How to Question Your Boss (and Be Loved for Being Obnoxious)

Rude is not always loud. Yes, the person who speaks over everybody in a meeting is a bit obnoxious. But the person fading into the corner of the room can be even worse. No curiosity. No clarity. Nothing bold. Quietly letting the world and the work pass them by.

This clammed-up person is not being rude on purpose, of course. Like most people, they are just trying to be nice and get along.

But the opposite is true. The person who hides in comfortable silence is being cruel — by not asking tough questions when tough questions need to be asked. (Which is almost every day.)

Being quiet is a survival tactic — especially in large companies. Most people do not speak up because it keeps them safe and they are unsure of what to say. They do not know what to say because leadership teams do not have a clear vision and, if they do, no one knows what it is. That makes it hard to evaluate new ideas. So people just nod along, confusion abounds.

If the entire organization is muddling with confusion, the person who acknowledges the lack of understanding or frustration may as well paint a target on their own back. Who are they to question a decision or strike back against the status quo?

But consider that if you feel perplexed, the whole team probably does too. If everyone operates without understanding the big picture, very little of value gets done. So if you are a person of ambition and integrity, you need to be more obnoxious at work. In a productive way, of course. Recharge your curiosity and begin enumerating your questions.

Get analytical. Trust your ability to know when things do not add up, then say so.

Be frank. This might feel uncomfortable at first. And you do not want to come across as impudent. But you can ask “why” with respect — no need to be harsh or confrontational. Your co-workers will actually appreciate you for this professional “rudeness.”

It is possible to engage more fully in your work, ultimately becoming a better teammate. Here are five ways to get started:

Understand No task or action happens in isolation. You need to get a firm grasp on key strategic concepts, especially if they are related to big new programs. It would be wise to ask what has changed (for example, with your market or customer), how your company is changing course, and what part you have to play in that.

Listen You do not have to ask probing questions right away. Absorb as much knowledge and information as you can about everything related to your work. Careful observation will often reveal the gaps in reasoning. Make sure you understand all of the assumptions that have gone into what is being decreed before presenting your own thoughts. Why is someone recommending what they are recommending? Think about what their role is and how they see your input. Take into account both the external and internal forces that went into their guidance or request.

Connect Try to connect what is being proposed to any goals that have been presented. Can any ties be made? Is there a match? Remember that it is okay to be skeptical of requests that are not strategically aligned. And if there is no strategy, ask what outcomes are expected of the work and if that work will have the biggest impact on the business.

Think There is never just one solution to a problem. Question the recommended approach — even if it was your own idea. Hone your strategic thinking by contemplating alternatives and the advantages and disadvantages of each. You should be able to clearly explain the idea in a sentence or two and list the three benefits and challenges of the various approaches.

Share Give teammates access to your knowledge and expertise. Do this easily and freely, with no expectations that info will be shared with you in return. Speak up with a new recommendation if you believe it can help the team complete its goals more effectively or efficiently.

Be aware of what silence costs. It perpetuates a facade of agreement that is almost surely hurting the organization and the team.

It stunts your own growth. And it is keeping you from being fully engaged. Instead, be the one known for critical thinking and tough questions. Put the growth of your organization and yourself ahead of any nervousness or fear of what the reaction will be. Question with respect and kindness, but question nonetheless. Your team and company need you to.

Some may call it obnoxious — but I know your co-workers will love you for it.

What is the most important question you have asked at work?

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