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Severin Sorensen

Effective Questioning in Executive Coaching: Strategies for Success

We all ask questions, but do our questions serve powerfully in our coaching sessions? Do they inspire further investigation? Do they invite our clients to dive into issues, and ponder what their goals and ambitions are? If not, are they merely pushing the conversation along? Continue reading to explore what questions are, the usefulness of powerful questions, and seven practical tips on asking powerful questions. If this topic piques your interest, tune into Episode #1021 of the Arete Coach Podcast where we explore powerful questioning and the use of this tool in executive coaching situations.



Originally released in 2021, this article has been revised to incorporate four pre-questioning considerations.


What are questions?

Questions are statements that seek to clarify or further understand information or details. But what determines if they are “powerful” or “bad”? A question’s worth is determined by the usefulness it provides to a conversation.


Powerful questions support a client’s goals, inspire reflection, and help them reach their fullest potential. While there are many valuable questions to ask, the most valuable questions support a client’s journey to their best self. For example, powerful questions can be future-based such as, “Two years from now, where do you want to be?” This question addresses current goals by association to future completion and allows the client to pave their way to success in their own words.


Bad questions simply push the conversation towards an unimportant topic or only serve to avoid silence. For example, imagine if during a session you began to ask about the weather for a prolonged period of time. The weather has little to do with your client’s circumstances or goals, and only serves to avoid silence.


Why are powerful questions useful?

As stated previously, powerful questions push clients to ponder their situation and inspire them to reach their highest potential. According to Terry Heick, “questions seek and frame and expose” important information and topics (2021). Questions allow executive coaches a chance to learn more about their clients, and give clients an opportunity to follow a potentially new thought pattern. If a client has never directly been asked what their overall goal is, have they ever been given the opportunity to explore the idea? By voicing their thought process, they can further develop their own understanding of their goals and receive feedback, direction, and insights from their executive coach. Heick summarizes the importance of powerful questions in his quote:


“The right question at the right time can make a learning experience, because more than anything read, drawn, or even written, a question is acute and properly troubling. It creates a needle-point of light even as it suggests darkness.” -Terry Heick


As executive coaches, it is our job to teach our clients how to reach their full potential. This requires that both the coach and client develop an accurate understanding of what that potential is. This understanding is taught to the client through questions and supported by timely responses and a respect for silence. Allowing clients to ponder in silence offers immeasurable opportunities for growth in these moments of self-reflection.


7 types of powerful questions

Understanding By Design, a comprehensive work by Jay McTighe and Grant Wiggins, identifies seven essential aspects of powerful questions (2004-2012). These principles can be applied by executive coaches in their sessions to further their client’s learning and growth to their fullest potential and best self.


Open-ended questions

Open-ended questions do not typically have a single, final, or correct answer. They are questions that invite the client to open a dialogue of their choice. These questions are a lot like brainstorming. They make room for creativity in response and give the client the freedom to explain, elaborate on, or clarify topics that are important to him/her.


Questions like these allow for both the client to learn by pondering and the coach to learn by client-led revelations. Open-ended questions also offer advantages that closed questions fail to account for. According to Schuman and Presser, closed questions can create bias in the client by naturally seeking to maintain social desirability (1979). Open-ended questions offer the client free reign on how they will voice their beliefs. An example of this can be seen in the following conversations:


Open-ended question

Coach: “How do you feel about your employee’s behavior in the office?”

Client: “I feel like it was justified, but still inappropriate for the workplace. I think I will need to take disciplinary action regardless.”

Coach: “What do you think the best outcome would be for the situation?”


Closed question

Coach: “Do you think that your employee’s behavior was wrong?”

Client: “Yes, I think in some ways.”

Coach: “Are you going to write them up?”

Client: “Probably”


The coach who asked the closed questions lost valuable information about his client’s opinions and stance towards the topic at hand. The closed question coach doesn’t know that the client feels his employee’s behavior was justified or his employee’s plan of action.


By asking an open-ended question, the coach in our example was able to ask more questions and gain additional insight into the topic at hand. Their discussion began with the topic of an employee’s behavior and then invited the client to ponder what they believe would be the best outcome. This open-ended conversation helps the client understand what they want out of the situation at hand and gives the coach insight to their desires which allows them to aid the client better.


Thoughtful questions

Thoughtful questions spark discussion or debate. They invite the client to question their stance on their goals and beliefs. These questions support intentional action that moves the client from reaction to thoughtful decision.


David Wind, CEO of Eduflow, suggests a few types of questions that provoke thought. Wind states that “the ability to consider many possible solutions instead of just one” is a valuable way to invoke thought (2020). Questions that widen the frame of perspective for clients allow them to ponder other potential courses of action and different ways of reaching their goals. The goal of these questions is to move the client from “passive receptor” to “active participant” in the creation of their own goals, the development of their best self, and the understanding of their “unique perspective” (Wind, 2020).


Higher-order analysis based questions

These questions encourage clients to analyze and practice higher-order thought of what they have learned in their experiences with their own career path, their coach, or materials provided outside of the coaching session (Wind, 2020). Questions like these often use what Wind calls “causal reasoning” (2020).


Causal reasoning leads clients to refer to the knowledge they currently have and apply it to their life. An example of causal reasoning would be asking a client: “Based on the reading I gave you after our last session, what are some changes you might make to your daily life practices?” This question specifically asks clients to question the cause-and-effect that the reading had on their life. By intentionally asking questions that analyze information and previous learnings, clients can become more comfortable with analyzing their current situation based on new information and experiences.


Questions that focus on important ideas

Powerful questions hone in on the important ideas at hand. These questions refrain from beating around the bush and directly tackle issues. Unfortunately, this can be a challenge to new and experienced coaches alike. It can be daunting to ask questions that confront issues or inconsistencies, but it is essential for growth and can be done with tact.


Mcdaniel of Vanderbilt University recommends that before entering potential “hot button” topics into the discussion, consider how they will be valuable for the client (2021). Will they careen the client into action towards their highest-self? Will they appreciate the confrontation later on in life or will it only discourage the client? Being purposeful in times of difficult discussion is challenging, but important. In the words of Christopher Hitchens:


“There can be no progress without head-on confrontation” - Christopher Hitchens

By choosing to focus on important topics and asking relative questions, we can embrace the potential that comes with confrontation and change.


Additional questions

Additional questions offer the client more time for reflection and reaffirmation of established ideas. Often referred to as follow-up questions, additional questions dive deeper into the present goals and concerns addressed by the initial answer.


In an article by Winston Resources, there are three central ideas that can be used to formulate additional questions. The first of these ideas is “asking the original question in a new way” (Why, 2014). By repeating questions the client can be encouraged to go into more detail and dive deeper into their reasoning. It is important when re-asking questions to remember that silence between the answer and question is okay and encouraged. This silence allows the client to ponder on the issues at hand in a deeper more purposeful way.


Secondly, it is recommended that you “link” a client’s answers together. This tells clients that you are painting a full and more detailed picture of them and also gives them the opportunity to correct you as the coach if needed (Why, 2014).


Lastly, ask clients about the “ramifications” of their answers (Why, 2014). This leads clients in further analysis of their own ideas and gives an opportunity to confront any unmet goals that may arise as a result of decisions.


Questions that need additional support

Questions that need additional support often regard asking a client their opinion or belief on specific situations. By talking with clients about their reasoning and justification for their actions and behaviors, coaches can encourage more intentional action based on the goals that their clients want to achieve. This reflection can give way to further realization of the gaps between their reality and their goals. Answers that require evidence and information to back up claims strengthen the client’s claims or encourage the client to address possible misconceptions and errors of logic that they may hold.


Repeated questions

Repeated questions allow both the client and coach to monitor the growth and progress that is being made after attending sessions. It is recommended that coaches keep notes of the goals and measurable actions that have been given to clients between sessions.


Revisiting these goals and topics offers the client and coach an opportunity to celebrate success or address potential issues. When potential issues with the former plan of action are addressed, a conversation can be built around why this plan didn’t work for the client and what other plans could be made to help them achieve their goals.


If the goals were achieved, a moment of celebration helps the client realize the benefit that they are receiving from their coaching sessions. Having moments of reflection on success further establishes the importance of the actions taken to achieve the goal and increases the confidence of the client in their own ability.


Examples of powerful questions

  1. Open-ended questions

    1. “What is the best outcome that you believe could come from this situation?”

    2. “Can you explain…”

    3. “Tell me more about…”

    4. “How will you know if this implementation is on track?

    5. “What would success look like…?

  2. Thoughtful questions

    1. Tell me what you think your employee’s stance on this issue is?

    2. Have you considered…?

    3. I’m puzzled about ____, can you tell me more about…?

  3. Higher-order analysis based questions

    1. Based on your previous experience with this individual, what do you think…?

    2. In our last session, we talked about teaching independence. What do you think a good outcome of that discussion was?

  4. Questions that focus on important ideas

    1. You recently stated that you are interested in a new business venture, what are some concerns that are holding you back?

    2. What is the most important goal you have right now?

    3. Can you tell me more about how this goal is important to you?

  5. Additional questions

    1. What kind of effect do you think this decision will have on others?

    2. Can you clarify your goal in this situation for me?

  6. Questions that need additional support

    1. Why do you think this is your best course of action?

    2. How will this lead you to your overall goal?

  7. Repeated questions

    1. How has your goal of … been going?

    2. What are some differences you’ve made this past month to help you reach your goal?


4 considerations for asking the right questions

Equally crucial to knowing which questions to ask is grasping the factors that warrant consideration before posing any questions at all. Below are four key considerations to keep in mind before asking questions, ensuring that you effectively guide executives and leaders toward valuable insights and growth.


Avoid asking “why”

When framing questions for effective coaching, avoid using "why" as it might come across as confrontational. Instead, explore intentions or reasons behind actions with questions like "What was your intention with that?" This approach allows for a more engaging and insightful conversation with your direct report (Jen Su, 2014).


Aid clients in self-discovery

When collaborating with executives, it's common for individuals to become defensive when their weaknesses are brought to light. As executive coaches, our objective is to help clients cultivate a deeper self-awareness, ultimately reducing the inclination to become defensive. This transformative process typically begins with a simple question: “What am I not seeing?” (Schwartz, 2022).


Encourage adaptive leadership 

The article "Asking the Right Questions About Leadership" from the "American Psychologist" journal presents five critical questions that reshape our understanding and research of leadership. These questions, along with the insights derived from them (as shown below), are crucial for executives working on leadership development and coaching. They provide a framework for understanding the dynamic and context-sensitive nature of leadership, emphasizing the importance of adaptability, individual traits, and learning from experiences (Hackman, 2007).

  • Context Sensitivity: Understand when leadership is most impactful, recognizing the influence of external factors like resource availability.

  • Individual and Situational Synergy: Encourage leaders to blend their unique traits with the demands of their specific situations, promoting diverse leadership styles.

  • Differentiating Leadership Quality: Help leaders understand the qualitative differences between effective and ineffective leadership, focusing on key functions rather than control.

  • Redefining Roles: Promote a fluid understanding of leadership and followership, encouraging shared responsibilities and collaborative decision-making.

  • Facilitating Learning: Guide leaders to learn from experiences, especially failures, by challenging their assumptions and fostering emotional maturity (Hackman, 2007).

Center yourself before beginning a session

Before starting your coaching session, take a moment to center yourself. Allocate a few minutes to engage in deep breathing and reflection, setting aside any distractions from your day. This time is also ideal for reviewing your notes from the previous coaching session, helping you reorient and continue the conversation effectively. This preparatory step ensures you're fully present and ready to listen actively during the coaching session (Jen Su, 2014).


References

Arete Coach Podcast, e:1021, “Exploring Powerful Questioning,” 3/29/21, with podcast host Severin Sorensen.


Hackman, J. & Wageman, R.. (2007). Asking the Right Questions About Leadership: Discussion and Conclusions. American Psychologist. 62. 10.1037/0003-066X.62.1.43. 


Jen Su, A. (2014, December 12). The Questions Good Coaches Ask. Harvard Business Review. https://hbr.org/2014/12/the-questions-good-coaches-ask.


Mcdaniel, R. (2021, February 18). Difficult Dialogues. Vanderbilt University. https://cft.vanderbilt.edu/guides-sub-pages/difficult-dialogues/.


Schuman, H., & Presser, S. (1979). The Open and Closed Question. American Sociological Review, 44(5), 692–712. https://doi.org/10.2307/2094521.


Schwartz, T. (2022, November 21). To Coach Leaders, Ask the Right Questions. Harvard Business Review. https://hbr.org/2022/11/to-coach-leaders-ask-the-right-questions.



Wiggins, G., & McTighe, J. (2004-2012). Understanding by design. Association for Supervision and Curriculum Development.


Wind, D. K. (2020, September 28). How to Write Discussion Questions That Actually Spark Discussions · Eduflow blog. RSS. https://www.eduflow.com/blog/how-to-write-discussion-questions-that-actually-spark-discussions.


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