If you’re a new CMO and you’re not making people a little uncomfortable, you’re not doing your job.

You weren’t hired to maintain the status quo. You were hired because the status quo was broken. You were hired to be a change agent, a disruptor, a challenger.

That truth isn’t just for CMOs. It’s for anyone in leadership. And in the current housing market—where affordability pressures, consumer skepticism, and operational strain are daily realities—playing it safe isn’t leadership. It’s [capitulation to] slow decline.

Unpopular but Necessary

When I first joined Taylor Morrison, one of my earliest moves was not popular. Our field marketing teams were used to local creativity: one-off logos, clever taglines, campaigns that had personality but no cohesion.

I had to shut that down.

We centralized brand and strategy. We traded local flair for a consistent national identity that could actually scale. At the time, it stung. People felt their creativity was being clipped. But what we gained was a recognizable, trusted, enduring brand—one strong enough to win “America’s Most Trusted® Home Builder” for 10 years straight.

Sometimes leadership means being disliked in the moment to be respected in the long run. And if you’re waiting to make every change with unanimous applause, you’re not really leading.

Courageous Conversations That Count

Growth happens in conversations that feel uncomfortable. These five, in particular, are non-negotiable for any marketing leader:

1. The “What’s Broken?” Talk with Sales. Skip the glossy dashboards. Ask directly: What’s the biggest obstacle you face every day? Then shut up and listen.
2. The “How Do We Really Make Money?” Talk with Finance. Sit with your CFO. Walk the P&L. Understand margins, costs, and levers. Until you can connect campaigns to dollars, you’ll be treated as a cost center, not a business driver.
3. The “What Keeps You Up at Night?” Talk with the CEO. Hard question, harder answers. But it’s the only way to align your work with what truly matters at the top.
4. The “What’s Our #1 Complaint?” Talk with Customer Service. Every company has one complaint that shows up again and again. Solve it, and you don’t just improve the experience—you earn a story worth telling.
5. The “What’s My Blind Spot?” Talk with Your Team. This one stings. Ask, What’s one behavior I need to change to be a better boss? You’ll hear the truth if you’re ready for it.

Each conversation is awkward. Every one of them is critical. And worth their weight in gold.

Carrying the Boulder

Discomfort doesn’t just show up in tough conversations. Sometimes it’s the uphill grind of pushing an idea nobody else believes in — until they do.

For five years, I pushed to create an online home reservation system at Taylor Morrison. For five years, the answer was “no.” Nobody thought consumers would ever buy homes that way.

Today? That system converts at 60%. It drives higher prices, more option revenue, and less reliance on brokers. The same skeptics now celebrate it as a game-changing innovation.

But the truth is: if I had stopped at “no,” it never would have happened. Carrying that boulder felt lonely, exhausting, and frankly, a little crazy. But the view from the top proved worth it.

Discomfort as Strategy

The instinct in tough times—like the one our industry is living through right now—is to retreat to comfort. Stick with what we know. Avoid risks. Wait it out.

That’s a trap.

The brands and businesses that survive this moment will be the ones willing to lean into discomfort:

• Making bold bets while competitors freeze.
• Challenging operational habits that no longer serve the customer.
• Owning up when promises don’t match reality—and using that gap to raise the bar.

Comfort is not a growth strategy. It’s a stall.

The Call for Courage

Here’s an uncomfortable truth: leadership isn’t about creating harmony in every room you walk into. It’s about moving the business forward—even when it rattles people.

Courage looks different depending on your role. For some, it’s saying “no” to another low-impact marketing request to protect your team from burnout. For others, it’s pushing a digital initiative that seems impossible until it isn’t. For CEOs, it’s acknowledging that what worked before may not work now.

The common thread? Courage creates progress. Discomfort signals you’re in the right place.

Closing the Trust Vault

Trust doesn’t come from playing it safe. Trust is built when leaders push through resistance to deliver something stronger than what they inherited.

So, the next time you feel that knot in your stomach before saying the hard thing, or when the room goes quiet after you push for a bold change—don’t mistake it for failure.

That’s the evidence of leadership.

And if you’re not feeling at least a little uncomfortable? You’re probably not doing your job.