Challenging Bosses.
A firsthand narrative exploring the impact of untrained marketing leadership.
Have you struggled with a challenging boss as a Product Marketer? Join the conversation; submit your questions and thoughts to be discussed in our monthly advice column.
Navigating Leadership Landmines: From Car Shows to Boardrooms
By: Alex Virden
My first job in marketing was working in events—car events—that were part of a larger company that does real estate development across the country. The concept made sense in theory. In practice? Not so much. However, my boss was a man I had known for years, so I dove in.
Much like many challenging bosses, everything was fine until it wasn't.
One defining incident occurred during a car show miles away from home. My colleague and I were settling into our shared room when we overheard my name being uttered alongside a barrage of profanities. My boss expressed opinions about me that were far from flattering or accurate.
My colleague and I were terrified—it was loud, the event hadn't begun, and we were stuck. Fortunately, my male colleague, whom this boss was talking to, repeatedly defended me. But the damage was done.
Things only got worse with my boss due to things out of my control, like tension with the founder, mismanaging funds, and making bad business bets. There was no HR department, so I approached the founder and the CFO, who believed in me and what I was saying. They addressed my boss's unacceptable behavior. I moved on months later, but the experience left a lasting impression on me.
The incident underscored the array of managerial styles and personalities you encounter throughout a career. Despite endless HBR articles and training available, most managers I have experienced, read about, or heard of through networking have yet to be trained in the art of management. In some cases, the downside of this is mild; in other cases, it can be pretty extreme.
My first boss in product marketing, Lisa Sherr, was the gold standard. Kind and funny with the right approach to feedback, empowerment, and building a connected team.
She inspired our small team to take the initiative, grow professionally, commit deeply to organizational goals, and truly own our portfolios of educational products, which included upwards of 15 courses with thousands of users and top-tier sponsors.
She’s someone I try to emulate.
Product marketing can be challenging to navigate due to internal dynamics: old guard vs. new guard, marketing vs. product, founder vs. GTM. In start-ups, it can often feel like the bullseye is on your back. One wrong move and the fingers point at you.
I've personally experienced the repercussions of such dynamics, where the actions of individuals beyond my direct manager significantly impacted my role and well-being within an organization. Feeling stifled by a toxic culture perpetuated by a founder known for his verbal tirades against leadership and staff, coupled with an entrenched old guard unwilling to challenge the status quo, I reached a breaking point that culminated in my decision to quit.
What struck me as particularly unsettling was the complicity of those around me. Despite sharing my concerns with other go-to-market leaders and my newly appointed manager, the prevailing attitude was one of resignation rather than action. No one stepped up to advocate for change or offer a path forward, leaving me feeling isolated and unsupported.
In hindsight, leaving that toxic environment was the best decision I could have made for myself.
It served as a stark reminder not to compromise my self-respect by remaining in a situation where neither my efforts nor my well-being were valued.
While product marketing undoubtedly presents opportunities for meaningful impact, it also exposes individuals to potential backlash, scapegoating, and an undue burden of responsibility.
So, what's the solution? Managers must proactively invest in their development as leaders.
I get it.
Many managers find themselves trapped in a vicious cycle of being tasked with "do more with less," which leads to frustration and a tendency to take out their frustrations on their teams. Others find no way to move up but become people managers—a role they were never truly suited to.
To combat these pressures, I wish more managers would:
Promote a culture where team members feel empowered to suggest solutions rather than just pointing out issues, fostering proactivity and initiative.
Build a sense of belonging by actively listening to and addressing team concerns while leading with the values and behaviors you want to promote to build alignment and a sense of belonging.
Delegate tasks effectively, leveraging team members' strengths to foster growth and development.
Foster a culture of continuous learning and development, providing opportunities for skill-building and personal growth.
Be adaptable and flexible in your management approach, recognizing that what works for one individual or team may not work for another.
By embracing these principles, many of which were held by my first product marketing boss, Lisa, managers can create healthier, more supportive work environments that empower their teams to thrive.
A huge thank you to Alex Virden for sharing her story with us this month, follow her on LinkedIn for more of her great insights.
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