The Empathy Blindspot: What B2B Leaders Get Wrong About Underperformers
August 3, 2025
What makes a great marketing leader? Strategy? Vision? Results? Of course. But there’s a harder, more uncomfortable trait that separates good leaders from great ones: the ability to make decisions that are empathetic to the whole team—even when that means letting someone go.
In this post, I walk through one of the biggest mindset shifts that shaped how I lead: reframing empathy. Not just toward individuals—but toward your entire marketing org.
If you’ve ever struggled with a team member who’s holding things back (but you’re not sure what to do about it), this post is for you.
I was walking the streets of Boston, listening to Dave Ramsey’s EntreLeadership—and I heard something that’s stuck with me for over a decade.
“When you’re being empathetic to one underperformer, are you being fair to the rest of your team?”
At the time, I had a team member struggling to keep up. I was doing everything I could—coaching, feedback, second (and third) chances. But deep down, I knew they weren’t going to make it.
Ramsey’s challenge reframed it: I wasn’t just helping that one person. I was hurting everyone else.
That was the moment I started viewing marketing leadership through a wider empathy lens—not just the individual in front of me, but the team around them.
If you’re leading a marketing org today—whether that’s 3 people or 30—you’ve probably encountered one (or more) of these four personas. And maybe, like me, you’ve wrestled with how long to hold on.
This one’s tricky. Because they’re often producing results—and causing chaos.
Whether it’s gossip, drama, or subtle undermining, these behaviors chip away at team trust. And the longer they stick around, the more you signal that performance matters more than culture.
I’ve had to let go of team members who delivered great results but left psychological damage behind. That’s not the kind of marketing org I want to lead.
(Related: Our conversation on scaling culture and leadership to $750M+ goes deeper into how strong marketing teams grow with aligned values.)
This is often someone everyone likes—but who just isn’t getting it.
They need more training. More follow-ups. More hand-holding. And despite being a great culture fit, they struggle to meet the standard.
I’ve had some of the kindest, most well-meaning people in this category. But good intentions don’t build pipeline. And constant mentoring drains your high performers.
If someone can’t keep pace, even after support—it’s time for a tough conversation.
You know the one: always out, always slow to respond, always conveniently unavailable when crunch time hits.
I’m a huge proponent of work-life balance. But accountability and follow-through matter. When others are picking up the slack, resentment builds fast.
If someone’s showing up inconsistently and delivering inconsistently—it’s a red flag for your team culture.
(Related: We talk about modern marketing org dynamics and how leadership sets the tone for team performance.)
This one’s the hardest.
I’ve worked with people who were amazing contributors for years. But when our company grew, or our strategy shifted, they just couldn’t adapt.
Marketing orgs evolve. Structures, tools, and expectations change. And someone who thrived in the early days may struggle in the next phase.
Loyalty matters. But so does forward momentum. If someone can’t—or won’t—grow with the team, you owe it to everyone else to re-evaluate.
Every marketing leader wants to be kind. But kindness without accountability is a leadership trap.
When you over-index on being empathetic to an individual, you risk being unfair to everyone else.
Ask yourself:
The best marketing executives I’ve seen are the ones who make hard calls with heart. They give support and second chances—but they protect the culture and energy of the entire team.
(Related: Read how great CMOs balance empathy and accountability.)
If this resonated, here are three things to reflect on this week:
You don’t need to make sweeping changes overnight. But clarity creates courage. And courageous leadership creates high-performing marketing orgs.
Marketing leadership isn’t about avoiding conflict. It’s about serving your team by making the hard calls, the right way.
If this post sparked reflection or a tough next step—you’re doing it right.
(Related: Explore how CMO-CFO alignment impacts org decisions.)
I built the CMO mentorship I wish I had—because too many marketing leaders are figuring it out alone. At Growth Activated, we help B2B marketers bridge the gap between execution and executive leadership, equipping you with the strategic mindset, frameworks, and hands-on guidance to drive impact at every stage of growth. From scaling multi-million-dollar organizations to leading SaaS startups, I’ve been in your shoes—and now, I’m here to help you step into the marketing leader you’re meant to be. Whether you need a strategic marketing plan, expert coaching, or team training, Growth Activated gives you the tools to lead with confidence and deliver measurable results.
