How I Challenge My Coaching Clients Without Overstepping

(Lessons from My Executive Coaching Practice)

Over the years as an executive coach, I’ve learned that one of my greatest responsibilities is to challenge my clients — to push their thinking, question their assumptions and help them see opportunities they may be missing.

But there’s a fine line here. If I push too hard, it can feel like I’m imposing my ideas. If I’m too soft, I risk letting them stay comfortable in patterns that limit their growth.

I’ve seen both extremes — and I’ve lived the consequences.

When Direct Questions Backfire

In my early coaching days, I believed the safest way to challenge someone was by asking a direct question:

• “Why don’t you try restructuring your team this way?”
• “Have you considered dropping that product line?”

It sounded harmless enough, but here’s what I noticed:

Sometimes, these questions felt like leading questions — where I already had the “right” answer in mind. And the client could sense it. This made them defensive or hesitant to fully explore their own thinking.

Other times, they interpreted my question as a subtle directive:
“Oh, so you think I should do that?”

One senior executive I worked with even said, half-jokingly, “Vikas, just tell me if this is your idea or mine.” That was a wake-up call — I needed a better way.

The ‘Permission First’ Shift

Here’s what I do now. Instead of diving in with a challenge, I start by asking permission to share my observation:

• “Would it be okay if I shared something I’ve noticed in our last few conversations?”
• “Can I offer a perspective that might be worth exploring?”

It seems like a small thing, but the change in the conversation is huge:

1. They feel in control — it’s their choice to hear me out.
2. They lower their defences — they’re more open because I’m not forcing it.
3. It becomes a partnership — we’re exploring together, not me telling them what to do.

A Real Example: The Overworked Sr. Vice President

I once coached an SVP who constantly complained about feeling overwhelmed. My instinct was to tell him bluntly, “You need to delegate more.”

Instead, I said:
“I’ve noticed that many of your long days are spent on operational issues rather than strategy. Would you like me to share a thought about how that might be impacting your leadership?”

He said yes, and that “yes” changed everything. I wasn’t telling him what to do — I was inviting him to explore the impact of his current approach. We ended up building a delegation plan that he created himself, not one I imposed.

Detachment is Key

Once I share an insight, I detach from it completely. I’m not there to convince them to agree with me.

In fact, I’ve had clients listen carefully and say, “I hear you, but I’m not ready to make that change.” And that’s fine. The point isn’t to win an argument — it’s to create awareness. Sometimes that seed takes root weeks or months later.

Clarifying Expectations Early

Nowadays, I make it a point to explain this to every new client during our first session:

• I will sometimes share observations or insights that may challenge your current thinking.
• You are free to accept, adapt or reject them.
• My job is to provoke thought, not dictate action.

This transparency builds trust. They know I’m not here to take control of their decisions — I’m here to help them think differently.

Another Example: The Risk-Averse Business Owner

A business owner I coached was missing out on a big market opportunity because of his risk-aversion. Rather than saying, “You’re being too cautious,” I asked:
“Would it be okay if I shared what I’m noticing about how you’re approaching this expansion decision?”

When he agreed, I explained how his current approach mirrored a situation from two years earlier when the company lost market share to a faster-moving competitor. He made the connection himself — and within three weeks, had a revised expansion plan in place.

The key? He owned the decision, because he wasn’t told what to do.

Why This Works So Well

This method combines two beliefs I hold deeply about coaching:

• Growth needs provocation — clients must be nudged outside their comfort zone.
• Transformation needs partnership — clients must feel respected, empowered and in control.

When I challenge in this way, I see clients open up to bigger ideas, take bolder action and make changes that stick — because the change is theirs, not mine.

My Invitation to Fellow Coaches

If you’re a coach, try this the next time you want to challenge a client:

1. Pause.
2. Ask permission.
3. Share your insight without attachment.

Watch how the energy shifts. Notice how much more ownership your client takes.

In my experience, that’s where the real magic of coaching happens — not in the brilliance of our advice but in the brilliance we help our clients uncover in themselves.