CMO Leadership Lessons That Took Too Long to Learn

We recently asked a group of CMO’s a simple question:

"What's one lesson about leading people that took you too long to learn — and what did it cost you before you learned it?"

The conversation became a masterclass in leadership scars, hard-earned wisdom, and the hidden costs of waiting too long to act. Here are the 10 lessons that emerged.

1. Delaying people decisions is rarely kindness; more often, it’s avoidance.

Multiple leaders admitted they knew someone wasn't in the right role long before they acted. As one CMO put it:

"Never compromise on talent fit and move quickly."

Another offered an even sharper version:

"The second you have to ask yourself if this person should go, it's already too late."

For leaders who care about people, there is always a ‘what if I’m wrong, or what if I can help them,’ but the lesson is that it does not usually come to fruition, and in fact it leads to loss of team trust, reduced energy, cultural drag, and leaders spending disproportionate amounts of time compensating for a poor fit.

2. An empty seat usually creates less damage than the wrong person in it.

The pressure to fill vacancies creates urgency. Urgency creates mistakes.  One leader shared perhaps the most memorable lesson of the day:

"Better a hole than an asshole."

The point wasn't about personality. It was about the damage that happens when leaders hire quickly to solve a short-term capacity problem and create a long-term people problem instead.

3. Evolving from doing the work to enabling others to do it.

Several leaders described the painful transition from individual contributor to executive leader. One recalled telling his boss he was drowning under the workload. The response?

"Are your people saying the same thing to you?  You have people. Use your people."

Too many high performers get promoted because they're exceptional at doing the work. Then they struggle because they continue doing everyone's work. Learning how to delegate and empower become critical skills.

4. Don't let your C-players consume the attention your A-players deserve.

One participant shared a counterintuitive insight.

For years, she invested most of her coaching energy in underperformers because the others were strong and the least of her worries. A mentor challenged her to spend more time with the people who represented the future of the organization.  As she reflected:

"The amount of time it takes to get a 3 to become a 5 versus an 8 to become a 10 is totally backwards."

The result? Higher engagement, stronger succession benches, and dramatically better returns on leadership time.

5. Feedback delayed is feedback denied

Many leaders admitted that early in their careers they avoided difficult conversations. Others delayed developmental feedback because they wanted to find the perfect words. One leader now advocates for immediate coaching moments:

"Fast follow-ups."

Another described it as:

"Curbside coaching."

The principle is simple. Great feedback loses value when it sits in your notebook for three weeks.

6. Clarity is kinder than patience

One of the most powerful reflections came from a leader who realized she was mistaking patience for support. She wanted people to succeed. She believed they'd eventually get there. What she failed to provide was absolute clarity on expectations and performance gaps. Her conclusion:

"Being clear is often kinder than being patient."

The moment she shifted from hoping people would figure it out to explicitly telling them where they stood, everything improved — for individuals, the team, and the business.

7. Invest in the Human, not just the employee

COVID changed leadership for many people. One executive admitted he had previously approached leadership almost entirely through a performance lens.  Remote work forced something different. Daily check-ins became personal conversations; Relationships deepened; Trust increased; Performance improved.  In his words:

"I've since realized how much more you can get out of people, how much more joy it brings me as a manager and the overall connectedness of a team."

8. Never project your ambitions onto someone else's career.

One of the most painful stories came from a leader who lost a highly valued employee. Everyone assumed this person wanted a promotion and greater responsibility. She didn't. By the time the truth emerged, it was too late. The lesson?

"Always consider the no."

Not everyone defines success the same way. Not everyone wants the next rung on the ladder. Not everyone is motivated by title, status, or money. Are you clear on where your people want to go?

9. Believe people when they show you who they are

Several leaders reflected on giving too many second chances. They wanted to see the best in people. They rationalized behaviour. They hoped things would improve. Eventually they realized the cost wasn't only personal stress. It was team culture. One executive summarized it simply:

"When people show you who they are, believe them."

Because teams are always watching. They notice what leaders tolerate. They notice who gets away with behaviour that damages the culture.

10. Culture-add beats Culture-fit

One leader reflected on hiring a team full of people who looked and thought like her – ambitious, assertive, competitive. It seemed like a strength until it wasn't.  The result was internal friction, organizational conflict, and a team lacking the complementary strengths needed to succeed.

The insight?

High-performing teams aren't built through similarity.  They're built through complementarity. As the group discussed, the goal isn't culture fit.  It's values fit and culture add.

The Bigger Lesson – The Consistency of the Cost

Whether the issue was hiring, delegation, feedback, coaching, team design, performance management, or career development, leaders described the same consequences:

• Lost time

• Lost trust

• Lost energy

• Lost culture

  
  

The hard truth of leadership is that while there are always exceptions, most people problems don't get better with time. They get more costly. Lucky for the marketing community, this is a representation of CMOs who put people first and are trying to do the right thing for their people, their culture, and their business.