Clean the Lint Filter by Work Shouldn't Suck

Month 3 of 7

The Art of Really Listening

Looping, seeking to understand, and the skill everyone thinks they have.

This month's lens comes from non-caucused mediation, with hostage negotiation as its stress test.

Most people listen to respond. This month is about learning to listen to understand, which sounds obvious and is genuinely difficult, and looks completely different in practice. The cross-sector insight comes from two unlike places: professional mediation and hostage negotiation. Both fields discovered through hard empirical testing that the fastest way to get somewhere is to make the other person feel completely heard first.

Download this month's worksheet (PDF)
The central lens

Looping is a technique from mediation practice: you reflect back what you heard until the other person says “yes, that's it.” This is harder than paraphrasing. It is not a summary. It is the experience of being understood. When it works, it changes the chemistry of a conversation in ways that are hard to describe but immediately recognizable when they happen.

This month also introduces the levels of listening, a framework developed across coaching, organizational learning, and communication research that describes how we move from self-focused listening (planning your response while someone speaks) to focused listening (attending to their words) to global listening (attending to tone, body, and what is not being said). Most people in most workplace conversations are listening at the first level. Looping requires the third.

This month’s move: Looping. Once a day, in one exchange, make it your only job to reflect back what you heard until the other person says “yes, that’s it,” before you say anything about your own view. Use the prompts: Do I have it right? Is there more? What matters most to you about this?

Recognition cue: A conversation is ending and you realize you understood their position but not what matters to them about it, or you notice you could not restate their view in a way they would accept.

Write one line on your log each day you run it.

The solo variant

Run the rep in any conversation, work or not. Looping does not require a partner who is also doing the curriculum. Find one person for a single 10-minute looping exercise mid-month, then debrief what it felt like to be on each side.

Live Session Agenda (90 minutes)
Run of Show
0:00–0:10Check-in Share one moment from Month 2 where you caught yourself mid-story.
0:10–0:25Core concept Looping for understanding. The levels of listening. Why reflecting is not agreeing.
0:25–0:55Looping practice in triads One speaker, one listener, one observer. Rotate. Use real workplace situations.
0:55–1:15Debrief What did it feel like to be truly heard? What made it hard to loop accurately?
1:15–1:25Set the daily rep and meeting hook.
1:25–1:30Close.

Looping prompts:

  • Do I have it right?”
  • “Is there more?”
  • “What I am hearing is ... Is that accurate?”
  • “So from your perspective, what matters most is... Is that right?”
  • “And the impact on you is that you feel ... Is that close?”

Meeting hook for this month: In one conversation where tension is present, make it your only job to loop until the other person says “yes, that's it” before you say anything about your own perspective. Use the looping prompts.

Session handouts & frameworks
Session HandoutLOOPING (Understanding in Conflict)

Looping is not paraphrasing. You reflect back what you heard until the other person says “yes, that's it.”

The sequence:

  1. Listen without planning your response.
  2. Reflect back what you heard in your own words, not a transcript.
  3. Check: “Do I have it right?”
  4. If the answer is not a clear yes, ask “Is there more?” or “What am I missing?”
  5. Repeat until they say yes.

Prompts:

  • “Do I have it right?”
  • “Is there more?”
  • “What I am hearing is... Is that accurate?”
  • “What matters most to you about this?”

What this is not: agreement. You can loop someone fully and still disagree. The loop creates the conditions for the real conversation.

Session HandoutNVC: NONVIOLENT COMMUNICATION (Marshall Rosenberg)

Four parts, in order:

  1. OBSERVATION: What I saw or heard. No evaluation. “When I see/hear…”
  2. FEELING: What I feel in relation to what I observed. “I feel…” (not “I feel that you…”)
  3. NEED: The underlying need connected to the feeling. “Because I need/value…”
  4. REQUEST: A specific, doable action. “Would you be willing to...?”

Example: “When the meeting ends without a decision (observation), I feel frustrated (feeling) because I need clarity to do my job (need). Would you be willing to close with a clear next step? (request)”

Session HandoutLEAP (Dr. Xavier Amador)

For working with someone resistant, entrenched, or seeing the situation very differently:
L — Listen. Fully. Without planning your response. Your job is to understand, not persuade.
E — Empathize. Demonstrate you received what they said: “That sounds really frustrating.”
A — Agree. Find any genuine point of agreement, even one thing. Not false agreement.
P — Partner. “What would it look like for us to work on this together?”

The sequence is deliberate: you cannot move someone toward your position until they feel fully understood in theirs.

Practice scenarios

SCENARIO 1
A board member opposes a strategic direction and seems unwilling to engage with evidence. In pairs, one plays the resistant board member. The other’s only job for five minutes is to loop them until they say “yes, that’s it.” No persuasion. What is hard about staying in the loop?

SCENARIO 2
A colleague tells you in a one-on-one they feel left out of decisions. Write what you would say using NVC: observation, feeling, need, request. Then say it aloud. What feels awkward?

SCENARIO 3
Two colleagues keep having the same disagreement. Person A states their position for two minutes. Person B loops it. Person A confirms or corrects. Swap. Does anything shift when both people feel genuinely heard before anyone advocates?

Cross-sector lens
From the FieldHOSTAGE NEGOTIATION (FBI)
Former FBI lead hostage negotiator Chris Voss built his methodology around tactical empathy, not as warmth but as strategy. The fastest way to de-escalate a crisis is to make the other person feel so completely understood that their nervous system begins to settle. Understanding is the precondition for agreement, not agreement itself.
From the FieldTRANSFORMATIVE MEDIATION
The transformative approach argues that what people in conflict most need is a shift, from weakness to strength (empowerment) and from self-absorption to openness to the other (recognition). Problem-solving before those shifts happen produces agreements that do not hold. The listening phase is not a preamble to the real work. It is the real work.
From the FieldNONVIOLENT COMMUNICATION (MARSHALL ROSENBERG)
Learn more: Free NVC resources
NVC asks us to separate observation from evaluation, and to identify feelings and underlying needs before making requests. The listening practice in NVC is active investigation into what the other person needs, beneath what they say they want.
From the FieldLEAP METHOD (DR. XAVIER AMADOR)
Learn more: LEAP overview
Amador developed LEAP, Listen, Empathize, Agree, Partner, for working with people who resist help or see a situation very differently. The sequence is the point: genuine understanding changes what is even necessary to say. LEAP works with an entrenched board holdout, a betrayed donor, an angry community member. The context changes; the sequence does not.
From the FieldIMPROV THEATER
The improv director in this curriculum’s opening developed their practice in real time with real audiences. The core discipline is presence. “Yes, and” requires you to fully receive what the other person offers before adding to it. You cannot “yes, and” someone you have not heard. Blocking, rejecting what your partner brought, is the organizational equivalent of planning your response while someone is still speaking. Patricia Ryan Madson, who taught improvisation at Stanford for thirty years, frames the most important skill not as wit but as paying attention. That is exactly what looping trains.

Media for this Month
Required before the live session: the Voss podcast (item 1). Budget for it; it runs about an hour and is worth every minute.

Media for this month
  1. REQUIRED · LISTEN Knowledge Project: Chris Voss The FBI's lead hostage negotiator on tactical empathy and looping.
  2. LISTEN Negotiate Anything: The Compassionate Curiosity Framework Explained (Kwame Christian) The host of the popular negotiation podcast on his three-step framework, validate emotions, get curious with compassion, joint problem-solving, which maps almost one-to-one onto looping before you advocate.
  3. WATCH Julian Treasure: 5 Ways to Listen Better TED Talk
  4. ARTICLE The Heart of Nonviolent Communication (Marshall Rosenberg) An excerpt from Rosenberg's book introducing the NVC framework directly in his voice
  5. ARTICLE Marshall Rosenberg Article Archive (NVC Center) Collection of interviews and short pieces by Rosenberg directly in his voice
  6. ARTICLE Excerpt: You're Not Listening (Kate Murphy) The opening chapters that set up the book's central argument
  7. ARTICLE A Conversation With Kate Murphy on Listening Murphy interviewed on why listening is a skill, why we lose it, and what it costs us. It’s a sharp read applicable to any team context
  8. ARTICLE BIFF: 4 Ways to Respond to Hostile Comments (Bill Eddy, Psychology Today) Overview of the BIFF method (Brief, Informative, Friendly, Firm) for responding to charged written communication without escalating. Applies to email, Slack, donor letters, social media, and any inbox message that raises your pulse.
  9. WATCH Oprah Winfrey talks with Thich Nhat Hanh about deep listening Thich Nhat Hanh on compassionate, deep listening: listening with the single purpose of letting the other person empty their heart. Ten minutes that reframe the entire month.
  10. OPTIONAL | BUY THE BOOK *You're Not Listening* (Kate Murphy)
  11. OPTIONAL | BUY THE BOOK *Improv Wisdom* (Patricia Ryan Madson)

Total time for required media this month: approximately 2 hours 30 minutes. The Voss podcast is the longest single item at one hour.

Weekly journal prompts

Week 1: In your next significant meeting, track how long you go before you stop listening and start planning your response. What prompted the shift?

Week 2: Practice looping once in a non-work conversation. What changed about how the conversation moved?

Week 3: Think of someone whose perspective you find genuinely hard to understand. Apply the 5 Whys to their position. Keep going until you find something you did not expect.

Week 4: Think of a recent message you received when someone was clearly activated. Rewrite your reply using BIFF: Brief, Informative, Friendly, Firm. What had to change?

Practice between sessions
Spot the moment (self-check)

Five quick recognition checks. No grades, no tracking. Pick the answer, see the why, move on. Three minutes.

1You loop a colleague and they respond, “sort of.”

What do you do?

Reveal answer

c. “Sort of” means the loop is not closed. The standard is “yes, that's it.”

2A teammate says the budget process is rigged against their department. You loop it back until they say “yes, that's it.”

Have you agreed the process is rigged?

Reveal answer

b. You can loop someone fully and still disagree completely.

3Two different signals, two different moves.

Which moment calls for looping rather than STOP?

Reveal answer

b. Somatic activation is Month 1. A comprehension gap is Month 3.

4The other person finally says “yes, that's it.”

What has just become possible?

Reveal answer

b. The loop is the precondition, and now the real exchange starts.

5A colleague interrupted you twice in front of a client.

Which opener is consistent with this month's frameworks?

Reveal answer

b. Observation, feeling, need, request, in that order, with no verdicts smuggled into the observation.

Study guide

Discussion questions for pairs or the full group:

  • What did it feel like to be looped, to have someone reflect back until you felt understood?
  • How often does that happen in your regular work?
  • What made it hard to loop accurately?
  • Where did you find yourself wanting to jump to your own response?
  • How does the NVC distinction between observation and evaluation show up in how this team communicates?
  • What would change in our meetings if we made “do I have it right?” a standard question before anyone advocates?

Before the next session, check in with yourself:

  • Did I loop at least twice in real conversations this month?
  • Did I act as conflict miner in at least one meeting?
  • Can I distinguish between understanding a colleague’s perspective and agreeing with it?
Facilitator guide
  • The triad exercise is the most important practice in Month 3.
  • Give it the full 30 minutes.
  • The observer’s job is to say what they noticed, not what they would have done differently.
  • After the triad, ask speakers what it felt like to be looped, then ask listeners what was hard about doing it.
  • The contrast is the learning.
  • One note on NVC, which appears in this month's handouts: social justice practitioners raise a fair critique that NVC, used badly, slides into tone-policing, privileging calm delivery over legitimate grievance.
  • Teach it as a tool for the speaker's own clarity, never as a standard to impose on how someone else expresses hurt.
  • The looping prompts feel stilted at first.
  • Name that.
  • The goal is to internalize the intent, not memorize the prompts.
  • If the group is large, run multiple triads at once and debrief together.
  • Watch for listeners who paraphrase their interpretation rather than reflecting what was said (ask: did the speaker say that, or is that your interpretation?), speakers who choose easy scenarios (encourage real tension), and the person who says “I already do this” (invite them to demonstrate; almost everyone finds room to grow).
  • Month 3 is often when the group starts to feel like a learning community rather than a task group.
  • That shift is significant.
  • Name it.