Where are U: 

Shadowing is part of the seeing and sensing phase on the left side of the U.

At a Glance: 

Shadowing means that a person accompanies somebody for a defined period of time to observe him/her during work and learn from this observation.

Shadowing allows the person who shadows someone to:

  • Observe and learn from an experienced practitioner/leader
  • Step into someone else’s daily work experience
  • Connect to someone who is facing similar challenges

The purpose of shadowing is to observe and absorb practical and intuitive knowledge from a colleague, customer, or an otherwise interesting person, and by doing so, gain a new perspective on your own work.

Uses & Outcome: 
  • Real-time insights on practices of an experienced leader
  • Informal access to the daily routines of leadership work without being “on stage”
  • A deeper understanding of the leader’s work
  • The identification of barriers to and opportunities for leadership that need to be addressed
  • An expanded personal network
  • New ideas for your own leadership practices
  • Enhanced clarity about your own leadership challenge profile through the lens of the shadowing experience.
Set Up: 

People & Place
Participants identify a possible shadowee, and then visit the person for a day.

Minimum of half a day; a full workday is preferred.


Step 1
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.

Step 2

  • Make an appointment with the shadowee.
  • Let the person you wish to shadow know that you are interested in just following her daily practice and routines and that there is no need for any special program or treatment.
  • There is no need for 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.

Step 3
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—and 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 below.

Step 4
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 realizing 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 summarize results.

Step 5
"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 was your shadowee facing today?
  4. What was an intervention the shadowee made that changed the course?
  5. Reflect on interventions that have failed.
  6. Were there moments I felt uncomfortable with how things went? Why?
  7. Were there moments I felt inspired during the day? Why?
  8. What other things did you notice about your self?
  9. Other observations or key take-aways?

Step 6
Send a thank-you note: close the feedback loop by sending your shadowee a brief email or voice mail to say thank you for the day (within 24 hours). You can also use it to say something about the most important insight you gleaned from the day or the closing interview.


Shadowing works best when participants select a person they don’t know and a business area that is unfamiliar or “at the other end of the corporate universe.”
Shadowing is not an interview or a visit with an old buddy. It does not follow a structured program.

Suspend your voice of judgment (VOJ) to see the situation with fresh eyes. Observe. Observe. Observe. Try to look at the situation from the perspective of a video camera, or a first day at work, or that of a researcher. You haven’t visited or been to meetings in this company before. You just see this person working through the day trying to get things done. What matters at this point is not whether or to what extent his working environment, meetings, or colleagues are similar to or different from yours. You can assess that at a later point. You are there to observe and become immersed in how the day is evolving.

Access your ignorance: As the day unfolds, pay attention to and trust the questions and observations that occur to you; record questions and important observations in your notebook.

Be empathic with the person you shadow and his/her environment: try to observe from the other person’s perspective. Sympathize with the person and his/her task, and appreciate his/her approach and way of handling things.

Use with...: 

Listening and mindfulness tools


At the beginning of a leadership development program, all participants were paired up, and shadowed another participant for a day. This allowed them not only to quickly dive into another part of the organization but also see their own work from a new perspective. Both parties, shadowee and shadower, gained new insights, and questions about their work. This experience became the kick-off for more comprehensive leadership work.


C. Otto Scharmer, (2009) Theory U: Learning from the Future as it emerges. Berrett- Koehler: San Francisco. Chapter 21.