How to Tell Your Boss Off . . . Respectfully

Not every workplace makes it safe to speak up. I acknowledge this is written with the privilege of working with leaders who are open to feedback. These tips can help your feedback land well with even the prickliest of bosses.

Learning how to assert yourself can be crucial, especially when it’s time to tell your boss off…respectfully.

How often have you been in this position? A brand-new initiative comes down from the desks of leadership, and upon reading it you realize that it’s detached from reality.

• A new “top priority” piled on top of existing ones.
• A demand to get more done with fewer hours and fewer resources than ever before.

Often, these plans may not seem all that outrageous. Heck, on paper they can look perfectly logical – and I guarantee they were carefully thought through, likely balancing a bunch of competing priorities before they ever reached your desk.

But for the folks responsible for carrying them out, it can feel like juggling too many bowling pins . . . and someone just threw in a chainsaw.

Now, if you’re reading this and you’re the decision-maker, this might help you see the other side of the coin. But if you’re the juggler, you need a way to speak up. Learn how to tell you boss off with respect.

The good news: There’s an art to it. The art of managing up. One that can actually earn you more respect.

Burnout often points to a breakdown in communication. Leaders need to be willing to listen, and employees need to be able to articulate their workload constraints.

Rule 1: Stay calm under pressure

If you’re buried in work and burnout is creeping in, snapping is easy. But being reactive rarely helps – it’s usually your nervous system sounding the alarm after being pushed too far.

 If something sets you off, try taking a quick walk around the block before replying to that email. A short pause can reset your brain, and that moment of calm might be exactly what you need to respond with clarity instead of frustration.

Calmly explaining timelines, competing priorities, and pain points gives your leader something tangible to work with, whether that means reprioritizing, delegating, or removing tasks altogether.

However, if you lash out, it can throw off your leader’s emotional balance, triggering unintentional defensiveness that only makes things worse. Think of it like a snowball effect, except it’s rolling downhill toward hell.

Burnout often points to a breakdown in communication. Leaders need to be willing to listen, and employees need to be able to articulate their workload constraints.

Rule 2: Share challenges collaboratively

It can be frustrating for leaders to hear “This is impossible,” but remember, they often don’t have the same perspective you do.

They’re not seeing your systems or constraints firsthand. If you’re struggling with an outdated computer that takes forever to pull reports, vendors who are slow to respond, or a staffing shortage, those challenges might not be on their radar.

Executives are often operating within their own realities, making decisions based on broad statistics, meetings you weren’t a part of, and pressures you may not be aware of. That could mean a sudden pivot due to market volatility or fallout from a particularly spicy board meeting.

This is where you come in. Help them grasp the true weight of a new initiative by showing its impact clearly and collaboratively.

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One of my favorite recommendations: Ask for help.

Leaders often rise through the ranks either by sheer drive and ruthless efficiency, or more optimistically, through a genuine passion for helping their teams succeed and grow. Think about how it feels when someone asks you for help – there’s usually a sense of respect for their transparency, empathy for what they’re facing, and pride in being able to support them. Maybe you even feel good on the drive home that day.

Getting help from your leaders can be a fast pass to removing roadblocks. Straight from the source, you can learn what can be postponed and what absolutely needs attention now. This often leads to more strategic use of the scissors, cutting out tasks that are no longer mission critical.

And remember, not every pushback needs to be a big conversation. Sometimes it’s just a quick check-in: “Just confirming, should this replace Project A or run alongside it?”

Getting help from your leaders can be a fast pass to removing roadblocks.

Rule 3: Help shape the fix

Here’s the magic formula – the tip above all tips that can take you from being just the bearer of bad news to standing out among your peers: Don’t stop at pointing out problems. That part’s easy, anyone can do it. Bring solutions to the table. Suggest what could be postponed, where resources might be reallocated, or propose a timeline adjustment that allows for a smoother, more realistic path forward.

When you offer solutions, your perspective gets woven into the final plan rather than leaving leaders to solve it alone, which risks another out-of-touch decision. This is the art of managing up.

Put yourself in your leader’s shoes. How would you want to be approached? Would you prefer a problem dropped in your lap, or someone showing up with the start of a solution?

Working together to solve the problem builds trust and strengthens rapport with your leadership team.

As a leader, remember this important fact: When people feel safe flagging issues, organizations move faster and more efficiently. You need a full picture of how your business actually runs before you can crank up the speed.

Your team must be able to speak up, especially when major organizational moves are being plotted. But they also need the emotional intelligence and communication skills to do it effectively. And here’s an important note: Be gentle with your teams if they’re stressed, it means they care. If they lash out, it’s often a symptom of a long-overlooked issue – something you should have been aware of long ago.

So, the next time you’re tossed a chainsaw, ask if it’s okay to put down the bowling pins, or if another juggler can be added to the act.

Above all else, stay calm: The last thing we need is angry jugglers with power tools.

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