Creating Better AI Prompts for One-on-One Manager Conversations
How thoughtful questions lead to better coaching, not canned answers
As more managers begin using AI tools to prepare for one-on-one conversations, an important distinction is emerging:
The value of AI depends almost entirely on the quality of the prompt.
This builds on an earlier post exploring how AI can support one-on-one conversations without replacing human leadership.
AI does not think for managers; it reflects their thinking back to them. Vague prompts produce generic responses. Thoughtful prompts lead to insight, clarity, and better conversations with direct reports.
For leaders using general GPT tools or strengths-based platforms such as Gallup AI, learning how to craft effective prompts is quickly becoming a practical leadership skill.
This post is part of a short series exploring how managers can use AI thoughtfully to strengthen one-on-one conversations—without replacing human judgment or connection.
Start with Intent, Not Efficiency
The most common mistake managers make with AI is treating it like a shortcut.
“Give me questions for a one-on-one” may save time, but it rarely improves the conversation.
Strong prompts begin with intent:
What do I want this person to leave the conversation thinking or feeling?
Am I trying to coach, clarify, support, or challenge?
What is happening in this employee’s work right now that truly matters?
When managers clarify intent first, AI becomes a thinking partner—not a script generator.
In my own coaching work, I’ve noticed that when I pause to clarify my intent before using AI, rather than asking for “good questions” the quality of both the preparation and the conversation improves dramatically.
What Makes a Strong AI Prompt for Coaching?
Effective prompts for one-on-one preparation tend to share four characteristics:
Context-rich – They include relevant information about the role, situation, or working relationship
Strengths-aware – Strengths-aware prompts reflect how the individual does their best work, often informed by tools such as CliftonStrengths® or DiSC®.
Curiosity-driven – They seek understanding, not compliance
Human-centered – They support conversation, not automation
AI tools perform best when they are given enough context to think alongside the manager, not replace them.
Sample Prompts Managers Can Use Today
The following examples are designed for pre-meeting preparation or post-meeting reflection, not live use during the conversation. Managers should adapt the language to their own voice and organizational context.
Preparing for a Coaching-Focused One-on-One
I’m meeting with a direct report, [name], for a one-on-one coaching conversation. Their role is [role], and they are currently working on [project or priority]. Help me clarify my intent for this conversation and suggest three to four open-ended questions that would support reflection, ownership, and learning. If helpful, note a natural flow for how these questions might unfold.
Why it works
This prompt keeps the manager in control of the conversation while using AI to sharpen intent and question quality. It avoids rigid agendas while supporting thoughtful preparation.
Strengths-Based Preparation
Prompt
A direct report with Top 5 CliftonStrengths [list strengths] or DiSC style [enter style] is experiencing [describe challenge]. Help me think through how their strengths may be showing up in this situation and suggest at least three open-ended questions that encourage ownership, problem-solving, and confidence.
Why it works
AI is used to surface patterns and possibilities, not label the person. The manager interprets the insight and chooses how to engage, reinforcing a strengths-based coaching mindset.
Supporting Engagement and Wellbeing
Prompt
Help me prepare for a one-on-one conversation with my direct report [name] focused on engagement and wellbeing. Suggest open-ended questions that would help me understand what is energizing them, what may be draining them, and where clarity or support would be most helpful.
Why it works
This prompt broadens the conversation beyond tasks without drifting into generic advice. It helps managers listen for patterns and signals rather than jumping to solutions.
Preparing for a Difficult or Sensitive Conversation
Prompt
I need to address a performance concern with direct report [name]. Help me think through how to frame this conversation in a strengths-based way that is clear, empathetic, and encourages ownership and accountability.
Why it works
AI supports thoughtful framing while leaving delivery and judgment firmly with the manager. Accountability remains central, alongside care and clarity.
Reflecting After a One-on-One
Prompt
Here is a brief summary of my one-on-one conversation with [name]: [paste summary]. Based on this summary, help me reflect on key themes, unresolved questions, and potential follow-up areas to explore in our next one-on-one. Focus only on what is present or implied—do not make assumptions.
Why it works
Used after the meeting, AI becomes a reflection partner rather than a decision-maker. This supports continuity across conversations while keeping interpretation grounded in what was actually discussed.
These examples are not templates to follow rigidly, but starting points managers can adapt as their confidence and fluency grow.
What to Avoid When Prompting AI
Managers should be cautious of prompts that:
- Ask AI to “solve” employee problems without conversation
- Generate scripts to be read verbatim
- Replace listening with efficiency
- Ignore individual differences or strengths
The goal is better dialogue, not better automation.
Teaching Managers to Use AI Well
Organizations introducing AI into leadership development should focus less on tools and more on thinking habits, including:
clarifying intent before meetings
asking better questions
reflecting after conversations
anchoring discussions in strengths and trust
When managers learn how to prompt AI effectively, one-on-one conversations become more focused, more human, and more impactful.
Leading Forward, Thoughtfully
AI is neither a threat nor a solution to leadership challenges. It is a tool. Like any tool, its impact depends on how and why it is used.
When leaders use AI to sharpen their thinking, deepen their preparation, and reinforce strengths, one-on-one conversations improve. Not because the technology is impressive, but because the manager shows up better prepared to lead like a human.
Want to help your managers use AI to strengthen, not shortcut, coaching conversations?
Let’s explore practical, strengths-based ways to build this capability into leadership development efforts.
