Quick Prompts: Coaching & Mentoring
Real-time AI assistance for coaches, mentors, and advisors guiding others' development.
Coaching & Mentoring quick prompts help you be a more effective guide for your clients, mentees, or team members. Whether you're a professional coach, an executive mentoring rising talent, or a manager developing your team, these prompts help you ask better questions, facilitate deeper insight, and support meaningful growth.
Each goal category supports a different aspect of effective coaching. Use "Powerful Questioning" to prompt insight, "Client-Led Discovery" to reflect and synthesize, "Goal Clarification" to establish clear objectives, and "Action Planning" to drive toward concrete results.
Goal: Powerful Questioning
When this applies: You want to ask questions that catalyze insight, challenge assumptions, and help your client or mentee think more deeply. The right question at the right time can unlock significant growth.
Ideal settings: Coaching sessions, mentoring conversations, development discussions, any conversation where you're guiding someone toward their own insights.
💡Deepen insight
What it does: Suggests a powerful question designed to help your client gain deeper insight into their situation—one that challenges assumptions, reveals new perspectives, or connects dots they haven't connected.
When to use it:
The conversation is staying at a surface level and needs to go deeper
You sense there's more beneath what they're saying
They seem stuck in familiar patterns of thinking
A breakthrough insight feels close but hasn't emerged
Example scenario: Your mentee is describing a conflict with their manager. They've told you the facts, but they're not examining their own role or assumptions. You need a question that helps them see the situation more fully without telling them what to see.
What to expect: A powerful, open-ended question tailored to the current conversation that could unlock deeper understanding or new perspective.
💡Explore values
What it does: Suggests a question that helps your client connect their current situation or challenge to their underlying values and motivations—what truly matters to them.
When to use it:
The conversation would benefit from grounding in values
Decisions are being made without considering what really matters
They seem disconnected from their deeper motivations
Values clarification would help them move forward
Example scenario: Your client is weighing a job offer that's objectively great—more money, better title—but something is holding them back. A values exploration might reveal what's really at stake for them.
What to expect: A question designed to connect the current topic to underlying values, helping them understand what truly matters in this situation.
💡Challenge assumptions
What it does: Suggests a thoughtful question that gently challenges a limiting belief or assumption your client seems to be operating under, opening new possibilities.
When to use it:
You notice beliefs that might be limiting their options
They're treating assumptions as facts
Self-imposed constraints are blocking progress
A mindset shift could change everything
Example scenario: Your mentee keeps saying "I can't push back on my manager" as if it's an immutable fact. But is it? The assumption itself might be the main obstacle. How can you challenge this gently?
What to expect: A question that invites them to examine a limiting belief without being confrontational, opening space for them to reconsider their assumptions.
💡Future perspective
What it does: Suggests a future-oriented question that helps your client envision possibilities, desired outcomes, or their ideal situation—shifting from problem-focus to solution-focus.
When to use it:
They're stuck in problem analysis and need to look forward
Vision and possibility would be more energizing than problem-solving
They need to connect current actions to future goals
Hope and aspiration could motivate better than fear
Example scenario: Your client has spent the entire session analyzing what's wrong with their current situation. They're stuck in complaint mode. A future-focused question could shift their energy toward what they want to create.
What to expect: A question that helps them envision a desired future state, shifting perspective from problems to possibilities.
💡Reframe situation
What it does: Suggests a question that offers a different lens on the situation, helping your client reframe their understanding in a way that creates new options or insights.
When to use it:
They're locked into one way of seeing a situation
A different perspective could be transformative
The current frame is creating limitations
You see another angle they might not have considered
Example scenario: Your mentee sees their new assignment as a demotion and punishment. But could it also be seen as an opportunity to prove themselves, or a chance to develop new skills? A reframe could change everything.
What to expect: A question that gently offers a different perspective on their situation without dismissing their current view.
Goal: Client-Led Discovery
When this applies: You want to support your client's own discovery process rather than telling them what to do. Great coaching helps people find their own answers. These prompts help you reflect, synthesize, and hold space effectively.
Ideal settings: Deep coaching conversations, when the client is working something out, when reflection and synthesis would be valuable.
💡Reflect meaning
What it does: Suggests a powerful reflection that captures the deeper meaning, feelings, or themes beneath your client's words—demonstrating deep listening and helping them feel truly understood.
When to use it:
They've shared something important that deserves acknowledgment
The emotional content beneath the words is significant
You want to demonstrate that you're truly hearing them
Reflection would help them process what they're experiencing
Example scenario: Your client has been describing a difficult decision, ostensibly about career moves, but beneath the surface there are themes of identity, fear of failure, and family expectations. A reflection could name what's really at stake.
What to expect: A reflection that captures deeper meaning or emotional content, helping them feel understood and enabling further exploration.
💡Identify strengths
What it does: Identifies strengths, resources, or capabilities your client has demonstrated in their sharing—assets they might be overlooking that could help them move forward.
When to use it:
They're focused on problems and not seeing their resources
Confidence seems low despite evident capabilities
Their strengths are obvious to you but not to them
Building on strengths would be more effective than fixing weaknesses
Example scenario: Your mentee is anxious about an upcoming presentation, convinced they'll fail. But in describing past situations, they've revealed resilience, preparation skills, and subject matter expertise that they're not acknowledging.
What to expect: Identification of specific strengths evident in what they've shared, with suggestions for how to reflect these back in a way that builds confidence.
💡Summarize progress
What it does: Provides a concise summary of the key insights, realizations, or progress your client has made in this conversation, helping them see the arc of their own discovery.
When to use it:
The session is approaching its end and consolidation would help
Multiple insights have emerged that should be connected
They might not recognize how much progress they've made
A summary would reinforce key learnings
Example scenario: Your coaching client has had several realizations during your session, but they've come gradually and might not see the full picture. A summary could help them appreciate the journey they've taken in this hour.
What to expect: A summary of the key insights and progress from the conversation, organized to show the arc of their discovery.
💡Spot patterns
What it does: Identifies patterns, themes, or recurring elements in what your client has shared—observations that could deepen their self-awareness without imposing your interpretation.
When to use it:
You notice recurring themes across different topics
Patterns are emerging that the client might not see
Self-awareness would be served by noticing patterns
Similar dynamics seem to recur in different contexts
Example scenario: Across several topics, your mentee keeps describing situations where they take on too much, don't ask for help, and then feel overwhelmed and resentful. The pattern is clear to you—would they benefit from seeing it?
What to expect: Identification of patterns or themes, with suggestions for how to share this observation in a way that invites reflection rather than defensiveness.
💡Hold space
What it does: Suggests a way to create more room for your client's reflection and discovery—sometimes the most powerful thing you can do is be present and quiet.
When to use it:
They're processing something significant and need space
Silence would be more valuable than more questions
You're tempted to fill the space but shouldn't
Something is emerging that needs room to unfold
Example scenario: Your client just had a significant realization and is sitting with it quietly. The silence feels uncomfortable but important. You want guidance on how to hold space rather than rushing to the next question.
What to expect: Guidance on holding space—when silence is powerful, how to stay present without filling the void, and gentle ways to invite continued reflection when appropriate.
Goal: Goal Clarification
When this applies: You're helping your client define clear, meaningful goals. Effective coaching often starts with clarifying what someone really wants—and ensuring their goals are specific, aligned with their values, and appropriately challenging.
Ideal settings: Goal-setting sessions, new coaching engagements, when clients seem to be pursuing vague or unexamined objectives.
💡Clarify desired outcome
What it does: Suggests questions or approaches to help your client articulate their desired outcome more clearly, moving from vague aspirations to specific, meaningful goals.
When to use it:
Their goal is too vague to work with effectively
They're describing what they don't want rather than what they do want
Clarity would help them focus their energy
You need a clear target to coach toward
Example scenario: Your client says they want "better work-life balance." That's a worthy goal, but it's too vague to pursue effectively. What specifically do they want? How would they know they'd achieved it?
What to expect: Questions designed to sharpen their goal from vague aspiration to concrete, specific objective.
💡Make it measurable
What it does: Suggests ways to help your client make their goal more concrete and measurable—so they can track progress and know when they've succeeded.
When to use it:
The goal is qualitative but needs quantitative elements
They need to track progress over time
Success criteria are unclear
Accountability would be served by measurable milestones
Example scenario: Your mentee wants to "become a better leader." How will they know when they've achieved this? What would "better" look like in measurable terms? You need to help them define success concretely.
What to expect: Approaches for making the goal measurable, including potential metrics, milestones, or observable indicators of success.
💡Test alignment
What it does: Suggests questions to help your client assess whether their stated goal truly aligns with their core values and long-term vision—ensuring they're pursuing what genuinely matters.
When to use it:
You sense the goal might be externally imposed rather than internally motivated
They're pursuing something that doesn't seem to excite them
Values alignment needs to be verified before investing energy
The goal might conflict with other things they care about
Example scenario: Your client is pursuing a promotion to senior director, but something feels off. They don't seem genuinely excited about it. Is this really their goal, or something they think they should want?
What to expect: Questions to test whether the goal aligns with their values and authentic desires, not just external expectations.
💡Define success
What it does: Suggests ways to help your client create a vivid, detailed picture of what success looks like—both tangible outcomes and how they'll feel when they get there.
When to use it:
A clear vision would motivate and guide action
They're unclear on what they're working toward
Visualization would help them commit to the goal
Both tangible and intangible success measures matter
Example scenario: Your client wants to launch their own business. What does success look like? Not just the numbers—how will their life be different? How will they feel? A vivid picture of success can drive sustained motivation.
What to expect: Approaches for developing a rich, motivating picture of success that includes both tangible and intangible elements.
💡Balance stretch and feasibility
What it does: Helps you assess whether your client's goal strikes the right balance between being challenging enough to inspire growth and realistic enough to be achievable.
When to use it:
The goal seems either too easy or too ambitious
You need to calibrate expectations appropriately
Setting them up for failure or boredom serves no one
The goal needs adjustment to be optimally motivating
Example scenario: Your mentee wants to be promoted to VP within six months. Is this a stretch goal that will drive growth, or an unrealistic expectation that will lead to disappointment? You need to help them calibrate appropriately.
What to expect: An assessment of whether the goal is appropriately challenging, along with ways to adjust if needed.
Goal: Action Planning
When this applies: You're helping your client translate insight and intention into concrete action. Coaching isn't complete until learning becomes doing. These prompts help you drive toward tangible next steps.
Ideal settings: End of coaching sessions, when moving from exploration to execution, when accountability is needed.
💡Identify next steps
What it does: Helps identify one or two clear, specific next steps your client could take to move toward their goal—actions that are concrete and manageable.
When to use it:
The session is ending and you need to lock in action
Insight needs to be translated into behavior
They know what they want but not what to do next
Momentum requires a clear first step
Example scenario: Your client has realized they need to have a difficult conversation with their manager. Great insight—but what specifically will they do? When? How will they prepare? Next steps need to be concrete.
What to expect: Identification of specific, actionable next steps based on the session, designed to create momentum toward their goal.
💡Anticipate obstacles
What it does: Helps your client identify potential obstacles or challenges they might face in executing their plan—and consider how to overcome them.
When to use it:
The action plan needs stress-testing
Foreseeable obstacles could derail progress
Preparation for challenges increases success likelihood
They tend to be overly optimistic about execution
Example scenario: Your mentee has committed to delegating more to their team. Great plan—but what might get in the way? Their perfectionism? Time pressure? Lack of trust? Anticipating obstacles helps them prepare.
What to expect: Identification of likely obstacles based on the conversation, with approaches for addressing or preparing for them.
💡Support systems
What it does: Helps your client identify resources, people, or systems that could support them in achieving their goal.
When to use it:
They'll need help from others to succeed
Resources are available that they're not utilizing
Support systems would increase success likelihood
They tend to try to do everything alone
Example scenario: Your client is taking on a challenging new project. What support do they need? A mentor in that area? Time blocked for learning? A teammate to partner with? Help them think about the ecosystem of support.
What to expect: Identification of potential support systems—people, resources, structures—that could enable their success.
💡Build accountability
What it does: Suggests structures or approaches to help your client build accountability into their action plan—mechanisms that increase follow-through.
When to use it:
They have a history of not following through
External accountability would increase commitment
You want to set up check-ins or progress reviews
The goal is important enough to require accountability structures
Example scenario: Your client has made similar commitments before and not followed through. This time needs to be different. How can you build in accountability that increases the odds of success?
What to expect: Accountability structures and approaches tailored to your client's situation and patterns.
💡Timeline planning
What it does: Helps your client create a realistic timeline for their action steps, considering priorities, dependencies, and appropriate pacing.
When to use it:
Actions need to be sequenced appropriately
They're being unrealistic about timing
Deadlines would help maintain momentum
Complex goals need to be broken into phases
Example scenario: Your mentee wants to make a career change that involves building new skills, expanding their network, and eventually applying for new roles. What's a realistic timeline? What sequence makes sense?
What to expect: Help structuring a realistic timeline with appropriate milestones and sequencing.
Goal: Progress Assessment
When this applies: You're reviewing progress, celebrating achievements, and learning from challenges. Good coaching includes regular assessment of how things are going—not just setting goals but tracking movement toward them.
Ideal settings: Check-in sessions, progress reviews, when the client is reporting on actions taken since last session.
💡Recognize achievements
What it does: Identifies specific progress, achievements, or growth your client has demonstrated—especially ones they might be overlooking or minimizing.
When to use it:
They're being hard on themselves despite real progress
Achievements deserve acknowledgment and celebration
Positive reinforcement would increase motivation
They focus on what's not done rather than what is
Example scenario: Your client reports on their week, focusing on what they didn't accomplish. But listening carefully, you hear about several real wins they're dismissing. They need to see and celebrate their progress.
What to expect: Identification of specific achievements or progress from the conversation, with ways to help them acknowledge and appreciate what they've accomplished.
💡Learning from setbacks
What it does: Helps you turn setbacks or challenges into learning opportunities, extracting valuable lessons rather than dwelling on failure.
When to use it:
Things didn't go as planned and they're discouraged
There's learning to be extracted from what went wrong
Failure reframe could be valuable
They need to maintain momentum despite setbacks
Example scenario: Your mentee tried the new approach you discussed and it didn't work—they're discouraged and ready to give up. But failure contains information. How can you help them learn from this experience?
What to expect: Ways to extract learning from the setback and reframe failure as valuable feedback.
💡Measure progress
What it does: Suggests practical ways to assess your client's progress toward their goals, reviewing metrics, milestones, or other indicators of movement.
When to use it:
Time to review progress against the original goal
Objective assessment is needed beyond subjective feeling
Progress has been made but not quantified
You need to calibrate remaining effort
Example scenario: Your client wanted to improve their public speaking skills. You've been working together for three months. How much progress have they actually made? What evidence exists?
What to expect: Ways to assess and measure progress toward the stated goal, including specific indicators to review.
💡Adjust approach
What it does: Helps you and your client evaluate whether the current approach is working and consider adjustments to strategy or tactics.
When to use it:
Progress is slower than expected
The approach isn't producing results
New information suggests a different path
Flexibility and adaptation are needed
Example scenario: Your mentee has been trying one approach to building their network for two months with limited results. Maybe it's time to try something different. How do you help them pivot without abandoning the goal?
What to expect: Assessment of whether adjustment is needed and suggestions for how to modify the approach while maintaining commitment to the goal.
💡Celebrate momentum
What it does: Suggests meaningful ways for your client to celebrate their progress and accomplishments, reinforcing motivation for continued effort.
When to use it:
Milestones have been reached that deserve celebration
Positive reinforcement would boost motivation
They tend to move immediately to the next challenge
Marking progress would build confidence
Example scenario: Your client just hit a major milestone—they gave their first board presentation and it went well. They're already thinking about the next challenge. But this moment deserves celebration.
What to expect: Ways to meaningfully celebrate progress that acknowledge both the achievement and the effort it took.
Goal: Coach Development
When this applies: You're reflecting on your own effectiveness as a coach or mentor. Great coaches continually develop themselves. These prompts help you examine your own practice and grow as a guide.
Ideal settings: Self-reflection after sessions, when you feel stuck as a coach, when you want to develop your own practice.
💡Improve my listening
What it does: Suggests ways you could deepen your listening to better serve your client, identifying what you might be missing or assuming.
When to use it:
You're not sure you're fully understanding your client
Something feels off in the coaching dynamic
You want to develop deeper listening skills
The conversation feels more surface-level than it should
Example scenario: You're working with a new client and you sense you're not fully connecting. Something in your listening isn't quite working. What could you do differently?
What to expect: Suggestions for deepening your listening, including what you might be missing or where you could be more present.
💡Manage my assumptions
What it does: Identifies potential assumptions or biases that might be influencing how you're coaching, helping you see your client more clearly.
When to use it:
You want to check your own objectivity
You might be projecting your experience onto them
Your advice feels more prescriptive than curious
You want to ensure you're serving the client, not your agenda
Example scenario: You keep feeling like your mentee should just "be more assertive"—but is that your assumption based on what worked for you? Are you really seeing their situation, or projecting?
What to expect: Identification of assumptions or biases that might be influencing your coaching, with suggestions for how to set them aside.
💡Shift my approach
What it does: Suggests whether and how to modify your coaching approach based on how the session is going—being more or less directive, challenging, supportive, etc.
When to use it:
Your current approach doesn't seem to be landing
The client needs something different than you're providing
You want to be more responsive to what's emerging
Flexibility in style would serve the client better
Example scenario: You've been asking open-ended questions, but your client seems to need more structure and direction right now. Should you shift your approach? How?
What to expect: Assessment of whether a style shift is warranted, with suggestions for how to adapt your approach.
💡Improve my presence
What it does: Suggests ways to enhance your coaching presence—creating a more supportive, focused, and impactful environment for your client's growth.
When to use it:
You feel distracted or not fully present
The container you're creating could be stronger
Energy in the session feels flat
Your presence could better support their work
Example scenario: You've been coaching all day and you can feel your energy flagging. Your next client deserves your full presence. How can you reset and show up fully?
What to expect: Suggestions for enhancing your coaching presence and creating a more powerful container for the work.
💡Self-assessment
What it does: Provides an assessment of how effective your coaching appears to be, based on the client's engagement and progress, with suggestions for improvement.
When to use it:
You want honest feedback on your effectiveness
You're committed to continuous improvement
Something isn't working and you want to understand what
You want to develop your craft
Example scenario: This coaching engagement has been challenging—progress is slow and you're not sure if it's the client's circumstances or your approach. An honest assessment would help you calibrate.
What to expect: An assessment of coaching effectiveness based on the conversation, with specific suggestions for what might be more impactful.