Beyond Sessions 2: When Coaching Skill Stops Being the Problem

There’s a shift that happens in coaching practice that’s difficult to describe until you’ve experienced it.

It doesn’t announce itself clearly. It doesn’t arrive as failure. In fact, it often appears when the coaching itself is working. Sessions land well. Clients are engaged. Conversations are meaningful.

And yet, something feels unresolved. Not in the coaching. In the delivery.

Because the sessions are good, this tension can be easy to misinterpret. It often shows up as quiet self-doubt — a sense that you should have this figured out by now. But what’s surfacing here isn’t a lack of skill. It’s a developmental signal.

What I Hear at This Stage

When I sit with coaches at this stage, I hear a familiar set of observations.

A coach will describe sessions that feel solid — sometimes powerful. Clients are moving. Insight is happening. Then I’ll ask about the engagement as a whole, and there’s a pause.

“I’m not always sure where we are.”
“Every engagement feels different — I’m figuring it out as I go.”
“I feel like I’m carrying the entire journey in my head.”

These aren’t signs of incompetence. They’re signs that the structure needed to hold the journey hasn’t been installed yet.

Session-by-session delivery allows for responsiveness and honours what emerges. When coaching functions as occasional support, this works. The ceiling appears when you’re guiding someone through sustained transformation — when continuity across weeks starts to matter more than what happens inside any single session.

Without that structure, you have to improvise — session by session, decision by decision. That improvisation works for a time. Skill can compensate. Presence can carry things forward. But over time, improvisation becomes load.

When Coaching Skill Stops Being the Edge

When coaching skill stops being the edge, engagement leadership becomes the edge. This isn’t a failure — it’s a developmental stage with a predictable next step.

Coaching skill allows you to show up fully in the room. It gives you the ability to listen deeply, challenge thoughtfully, and stay with what’s emerging. What it doesn’t provide is clarity about the journey itself.

Skill alone doesn’t tell you what should happen before coaching formally begins, how discovery is meant to unfold across time rather than being compressed, how momentum is maintained when the work gets difficult, or when and how an engagement should move toward meaningful completion.

These aren’t coaching questions — they’re engagement leadership questions.

And for many coaches, delivery has been improvised — not because they are disorganised, but because no one taught them how to design it. This is a stage, not a failure.

The Cost of Carrying the Engagement

When a structure doesn’t exist, you become the structure.

Every decision about pacing, sequencing, and transition has to be held mentally. Each session begins with a quiet recalibration: Where are we? What’s next? What needs attention now?

Over time, this creates cognitive load that never quite eases, subtle pressure to perform in every session, difficulty articulating the value of the work beyond individual conversations, and uncertainty about whether transformation will integrate or simply fade.

Much of this effort is invisible to the client. But it’s felt by you. And when coaching is delivered this way over months or years, it doesn’t just feel effortful — it starts to feel unsustainable.

What This Tension Actually Points To

If you’re recognising yourself here, it doesn’t mean you’re behind. It means you’ve reached the point where coaching skill is no longer the bottleneck.

You can coach. You can hold presence. You can create insight. The work inside sessions is not the issue. What’s missing is a professional coaching delivery structure that allows transformation to unfold across a journey — rather than relying on you to carry everything moment by moment.

This is often the stage where structure stops feeling like a constraint and starts feeling like relief.

Who This Is For

This tension typically appears for coaches actively working with clients who feel confident in-session but sense improvisation becoming load rather than flexibility. If you’re still building coaching presence or focused on client acquisition, this likely isn’t your stage yet — and that’s fine.

Where This Leads

If this tension feels developmental rather than personal, you’re sensing what Beyond Sessions addresses. It’s a professional space where journey-level delivery becomes operational, not just conceptual. This shift from conceptual to operational benefits from freedom that is built upon structure and this is what Article 3 explores in depth.

This is part 2 of a 6 blog series helping coaches to elevate their professional impact.

Written by Dr Steve Jeffs & Erwin de Grave

Contributing Author:

Dr Steve Jeffs is a Master Certified Coach (MCC), business and organisational psychologist, and leadership transformation expert with over 20 years of global experience. Before becoming a full-time coach, Steve led large-scale leadership assessment and development programs, organisational change initiatives, and cultural transformation projects across the Middle East, working with government bodies, multinationals, and high-growth businesses. His early career as a registered psychologist and management consultant continues to shape his pragmatic, systems-oriented approach to coaching and leadership.

Today, Steve serves as Director of Coaching at The Coaching Tools Company, where he brings together his expertise in psychology, strategy, and personal development to create practical, impactful tools for coaches and leaders alike. He is also the Co-Founder of The Guiding Matrix, a company dedicated to helping coaches grow sustainable businesses while expanding their leadership capacity.

With over 5,000 coaching hours, Steve has worked with executives and teams in more than 20 countries, including in the UK, UAE, KSA, USA, Egypt, South Africa, and the Philippines. His coaching clients include leaders from organisations such as HSBC, Siemens, Roche Diagnostics, STC, Etisalat, Sanofi, and Dubai Holding. As one of the first MCCs in the Middle East, Steve has also trained and mentored over 1,000 coaches globally and continues to supervise coaches through their credentialing journeys.

Steve is a multi-award-winning coach, recognised globally for his work on leadership and innovation—including honours from the World Innovation Congress and CHRO Asia. He is co-author of Stuck No More: Practical Self-Coaching for Everyday Problems and Shift Up: Strength Strategies for Optimal Living, and is the creator of multiple strengths-based assessments and coaching tools, including the StrengthsMultiplier™. With a Doctorate in Leadership and a Master's in Organisational Psychology, Steve blends deep psychological insight with practical coaching to help individuals, teams, and organisations thrive.

Originally from Australia, Steve now lives in the UK having worked in the UAE for over a decade, bringing both global perspective and deep regional understanding to his work. When not coaching or creating tools, you’ll likely find him exploring deep caves or shipwrecks—he’s a certified technical diver and cave explorer who brings the same spirit of curiosity and courage to his coaching and leadership work.

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