The Coaching Crossroads: Converting Uncertainty into Opportunity
- Giridhar
- 2025/08/12
- Coaching

The Coaching Crossroads: Converting Uncertainty into Opportunity
The silence stretches for what feels like minutes. The energy drops and the silence becomes awkward when the coach is trying to move forward and starts having those nagging doubts on how to proceed. Sound familiar? That moment when your confidence wavers, and you wonder if you’ve lost your touch. Whether you’re two months or two decades into your coaching journey, these moments visit us all – they’re part of the coaching conversations. As a coach, I have had my own experiences of being in this situation. Over time, I have started to realise two aspects – First, getting stuck is not a sign of failure, it is part of the process, and second, these moments often precede a breakthrough moment.
Recognizing the Signs
When we feel stuck in a coaching conversation, it often reflects a deeper underlying dynamic. It might show up as focusing and being obsessed on the same point over and over, where the client circles back to the same issue. without gaining new insights. Other times, it feels like an invisible wall — the energy drops, and progress seems impossible. Occasionally, there’s a nagging sense that something critical is being overlooked, though we can’t quite pinpoint it. Our anxiety rises as we search for the “perfect” next question. We also tend to rephrase the same question in different ways thereby continuing to hover around the same issue. Often, we end up talking more than the client in these situations.
What’s intriguing about this feeling of being “stuck” is that it’s rarely without purpose. From my experience, it often indicates we’re on the verge of something significant — perhaps an unconscious block, a deeply held belief, or a truth the client isn’t yet ready to confront. Instead of trying to find a path around this imaginary wall, we unconsciously keep colliding with this wall.
I recently experienced this during a session where my client was exploring career transitions. As they repeated their concerns about job security for the third time, I noticed myself becoming increasingly anxious about finding the “right” question to break through. This awareness was my first step toward shifting the conversation.
Understanding the Block
The reasons are as varied as our clients, but some patterns emerge consistently:
First, we might be pushing too hard toward what we perceive as the “right” direction, unconsciously steering the client instead of following their lead. While this goes against the basic principle of coaching, this is something that need to master. I remember a session where I was so excited about a potential breakthrough that I missed my client’s subtle resistance signals. The conversation stalled until I stepped back and renewed my commitment to deep listening. Second, we sometimes get caught in the content trap, becoming too invested in the client’s story rather than the underlying patterns and energy. The details can be interesting, but our role is to help clients see beyond them. Third, and perhaps most importantly, getting stuck often appears when we’re approaching something transformative. Like the calm before a storm, these moments can precede significant shifts in perspective or awareness
Prevention Isn’t Always Possible
While we can minimize getting stuck through practiced presence and deep listening, trying to avoid it entirely might not be always feasible. Instead, I’ve learned to welcome these moments as valuable indicators that something important is happening beneath the surface.
That said, we can create conditions that support flow in our coaching conversations. Some of these include: Maintaining genuine curiosity about what’s emerging, staying attuned to energy shifts in the conversation holding back our assumptions, trusting the client’s innate wisdom and timing
Working with Stuck Moments
When you notice that stuck feeling creeping in, consider these approaches:
Name it with curiosity: “I’m noticing we might be in a holding pattern here. What are you noticing?” This simple acknowledgment often creates space for fresh perspectives to emerge. One client responded to this observation by revealing their fear of the changes we were discussing – a crucial insight we might have missed.
Shift the energy: Asking the right questions can help shift the energy in a coaching session. By prompting the client to reflect from a different perspective or challenge their current thinking, you can break the pattern and open up new possibilities for insight and growth.” Some of my standard question include, “If your future self was looking at this situation, what would they see?” or “What would you tell a friend facing this challenge?”
Step back: Asking the client to reflect on how they are engaging with their challenges or the coaching process itself, rather than just diving into the specifics of the issue at hand. It’s a way of gaining insight into the bigger picture or the underlying dynamics at play. “What might this moment of pause be trying to tell us?”or “How is this challenge showing up in other areas of your life?” These questions have led to some of my most profound coaching moments.
Return to the client’s agenda: Reconnecting with what the client truly wants from the session can help reset the conversation’s direction and energy. “Let’s revisit what you hoped to achieve today. How is this connecting to that?” This reset often provides fresh clarity and direction.
Finding Opportunities in the Struggle
Over the years, I’ve come to appreciate these challenging moments as opportunities for deeper connection and insight. They remind us that coaching is not about maintaining constant forward momentum, but about being present with whatever emerges.
Some of my most powerful coaching experiences have grown from moments when I felt most uncertain. By embracing the discomfort of not knowing, staying present with what is, and trusting the process, we create space for authentic transformation to occur.
Remember, feeling stuck doesn’t mean you’re doing something wrong – it might mean you’re right where you need to be for something important to unfold. Trust yourself, trust your client, and trust the process.
This post was first published in the ICF Delhi Newsletter
About the Author
Giridhar Sridhar is a Master Coach specializing in Executive and Leadership Development, helping leaders navigate pivotal moments in their journey. As the Managing Director of Reframing Visions, he brings deep insights from extensive coaching experience working with senior executives across industries.
Connect with Giridhar: Email: giridhar@reframingvisions.com
LinkedIn: www.linkedin.com/in/giridhar-sridhar