Discovering Artificial Intelligence in Leadership Coaching: Interview with Jack Glennon

Jack Glennon is the founder of Glennon Peak Coaching, specialising in leadership, emotional intelligence, and career transitions. With over two decades of experience in leadership across various industries, Jack combines his expertise with a personal story of resilience and reinvention. Having overcome redundancy and major health challenges, Jack is passionate about helping individuals and teams turn setbacks into opportunities for growth. Through Glennon Peak Coaching, Jack empowers clients to redefine their identity, lead with confidence, and achieve their goals.

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How do you tailor your coaching approach to meet the unique needs and goals of each individual you work with?

Tailoring my coaching is a bit like crafting a bespoke suit—it has to fit perfectly. I start by truly understanding the person in front of me: their challenges, aspirations, and quirks. I use a mix of open-ended conversations, assessments, and observation to piece together their unique leadership puzzle. From there, it’s about creating a dynamic approach that evolves as they do. Some clients need a strategic roadmap; others benefit from real-time role-play or gentle accountability nudges. It’s always about meeting them where they are, not where they "should" be.

How do you approach building trust and rapport with the leaders you coach?

I approach trust-building with a healthy dose of authenticity and curiosity. People can sense when you’re genuinely invested in their success—and that’s always my starting point. I also share a bit of myself (the good, the bad, and the "I can’t believe I just admitted that"), which often opens the door for them to do the same. Building rapport is about creating a space where it’s okay to be vulnerable and explore growth without judgment. Plus, a dash of humour always helps—it’s hard not to connect when you’ve just laughed together.

Can you share a specific technique or tool that you find particularly effective in helping clients develop their leadership skills?

The “Stop, Start, Continue” framework is a game-changer. It’s simple yet powerful: we identify behaviors they need to stop doing (like micromanaging), start doing (like delegating effectively), and continue doing (like fostering a positive team culture). It’s actionable and immediately impactful, creating clarity without overwhelming the client. I love how it encourages self-awareness while being forward-focused.

How do you ensure that your coaching relationships with clients are sustainable and have a lasting impact on their leadership development?

Sustainability comes from creating self-reliance. I don’t aim to be a permanent fixture in their lives—I aim to give them the tools, mindset, and confidence to lead effectively long after our sessions. This involves setting clear, measurable goals and embedding habits that align with their values and leadership style. We also reflect regularly on their progress, ensuring they see and own their growth. If I’ve done my job right, they’ll hear my voice in their head long after I’m gone (hopefully the good advice, not my coffee order).

How do you measure the effectiveness of your leadership coaching interventions?

I look at progress through both qualitative and quantitative lenses. On one hand, we set measurable goals at the start of our engagement—things like team performance metrics, communication scores, or specific career milestones. On the other hand, I lean heavily on feedback, both from the client and their teams. If their team is saying, “Wow, you’re showing up differently,” that’s the golden ticket. Ultimately, the proof is in the transformation, not just the spreadsheets.

What strategies do you use to promote your leadership coaching services and attract new clients?

I’ve embraced the power of storytelling. Whether it’s through LinkedIn posts, podcast appearances, or sharing client success stories (with permission, of course), I aim to show—not just tell—what coaching can achieve. Word of mouth has been a major driver for me too; when you genuinely help someone, they’re quick to recommend you. Lastly, I offer a free introductory session, which gives people a taste of my style without pressure. It’s like trying on shoes—if it feels right, you’ll stick with it.

Have you ever utilized artificial intelligence tools in your work as a leadership coach? If so, how has it enhanced your practice?

Absolutely! AI has been a fantastic sidekick. I use it to analyze trends in client feedback, streamline session prep, and even generate fresh perspectives for complex challenges. Tools like ChatGPT (shoutout!) can spark ideas for workshops or create custom scenarios for role-play exercises. But it’s never a replacement for the human connection—it’s more like having a really smart assistant who doesn’t need coffee breaks. It’s enhanced my practice by freeing me up to focus more on what truly matters: my clients.

The interview questions were created by Everneed AI.