The BCC Toolbox
AI-powered coaching tools designed to help leaders and emerging professionals build a genuine coaching culture in their organizations — session by session.
What Is the BCC Toolbox?
The BCC Toolbox is a library of AI-powered coaching tools organized by session across the full Building a Coaching Culture program. Each session includes up to four distinct tools — a Socratic Practice conversation, a Self-Assessment, a Reflection exercise, and a Peer Practice prompt. Together, they support four different moments in your learning: before, during, after, and alongside others.
These tools are designed for leaders, managers, and career college graduates who want to develop coaching skills and build a coaching culture in their organizations. You do not need to be a professional coach. You need a commitment to leading differently — and a willingness to practice.
Each tool opens in the AI platform of your choice (Claude, ChatGPT, Gemini, or Copilot). Copy the prompt, paste it in, and begin. The AI acts as an experienced executive coach — asking one question at a time, never giving advice, and helping you discover what you already know through Socratic questioning.
The Shift From Expert to Coach
4/4 tools liveExplore your default mode in conversations — when do you reach for advice and when do you stay curious?
Examine where your identity as “the one with answers” shows up most — and what it costs the people around you.
After a conversation this week, identify one moment where you coached instead of advised. What changed?
Have the same brief conversation twice — once as the expert giving answers, once as a curious coach asking questions. Debrief on the difference.
What Is a Coaching Culture
4/4 tools liveExplore what your organization’s current culture actually rewards — and the gap between that and a coaching culture.
Rate your team or organization on five markers of a coaching culture. Where are the biggest gaps right now?
Where did you see coaching-culture behaviours — or their absence — in your organization this week?
With a peer, map your team’s current culture: what gets rewarded, what gets punished, and what a coaching culture would look like instead.
The Power of Listening
4/4 tools liveExplore a moment when being truly listened to changed something for you — and what that tells you about how you listen to others.
Rate your current listening habits across five dimensions. Where are you strongest — and where does listening consistently break down?
After a full day, identify one conversation where you felt the pull to listen more deeply than you did. What stopped you?
Give a colleague 10 minutes of completely undivided listening — no advice, no redirects. Debrief on what you both noticed.
The Cost of Helping Too Much
4/4 tools liveExplore what drives your impulse to help quickly — and whose need it is actually serving in that moment.
Identify who on your team comes to you most often for answers. Map the pattern — and the cost of that dependency over time.
After this week, identify one moment where helping too quickly cost someone else an opportunity to think it through themselves.
In a real conversation this week, catch yourself starting to help and switch to a coaching question instead. Debrief with a peer on what happened.
Part 1 — Building the Foundation
Twenty-four sessions across four semesters. The core skills of the coaching leader: listening deeply, asking powerfully, holding space for real conversation, and applying those skills in the varied contexts of organizational life.
Semester 1: Listening and Presence
Radical Listening
1/4 tools liveIdentify your default listening mode and explore the gap between where you are and where you want to be.
Rate your Level 1/2/3 distribution across different conversation types and identify where you consistently fall short.
Debrief a specific recent conversation — what level were you listening at, what evidence do you have, what would you do differently?
One person listens at Level 2 for 10 minutes while the other talks about a real challenge. Debrief on what each person experienced.
Holding Silence
1/4 tools liveExamine what drives your discomfort with silence and what becomes possible when you stay in it just three seconds longer.
Across different conversations and people, how quickly do you typically fill silence? What situations trigger the fastest fill?
After using tactical silence in a real conversation this week, describe what happened — what you felt, what the other person did, what it produced.
One person asks a question; both wait in silence for 10 seconds before the other responds. Debrief on what that pause felt like from each side.
Noticing Patterns
1/4 tools liveSee recurring emotional and behavioural patterns in conversations rather than just responding to surface content.
Which types of patterns do you typically miss — emotional, behavioural, language, or relational? Describe a recent example of each.
After a conversation this week, write down any recurring themes you noticed. Did you follow them or move past them? What stopped you?
One person describes a team challenge for 5 minutes. The listener writes down patterns only (not content responses). Share observations.
Being Fully Present
1/4 tools liveExplore what full presence means, what fractures it, and what becomes possible when you deliberately return your attention.
List your top three presence killers. Which conversations or people trigger the most consistent fracture in your attention?
After using the STOP practice before a conversation this week, describe what you noticed — in yourself and in the quality of your attention.
Have the same brief conversation twice — once distracted, once fully present. Debrief on what the speaker noticed from each version.
The Advice Monster
1/4 tools liveIdentify which face of the Advice Monster shows up most in your leadership conversations — and what’s driving it.
Over one full week, note every time you gave advice before the other person finished explaining. Which face appeared most?
Pick a specific recent advice moment. Walk through what might have happened if you had asked “And what else?” instead.
In a 15-minute structured conversation, one person commits to asking only “And what else?” for the first 10 minutes. Debrief on what surprised you.
Listening as Care
1/4 tools liveConnect listening to relational care — and examine how consistently you offer that quality of attention to the people you lead.
Who in your organization currently feels most heard by you — and who feels least heard? What has the cost of that gap been?
After deliberately listening with care in one difficult conversation this week, describe what shifted and what you held back.
Have a 10-minute conversation where your only purpose is for the other person to feel completely heard. No advice, no redirects. Debrief afterward.
Semester 2: Powerful Questions
Open vs. Closed
1/4 tools liveExamine your question habits in a recent conversation and explore what drives the use of closed or steering questions.
Review your last three one-on-ones. Estimate the ratio of open to closed questions. Which topics or people pull you toward closed questions?
After your next one-on-one, identify the moment you steered instead of opened. Write the question you asked — and the genuinely open version.
Share three questions you regularly ask. Your peer identifies which are closed or leading and helps you build an open version of each.
The Seven Essentials
1/4 tools liveEvaluate your own questions against the seven criteria for powerful questions and rebuild a weak question from scratch.
Rate yourself on each essential (brief, open, clean, forward-focused, curious, singular, evocative) on a 1–5 scale. Where is your lowest score?
After your next meeting, identify the one question you asked that best embodied the seven essentials. What made it work?
Bring five questions you use regularly. Your peer evaluates each against the seven essentials and you rebuild the weakest one together.
Questions That Clarify
1/4 tools livePractice the Specificity Ladder — moving from vague language down through specific behaviour, impact, and meaning.
What words do you use most often that could mean different things to different people? For each, what specifically do you mean?
After a conversation this week, find one moment of vague language — yours or theirs — and walk it down the Specificity Ladder on paper.
Have a 10-minute conversation about a real work topic. Your peer’s only job: ask “What does that mean specifically?” every time vague language appears.
Questions That Unlock
1/4 tools liveWork through all five unlocking question types on a real situation where you’ve been going in circles — and discover which one shifts something.
Which of the five unlocking question types do you use naturally? Which one do you never use? What does that tell you?
After using an unlocking question in a real conversation this week, describe which type you used, how it landed, and what shifted.
One person describes something they’re genuinely stuck on. Their partner selects one unlocking question type to try. Debrief on what opened.
Following Curiosity
1/4 tools liveExamine a specific moment you noticed something in a conversation but moved past it — what you noticed, what you did, and what you were protecting.
What are your top three reasons for not following curiosity in conversations — agenda, discomfort, wanting to appear competent? Which is most dominant?
After a conversation this week, identify one moment of genuine curiosity you bypassed. What would following it have looked like?
Have a conversation where you commit to following every thread of genuine curiosity — no agenda, no plan. Debrief on where it led.
Avoiding Leading
1/4 tools liveExamine a leading question you’ve recently asked, identify which of the four leading forms it matches, and rebuild it as a genuinely open question.
Over your next three one-on-ones, mark every question that contains a direction, evaluation, or implied answer. What patterns do you see?
After catching yourself asking a leading question this week, explore what you were afraid would happen if you had asked it cleanly.
One person asks a question. Their partner identifies whether it’s leading, names the form, and together they rebuild it as a genuinely clean question. Run five rounds.
Semester 3: Conversations That Shift
The Coaching Arc
1/4 tools liveExamine the structure of a recent conversation against the four arc stages and identify which stages were present, rushed, or missing.
Across your last five one-on-ones, which stage do you most consistently skip or rush? What does that pattern cost the people you’re talking with?
After your next structured conversation, map it against the four stages. If you ran it again with the full arc in mind, what would you do differently?
One person leads a 15-minute conversation while their partner maps it against the four stages in real time. Debrief on what landed and what was skipped.
Naming What’s Real
1/4 tools liveIdentify something you’ve been observing about someone on your team but haven’t named — and practice framing it as an observation that could be received.
List the observations you’ve been sitting on about people on your team. For each, what has stopped you — fear of reaction, uncertainty, or something else?
After naming a real observation in a conversation this week, describe how you framed it, how it was received, and what it produced.
Observe your peer for five minutes while they describe a real work challenge. Share one observation about what you noticed (not an interpretation). Debrief on how it landed.
Holding Discomfort
1/4 tools liveExamine your rescue patterns — what triggers them, whose discomfort you’re actually responding to, and what might happen if you stayed in the tension longer.
What emotions, situations, or types of people most reliably trigger your rescue reflex? How quickly do you typically move to fix or reassure?
After a conversation this week where you deliberately held discomfort instead of rescuing, describe what it felt like and what happened when you did.
One person describes something genuinely difficult. Their partner asks one question and then stays completely silent for 60 seconds. Debrief on what not rescuing felt like.
Working with Resistance
1/4 tools liveExamine a specific instance of pushback — what form it took, how you responded, and whether your response amplified or dissolved it.
When faced with pushback, what’s your most common default? Which form of resistance is hardest for you to stay with without reacting?
After a conversation with resistance this week, describe what form it took and what you now think it was protecting.
One person takes a position. Their partner pushes back using one of the three resistance forms. Practice staying with it for three exchanges before shifting.
Commitment and Action
1/4 tools liveExamine how your conversations close — whether the commitment that emerges is specific and owned, or a general intention handed from you to them.
Think back over your last five one-on-ones. How many ended with a specific, owned, time-bound commitment vs. a general intention?
After your next one-on-one, did you use the scaling question? What did it reveal? If you didn’t, what would it have surfaced?
Lead a 10-minute conversation with a peer on something they’re genuinely working through. Practice the full close: scaling question, obstacle check, owned commitment.
Closing Well
1/4 tools liveExamine the last few minutes of a recent conversation — who named the insight, who made the commitment, and which closing pitfall appeared.
Which of the three closing pitfalls (topic creep, coach-led summarising, social collapse) do you recognise most consistently in your own conversations?
After your next conversation, write down as precisely as you can the last three things said. Who named the insight? Who made the commitment?
Practice just the final three minutes of a conversation. Your peer observes and gives feedback on which pattern emerged and what one thing you could do differently.
Semester 4: Coaching in Context
Coaching Peers
1/4 tools liveExamine a peer relationship where you play an informal support role — what mode you default to, and whether you’ve ever explicitly contracted the role.
For three peers who regularly come to you, what mode do you most often use? Have you ever explicitly asked what they actually need from you?
Did you choose your mode deliberately or default into it? Looking back, what would have been more useful for this specific person in this moment?
Open your next peer conversation by asking: “What would be most useful from me right now?” Debrief on what changed.
Coaching Upward
1/4 tools livePrepare to offer a coaching-quality observation to a senior leader — separating the observation from the interpretation and finding the permission question.
What patterns in senior leaders around you have you noticed but never named? For each, what specifically has stopped you?
After delivering an upward observation, describe how you framed the permission question, how the observation landed, and what you would do differently.
One person plays the senior leader. The other practices the opening permission question and the clean observation sequence. Debrief on tone and framing.
Coaching in the Moment
1/4 tools liveFind coaching opportunities in brief, unplanned conversations — identifying the three signals and the single question that could shift the exchange.
Over one full workday, note every brief unplanned conversation. How many contained a coaching signal? How many did you catch in the moment?
After using a coaching-in-the-moment question in an unplanned conversation, describe the signal you caught, the question you asked, and what happened.
One person describes their day in 3 minutes. Their partner listens only for coaching-in-the-moment signals. After, the partner names what they noticed.
Ethics and Boundaries
1/4 tools liveExamine the ethics of a current informal support relationship — whether it primarily serves the other person, and whether a dual role exists.
For every developmental or support relationship you currently hold, apply the dual-role test honestly. Are you the right person — and is this primarily serving them?
After applying the dual-role test to a specific relationship, describe what you found and what conversation might need to happen.
Describe a current support relationship to a peer (anonymized). Ask them: “Does anything concern you about this setup?” Use their perspective to stress-test your assumptions.
Measuring Growth
1/4 tools liveAssess observable growth in a developmental relationship — distinguishing between what is concretely different and what is merely hoped-for.
For one person you’re developing, list only the observable, concrete changes since you started. What’s missing from the list?
What did the person say about their own growth? Did it match your observations? What does the gap — or alignment — tell you?
Describe a developmental relationship to a peer. They ask you three questions to help you identify whether sessions have become comfortable in a way that signals drift.
Foundations Capstone
1/4 tools liveAn integration conversation across all four semesters — what has changed, where the gap between understanding and behaviour is still largest, and what’s next.
Rate yourself on the core skills from each semester. Where has growth been most visible? Where is the gap still largest?
Describe specifically how you handled a difficult leadership conversation 6 months ago vs. how you handle it now. What is concretely different?
Ask a peer who has worked alongside you to reflect back what they’ve noticed has changed in how you show up. Listen without defending.
Part 2 — Expanding the Culture
Building on the foundations of Part 1, these four semesters take coaching culture skills deeper — into pressure, complexity, systemic change, and lasting legacy.
The Coaching Leader Under Pressure
How do your listening, questioning, and conversation skills hold up when you’re stressed, rushed, or in conflict? This semester examines what breaks down first — and how to rebuild it deliberately.
Coaching Across Difference
Coaching skills don’t work the same way across cultures, generations, personality types, and power differentials. This semester builds the adaptive range to meet people where they actually are.
Culture Change from the Inside
Individual coaching skill is necessary but not sufficient. This semester focuses on the systemic and organizational conditions that allow a coaching culture to take root — and what leaders can actually do to create them.
The Coaching Leader’s Legacy
What does it mean to build something that outlasts you? This semester focuses on embedding coaching culture as an organizational capability — measuring it, sustaining it, and developing the next generation of coaching leaders.