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Ten Signs You Are Over-Engineering Your Coaching

29 January 2026 by Keith Rosen

Coaching doesn’t break because of bad frameworks. It breaks when presence gets replaced by performance and control replaces creation and connection. If coaching feels heavy, scripted, or exhausting, you’re not developing people, you’re managing a process and are driving your agenda. Here are the top ten areas where managers get stuck when coaching, and how to overcome them.

1. You’re Trying To Follow A Script Instead Of A Person.
If you’re focused on “getting the framework right” rather than listening, you’ve left the conversation and are allowing the framework to grip you, instead of making it organic.

2. You’re Stacking Multiple Questions At Once.
If you catch yourself asking two questions in one breath, that’s not coaching, that’s interrogating. One question. One moment. One direction.

3. You Feel Pressure To Give The Perfect Coaching Question.
Great coaching isn’t perfection. It’s presence. When you’re trying to sound brilliant, you’re no longer curious, and if you’re thinking about that perfect question, you’re no longer listening, making your question irrelevant. Stop trying to be perfect and start being human.

4. Coaching Sessions Start To Feel Like Workshops.
If you’re teaching, preaching, or presenting information more than 20% of the time, you’re no longer coaching; you’re consulting, training, or advising.

5.  You’re Searching For A Solution Instead Of Their Truth.
The more you try to solve, the more they sit back and wait for you to save them. That’s dependency, not development. Development happens in the unknown, not in the outcome.

6. You’re Over-Preparing For Coaching Conversations.
If coaching feels like you’re preparing for a board presentation and the pre-work takes longer than the conversation, you’ve overcooked it. Now, you’re building mini-strategies, and, “what if” scenarios before every 1:1. You’re coaching the fantasy, and what hasn’t happened yet, which is an impossibility. Coach what is, not what could be.

7. You Feel Responsible For Their Breakthrough.
Coaching becomes heavy when you forget they own the outcome. Your job is the question, not the finish line. Whether it’s a mind shift, behavioral shift, or a skill and strategy shift, let them create it so they own it, and act on it with confidence. We don’t judge what valuable coaching is. They do.

8. You’re Avoiding Silence Because It Feels Awkward.
Quiet moments aren’t dead space. They’re where people access new thinking and have a safe, non-judgmental space and the time to process their way, which is something we all don’t get enough of. Honor their thinking process, not yours. If you fill the silence, you steal the breakthrough.

9. Coaching Feels Like Extra Work Instead Of The Work.
If every conversation feels mentally draining, and harder than it should, you’re managing steps, tools, frameworks, and your agenda, instead of simply connecting with people.

10. Coaching Feels Like Running A Meeting Instead Of Developing A Person.
When you’re checking boxes and tracking action items more than insights, and positive change, you’re managing activity, not coaching and growth.

The post Ten Signs You Are Over-Engineering Your Coaching first appeared on Keith Rosen.

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