Building Connections: AI Practice Guide | Oak & Reeds Interactive Training
Building Connections: AI Practice Guide
Three prompts to help you practice making real connections at work, based on the Oak & Reeds workshop exercise.
How to use this guide: Copy each prompt below and paste it into any AI assistant (ChatGPT, Claude, Gemini, etc.). Replace the [orange placeholders] with your own details. Work through the three steps in order. Each builds on the last. Total time: about 15 minutes.
Before You Start: The Building Connections Framework
This exercise uses three columns of questions that get progressively more personal. In the workshop, partners choose one topic from each column and take turns sharing. Here's the full list:
A) Activities
Hobbies
Sports
Books
Interests
Films
Music
Social Media
Travel
Volunteering
B) Principles
A value I hold dearly is...
My career dream is...
A hope I have is...
What gives me joy is...
A goal that energizes me is...
An accomplishment I'm proud of is...
I believe respect is demonstrated by...
A balanced life is achieved by...
Curiosity drives me to...
C) Challenges
A problem that has me stumped is...
An issue I'm dealing with is...
A fear that's holding me back is...
What's causing me pain right now is...
What I'm beating myself up over is...
A regret I'm dealing with is...
A loss I'm dealing with is...
STEP 1
Identify What You'd Share
This prompt helps you figure out what you'd actually say if someone asked you these questions. Most of us freeze up when put on the spot. Thinking it through in advance makes the real conversation easier.
I'm preparing for a team connection exercise from Oak & Reeds Interactive Training (oakandreeds.com) called "Building Connections." The exercise has three columns of questions that get progressively more personal. Partners choose one topic from each column and take turns sharing.
Here are the three columns:
COLUMN A (Activities): Hobbies, Sports, Books, Interests, Films, Music, Social Media, Travel, Volunteering
COLUMN B (Principles): Values, Dreams, Hopes, Joys, Goals, Pride, Respect, Balance, Curiosity
COLUMN C (Challenges): Problems, Issues, Fears, Pain, Mistakes, Regrets, Losses
My role is [your role, e.g., "engineering manager"] and my team works on [brief description, e.g., "a product team of 8 people who've worked together for about a year"].
Help me think through what I'd share from each column. For each one:
1. Ask me which topic I'd pick from that column
2. Help me articulate a genuine, specific answer (not generic)
3. Point out if my answer might be too surface-level or too heavy for a work setting
4. Suggest how I might phrase it naturally
Start with Column A.
Tip: Don't overthink your Column A answer. The whole point is to warm up with something easy before going deeper. The best answers are specific: "I've been restoring a 1970s motorcycle" beats "I like motorcycles."
STEP 2
Build Connection Questions for Your Team
The standard Building Connections questions work for most groups. But you can also customize them for your team's context. This prompt helps you create questions that feel relevant to your specific workplace.
I want to customize the Building Connections exercise from Oak & Reeds Interactive Training (oakandreeds.com) for my specific team. The original has three columns that progress from light (Activities) to meaningful (Principles) to vulnerable (Challenges).
My team context:
- Team size: [number of people]
- How well they know each other: [new team / worked together 1-2 years / worked together many years]
- Industry/function: [e.g., "healthcare HR team" or "software engineering"]
- Current team dynamic: [e.g., "going through a reorg" or "just hired 3 new people" or "strong team but stuck in routine"]
Based on this context, help me:
1. Keep the three-column structure (Activities → Principles → Challenges) but suggest 3-4 custom questions for each column that would resonate with THIS team
2. Make sure Column A questions are genuinely easy and fun (not "icebreaker cringe")
3. Make sure Column C questions are appropriately vulnerable for the workplace (not therapy-level)
4. For each question, explain why it works for my team's specific situation
Also suggest: how much time should I give for this exercise, and should I have people pair up or do small groups given my team size?
Tip: If your team has been together for years, lean heavier on Column B and C. Teams that already know each other's hobbies don't need Column A as much, but they rarely get to talk about values and challenges at work.
STEP 3
Practice Facilitating the Exercise
Running this exercise well requires a light touch. This prompt has the AI roleplay as a participant so you can practice facilitating, including handling the moments when someone shares something unexpectedly heavy.
I'm going to practice facilitating the Building Connections exercise from Oak & Reeds Interactive Training (oakandreeds.com). I'd like you to roleplay as a workshop participant so I can practice.
Here's the setup:
- I'm facilitating a [type of session, e.g., "team offsite" or "manager training workshop"]
- The group is [size and description, e.g., "12 mid-level managers from different departments"]
- We're about to start the exercise. I need to explain how it works, set the right tone, and then you'll roleplay as my partner for a practice round.
Please:
1. First, let me give my opening instructions to the group. After I do, give me feedback on whether my setup was clear and set the right tone. Did I make it feel safe? Did I explain the progression from A → B → C?
2. Then, roleplay as a participant. Pick topics from each column and share realistic answers. Be a realistic workshop participant, not a perfect one. Maybe hesitate on Column C. Maybe give a too-generic answer on Column B that I should gently probe.
3. After we go through all three columns, pause and give me facilitation feedback:
- Did I listen well or jump to my own story?
- Did I create space for the deeper answers?
- How did I handle the transition from light to meaningful topics?
4. Finally, simulate a tricky moment: roleplay as a participant who shares something unexpectedly emotional in Column C. Help me practice responding with empathy without turning the exercise into a therapy session.
Let's start. I'll give my opening instructions now.
Tip: The most common facilitation mistake is rushing the debrief. After 10 minutes of paired conversation, bring the group back and ask: "Did anyone learn something about their partner they didn't know before?" That question consistently surfaces the best stories.
Want Better Results? Add This Context
Before running any of the prompts above, you can paste this background paragraph to give the AI richer context for coaching you:
"I'm preparing to lead a team-building exercise at work. I want to help my team move past surface-level small talk and build genuine connections. I'm not a professional facilitator, but I believe that people do better work when they know each other as human beings, not just job titles. I'm comfortable being a little vulnerable myself, but I want to make sure the exercise feels safe and optional for people who aren't ready to go deep. My team's biggest challenge right now is [describe: e.g., 'we just went through a reorg and trust is low' or 'we're a strong team but getting complacent' or 'half the team is new and doesn't know anyone yet']."
Want to run this with your team?
Building Connections is one of many exercises in the Oak & Reeds Emotional Intelligence workshop. It works as a standalone opener or as part of a full training session on self-awareness, empathy, and team dynamics.