How to Push Back on the Boss Like a Boss

Jessica Gardiner
say no to a difficult boss like a boss

Being able to say “no” and push back when you are your boss’s right-hand woman (or man!), responsible for making sure everything is in order and that their workflow is seamless, can be challenging to say the least – no one enjoys it. At one point in my career, I felt that saying ‘no’ equalled failing and that I was being unprofessional because of it.

If anything, saying no in the right circumstances can demonstrate that you understand the importance of prioritising and sticking to set deadlines, an important quality in any organisation.

If you feel the need to push back on a task and say no, make sure you have considered the below points to make sure you are doing so, like a boss!

HAVE A VALID REASON

Make sure you have a valid reason why you are saying no rather than just not wanting to do the task being asked of you.

You need to make sure you can express this reason clearly and confidently as only a valid reason is likely to be taken seriously. 

For example, let’s say your boss asks you to work late on a Friday evening to prep for a Monday meeting but you have plans with your family that you cannot change. Explain that you understand the importance of the meeting but also need to make time for your family. An understanding boss will be likely to then at least consider your other commitments, which may lead to the result you want, as opposed to keeping quiet, which inevitably will not.

Offer an alternative

If you push back without an alternative option readily available, how will the original task be managed?

As administrative professionals, we are meant to help our bosses limit and streamline their workload so they can focus on the important things, so not providing a solution will not be well received; make sure you have an alternative solution ready. 

Using the above example again, an alternative could be that you offer to go in early on the Monday before the meeting, so that you can still prep before the meeting starts.

You still get to spend time with your family, and your boss still gets the help they need to prep. Simple!

If it’s a workload issue, prove it.

Maybe you are pushing back because of your workload. It could be possible that you support more than one exec, or you are working on a big project. 

Show your boss what you are working on at the time in the form of a progress report or a simple list, making sure to also include deadlines. If your boss then decides that what they are asking of you is more important than another task they have set you, they can let you know and you can amend your priorities. 

This is also a great way to remind them of how awesome you are by managing multiple tasks, all of which are to make their lives easier!

Be firm and to the point (but avoid a power struggle!)

It is important to not beat around the bush when pushing back on a task. Be firm and explain why you are saying no and offer your alternative, both of which you would have established by this point. 

Do remember who is actually the boss and make sure they know that you are aware that they make the decisions. 

You could use phrases like “I appreciate how important this task is and that ultimately the decision is in your hands” to avoid any power struggle. Be sure to end your response with a clear closing statement like “thank you in advance for your understanding” preventing the likelihood of push back from your boss.

Pushing back and saying no is something that none of us enjoy and it doesn’t come naturally, so really understanding why you are saying no and how you will ensure the task is still completed well is critical.

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