Shadow sessions — how to watch the work

TL;DR. A shadow session is a 90-minute observation, not an interview. The operator does their work; you watch and record three columns — what they did, why (when volunteered), where the friction is. Friction is the most underrated signal. The closing three questions extract the highest-density information.

The principle#

You are not interviewing. You are watching. The operator does their work; you ask the minimum questions needed to follow what they are doing. The interview comes later, in the Co-design beat.

The setup#

• 90 minutes, scheduled at a time the operator is doing real work.
• One observer; never two — two observers signal "we are auditing you."
• Screen sharing or in-person, with permission to take notes.
• A defined boundary: which workstream you are shadowing, not "your whole job."

What to record#

Three columns in your notes:

• What they did — concrete steps in the operator's words.
• Why — only when the operator volunteers it; do not interrogate.
• Friction — pauses, sighs, copy-paste, switching tools, reaching for a sticky note.

Friction is the most underrated column. It is where the workflow improvements live. The operator may not even notice the friction; you have to.

What to ignore (in this session)#

• Tool ideas. They will come naturally in Co-design.
• "Why don't you just …" suggestions. Not yet.
• Documentation discrepancies. Note them; do not correct them.
• Anything that requires judgment about whether the work is good.

The closing 10 minutes#

Three short questions, asked in order:

1. "What part of this would you most like to never do again?"
2. "Where do you most often have to redo something?"
3. "Where do you most often help someone else who is doing this?"

Capture answers verbatim. They are the highest-density signal you will get from the whole session.

After the session#

Within 24 hours:

• Tidy the notes.
• Identify 3–5 friction points worth probing in Co-design.
• Identify 1–2 candidate Cowork workflows.
• Share notes back to the operator for accuracy. Their corrections are themselves diagnostic — what they correct tells you what they care about.

Common shadow-session mistakes#

• Talking too much. Talking to learn instead of watching to learn.
• Interrupting to suggest a tool. Save it.
• Trying to fix the workflow during the session. Save it.
• Recording what the operator says they do, instead of what they do. The two diverge often, and the divergence is the gold.

How many shadows per role#

• Two for each highest-leverage role.
• One each for adjacent roles.
• For the pilot owner: a Tinkso engineer shadows them for half a day.

Tinkso's take#

The session before lunch is always more productive than the session after. People who are tired do their work differently — and that difference is itself useful, but only if you have a baseline. Shadow people fresh first; tired second.

Try this#

Before your next pilot, run one 90-minute shadow on the role you think is the highest-leverage. Take notes in three columns. The exercise will either confirm that you picked the right role, or redirect you to a different one. Either result is a win.