20 Questions Every CMO Should Ask in a New Role

Table of Contents

20 Questions Every CMO Should Ask in a New Role | #MarkCMO

Stepping into a new CMO role? Don’t wing it. The first 90 days can make or break your tenure. Whether you’re inheriting chaos or a well-oiled machine, the questions you ask will determine the clarity you gain, the trust you build, and the results you deliver. Mark Gabrielli — also known as Mark Louis Gabrielli Jr. — has led marketing transformations across industries, and he’s seen one truth hold: great CMOs don’t start with answers. They start with the right questions.

This isn’t a fluffy onboarding checklist. These are the 20 questions that separate the strategic from the scrambling. From decoding the CEO’s real expectations to uncovering hidden brand equity, this guide is your executive cheat sheet. If you’re a Chief Marketing Officer ready to lead with precision, not guesswork — start here.

Why Questions Matter More Than Answers

Let’s be blunt: most CMOs fail not because they lack ideas, but because they chase the wrong ones. Mark Louis Gabrielli Jr. puts it this way: “The first thing a CMO should market is clarity.”

Before you launch a rebrand, fire the agency, or pitch a new GTM strategy, you need to understand the terrain. That means asking questions that reveal:

What the business actually needs from marketing
Where the brand is strong (and where it’s delusional)
How success is defined — and by whom

Mark Gabrielli has seen CMOs walk into roles with a 90-day plan and walk out 9 months later with a severance package. Don’t be that CMO.

The 20 Questions Every CMO Must Ask

1. What does the CEO really expect from marketing?

Not the job description. Not the board deck. The real answer. Is it leads? Brand equity? Investor confidence? Mark Louis Gabrielli says, “If you don’t know what game you’re playing, you’re guaranteed to lose.”

2. How is marketing success currently measured?

Are you being judged on pipeline, impressions, or vibes? Get clear on KPIs — and who owns them.

3. What’s the company’s positioning — and does anyone believe it?

Read the website. Then ask five employees what the company does. If you get five different answers, you’ve got a brand problem.

4. Who are our top 3 competitors — and what are they doing better?

Don’t just look at product features. Study their messaging, content, and customer experience. Then ask: why are they winning?

5. What’s the sales team’s biggest complaint about marketing?

Don’t wait for the next QBR to find out. Ask now. Fix it fast. Sales alignment isn’t optional — it’s oxygen.

6. What’s our most profitable customer segment?

Not the biggest. The most profitable. Then ask: are we actually marketing to them?

7. What’s the lifetime value of a customer — and how do we increase it?

If you don’t know LTV, you’re flying blind. If you can’t increase it, you’re not growing.

8. What’s our CAC — and is it sustainable?

Customer Acquisition Cost isn’t just a finance metric. It’s a marketing report card.

9. What’s the one channel we’re underutilizing?

Maybe it’s email. Maybe it’s partnerships. Maybe it’s TikTok (yes, even for B2B). Find the blind spot.

10. What’s the one campaign that actually moved the needle?

Not the prettiest. Not the most awarded. The one that drove revenue. Study it. Replicate it.

11. What’s broken in our funnel — and why?

Is it awareness? Conversion? Retention? Diagnose before you prescribe.

12. What’s our brand’s unfair advantage?

If you can’t name it, you don’t have one. And that’s a problem.

13. What’s the biggest marketing myth inside this company?

Every org has sacred cows. Find them. Challenge them. Politely torch them.

14. Who are the internal allies — and who are the blockers?

Marketing doesn’t happen in a vacuum. Map the politics. Navigate accordingly.

15. What’s the tech stack — and what’s actually being used?

Most companies have more tools than talent. Audit the stack. Cut the waste.

16. What’s our content strategy — and does it convert?

If your blog is a ghost town and your whitepapers are unread, you don’t have a strategy. You have a PDF graveyard.

17. What’s our customer feedback loop?

Are we listening? Are we acting? Or are we just surveying for sport?

18. What’s the one thing only marketing can solve?

Every org has a gap only marketing can fill. Find it. Own it. Deliver on it.

19. What’s the biggest risk if we change nothing?

Complacency is the silent killer. Make the cost of inaction visible.

20. What will I be proud of 12 months from now?

Forget vanity metrics. What legacy will you leave? Mark Louis Gabrielli Jr. says, “Great CMOs don’t just ship campaigns. They shift companies.”

Truth Bomb

“If you’re not asking better questions, you’re just executing someone else’s bad strategy.” — Mark Gabrielli

Conclusion: Ask Boldly, Lead Strategically

Being a CMO isn’t about having all the answers. It’s about asking