Asking Better Open Questions: Whose Perspective Really Matters?

In mentoring, questions are your most powerful tool. They shape the direction of the conversation, influence how deeply a mentee reflects, and determine whether they leave the session with genuine insight or simply with your opinion dressed up as guidance.

But there’s a subtle trap that even seasoned mentors fall into: Are you asking the question from your perspective, or theirs?

The Temptation to Lead the Witness

Open questions are often celebrated as the gold standard of mentoring: broad, inviting, and reflective. But even an open question can become loaded if it stems from your assumptions, expertise, or agenda.

For example:

• “What made you think that strategy would work?”

• “Have you considered doing X instead?”

  
  

These may be open in structure, but they lean heavily toward validating your own opinion. They point the mentee in a direction you’ve already chosen. In effect, the question becomes a suggestion wearing a thin disguise.

This is natural; mentors have experience, patterns, and solutions that come quickly. Yet when questions come from this stance, the mentee is less likely to build confidence or independent thinking. They are simply navigating your map, not their own.

Shifting the Perspective Back to the Mentee

A mentee-centred open question feels different. It leaves room. It honours uncertainty. It shows curiosity rather than confirmation.

For example:

• “What options have you explored so far?”

• “How do you see this situation from where you stand?”

• “What feels most important to you in this decision?”

  
  

Here, you are not steering - you’re creating a space where the mentee can step forward, articulate their thinking, and discover what they already know. This is where transformation happens.

A sound internal check is to pause before you speak and ask yourself: “Am I asking this question to learn about their thinking, or to guide them toward mine?”The answer will reveal whether your question invites clarity or subtly prescribes it.

When Mentor Perspective Is Useful

There are moments when offering your perspective is valuable - especially when a mentee explicitly asks for guidance or is at a learning stage where modelling is appropriate. But even then, you can frame your expertise as an option, not a directive.

For example:

• “Would it be helpful if I shared an experience from a similar situation?”

  
  

This keeps the mentee empowered, not overshadowed.

Two Key Takeaways to Put Into Practice

1. Run the “Agenda Check” Before Asking Anything

Before you speak, silently ask:“Whose answer am I really pursuing - mine or theirs? ”If it’s yours, reframe the question to be more exploratory and less leading.

2. Replace Prescriptive Curiosity with Genuine Curiosity

Shift from:

• “Why didn’t you…?”

  
  

  To:

• “What was influencing your choices at the time?”

  
  

This reduces defensiveness and increases self-reflection ...the key ingredients in effective mentoring.

Am I leading the witness ??