Leadership Coaching Questions

Leadership coaching questions are the types of questions used when you're coaching someone to guide them on this journey you've commenced together. We've looked at how to identify great coaches and now we're moving onto the particulars of questions used in a coaching environment.

We can't stress enough how interesting and important this section is for learning and being trained to coach WELL. Further than that, the hope of every coach is that the person being coached will be able to take on the skills themselves to partially coach themslves through situations and then pass on this ability to coach others.

Leadership coaching questions are the bread and butter of life coaches, but also anyone in a coaching situation of any kind. Great questions will help you succeed and find out the information necessary for quick and efficient resolution. Too many 'coaching' conversations follow the following pathway'



Coach: So, how have you gone since we last talked?


Coached: Oh pretty good really...

Coach: How have you gone implementing the goals we discussed last time?

Coached: Yeh, i've started doing it and it's working

Coach: Great! Is there anything else you want to talk about?

Coached: ... Ummm i'm not really sure.

Coach: Ok...


This is not helpful at all - it's great to follow up and find out but how could we develop this conversation? Maybe ask probing questions about how exactly the goals have been outworked? Talk about the cconsequences of what's been applied?

Developing Coaching Conversations and Questions

Before i go ahead and take you through the different types of questions I wanted to give some credit to a leader who helped teach me about these questions. Scott Wilson who is the creator of the Institute for Creativity, Leadership and Management changed my own leadership journey dramatically and through his training I learnt a vast amount including some of this material. Scott is a great voice in the leadership/management world and has had a great impact on my perception of positive leadership.

Questions are the foundations of conversations, great questions will help guide a great conversations but bad questions will do the opposite. You may ask what are good questions? And the answer to this is; the best question for the situation. Follow the different types of questions below.

  • Open Questions are ones which allow the respondent to share anything they want to say and give them the ability to lead the conversation to place they desire. Open questions are usually short and include the why, who and how kind of language.
  • Closed Questions are generally used by the coach to evoke an end to a particular line of conversation or push out a particular answer. They often imply a yes or no type of answer and don't let the respondent reply with a longer more open answer.
  • Extremely open Questions usually follow on from open questions to delve a little deeper. It usually implies how the respondent feels about something or what they thought about a certain situation they responded about. It opens the door to take a conversation to the next level. This is one of the best leadership coaching questions as it takes a conversation in a deep direction which will reveal some interesting motivations.
  • Leading Questions are used by coaches to lead a conversation in a certain direction. Usually the coach will have an idea about where the conversation needs to go to be useful and bring answers that the respondent needs. Leading questions are very strategic and directive but used properly help to keep the conversation on topic and actually making ground on a resolution.
  • Probing Questions are always a lot of fun. Coaches use these to probe into what's happening in the respondents mind and usually helps unlock thoughts and feelings the respondent never knew existed (usually helping to bring the current issue to a close). As far as leadership coaching questions this one will help reveal a good amount of information about the resondent.
  • Hypothetical Questions bring in the creative part of conversations. Usually the coach will ask a hypothetical question to see what the respondent would say or do in a made up situation which reveals a lot to the coach about the respondent. Often thinking outside of a situation will help to open up the respondent to a new way of thinking and application of their response to current issues.
  • Open Self Persuasion Questions are linked in with hypothetical questions but help develop the paradigm of the respondent convincing themselves of a certain (good) outcome. This tactic is used well in life coaching in-particular as it enables the respondent to find the answer within themselves rather than being told what to do and therefore developing self-reliance.
  • Empathetic Questions help the respondent understand the feelings of others. This is really important as often in all situations we are unaware of how our decisions and lives impact others. Empathy is vital in leadership, especially when it comes to people. Understand that others will feel differently than you.
  • Consequence and Analysis Questions help open up our minds to acknowledge that our leadership decisions will affect others. There are usually huge ramifications on others through the decisions that the respondent will make and ultimately they will be held accountable for this. Consequence questions shouldn't be brushed by in a holistic approach to coaching.
  • Stage Dive Questions help the coach bring the conversation back to where it should be. Sometimes the respondent takes things off topic or starts to become extremely negative about something - which is a sign to move on. The coach takes a stage dive and changes the conversation immediately to something completely different.
  • Socratic Questions bombard the respondent to get them into a place of thinking about why they're answering the way they are. It often takes the shape of the coach continually asking "But why?" after everything the respondent says. This is one of the more hardcore and assertive type of leadership coaching questions.

These are a survey of great leadership coaching questions. We can't stress how important it is to have a diverse arsenal of questions when coaching. You wont get very far with a standard set of 'Hi, how are you?" you'll certainly need a strategy and plan to help the respondent.

For more resource around leadership coaching questions head back to our coaching and mentoring hub.

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