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Coaching Executive Leaders

Insights from Dion Leadership’s Annual Coaches Panel Webinar

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5 minute read

Dion Leadership Webinar Unlocking Leadership Potential on a laptop screen.

I recently moderated our fifth annual coaches panel webinar (recording available on YouTube) and was inspired by the insights shared by our distinguished panel of executive coaches. This popular event is designed to help talent development professionals understand the challenges leaders face today and how coaching can be beneficial for both leaders and organizations. It also provides an insider’s view of the entire coaching process and the intricacies of a typical coaching session.

The 2024 Coaches Panel

  • MaryAnn Rivers: Drawing from her extensive experience, including as a CEO, MaryAnn advocates for sustainable leadership development and personal growth. She believes coaching would have been invaluable during her time as a CEO.
  • Kelly Scheer: A former healthcare executive turned coach, Kelly got into coaching to find the accountability and guidance she desired in her own career.
  • Jim Taigman: With a background as a human resources executive, Jim finds his passion in supporting leadership teams. He engages clients on all levels, focusing on the whole person.

Discussion Highlights

1. Choosing the Right Coach with a Chemistry Call

Questions: What is a chemistry call? What happens during these calls? Should the coach be similar to or different from the coachee?

Insights: At the beginning of any coaching assignment, the Dion Leadership team arranges for the coachee to interview up to three coaches. These chemistry calls are a crucially important step in the process as they aid in creating an ideal fit between coachee and coach. MaryAnn emphasized the importance of comfort and vulnerability during this initial interaction. She conducts mini-coaching sessions to set clear expectations and ensure a good fit, prioritizing confidentiality and safety. Jim and Kelly agreed that the right match often involves a coach who can help the coachee stretch outside of their comfort zone. Jim explained that coaching, not consulting, is key. Kelly added that coachees often appreciate a coach who matches their energy level and provides an open invitation to challenge them and help them grow. While understanding the particulars and language of the coachee’s industry can be helpful, Kelly finds that objectivity can be even more beneficial. Jim noted that leadership experience, rather than industry experience, builds comfort. MaryAnn stressed that communication, relationships, and leadership behavior transcend industries.

2. Most Common Coaching Focus Areas in 2024

Questions: What specific areas do you typically coach to? What are the common issues that leaders are facing today?

Insights: Jim discussed how generational differences are frequently impacting leaders today. He often works to help his clients accept and understand diverse perspectives.

MaryAnn’s coachees will often ask her for strategies and tactics for managing up as well as establishing a stronger executive presence. While helping the coachees realize that they do not have to be at the mercy of their bosses, she emphasized that she often encourages leaders to truly see their bosses’ perspective when working through challenging situations.

Kelly frequently deals with leaders who are struggling with imposter syndrome, stating that 90% of her coachees seem to struggle with their worthiness to be in their role. The loneliest place on the org chart, she says, is in the C-suite. She guides these leaders through a process for building their confidence and developing their leadership brand. She reminds them that remaining true to that brand will help them bring their authentic self to their work and relationships. She recommends Adam Grant’s book Think Again and Kim Scott’s book Radical Candor for leaders looking to transcend impostor syndrome.

3. Inside a Coaching Session

Question: What actually happens during a coaching session?

Insights: Jim outlined the arc, as he put it, of a typical session. The coaching session starts with a review of the previous session’s action items, accountability, and ownership. The coachee drives the conversation, with the coach facilitating problem solving and action planning for current real-work situations. The coach helps the coachee look at issues differently by asking powerful questions. The coachee should be talking 80–90% of the time. Once the issue is understood, the coach and coachee explore and then develop new and different steps for working through the issue in a healthier and more productive way. Flexibility is also crucial, as sometimes critical current-day issues arise. A good coach will help the leader process that issue before focusing again on the original coaching action plan.

4. The Power of Feedback and Data in the Coaching Process

Questions: How do you use assessments as part of the coaching process? Why are they helpful?

Insights: Kelly highlighted the importance of 360-degree assessments and stakeholder interviews. The data gathered in a quantitative manner helps align the leader’s perception with reality and provides a foundation for development. Seeing the gaps between self-ratings and those from other people, or between different rater groups, can be a powerful experience to help a leader better understanding of the impact of their behavior. Kelly references the data again and again throughout the coaching engagement and uses the data to help the coachee defy their inner critic.

MaryAnn made the point that assessment data is always contextual, not inherently good or bad. The stakeholder interview meetings bring a richer, deeper dimension to the feedback. The context of the leader’s role determines what skills or strengths need development. A good coach will be able help debrief the data with these nuances in mind. Assessments also allow leaders to prioritize key areas and let go of less critical ones.

5. Shifting Mindsets

Questions: What kind of leader really benefits from coaching? Can coaching encourage a fundamental mindset shift?

Insights: The ultimate purpose of coaching is to change one’s mindset. All new behaviors grow from that change. Kelly believes coaching is mostly beneficial to those leaders who are eager to improve, making it a highly worthwhile investment.

While using coaching as a last resort for problematic leaders is less ideal, MaryAnn shared that even challenging turnaround situations can succeed, sometimes resulting in win-win outcomes like role changes within the organization. MaryAnn uses deep reflection questions to challenge limiting beliefs and encourage new perspectives. She emphasized that leadership is an inner game, focusing on self-awareness and mental noise. Asking questions like “Is that confirmed or assumed?” can help shift one’s internal dialog, resulting in profound mindset shifts.

Books you can read to help sharpen your skills to coach others in mindset shifts include The Courage to Be Disliked by Ichiro Kishimi and The Untethered Soul by Michael Singer.

Conclusions

We closed the session noting that coaching is an investment in the future of the organization and creates an “all boats rise” scenario. The best coachee is someone who you think has “got it” and “could be even better if.” When coaching is a last-ditch effort, after the organization feels that it has tried everything else, the results can be mixed. Many times, even after a rocky start, coaching can turn the situation around and result in finding the right role or situation to make the person a value-added member of the organization.

This excellent webinar offered a deep dive into the real-world application of leadership coaching. By understanding the nuances of coaching sessions, the challenges leaders face, and the transformative power of coaching, talent development professionals can better support their organizations.

If this summary piqued your interest, please watch the full webinar replay for a deeper level of insight and understanding.

As Kelly Scheer aptly put it, “If you know better, you do better.”

Stay tuned for more insights from Dion Leadership as we continue to explore the transformative power of leadership coaching.

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Steve Dion-Steve Dion-Founder and CEO-Dion Leadership-23.png

Steve Dion

Founder & CEO

Steve has dedicated his career to understanding and improving organizational cultures through the creation and deployment of innovative assessment, leadership, and team development programs. He is a regular contributor to CEOWORLD magazine, Chief Executive, Fast Company, Training Industry, and HRCI’s HR Leads Business Blog. Steve and his Dion Leadership colleagues have recently launched a new
e-learning course that supports
 work-life alignment.

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