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Writer's pictureJessica Grossman

Unlocking Wisdom: Key Insights from 30+ Leaders in 2024

This year, I coached 30 leaders from diverse industries, each with unique strengths and challenges. Common themes emerged in their leadership journeys, guiding our work. Below are the key challenges faced, their implications, and insights for progress.


Prominent Challenges


#1 Tough Calls on Talent: When to Coach, When to Cut Ties

Many leaders struggled with addressing performance gaps, hesitating to act due to self-doubt and avoidance of discomfort. At times it felt like underperformance often felt less like an issue with their team member fit and more like a reflection of their leadership.


Questions like these echoed in their minds:

  • Is it me or them? Are my expectations too high?

  • Am I failing to inspire or communicate clearly?

  • How much time should I spend getting someone up to speed?


This internalized self-blame led to delays in decision-making, creating a self-fulfilling cycle. Leaders feared that addressing a performance gap might expose their perceived shortcomings, making it harder to take decisive action.


#2 Feeling that Self-Doubt

This year, many leaders I coached felt an unrelenting need to prove their value and showcase their expertise—a pattern that, ironically, often hindered their ability to build trust and meaningful relationships. Instead of believing in their inherent worth and leading from a place of confidence, they focused on pleasing others and seeking external validation.


Thoughts like these frequently crossed their minds:

  • I need to prove to them I belong

  • It has to be perfect so that I don't look stupid

  • What if they find out I don’t really know what I’m doing?

  • I have to keep working harder so no one notices I’m not good enough

  • If I ask for help, they’ll think I’m incompetent

  • If it’s not flawless, they’ll think less of me


This mindset led to burnout, reluctance to advocate for themselves, and a disconnection from their core values.



#3 Fears Around Micro-Management

The fear of being seen as “that manager” led many leaders to shy away from necessary oversight.


Common thoughts included:

  • I don’t want to burden my team.

  • I want them to feel trusted.


In trying to avoid micro-managing, leaders often withheld critical guidance, inadvertently causing misalignment and confusion. While the intent was to empower teams, the lack of direction sometimes led to performance gaps and resentment



#4 Managing Up & Balancing Team Expectations

Leaders often found themselves navigating the challenging process of managing up, acting as the bridge between their teams and upper management.


Key thoughts included:

  • How much should I shield my team from upper management’s pressure?

  • Managing up feels “icky”


This balancing act left leaders torn between advocating for their teams and meeting their leaders’ expectations. Over time, many overextended themselves, losing their sense of self and clarity in trying to meet everyone’s needs.


Implications

  • Lack of Boundaries Set

    Leaders struggled to establish clear boundaries, often blurring the lines between their responsibilities and others’ demands. Without clarity, they felt overwhelmed, taking on too much while neglecting their own needs.

  • Delays in Hard Conversations

    Avoiding tough discussions about performance or expectations allowed issues to linger, leading to frustration, misalignment, and strained relationships.

  • Burnout

    Leaders stretched themselves too thin, juggling competing priorities without clear boundaries or self-care. This left them physically and emotionally drained, impacting their ability to lead effectively.


How did we resolve these challenges? Let’s connect and discuss how coaching can help you or your team overcome these hurdles. Schedule a call today!




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