanted." In the past tense, such statements represent failures. In the present tense, they merely represent the clarifying of expectations: "Let me make sure we agree together on what I'm going to do next, so that I can do it for you."

If that doesn't make it any easier to question your boss, here's something that will: a history of people doing so. Relationships, as it turns out, are built on patterns. We learn to expect from each other what we're used to from our history and our surroundings. If you've always been one to ask clarifying questions, it's much easier to ask the next one. And, if everyone else in your peer group is always asking clarifying questions, it's much easier for you to ask your first one. So, all you have to do to make it easier to clarify and question with your boss, is to have already had a history of doing so.

This is Catch 22 at its finest. If it's easy, you'll do it, but it's only easy if you're already doing it. So, I can only suggest that both sides get started today.

Employees can begin with small, safe questions around commitments already made: "Just to clarify, I promised to deliver that report by Friday, and I will do so by the end of the day. Is that OK, or do you need it by 3 p.m.?" Getting your boss in the habit of clarifying needs when there's no debate or misunderstanding will make it easier to have such a conversation when things are more nebulous.

Managers can begin too, by inviting such questions: "I'll need at a minimum this information by Friday. Do you understand what I'm asking for, and do you believe it's an achievable request?" Opening the door for your employees to speak up when you think they already understand you will help enable them to speak up when they don't. You might also be surprised to learn that you're not as clear a communicator as you thought.

Of course, if this pattern of behavior isn't common in your workplace, you'll need to be careful about how you start it and how quickly you grow it. You certainly don't want to put unnecessary strain on such an important relationship as your relationship with your supervisors or employees. But, good relationships do grow and change, and if you're expecting to be in your current boss-employee relationship for a while, there's no reason not to try to nudge it toward the better.

And while I can imagine many objections -- "my boss won't go for it," "I don't have time to talk like this with my employees," and the ever-popular "my job sucks" (or variants thereof) -- I'm here to tell you that I've worked in and around many organizations where this behavioral practice is in place. It works, and it makes things work a whole lot better. People stop wasting energy trying to figure each other out, and instead get on with doing the work needed to make the enterprise succeed. It's not a bad thing to encourage.

Give it a try, starting as slowly and tentatively as you wish. You may be surprised at how much impact you can have.

And if you have any questions about how to get started, just remember, you can ask me anything.