Obstacle Remover vs. Obstacle Creator: Dan Gingiss, CSP on Leadership Archetypes

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Dan Gingiss, CSP

LinkedIn Author

Customer Experience Keynote Speaker 💡 | Certified Speaking Professional 🎤 | 3X Author 📚 | Fortune 200 Exec at Discover, Humana & McDonald’s | Helping corporations, franchises & associations create Experience Makers

In a recent LinkedIn post, Dan Gingiss, CSP, a recognized expert in customer experience, shared his distinct perspective on leadership, categorizing bosses into two fundamental types based on their approach to problem-solving and obstacle management.

Gingiss, drawing from over two decades of experience in corporate America, posits that leaders can be broadly classified by how they respond when their teams encounter challenges. He highlights the universal experience of hitting a roadblock, whether it’s a vendor issue, a stalled process, legal hurdles, or an escalated customer complaint.

“At some point, every one of us hits a brick wall: a vendor drops the ball, a process stalls, Legal says no, a customer escalates, and suddenly you’re stuck.”

The Two Boss Archetypes Defined

According to Gingiss, the critical differentiator lies in the leader’s reaction to these inevitable setbacks. He contrasts the proactive, problem-solving leader with the one who inadvertently exacerbates the situation.

The first type of boss, as described by Gingiss, is the one who actively assists in overcoming the obstacle. He uses a vivid metaphor to illustrate this:

“One kind of boss stands there with you, sledgehammer in hand, ready to knock a hole in the wall so you can keep moving.”

Conversely, Gingiss presents the second type of boss as someone who, rather than facilitating progress, adds to the difficulty. He explains:

“The other kind shows up with… more bricks. They make the wall higher. The job harder. The momentum disappear.”

Applying the Leadership Lens

Gingiss emphasizes that this framework is not merely an observation but a lens through which he now evaluates leadership. His core message is a call to action for leaders to consider their impact on team momentum and problem resolution.

The Central Question: Removal or Reinforcement?

The crux of Gingiss’s argument centers on the fundamental role of a leader in an organization. Are they agents of progress, clearing the path for their teams, or do they, perhaps unintentionally, become impediments themselves?

He urges leaders to reflect on their own behavior and its consequences, posing three pivotal questions to his audience:

  • Which kind of boss do you have?
  • Which kind of boss are you?
  • Which kind of boss do you want to be?

By framing leadership through this ‘brick wall’ analogy, Dan Gingiss, CSP encourages a deeper examination of how leaders influence team performance, morale, and overall organizational effectiveness. His insights underscore the importance of supportive leadership in navigating the complexities of the business world and fostering a culture where obstacles are overcome, not amplified.

📝 About This Content

This article is based on insights shared by Dan Gingiss, CSP on LinkedIn.

📅 Originally posted on June 19, 2026 | View original post on LinkedIn →