Whether you provide 1-1 coaching, team coaching workshops, training or organizational consulting, these prompts can be leveraged to by you and your clients to better support ongoing development in the flow of work in between sessions, trainings and live touchpoints.
Things to note:
You no longer need to use the “@” when typing someone’s name
If there are people with the same first name, you may need to put their last name
Currently, a client will need to be on a team to be able to use team prompts.
1-1 Coaching
For self:
What should I be aware of when I’m under stress?
What kind of feedback am I most likely to respond to?
When am I most productive during the day?
What blind spots do I consistently overlook in how I work with others?
How do others likely perceive my communication style?
What situations cause me to withdraw or dominate in a conversation?
About another individual:
What motivates [Name] in their work?
What blind spots might [Name] have when working independently?
How does [Name] prefer to receive recognition?
What kind of work drains [Name] or creates stress over time?
How does [Name] prefer to structure their day or workflow?
How does [Name] typically respond to change or uncertainty?
What kinds of communication might frustrate or confuse [Name]?
What are helpful ways to support [Name] when they feel overwhelmed?
For coach and client together:
What coaching style will resonate best with [Name], directive, exploratory, practical?
What barriers might [Name] have to opening up or embracing new ideas?
How might I unintentionally reinforce behaviors [Name] is trying to grow out of?
What are key conversation strategies I should use with [Name]?
Team Coaching
For the team as a whole:
What are the most common sources of tension on [name of team]?
How does this [name of team] tend to handle conflict?
Where does [name of team] get stuck when collaborating?
What values unify [name of team], and where might there be tension?
How do different thinking styles influence how [name of team] solves problems?
What are early warning signs that [name of team] is avoiding necessary conflict?
What slows down [name of team]’s ability to make decisions?
About two team members:
How do [Name1] and [Name2] differ in communication style?
What dynamics should I be aware of when [Name1] and [Name2] are in meetings together?
What misunderstandings might arise between [Name1] and [Name2] based on how they process information?
What’s one thing [Name1] could do differently to better support [Name2] within [name of team]?
How can we build trust more intentionally between [Name1] and [Name2] on [name of team]?
About individual contributions:
What unique value does [Name] bring to this team?
Who on the [name of team] is most likely to avoid conflict?
What kind of environment allows [Name] to do their best work within [name of team]?
How does [Name] respond to structure in the context of [name of team]?
What is one behavior that could limit [Name]’s impact on [name of team]?
What kind of conflict might [Name] avoid—and how could that affect [name of team]?
What motivates [Name] to fully engage in [name of team]’s goals?
Where might [Name] feel unseen or undervalued on [name of team]?
Enneagram Workshops
For self-awareness:
What’s my Enneagram type’s biggest strength at work?
How does my Enneagram type typically respond to feedback?
What does Enneagram growth look like for my type?
How do I typically react when things feel out of control?
What does growth look like for someone with my Enneagram type?
When do I feel most seen and valued on [name of team]? (If putting people on teams)
For others:
What does [Name] need to feel seen or appreciated?
How does [Name] typically react when under pressure?
How can I adapt my approach when working with someone who has a very different Enneagram type than me?
How does my Enneagram type shape the way I give or receive feedback?
When might my type’s communication style unintentionally cause friction between myself and others? (caveat: you can also ask about a specific team here and say between myself and others on [team name])
For pairs or the team:
What stress behaviors should I watch for with [Name]?
Which Enneagram types are most likely to challenge each other on [name of team]?
How do [Name1] and [Name2] each prefer to express themselves, and what gets lost in translation?
How might [Name1] misinterpret [Name2]’s tone, pace, or intention based on their Enneagram types
What shared values could serve as common ground between [Name1] and [Name2]?
What’s one behavior that would build trust between [Name1] and [Name2]?
DISC Workshops
Individual exploration:
What DISC style am I most similar to, and how does it show up in my day-to-day behavior?
What energizes and drains me based on my DISC profile?
What DISC traits show up most strongly in how I approach my work?
When I’m at my best, what does my DISC style make possible for others?
How do I respond when working with someone who has a very different pace or communication style?
How might my DISC style impact how others interpret my emails, tone, or silence?
How can I recognize when my DISC style is over-functioning in conflict?
Who on [name of team] helps balance out my DISC style, and what can I learn from them?
For coaching pairs or group discussion:
How might [Name1] and [Name2] respond differently to change?
What’s one way [Name1] can adjust their communication to match [Name2]’s DISC style?
Where might [Name1] push for action while [Name2] wants more details, or vice versa?
What does it look like when [Name1] and [Name2] feel overwhelmed, and how can they recognize it early?How can [Name1] help [Name2] stay engaged without applying the wrong kind of pressure?
What communication behaviors from [Name1] might unintentionally cause [Name2] to shut down?
Team-level insights:
What’s [name of team] collective comfort level with risk or uncertainty?
How does this blend of DISC styles influence [name of team]’s ability to take action, analyze, relate, or stabilize?
Where might [name of team] lean too heavily on one approach like speed, harmony or precision?
Where might certain styles DISC dominate conversation on [name of team] and how can we create more balance?
What DISC styles on [name of team] might avoid conflict, and which might escalate it?
What does “safety” mean for each DISC style and how can [name of team] support that?
Leadership Development Training
For emerging leaders:
Self-Awareness & Style
How does my personality influence the way I lead under pressure?
What leadership behaviors feel natural to me, and which require more intention?
When I take charge, how do others typically respond?
Confidence & Influence
What strengths do I bring to leading a team or project?
How do I influence others when I’m not the most experienced person in the room?
Where do I hesitate to speak up, and what’s behind that?
Delegation & Control
What kinds of tasks am I most reluctant to delegate?
Where does my need for control support my leadership, and where might it hold others back?
How can I build trust while letting go of perfection?
Growth Opportunities
What feedback have I resisted, and what might it be trying to show me?
What behaviors from senior leaders do I admire and want to develop in myself?
How do I want others to experience me as a leader?
For Middle Managers
Self-Awareness as a Leader
How does my personality influence how I handle competing priorities?
What does my style say about the kind of structure I need, or resist?
Where might my strengths become overused when I’m under pressure?
What kind of leadership presence do I naturally project, and how is it perceived?
Managing Up, Down, and Across
How do I adjust my communication when navigating different personality styles across levels?
Where might my behavioral tendencies cause me to over-explain or under-communicate?
What motivates me, and how might that shape how I try to influence others?
Where am I most likely to misinterpret signals from senior leaders, peers, or direct reports?
Communication, Feedback & Decision-Making
How does my DISC or Enneagram style affect how I deliver feedback?
What does my preferred decision-making style look like, and how does that impact collaboration?
Where might I unintentionally shut down voices that don’t match my communication pace or tone?
When I’m under pressure, how does my behavior shift, and what message does that send?
Coaching & Developing the Team
What do my assessment results suggest about how I support and challenge my team?
Where might my own preferences make it harder to flex to others’ development needs?
How can I better tailor recognition and motivation to individual team members?
Who on [name of team] might need a different kind of support than I naturally offer?
For Senior Leaders:
Team Dynamics & Culture
How does my communication style set the tone for this team?
What values do I model consistently, and what gaps might my team notice?
Where might I be unknowingly rewarding behavior that undermines collaboration?
Adaptability & Impact
How do different personality styles on [name of team] respond to my leadership approach?
Where do I need to flex my style to support both speed and inclusion?
What signs of disengagement or friction might I be overlooking? [if relevant, add [name of team])
Strategic Leadership
What signals do I send about what matters most—results, relationships, efficiency, or innovation?
When I make decisions quickly, how does it affect trust or alignment?
How do I balance driving performance with developing people?
Reflection & Growth
What habits might be limiting my leadership right now?
What’s one leadership behavior I need to unlearn to scale my impact?
Who challenges me in a productive way, and how often do I seek that input?
Conflict Management Training
For diagnosing root issues (for the practitioner):
What behaviors might escalate tension on [name of team]?
Who is most likely to avoid conflict on [name of team], and how can I draw them in productively?
What behavioral styles on [name of team] are most likely to dominate in conflict?
What underlying personality traits may cause tension to build silently on [name of team]?
Where might differences in pace, tone, or decision-making style contribute to misalignment on [name of team]?
For one-on-one coaching:
What’s my typical response to conflict, and how might that affect others?
What triggers should I be aware of in high-pressure situations?
How do I behave when someone challenges my authority or opinion?
What types of conflict am I most likely to avoid, and why?
What is my natural response style: direct, diplomatic, passive, or reactive?
To help resolve a team issue:
How can we structure a conversation between [Name1] and [Name2] to ensure both feel heard?
What shared values might help [name of team] reconnect after a conflict?
What behavior differences between [Name1] and [Name2] might cause friction?
What repair strategy would align best with the motivation style of [Name1]?
What roles might different team members naturally play in conflict resolution on [name of team]?
Organizational Development Training
For broader system analysis:
What assessment data points to communication or cultural gaps on [name of team]?
Where are there mismatches between values and behavior on this team?
What personality styles are over- or underrepresented on [name of team], and how does that shape culture?
Where might communication gaps stem from differences in processing speed, structure preference, or interpersonal energy on [name of team]?
What are the dominant values expressed by this [name of team], and where might those values be out of sync with behavior?
Where might the [name of team] current norms unintentionally suppress diverse thought or working styles?
What type of psychological safety is needed, but missing, for [name of team] to thrive?
For change leadership:
Who might struggle most with an upcoming organizational change on [name of team]?
What coaching can I provide to help [name of team] build trust and clarity?
How do people on [name of team] respond to ambiguity, and how can we use assessment data to guide clarity?
Which motivational drivers (security, recognition, growth, clarity) need to be supported for [name of team] to engage with change?
For role design and org structure:
Who thrives in autonomy, and who needs structure to succeed on [name of team]?
What roles might align well with [Name]’s natural strengths?
Who on [name of team] works best with autonomy, and who thrives with clearly defined roles?
What level of interpersonal interaction does [Name] need to stay engaged and energized?
What behavioral traits suggest [Name] is suited for fast-paced, flexible roles, or more stable, process-driven ones?
Where does [Name] need coaching to stretch into a role that doesn’t fully match their preferences?
C-Suite Executive Coaching
For strategic self-reflection:
How do I show up in high-stakes situations?
What’s my default leadership style, and how is it perceived?
How does my decision-making style affect how others perceive my decisiveness or openness?
Where might I default to execution over reflection, or vice versa?
What blind spots does my personality style create at this level of leadership?
What am I modeling through my stress responses, and is that intentional?
For managing executive team dynamics:
Where is trust strong and where might it be fragile among [name of team]?
What tension exists between speed of execution and relational alignment on [name of team]?
Which personalities on [name of team] need more direct communication, and who needs more processing time?
How might [name of team’s] combined behavior styles reinforce urgency over relational alignment?
For supporting the broader org:
What do people on [name of team] need from me to stay engaged?
How am I shaping the organizational culture through my daily behavior patterns?
What values am I signaling, intentionally or not, through my communication style?
What kind of psychological environment am I creating for those two levels below me?
How does my leadership style enable or discourage upward feedback?
What motivation styles exist on [name of team], and how can I speak to them more clearly?
Sales Training
For individual reps:
What kind of client relationships do I build most naturally?
How does my personality influence my sales approach?
How does my DISC or Enneagram style influence my prospecting approach?
When under pressure, how does my personality affect how I engage with a hesitant buyer?
What kind of client relationships do I find most energizing, and which are most draining?
Where might my natural communication style miss buyer cues or preferences?
How do I build credibility: through data, connection, momentum, or reliability?
For manager-coaching:
How can I coach [Name] to handle rejection more effectively?
What motivates [Name] to hit stretch goals?
How does [Name] typically respond to rejection, and how can I coach through that lens?
What personality strengths can [Name] lean into when sales are slow?
What behavior patterns are helping [Name] build trust, and which are unintentionally limiting?
How does [Name] best receive encouragement, feedback, or redirection?
Where might [Name] be relying on their natural strengths at the expense of growth?
For sales teams:
Where does [name of team] excel in influence, and where does it need more structure?
What types of clients might [name of team] naturally connect with?
What behavioral patterns show up across [name of team], urgency, harmony, perfectionism, or adaptability?
How does [name of team] dominant communication style affect how they engage with different client types?
Where might overuse of a specific DISC style be limiting overall [name of team] agility?
What kind of buyer personas align best with this [name of team] natural selling approach?
How can we use each [name of team’s] strengths to build a more complete sales experience?