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Why Some Leaders Never Get the Marketing Team They Want

Aaron Cullers

Jun 15, 2026

*Cue the Spider-Man point gif*

One of the more uncomfortable truths I see is when leaders get visibly or actively frustrated by outcomes they are actively creating. It’s just… you know… super awkward.

 

Marketing? No exception.

 

Spend enough time around executive teams and you'll hear some version of the same complaints:

 

"We need marketing to be more… strategic."

"We need marketing to be more… proactive."

"We need marketing to think like business leaders."

"We need marketing to drive growth."

 

If and of themselves, these are expectations that fall solidly in the reasonable and important camp. The question that’s worth asking, though, isn't whether marketing is failing to meet those expectations - it's whether the company has created conditions where those expectations are possible in the first place. Because the marketing team a company gets is often a reflection of the environment leadership creates.

 

Not always.

 

But often. And undeniably so.

 

This site and these field notes are bullish on the concept that “most people say they want marketing to play a larger role in strategy, but when the day-to-day takes hold it inevitably trains marketing to become highly tactical.” It’s understandable that priorities change… but weekly? It’s common that requests take place in hallways and Teams chats and then urgency completely overrides all planning… but EVERY TIME?

 

Eventually, marketing adapts… not because they can’t be strategic or don’t know strategy from a hole in their shoe, but because the incentives placed around them demand reaction. And the result is predictable. Rapid execution is what’s actually rewarded.

 

Marketing isn’t stupid; marketing knows which behavior survives.

 

Now, take the concept of proactivity. Leaders often want marketing to bring new ideas, challenge assumptions, and identify opportunities. “Use your voice! Push us! You own this, I hired you to lead this function, let’s enable you for success!”

 

And then those ideas create friction and challenge existing priorities, and the well that might ideally drip with tradeoffs runs dry. That’s when the safest path becomes execution.

Again, not because the people changed… but because the environment responded around them.

 

This isn't about assigning blame. Leadership is hard, y’all. Marketing is hard. Companies and people are complicated.

 

It’s just… it’s worth remembering that culture isn't defined by what leaders say they want. It's defined by what gets rewarded, tolerated, and reinforced over time.

 

The strongest teams I've worked with weren't simply better marketers (though I’ve been fortunate that my career has let me work with countless Mount Rushmores of bad ass marketing talent). They were marketers who operated in environments with clear priorities and understood business goals and consistent feedback and shared accountability. Where strategic thinking was encouraged repeatedly, and not occasionally.

 

So. When leaders feel frustrated by the marketing team they have, the first question shouldn’t be: "What's wrong with marketing?"

 

It should be: "What conditions have we created for marketing to succeed?"

 

The answer to that question often explains far more than any campaign review ever will.









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