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The Audacity to Challenge Your CEO

I still remember the meeting. Sitting at a conference table, watching a decision unfold that I knew was wrong. Not just misguided—wrong. The kind of decision that would hurt people whose names I knew, whose families depended on them, whose trust we'd earned.

I said nothing.

I still remember the meeting. Sitting at a conference table, watching a decision unfold that I knew was wrong. Not just misguided—wrong. The kind of decision that would hurt people whose names I knew, whose families depended on them, whose trust we'd earned.

I spoke up. I advocated for our people. I challenged. I spoke up again. I advocated for our people. I challenged.

Similar scenarios.

Two very different times in my career.

It took me a long time to learn that discomfort is temporary, but the consequences of our silence are not.

I was the kid who never spoke in class until college. An introvert who physically felt the weight of every eye in a room. When I started speaking at conferences, I genuinely wondered if I might pass out on stage.

Eventually, as I learned and started to challenge and change myself, I started caring more about the people counting on me than about my own comfort. I got comfortable with being uncomfortable, but within the boundaries that I needed to set for myself. I got braver. Not all of the time. But you don’t need to be brave all of the time. You just need to be brave for a few minutes at a time!

We talk a lot in HR about being strategic business partners, about having a seat at the table. (Which we should stop doing, that’s an awful phrase and we need to take that seat if it’s not given to us!) But having that seat does not matter if you are not willing to use that seat to say the hard things.

CEOs don't always see what's happening on the ground. We do. But managers see it first. They're closest to it.

As HR professionals, we coach managers to recognize what they're seeing and give them tools to address it. We create the systems and help foster a culture where it's safe for them to escalate. We see patterns across the organization that individual managers can't see from their vantage point. And when issues are systemic or beyond what managers can solve at their level, we bring it to the CEO.

That employee being overlooked because of unconscious bias? Their manager likely sees it. Have we coached them to recognize it? Have we helped foster a culture that made it safe to speak up? When they bring an issue to us, do we act? And if it's a pattern across multiple teams, are we taking it to leadership?

That policy that sounds good in the boardroom but will devastate the front line? Managers will be the first to tell us if we've built relationships where they trust us with the truth. Are we listening? Are we escalating their concerns?

We're not the only ones responsible. But we are responsible for creating the systems, learning, and fostering a culture that helps issues surface. And we are responsible for having the courage to take them where they need to go when managers can't solve them alone.

The audacity to challenge starts way before you need it. It starts with building trust and demonstrating value. Early on at The Granite Group, I spent time learning the business inside and out. Not HR - the actual business. How we went to market. What kept branch managers up at night. Their challenges, frustrations. The customers. The business software. I made it my mission to understand the business as well as I understood people.

Why? Because when I eventually needed to challenge a direction, I could do it from a place of credibility. I wasn't "the HR person" with an opinion. I was the member of the executive team leading the people function.

The relationship with your CEO needs to be real. You need to genuinely like, respect, and trust each other. (Or at least respect and trust!) That happens through consistent demonstration that you're there to help the business, the people, and to help them succeed, and that when you bring them something, it matters.

What does challenge look like? Real challenge looks like partnership. When we were drowning in paperwork at The Granite Group, I didn't complain. I came with a plan for how technology could solve it, what the ROI would be, and how it would free up time for what actually mattered.

Sometimes challenge looks like asking the question no one else is asking: "Have we thought about how this will land with our team?" or "What are we not seeing here?"

Sometimes it's being direct: "I'm concerned about this direction, and here's why.” followed by the impact you're seeing or anticipating.

And sometimes it's simply: "I disagree, and I think this could hurt people. Can we talk about alternatives?"

The first time I challenged a CEO decision, I had a hard time getting the words out. But I did it anyway, because the alternative was unacceptable.

The second time was slightly easier. The tenth time, easier still. Bravery is taken action even when you are afraid. And like any muscle, it gets stronger with use.

What You Can Do This Week:

Ready to start building this muscle? Here are some practical steps you can take right now:

Build the foundation:

• Schedule regular one-on-ones with your CEO if you don't have them. Even 30 minutes biweekly makes a difference.
• Share one business insight per week that has nothing to do with HR. Show you understand the whole picture.
• Ask your CEO: "What keeps you up at night?" Then listen. Really listen.

Practice in lower-stakes moments:

• In your next leadership meeting, ask one clarifying question that others might be thinking but not saying.
• Offer a different perspective on something small when the opportunity presents itself. Not to be contrary, but to add value.
• Notice how it feels. Notice that nothing terrible happens.

Prepare for the hard conversation:

• Write down the specific impact you're concerned about. Use names, numbers, concrete examples.
• Identify 2-3 alternative approaches. Never just bring the problem.
• Practice saying it out loud. Literally. In your car, to a trusted colleague, wherever. Hear your own voice saying the words.

Frame it as partnership:

• Start with: "I want to think this through with you" not "I think you're wrong."
• Use: "I'm seeing something that concerns me" or "I have a different perspective that might be useful."
• End with: "How can we approach this differently?"

After you speak up:

• Follow up in writing with the key points discussed and any agreed-upon next steps.
• Don't apologize for raising the issue. Thank them for hearing you out.
• If it didn't go well, debrief with a trusted peer. Learn. Try again.

Find your people:

• Join one HR community this month where real conversations happen (not just networking).
• Reach out to one HR leader you admire and ask them about a time they had to challenge up.
• Build your support system before you need it.

Start with one thing. Just one. Then next week, do one more.

If you're thinking "I'm not that person" or "I could never do that," I wasn't that person either.

I'm still an introvert who'd rather read than party. I still feel nerves before hard conversations. I still sometimes wonder if I should just keep quiet. I’m still autistic and often challenged in social situations, even more so amidst conflict.

However, I've learned that making things easier in the moment makes them harder in the long run. For the people counting on us. For the culture we're building. For the business we're growing.

You don't have to transform your personality. You don't have to become fearless. You just have to care enough to be uncomfortable for five minutes. And then five more.

The people you serve deserve someone in that room who will speak up for them. Who will bring the perspective others miss. Who will be brave enough to say what needs saying.

They deserve you, with all your hesitation and fear, but also with all your insight and care.

The audacity to challenge your CEO is about recognizing that silence has a cost you're no longer willing to pay.

So take a breath. Trust the relationships you've built. Remember why this matters. And speak up.

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COMMUNITY

One of the most interesting things I've had the opportunity to do over the past year (and I've been fortunate to have a lot of interesting things to do!) is attend some, and co-host some, sponsored dinners with wonderful HR tech partners and people leaders.

When Emma Biskupiak reached out and asked me to attend the CandorIQ people leader dinner in Boston, I was thrilled to go - especially because I was at a client that day less than 20 miles away! (CandorIQ is a unified platform to streamline compensation, headcount planning, and retention for people-focused organizations.)

It was a fun evening with great food and better company, and I got to spend time with people I really like, in a much more intimate setting than a conference.

What a beautiful way to build community.

I'm already looking forward to the next one! Want to learn more about CandorIQ, and when they are coming to Boston or your city again? Click below!

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CandorIQ

Connect with me on LinkedIn here!

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COFFEE

It's not coffee, but this is my view every day when I'm working from home.

And yes, every day it scares me, either this skeleton or the unpictured one sitting at the table outside!

Our kids are older. We have three houses in our neighborhood. No one really cares if we decorate or not. But it's fun, and adds a little bright spot (and sometimes a brief frightening moment to the day.)

I can't stop writing this without sharing some coffee stuff, though. What we're drinking lately? Mocha Joe's Cameroon Espresso Roast. I ran out mid-grind today (!!!!) and fortunately Dave was on his way through Vermont, the only place you can find this VT-based coffee. So we're back to where we should be!

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Have a great week ahead!

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ETC....

My business is constantly evolving to meet the needs of my clients and future clients (and stay tuned for a big announcement or two coming up on that!)

Everything I do is custom. Which is a lot, but it is the right thing to do for my clients who trust me to deliver a keynote, my advisory and fractional clients, and those that hire me to deliver a workshop.

I'm developing some workshops, both through Tracie Sponenberg LLC and with partners, focusing on HR Transformation in small and mid-size companies, AI in HR in small and mid-sized manufacturers and distributors.

Is this something you'd like to learn more about? I'd love to chat as we build, so we can make sure that the products are amazing. Reply to this email and we'll set up a time.

(**My custom workshops are limited but available now to book for Q1 2026**)

Want to chat more about your HR challenges? Want to submit a question that's on your mind? Click the button below!

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Questions and Feedback

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Until next time....... thanks for reading!

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Tracie

My Partner Spotlight ​ WorkStory makes the review process easy - and while maybe not fun, much more human - through using AI. I'm thrilled to continue to partner with WorkStory! Click on their logo to find out more. You'll also find part one of my three part series on performance management there!

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