Empathy interviews for transformational coaching

Empathy interviews for transformational coaching

I coach and mentor leaders in organizations that want to transform and learn to adapt to change successfully. As a coach starting to serve an organization, I need to learn a lot in order to be an effective agent promoting change.

Understanding the people involved is critical to a successful engagement. I also want to go beyond the individual and see where patterns start to emerge.

Empathy interviews are a technique I have used to help with these goals.

What are empathy interviews?

Empathy interviews were initially associated with Design Thinking and were used to relate to and build empathy around customers. They are one-to-one conversations where open-ended questions are used to better understand customer experiences, emotions, needs, and behaviors.

I first heard about empathy interviews related to workshop facilitation from Jean Tabaka back in 2016. I have interviewed stakeholders and participants for large, important meetings and workshops. The interviews absolutely have revealed important considerations to me as a facilitator.

I have discovered stakeholder conflicts over meeting intent, organizational political concerns, gaps in understanding, and other issues. I have resolved issues prior to meetings and revealed issues in order to ask related questions during meetings. The result has been more successful interactions and collaborations.

I won’t go into further detail here regarding facilitation-related empathy interviews. There is an excellent series of posts on Elevate To’s blog by Erik Willeke and Rosemary Astra-Blossom. It is worth reading if you want to know more.
Empathy interviews for transformational coaching

What am I trying to understand through interviewing?

I want to understand things about the interviewee, including their values, motivations, perspectives, ideas, and perceptions.

I also want to understand how they view the organization. What are the outcomes they want to see in its transformation? What are their expectations? How do they view the organization and its challenges and opportunities? What are their behaviors? And how do they support their perspectives?

I also want to know enough to draw a bigger picture. How common are the perceived challenges people discuss? What is the language people use? What circumstances are they reacting to? What are they saying that may reveal common cultural ideas? What barriers do they feel they have control over and which have they accepted as intractable?

How do I hold interviews?

I try to keep the interviews to half an hour in length. If I am meeting with a stakeholder for the first time, I may extend this to 45 minutes to account for introductions and for building trust and understanding. In my experience, going for an hour tends to be too exhausting for the people being interviewed.

A primary goal is to have an open conversation. I refrain from providing input or perspective during the interview. My goal is to hear as much as possible from the person I am interviewing.

While I have a set of prompting questions I draw from related to transformation context, perceptions, and intent, I keep the conversation loose. This leaves room for clarifications, some deeper dives into an area where there is a lot of energy, and unexpected insights.

I agree to keep the specific conversation confidential at the start of the session. I do, however, reserve the right to aggregate the results of the interviews into presentations, and I mention that I may share some selected ideas or paraphrase comments without attribution with leaders and other coaches to help the transformation along.

Ideally, the interviews are done with three people — the interviewer, the interviewee, and a notetaker. The notetaker’s role is to capture responses (ideally, the exact wording) as well as other observations. I ask the interviewer to pay close attention to not just the words but the interaction and reactions. There have been times I have done the interviews one-on-one; however, I find it challenging (actually, impossible) to capture all the details I’d like when I do.

Whom do I interview?

Depending upon the context, I may interview around 10 to 15 people. I target people within each silo or group involved with the change. One organization I worked with had a few business stakeholder departments, a transformation office, a PMO, and the target delivery organization. I interviewed select people from each of these groups with the target organization as a focus.

I also try to engage multiple levels within the target organization. I recommend interviewing some middle management and delivery team members as well as the C or director levels to help get a holistic picture of the environment, organization, politics, and culture.

What are some of the questions I ask?

Half an hour isn’t a lot of time for an interview, and I also don’t want to rush the conversation. After accounting for opening and closing the conversation, I may have time for between three to six prompt questions (perhaps with some follow-up questions), depending upon where and how the conversation goes.

I do have some common, open-ended prompt questions I ask, but I also come up with contextual questions.

Some common prompt questions I select from include the following:

  • What is your experience with this kind of transformation in this organization or outside of it?
  • What outcomes are you looking for in this transformation?
  • What are your personal goals in this transformation?
  • What will the change call for in you and your role?
  • As you think ahead to this transition, what has you feeling motivated?
  • As you think ahead to this transition, what has you feeling concerned?
  • Based upon your experiences, how effective do you think this group will be in the transformation?
  • If you were me, what question would you be asking?
  • What should I know that we haven’t spoken about?
  • What questions do you have for me?

I’ve also asked contextual prompt questions.  Samples include the following:

  • What will work best for bringing the business and technology people together for this transformation? What is getting in the way?
  • Previous coaches seem not to have worked out here. What happened with those engagements?

How do I process the interviews?

If someone acted as a notetaker, I ask them to help me process the interviews. Because they are focused on the interaction and comments during the interview, they have valuable perspectives to lend.

I previously used a spreadsheet or document to process what the people I interview heard, saw, said, thought, and felt. I now use an empathy map as a visual organization tool. It helps me to group common things together more easily and see patterns that emerge.

I may also process the results based upon a framework, focus areas, or other lenses to help me see interview comments in a different light. One thing I am starting to experiment with is organizing comments into four integral areas related to Leadership & Mindset(I), Practices & Behavior(It), Organizational Architecture & Systems(Its), and Culture & Relationships(We).

Viewing the situation through this lens helps me understand where the organization (and the people inside it) gravitate. This leads to me being more effective in meeting the organization where it is and opening up transformation possibilities related to their needs and motivations.


Empathy interviews are one way to deepen connections with the organizations I work with. Taking the time to interview and understand people in the organizations lets me empathize with them more deeply, which leads to better relationships. Assessing the interview results reveals things to me I wouldn’t otherwise see, leading to better possibilities for successful transformation.

What do you think helps you better understand the people and organizations you work with?  Join me in conversation on LinkedIn to discuss! (You need to be a member of that LinkedIn group. Request entry here if you’re not a member.)

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This is an Agile Alliance community blog post. Opinions represented are personal and belong solely to the author. They may not represent the opinion or policy of Agile Alliance.

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Kenneth Roberts

Kenneth Roberts

Ken Roberts is owner and trainer at Better Ways Agility, LLC. He is passionate about creating environments where learning cultures emerge and organizations can adapt to change. He believes the power of collaboration helps people and companies grow. Ken is an experienced Transformation Consultant. He has helped organizations large and small shift the way they work, resulting in better customer value delivery and deeper engagement through collaboration. Ken has been involved with multiple industries including…

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