Most organizations eventually face a moment when a leader’s behavior starts to raise eyebrows, along with questions, concerns, or even HR complaints. This can result in the leader being labeled as “challenging” or “difficult.”
Sometimes an HR partner reaches out to me wondering whether coaching can help them navigate the dynamics of working with a difficult executive. Other times, executives seek me out themselves because they’ve been labeled as challenging.
Over my years coaching senior leaders in tech, I’ve found that companies often misdiagnose the real issue. They focus solely on “fixing” the executive instead of also understanding the system surrounding them.
Managing a challenging executive not only requires nuance and clarity, but most importantly, a shift in how organizations think about the problem.
An important note before we go any further: Coaching shouldn’t be punitive. It also shouldn’t replace honest, direct feedback. Instead, when applied thoughtfully and as part of a larger strategy, coaching can absolutely transform workplace dynamics and performance, especially when a leader is engaging in behaviors that disrupt momentum.
To make sense of what’s really happening, organizations must look beyond the individual leader and explore a holistic set of factors that shape executive behavior:
1. Labels need to be used judiciously.
The phrase “labels are for food, not people” may sound cliché, yet there’s some truth to it. This includes the label “difficult executives.”
Leaders are not inherently difficult. What’s difficult is responding to behavior that feels disruptive while staying grounded, authentic, and aligned with your values and business goals.
I encourage leaders and organizations to focus on the specific behavior that needs to shift. Precise language drives accountability.
Disruptive leaders can make it difficult for teams to operate efficiently, so learning strategies to best work with them ensures your team can move forward successfully.
2. Organizations must be trauma-informed.
Trauma isn’t an excuse for poor behavior, but it can provide context for why a leader is showing up a certain way.
As I shared in Entrepreneur, “While trauma is often thought of as personal, our current workforce has been shaped by shared traumatic experiences like workplace violence, the pandemic, economic uncertainty, the environmental crisis, and more… the world is experiencing increasing collective trauma.”
Because I’m a trauma-informed coach, I believe leaders who are exhibiting problematic behaviors are most effective when they honor and acknowledge the role trauma may play in their work and life.
This doesn’t require their manager to play therapist. Instead, it invites deeper understanding so the leader, their team, and the business can function at their best.
[Read: How To Know Whether You Need A Coach Or A Therapist]
3. Personal preferences matter.
Sometimes what gets labeled as “difficult” is simply a difference in how people prefer to take in information and make decisions. This is why I often turn to the Myers-Briggs Type Indicator® (MBTI®) assessment when teams are navigating a challenging executive.
The MBTI Team Report often reveals that the problem is not a difficult personality, but a personality preference mismatch.
For example, a team with predominantly Judging (J) preferences, who prefer structure and decisiveness, may struggle with an executive who prefers Perceiving (P), who tends to be more spontaneous and adaptable. The executive isn’t difficult; they’re simply wired differently.
I recently partnered with a leadership team in this exact situation. Their MBTI® Team Report showed a few “difficult leaders” had strong Perceiving preferences, while the rest of the team preferred Judging. It wasn’t about being difficult. They just had clear preferences for how they organized their world. Ultimately, the Judgers needed to practice being more adaptable, while the Perceivers agreed to try more structure.
4. Cultural communication preferences influence more things than leaders think.
Similarly, the Intercultural Conflict Style Inventory (ICS) highlights differences rooted in cultural backgrounds and communication styles.
I recall a leader who was told they were too passive for their executive role and needed to be more direct. Their ICS results showed that their communication style was less expressive and less direct than their colleagues and was influenced by their cultural upbringing.
They weren’t an ineffective leader. They simply communicated differently based on the cultural norms they had internalized. As a result of this discovery, they learned how to lean into the strengths of their natural style while also stretching beyond it when it was helpful. The result was a leader who was perceived as flexible, adaptable, and authentic.
5. Difficult executives often point to underlying organizational issues.
Difficult executives rarely exist in isolation. They’re shaped by their systems, and sometimes those systems reinforce problematic behavior.
Often, the so-called difficult executive is simply expressing a dysfunction the organization has quietly normalized.
As a coach, I must ask tough, strategic questions like:
- What toxic or unacceptable leadership behavior are you tolerating?
- Where will you draw the line consistently?
- What boundaries need strengthening to protect the team and business?
- What incentives or gaps in accountability are fueling this behavior?
Challenging executives live within a broader ecosystem of their peers, team, and organization. Truly understanding that landscape allows you to reveal whether its boundaries need updating, accountability needs tightening, or culture needs recalibration to reach your goals.
6. Not all leaders are ready to be coached.
Executive coaching, especially when paired with 360 feedback, provides a brave container for reflection, behavior change, and perception shifts.
Still, not everyone is ready for it. Coaching is a vulnerable, deep process that requires significant self-reflection, introspection, and a willingness to sit in discomfort. Some leaders may have internal protectors, limiting beliefs, or other emotional blocks that prevent them from engaging fully in the coaching process.
If a leader isn’t ready for coaching, that’s okay. It simply means you must decide whether their behavior will continue to be tolerated and if you’re willing to take on the cost to your organization.
Can Coaching Improve A Difficult Leader?
Sometimes! Coaching can transform how a leader communicates, collaborates, and shows up. Many leaders who engage in disruptive behaviors are unaware of the perception they’re inspiring and impact they are having. Coaching offers a confidential space in which to strengthen insight and shift behavior. That said, coaching only works if they’re willing and ready.
How Do Coaches Work With Challenging Executives?
While rapport building and trust are necessary in any coaching engagement, difficult leaders often require a slower, more methodical process. Trial and error is also critical, since conventional techniques and interventions tend to fall flat with challenging executives.
What If I’ve Been Labeled The Difficult Or Challenging Leader?
You’re not alone. Most people have engaged in workplace behaviors and later wish they had handled the situation differently. The key is staying open to the process, remaining vulnerable, and sticking with it when you feel uncomfortable. You’re not defined by one chapter of your career. You get to decide what happens next.
If your employer presents you with the opportunity to work with a leadership coach, strongly consider taking them up on the offer, as it means they see potential in you.
Final Thoughts On “Difficult” Executives
Coaching challenging executives is one of my specialties. The vast majority of my clients come through word of mouth, and I’m often brought in to help with the toughest cases, including senior leaders no one else dares take on.
If you’re looking to support a leader who is struggling, please reach out or schedule a consultation. I’m here for you! You’ve got this!
