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Writer's pictureMaya Grossman

How to Handle Pushback With Grace (and turn it into progress)

I learned how to handle pushback the hard way at Microsoft.


My manager had just asked me to find an agency to help grow our online presence, and I threw myself into the task. I researched extensively, compared options, and found a solution that would significantly save costs while meeting all our requirements.


I presented my case, confident in my recommendation.


The response? "No." My manager decided to go with a much more expensive option.


I was confused. Frustrated. And I did exactly what you shouldn't do - I hit reply all on the email thread and basically stated that going with the expensive agency would be a mistake, overriding my manager's decision in front of everyone.


Yeah... that didn't end well.

The Reality of Executive Pushback


Here's what I wish I had known then: pushback isn't personal (for the most part). It's not about you, and it's definitely not about destroying your ideas.


When executives push back, they're usually trying to protect something - their teams, their budgets, their objectives. They're not out to get you. They're looking out for their interests.


Think about it.


Every time you present something significant, you're essentially asking people to change something about their world.


Their hesitation isn't resistance - it's due diligence.


Understanding this distinction helped me come up with a much better way to handle pushback, and actually turn it into progress.


That's what I want to share with you today.




Handling Pushback Like a Pro (To Grow Your Executive Presence)

Remember my reply-all mistake at Microsoft?


That single moment did more than just create an awkward situation. It sent a clear message about my executive presence - and not the message I wanted to send.


When you don't handle pushback well, you're telling senior leaders:


  • You might not be ready for executive discussions

  • You can't manage complex stakeholder relationships

  • You let emotions drive your decisions

  • You're not seeing the bigger picture


If you are the kind of person who gets emotional quickly (I am!), you have to practice staying calm under pressure.


What usually helps is pattern interruption: breaking your thought pattern to stop the automatic reaction and give you a chance to keep your composure.


Keep a water bottle handy and take a sip before responding.

Take a few deep breaths or count to three (stupid but it works), and remember - the goal isn't to win an argument. It's to find the best solution together.


When you learn how to react calmly, understand the underlying questions, and manage the pushback with graceful assertiveness, even if you don’t get a ‘yes’ you earn respect.


If you want to handle pushback like a pro, use these three tactics I've seen work time and time again:



1. Ask Clarifying Questions


When you do face pushback, your first job isn't to defend your idea - it's to understand what's really being said.


Your goal isn't just to hear the words - it's to understand what's not being said.

Is the pushback about budget really about control? Is the concern about the timeline actually about team burnout?


When the CFO says "What's the ROI?" they might really be asking "How will this affect my team's priorities?"


When the Head of Engineering questions the timeline, they might be worried about overworking their team.


This is why clarifying questions are so powerful.


Try this:


"I want to make sure I understand your perspective fully. You mentioned resource concerns. Could you help me understand which teams would be most impacted specifically?"


"Just to clarify - is the main concern about timing, resources, or both?"


These questions aren't just polite gestures. They give you the intelligence you need to find real solutions. Plus, when people feel truly heard, they're more likely to work with you toward a solution.


2. Propose Hypotheticals


This is where you get creative. Instead of pushing your original idea harder, test potential adjustments.


"If we could implement this without pulling resources from your Q4 initiatives, would that address your main concern?"


Think of it as trying on different solutions for different sizes. You're not committing - you're exploring what might work.


This gives stakeholders an easy way to guide you toward an acceptable solution without having to oppose your idea entirely.



3. Ask for Their Advice


This is my favorite tactic, and here's why: it transforms critics into collaborators.


Instead of defending your position, ask them to show you how to make it work:


"Given your concerns about resources, how would you approach this project differently? What adjustments would make this work better for your team while still helping us achieve our core objectives?"


When you ask for advice, something magical happens.


People stop focusing on why your idea won't work and start thinking about how it could work.


They become invested in finding a solution.



Putting It All Together


If I could go back, I would have handled that pushback completely differently.


Instead of getting defensive and hitting reply all, I would have asked to understand why the more expensive agency was preferred.

Maybe there were factors I hadn't considered.

Maybe there were concerns about the cheaper option I could have addressed.

Maybe my manager was under pressure and had to say yes to keep his leadership happy (which I later found out was the case).


I might have proposed a hypothetical: "If we could get the same level of service from the less expensive agency, would that be worth exploring?"


And I should have talked to my manager privately, instead of reacting emotionally and taking it out on the entire executive team.


The point isn't that I would have definitely gotten my way.

The point is that I would have turned a bad confrontation into a collaboration.



Your Next Steps

Next time you face pushback on an idea, remember: pushback isn't personal. It's an invitation to collaborate on a better solution.


Before your next big presentation or proposal:


  • Prepare your clarifying questions

  • Think through potential hypotheticals

  • Be ready to ask for advice

I believe in you, and I’m rooting for you.

Maya ❤️

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