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

question the boss

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:

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.

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.

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.

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.

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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About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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  1. Jennifer

    Long time reader, first time commenter. You know, the quiet person.

    I would challenge your assessment of a quiet person. Often, they know far more than you are giving them credit for here. They have observed the interplay between people in the meeting, the silent tells, and the underlying story that’s not being spoken–the elephant no one sees or is willing to admit is there. They may need time to digest what is being said and put two and two together to come up with 5 (the big idea).

    Every performance review I’ve had brings up “you need to speak up more in meetings”. My unspoken response is “you need to shut up more in meetings and actually listen”. I don’t disagree with your overall premise, and your suggestions of increasing visibility and participation are spot on. I might tweak “share” a bit to include things like:

    1) Get a “buddy” to help you out of your shell. Ask them pre-meeting to give you an opening by asking you a question that prompts you to share your knowledge. Sometimes it’s easier to respond to a question that to initiate.

    2) Be a buddy without being asked to be one. This could be done different ways. Ask the person in the meeting a question or have a 1×1 with them and solicit their feedback privately. Then you can be their champion in the meeting “I was talking to Jane yesterday at lunch and she had a great idea…” This may help to build confidence that the quiet one has valuable knowledge to share and eventually they will be more confident in speaking up on their own.

    My overall point is that you shouldn’t dismiss the quiet person as being disengaged. For sure that’s sometimes true, but you might be surprised how deep still waters run. I highly recommend the book Quiet by Susan Cain for more insights.

    Love your posts and what you are doing with your company. Keeping my eye on it!

  2. Roland

    this article is a nice attempt but there are still a lot of unanswered questions about how to deal with problem people who pretend to be talking about work but it’s really about their personal problems.

  3. Danielle

    I would agree with Jennifer that ‘quiet waters run deep’ – the quiet ones often are observing every nuance of every communication spoken or unspoken and has chosen to stay quiet. There can be many reasons for this but – in my experience – the primary reason is that they feel their opinion and experience is not valued. Perhaps peers or management have talked over them in the past or made comments that invalidated their thoughts and ideas. If you want a quiet person to speak up, you need to treat them (and all others) with a focused respect that they deserve. This person was hired for a reason – hopefully that reason was to be more than a cog in a grind. When people speak up, if you notice others speaking over them or not respecting their time and thoughts/ideas, you should (as a good leader) ensure that the initial speaker has the chance to be heard and considered.


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