Posted by Sylvia and Julia from Plenum

Define the objective of the process and identify an appropriate target person to shadow. The target person and the context should be both interesting and unfamiliar.

• Make an appointment with the shadowee.
• Let the person you wish to shadow know that you are interested in just following his/her daily practice and routines and that there is no need for any special program or treatment.
• There is no need for him/her to set aside extra time for you except at the end of the day for the closing/debriefing interview (30 minutes – 1 hour). This could also be done during lunch or dinner.
• Let the shadowee know what you are particularly interested in learning about. The shadowee can select the best day for your shadowing experience.
• Confidentiality: clarify that anything you observe or hear will be handled confidentially.

On the morning of the shadowing day, prepare and take 10-20 minutes prior to the exercise to:
• Focus on the purpose of the shadowing: what do you want to learn?
• Imagine the best possible outcome of the day for you and for your shadowee.
• Connect to the future that you want to create. Think about how your shadowing might be a small first step in that direction.

Once you arrive in the office of your shadowee, create transparency and trust about the purpose and the process of the shadowing exercise. Establish a personal connection early on; use observations in your interviewee’s office or return to themes that came up during the first moments of the conversation to establish a personal connection. Let your shadowee know that whatever you learn during the day is for your personal use only and won’t be shared with others. During the shadowing exercise listen with your mind and heart wide open, take notes, and follow the principles above.

Debriefing Interview: At the end of the day or during lunch, conduct a brief interview with the person you shadowed. Bring up any questions that the observations throughout the day sparked in your mind. Here are a few questions that you might consider.

Sample questions for de-briefing:
1. What journey brought you to your current position?
2. What good and bad examples of leadership have you experienced?
3. What key challenges are you currently dealing with?
4. What is your work as a leader? What in your organization would be missing without you? What value do you add?
5. When you started in this position, what did you have to let go of (unlearn), and what new competencies did you have to develop?
6. What barriers exist in the current system that prevent your team/organization from realising its potential more fully?
7. What personal practices do you use to tap into your best potential?
8. After all interviews have been completed, review the interview data, and summarise results.

“Debrief” and crystallize right away. Capture observations and insights in your journal. Don’t make phone calls or have conversations between your shadowing experience and recording your thoughts and impressions. Use a structured debriefing process as suggested below, if possible.
1. What are your 2-3 key observations from today?
2. What are their implications for your own work?
3. What were 2–3 important leadership challenges your shadowee faced today?
4. What was an intervention the shadowee made that changed the course of events?
5. Reflect on interventions that have failed.
6. Were there moments you felt uncomfortable with how things went? Why?
7. Were there moments you felt inspired during the day? Why?
8. What other things did you notice about your self?
9. Other observations or key take-aways?

Send a thank-you note: within 24 hours, close the feedback loop by sending your shadowee a brief email or voicemail to say thank you for the day. You can also use it to say something about the most important insight you gleaned from the day or the closing interview.