The hardest part of preparing for an Empathy Interview is figuring out which questions you need to ask. There’s no canned set of right or wrong questions to use, because each workshop’s outcome and the current state of the group participating directly influences the nature of the questions. When a group is new to experiencing proper facilitation, many of the questions will be about hidden concerns, elephants, and safety concerns. Later, the interviews may be much more transparently about interpersonal dynamics, behaviors, and hairy business challenges. Finding the perfect balance of questions will always be challenging, even for the most experienced facilitators. However, this post highlights some of the key challenges


Before writing questions, it’s important to ground yourself in three critical aspects that will help you achieve the proper mindset and framing as you prepare for the empathy interviews.

Goals of empathy interviews

The outcome of the interview is very focused: ensure the most impactful workshop experience possible. I explore a deeper list in this post, but the short version is incredibly grounded in this servant leadership mindset. Don’t let the process become mechanical or uninformative, because even the most repetitive cadenced leadership workshops will evolve every time and should be yielding fresh insights each time.

The purpose of the workshop

Every workshop should have a well-defined purpose before it’s scheduled, often in the format “TO <immediate outcome to accomplish> BY <key activities in the workshop> SO THAT <the larger purpose the outcomes are advancing>.” Reviewing these pieces carefully will help you align your servant leadership intent against the needs of the team in THIS workshop.

The journey of the attendees

Facilitated events take place in a context defined by the business pressures and the experience of the people in the room with both the mindset and the subject matter of the specific event. A key part of the empathy interviews is to both predict and validate where people are on this journey. Experienced participants will find themselves bored by elaborate instructions and the work to create intense clarity at the same moment that new attendees will find themselves bewildered by the cryptic activities and instructions. At the very same moment in the same room.


The process of generating your questions is fairly straightforward, and goes something like the following:

  1. Reflect on the context, as above.
  2. Write down questions exploring goals of the workshop.
    Explore the TO and SO THAT pieces for alignment traps and concerns
  3. Write down questions exploring any concerns you think people may have about the flow of the workshop.
    Explore the BY section for confusion and lack of readiness for the activities
  4. Write down questions to probe for any safety-related or “I’m in” concerns you might have.
    Reflect on any organizational drama or concerns you’ve heard about
  5. Capture questions teasing out the participants and any excess or missing people that could impact the safety of participants to fully engage or the success of the workshop.
  6. Capture questions that expose people’s reactions to the common risks encountered around incentives, team formation, low clarity, low safety, etc.
  7. Reduce your list to a small set of “must have” questions and a couple extra “like to have” questions.
  8. Share the selected questions with others familiar with the organization and update based on the feedback you receive.
  9. Wordsmith the questions till you’re happy and can feel natural asking them.


Questions to avoid

There are a few topic areas to avoid entirely:

  • Personal questions around home lives, medical conditions, etc. unless the interviewee brings it up as relevant. If it’s off limits for HR, it’s probably off limits for you too.
  • Accusational questions that make it sound like you’re attacking the interviewee or are already biased to the responses.
  • “Selfish” questions that focus on your immediate needs or objectives in the organization rather than the goals and outcomes of the workshop.
  • Factual questions easily answered elsewhere. This is like a sales rep showing up and asking “So what does your company do?” without looking at the website first.
  • Throw-away questions. Minimize small talk and demonstrate the value you put on your attendees’ time.

How many questions?

When it’s all said and done, most questions take 3-4 minutes to explore deeply, and relatively few take less than 2 minutes. As such, I encourage people to take the total time they have available, shave off 6-8 minutes for introduction and closing, and then divide the remaining time by three minutes per question. This becomes your “must have” allowance of questions. Then, add a couple extra questions that you’d love to explore if you have time.

Example #1: 15 minute interview: 9 minutes for questions, expect 3 answers, and have two extra ready.  
Example #2: 30 minute interview: 24 minutes for questions, expect 8 answers, and have two extra ready.

Example questions

This section has pairs of questions, first a poorly phrased question, followed by a better one. The general framing is to avoid closed (yes/no) questions, and wherever possible, ask questions that guide people into storytelling mode rather than factual answer mode.


Do you think the organization is well aligned?
Can you share an example of where alignment across managers either really helped or really hindered the organization?


Are people able to tell say what they mean?
What do you see that informs you if people feel safe to share their opinions?


Do people feel like it’s safe to make mistakes?
What stories do you have of how people are treated when they make a mistake at work? What happened?


What’s the strategy next year?
What do you personally think are the most important things for the organization to focus on next year?


Do people work together well?
How have you seen people work together most effectively here recently? Did that feel abnormal or different?

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