Managing Up in the Moment

Whether your boss is brilliant or a bit of a nightmare, there will always be times when we need to manage up.

In this episode of The Leader’s Kitbag, I’m sharing three actionable tips for managing up, especially when you need to push back on unachievable demands without damaging relationships or trust.

In this episode, you’ll learn:

• Why challenging upwards early and respectfully helps maintain credibility
• How to clarify ambiguous requests with sharp, specific questions
• How to explain trade-offs and get clarity around priorities

This episode is all about being proactive, courageous, and clear, even when you’re feeling squeezed.

Managing up isn’t about defiance; it’s about ensuring your team can do their best work without burnout or confusion.

If you’ve ever had to “speak truth to power” or felt stuck between a rock and a hard place, this one’s for you.

Podcast Transcript: Managing Up – How to Push Back With Respect

Regardless of whether you have an amazing boss or a truly difficult one, there will always be times when we need to challenge upwards, particularly when the demands being placed on you and your team are simply unachievable.

That’s exactly what we’re diving into in today’s episode of The Leaders Kit Bag.

Before we get into the practical tips, here’s a quick reminder of why appreciation at work matters.

A study by the University of California, Berkeley, found that when people feel appreciated by their manager, not just for what they do, but for who they are, productivity increases by around 43%.

That’s huge.

What leader wouldn’t want that kind of uplift in performance?

Now let’s get to the heart of today’s content: how to challenge upwards when you’re under pressure or need to speak truth to power.

Here are three strategies that will help you do that with impact and respect.

1. Challenge early, and do it respectfully.

If the workload or demands aren’t realistic, it’s far better to raise the flag early than to surprise your boss with delays later on.

You can frame it constructively with a simple, assertive statement like:

“With our current capacity, this may not all be achievable. Can we please discuss some options?”

It’s direct and respectful, and it invites a solution-focused conversation.

2. Clarify ambiguity with precision.

When you’re unclear about a task or priority, that confusion only multiplies when you try to delegate.

It’s on us as leaders to seek clarity, even if our boss is vague.

Ask questions like:

• “When you say ‘fix it’, what exactly do you mean?”

• “Do you mean by the end of the calendar year or the financial year?”

Getting specific helps you deliver first time and reduces frustration on both sides.

Because let’s face it, if something goes wrong, even when the original brief was unclear, we’re usually the ones picking up the pieces.

3. Explain the trade-offs and seek prioritisation.

When workloads clash or deadlines pile up, ask your boss to help you and your team prioritise. For example:

• “Given our current capacity, can you help us clarify what we must prioritise, and therefore what we can safely deprioritise?”

You could also ask:

• “To deliver this project to the standard you’re asking for, can you help identify which other project’s scope or quality can be reduced to make that possible?”

This approach keeps you solution-oriented while encouraging your boss to own the reality of what’s feasible.

Want More Insights?

So there you have it, three practical tips for pushing back when you need to respond reactively to your boss, manage up, or speak truth to power.

If you’re finding value in The Leaders Kit Bag,  subscribe to the Leaders Kit Bag email for more leadership tips and advice to help you become the best leader you can possibly be.

Until next time, look after yourself and those you’ve got the privilege and responsibility to lead.

Lead on.