HubSpot Rapport Exercise Guide for Stronger Sales Relationships

The famous rapport building exercise shared on the Hubspot blog reveals a practical way to create deeper human connection in sales teams, classrooms, and any group that needs trust. This guide walks you through how to run the exercise step by step so you can safely introduce vulnerability and build stronger relationships.

While the exercise became popular through a Harvard classroom story, it translates perfectly into modern revenue teams, sales kickoffs, customer success workshops, and remote meetings.

What Is the HubSpot Rapport Building Exercise?

The original story, featured on a HubSpot sales blog article, describes a professor who used an unusual exercise to break down barriers between students.

In simple terms, the exercise asks people to:

Pair up with someone they do not know well.
Share personal stories they usually keep private.
Listen actively without judgment or interruption.
Reflect on what they learned about themselves and the other person.

The result is rapid rapport, surprising empathy, and a more open group dynamic.

Why This HubSpot Rapport Exercise Works

This approach works because it deliberately moves people beyond small talk. Instead of surface-level questions, it invites them to share moments that actually shaped who they are.

Three core principles make the exercise powerful:

Mutual vulnerability: Both people take a risk, which builds trust.
Structured safety: Clear rules make it feel safe to open up.
Focused attention: Listening without distraction creates a rare feeling of being seen.

These are the same ingredients that make great sales discovery calls and long-term customer relationships so effective.

How to Prepare for the HubSpot-Style Exercise

Before running the exercise, set expectations and create a safe environment. Preparation is especially important if you are leading a sales or enablement session inspired by HubSpot content.

Define the Purpose Clearly

Explain why you are doing this and what success looks like. For example:

Strengthen trust inside the sales team.
Help new hires integrate faster.
Improve how people listen to each other.
Increase empathy for customers and colleagues.

When participants understand the purpose, they are more willing to participate fully.

Set Ground Rules for Psychological Safety

Borrowing from the spirit of the HubSpot rapport story, establish rules such as:

Everything shared is confidential and stays in the room.
No mocking, judgment, or side conversations.
Everyone participates; no one is forced to overshare beyond their comfort level.
Phones closed and laptops down during the exercise.

Make people verbally agree to these guidelines so the group norms feel real.

Step-by-Step: How to Run the HubSpot Rapport Exercise

Use this structured process to facilitate the experience smoothly.

Step 1: Form Pairs or Small Groups

Ask participants to pair up with someone they know the least. If you have an odd number of people, create one group of three.

Tips for pairing:

Avoid managers pairing with direct reports when possible.
Mix departments or territories to reduce existing bias.
In remote sessions, use breakout rooms to form pairs automatically.

Step 2: Provide Deep-Question Prompts

The original story that inspired the HubSpot article used questions that quickly sparked real conversation. Offer prompts such as:

“Tell me about a time you failed at something important. What happened?”
“What is something you are proud of but rarely talk about?”
“When have you felt most misunderstood in your life?”
“What is a challenge you are facing right now that most people do not see?”

Print these on a sheet or display them on a slide so everyone can see them easily.

Step 3: Set Time Limits and Speaking Order

Structure helps the exercise stay focused. For example:

Person A speaks for 4–5 minutes while Person B only listens.
Person B then reflects back what they heard for 1–2 minutes.
Switch roles and repeat.

Remind listeners that they are not there to fix anything. Their role is to listen, reflect, and understand.

Step 4: Coach on Active Listening

Before starting, give a quick mini-training on how to listen well, aligned with modern HubSpot-style sales coaching:

Maintain eye contact or look at the camera in remote calls.
Avoid interrupting, correcting, or jumping in with your own story.
Notice body language and tone as much as words.
Use simple reflections like “What I heard is…” or “It sounds like you felt…”

This reinforces skills that directly improve sales calls and customer meetings.

Step 5: Debrief as a Group

After everyone finishes, bring the full group back together for a debrief.

Ask questions such as:

“What surprised you about this exercise?”
“How did it feel to share something more personal?”
“How did it feel to be fully listened to?”
“What will you do differently in your sales conversations after this?”

Keep the focus on insights, not on retelling the private stories that were shared.

Using the HubSpot Rapport Exercise With Sales Teams

Sales leaders can adapt this exercise to improve performance, not just connection. Here is how to align it with revenue goals.

Connect Personal Stories to Customer Empathy

After the debrief, help your team draw clear lines between the exercise and everyday work:

Personal pain stories mirror the pain points prospects feel.
Feeling misunderstood is similar to how buyers feel with pushy reps.
Being truly heard is what customers want in discovery calls.

Ask your team to turn these insights into specific talk tracks or discovery questions.

Reinforce Skills in Coaching Sessions

Do not let the exercise be a one-time event. In future coaching sessions, reference it the way HubSpot sales enablement content often revisits core frameworks.

Play call recordings and evaluate listening skills.
Ask reps how they created psychological safety with a new prospect.
Use the same reflection techniques practiced in the exercise.

Adapting the HubSpot Exercise for Remote Teams

Remote and hybrid teams can still use this format effectively with a few tweaks.

Use breakout rooms for pairs in your video conferencing tool.
Encourage cameras on to preserve connection.
Ask participants to close other tabs to stay present.
Share prompts in chat so everyone can reference them easily.

Follow the same timing structure and debrief questions you would in person.

Best Practices and Common Pitfalls

To protect trust and maximize impact, keep these guidelines in mind.

Do This

Model vulnerability as a leader by sharing first.
Respect time limits so no one feels rushed or cut off.
Repeat the exercise periodically with new prompts.
Connect the experience to real sales and customer interactions.

Avoid This

Forcing people to share beyond their comfort level.
Allowing jokes that minimize someone’s story.
Skipping the safety rules to “save time.”
Turning the debrief into a performance review.

Where to Go Next After This HubSpot-Inspired Exercise

Once you see the impact of this exercise, you can build a broader system around it:

Create a recurring “story session” once a quarter.
Integrate listening skills into onboarding and enablement.
Replace one generic team icebreaker with this deeper format.

For more structured sales consulting and enablement ideas that complement HubSpot-style methods, you can explore specialized support from firms like Consultevo.

By deliberately designing moments of vulnerability and focused listening, you create what many sales teams and classrooms lack: genuine human connection. Run this simple rapport building exercise with intention, and you will see trust, collaboration, and customer empathy grow far beyond the session itself.

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