Chatbot Prompts for Managers 2024

In my continuing effort to help managers leverage the amazing value of chatbots, this article provides a large number of prompts you will immediately find helpful. If chatbots are new to you, please read my previous article “Practical Guide to Using AI Chatbots“.

As described in the above mentioned article, there are four good free AI chatbot options that you can use, ChatGPT, Bard, Claude, and Copilot. Each has been trained on a large data set and will provide good results for the prompts related to management. I recommend trying a couple of the chatbots to see which you prefer. If your company pays for any of the more advanced versions, I suggest you try it as well.

The first section of this article provides prompts across the most important aspects of management. Each aspect is broken down further to make it easy to find what you are looking for. While this is a long list, it is far from exhaustive, but it should give you a nice headstart. This is followed by a section on creating your own prompts. And finally, there is a discussion on chatting with the chatbot.

Note: I created the images for each section using Midjourney. I used the section heading as the prompt and selected the best image. I really like some and others not so much:)


Below are several prompts in each major area of management. These are written in a generic (non-industry and non-company) manner. They will help you to learn how to do something rather than provide you with specifics for you, your team, or your company. The next section will help you to provide the context to use prompts for your specific purpose.

Developing Strategy

Developing Strategy

External Environment and Industry Analysis:

  • How do I determine the key trends and disruptions impacting our industry, technology, and customer landscape?
  • What is the best way to identify our main competitors, and their strengths and weaknesses?
  • What are the political, economic, social, technological, and environmental (PESTLE) factors affecting our strategic planning?
  • What are the best ways to leverage emerging trends and opportunities to gain a competitive advantage?
  • What are some strategies to mitigate potential risks and threats to our strategy?

Internal Capabilities and Resources:

  • How can I determine our core strengths, weaknesses, opportunities, and threats (SWOT)?
  • What are the best approaches to determining key resources and capabilities, and how can we leverage them effectively?
  • How do I identify our biggest internal challenges and limitations?
  • How do I determine the skills and capabilities needed to develop to achieve our strategic goals?
  • What are the best approaches to attract and retain the talent needed to execute our strategy?

Decision-Making and Prioritization:

  • How do I determine the most critical decisions we need to make to move forward?
  • What are the approaches used to make sound strategic decisions based on incomplete information and uncertainty?
  • What criteria should I use to prioritize strategic options and initiatives?
  • How can I build consensus and alignment on the chosen strategy within the organization?
  • How do I address conflicting priorities and competing interests?

Implementation and Execution:

  • What are the key steps and milestones for implementing our strategy?
  • How do I determine the resources and budget to allocate to each strategic initiative?
  • What is the best practice in determining who is accountable for different aspects of the strategy?
  • What are the best approaches used to track progress and measure the success of our strategy?
  • How do I adapt and adjust our strategy based on changing circumstances?

Sustainability and Long-Term Vision:

  • How do I ensure our strategy is sustainable and adaptable in the long term?
  • What approaches can be used to determine potential future scenarios that need to be considered?
  • How do I make sure that my team stays agile and responsive to change?
  • What is the best approach to communicating our strategy and vision effectively to all stakeholders?
  • How do I continue to engage and motivate employees to deliver on the strategy?
Organizational Development

Organizational Development

Assessing the Need for Change:

  • How do I know if my organization needs to undergo organizational development (OD) initiatives?
  • How do I determine the current strengths, weaknesses, opportunities, and threats (SWOT) of our organization?
  • How can I understand the challenges are hindering our growth and performance?
  • How can I understand if employees are engaged and motivated, or if there are signs of dissatisfaction?

Defining Goals and Objectives:

  • What are the best approaches to determining the specific goals and objectives we want to achieve through OD initiatives?
  • How do I ensure that our goals align with our overall organizational strategy and mission?
  • How do I develop the metrics that we use to measure the success of our OD efforts?
  • Who are the key stakeholders involved in the OD process, and how can we engage them effectively?
  • How do I determine the right level of resources and budget to make available for OD initiatives?

Choosing the Right Approach:

  • What are the different approaches to OD, and how do I determine which one best suits our needs?
  • How do I decide if we should involve internal or external consultants for OD interventions?
  • In implementing OD, what training and development opportunities are needed for employees at different levels?
  • How do I create a culture of continuous learning and development within the organization?
  • How do I ensure effective communication and change management throughout the OD process?

Addressing Specific Challenges:

  • What are some approaches to improving communication and collaboration within our teams?
  • What are some best practices to attract and retain top talent in a competitive market?
  • How do I foster a more diverse, equitable, and inclusive workplace?
  • What are the best practices for managing conflict and building trust within the organization?
  • How can I increase employee engagement and motivation?

Measuring and Sustaining Change:

  • What are the best models and tools to track the progress and impact of our OD initiatives?
  • How do I make sure that we sustain the positive changes implemented through OD efforts?
  • How can I make continuous improvement a part of our company culture?
  • What resources and support are typically needed to maintain a healthy and thriving organizational environment?
Operational Management

Operational Management

Efficiency and Productivity:

  • How do we determine which processes are candidates to streamline to improve efficiency and reduce waste?
  • What metrics should we use to track and measure productivity?
  • How can we optimize resource allocation to ensure we’re maximizing resources?
  • How can we identify and address bottlenecks hindering workflow?
  • What tools and technologies can we leverage to boost operational efficiency?

Quality Control and Improvement:

  • How can we ensure consistent quality of products and services?
  • What are the most common quality control measures we should consider implementing?
  • How can we identify and address quality issues promptly?
  • How do I encourage a culture of continuous improvement within the team?
  • What data analysis and feedback mechanisms can we utilize to drive improvement?

Inventory and Supply Chain Management:

  • How can we optimize inventory levels to minimize waste and meet demand effectively?
  • What strategies can we employ to manage supplier relationships and ensure timely deliveries?
  • How can we mitigate risks associated with supply chain disruptions?
  • How can we leverage technology to improve inventory tracking and forecasting?
  • What cost-saving measures can be implemented without compromising quality or service?

Risk Management and Compliance:

  • How do we determine the key operational risks we face, and how to mitigate them?
  • How do I create a culture of safety and risk awareness within the team?
  • How do we identify areas where incident response and risk management plans are required?
  • How can we stay informed about evolving regulations and industry best practices?

Team Management and Communication:

  • How do I motivate and engage team members to achieve operational goals?
  • What communication strategies should I implement to ensure clarity and transparency?
  • How can I foster collaboration and teamwork within the operational team?
  • How do I effectively delegate tasks and provide constructive feedback?
  • How do I recognize and reward individual and team achievements?

Data-driven Decision Making:

  • How do we determine what data is most relevant and valuable for operational decision-making?
  • Are there best practices in collecting and analyzing data effectively to inform our decisions and choices?
  • What are approaches used to translate data insights into actionable plans and strategies?
  • How can we continuously improve our data-driven decision-making capabilities?
People Development

People Development

Identifying Needs and Gaps:

  • How do I identify skill gaps and development needs within my team?
  • What are the best methods for conducting performance reviews and development conversations?
  • How can I ensure individual development plans are aligned with both employee and organizational goals?
  • How do I assess the effectiveness of our current training and development programs?

Providing Learning and Development Opportunities:

  • What types of training and development programs are most effective for different learning styles and needs?
  • How can I leverage technology to provide flexible and accessible learning opportunities?
  • How can I encourage and support employee self-directed learning and development?
  • What resources can I offer to support mentorships and coaching within my team?

Creating a Culture of Development:

  • How can I create a culture that values and encourages continuous learning and development?
  • How can I empower employees to take ownership of their own development?
  • What are some approaches used to reward and recognize employees for their commitment to development?
  • What are innovative ways to overcome common challenges like budget constraints and time limitations?

Specific Skills and Areas of Focus:

  • How can I help my team develop essential skills like communication, leadership, and collaboration?
  • How can I support the development of digital skills and adaptability in a changing workforce?
  • How can I promote diversity, equity, and inclusion through learning and development initiatives?
  • How can I prepare my team for future changes and disruptions in the industry?


  • How can I effectively manage the cost and ROI of people development initiatives?
  • How can I stay up-to-date on the latest trends and best practices in people development?
  • What resources and tools can I utilize to support my efforts in people development?
Project Management

Project Management

Planning and Scoping:

  • How do I define a clear project scope and set realistic goals?
  • What is the best approach to breaking down the project into manageable tasks and sequences?
  • How can I estimate project timelines and resources accurately to avoid under- or over-allocation?
  • What risk management strategies should I implement to mitigate potential issues and impacts?

Resource Management and Team Dynamics:

  • What are the best practices to assign resources effectively to maximize team productivity and avoid overwork?
  • How do I ensure effective communication and collaboration among team members, even if they are geographically dispersed?
  • How can I foster a positive and motivated team environment conducive to achieving project goals?
  • How can I address conflicts and manage performance issues within the team constructively?

Execution and Monitoring:

  • What tools and techniques can I use to track project progress and identify potential problems early on?
  • How can I make data-driven decisions and adjust plans as needed to stay on track?
  • How can I effectively communicate project status and updates to stakeholders, including sponsors and clients?
  • What are the best practices to manage scope creep and maintain control over project budget and resources?

Agile and Adaptive Techniques:

  • How can I incorporate agile methodologies into my project management approach for faster adaptation and flexibility?
  • What tools and platforms can I leverage to facilitate iterative development and continuous improvement?
  • How can I cultivate a culture of openness and feedback to embrace change and iterate effectively?
  • How can I measure the success of agile projects beyond traditional metrics like deadline and budget?


  • How can I adapt my project management style to different project types, sizes, and complexities?
  • What are the ethical considerations in project management, especially when dealing with competing priorities and deadlines?
  • How can I continuously learn and develop my project management skills to stay relevant in a changing business landscape?
Hybrid / Remote Workers and Teams

Hybrid / Remote Workers and Teams

Communication and Collaboration:

  • How do I ensure effective communication across the team despite physical distance?
  • What tools and platforms can I use to facilitate seamless collaboration and information sharing?
  • How can I overcome communication barriers and ensure everyone feels heard and understood?
  • How do I build trust and rapport with team members I may rarely see in person?

Culture and Engagement:

  • How do great managers foster a strong team culture and sense of belonging despite physical distance?
  • How can I ensure everyone feels included and valued regardless of their location?
  • What are some recommended approaches to organizing virtual team-building activities and social events to promote connection and collaboration?
  • What can I do to prevent social isolation and loneliness among remote team members?
  • How do I maintain a culture of open communication and feedback in a hybrid environment?

Performance Management and Accountability:

  • What are the recommended approaches in setting clear expectations and goals for both remote and in-office employees?
  • What are examples of metrics I should use to measure the performance of hybrid and remote teams?
  • What are the best approaches to providing constructive feedback and coaching to remote employees without micromanaging them?
  • How do I ensure all team members, both remote and in-office, feel equally accountable and contribute meaningfully?
  • What are the best practices and examples to address potential performance issues arising from differences in work styles or communication preferences?

Technology and Security:

  • What technology tools and resources do I need to equip my hybrid team for success?
  • What can I do to ensure data security and privacy for remote employees accessing company information remotely?
  • How can I stay up-to-date on the latest technologies and trends relevant to hybrid work management?

Work-Life Balance and Flexibility:

  • How can I support healthy work-life boundaries for both remote and in-office employees?
  • What flexible work arrangements should I consider to accommodate different needs and preferences?
  • How can I ensure remote employees are taking breaks and avoiding burnout?
  • What are the best ways to address concerns about presenteeism or feeling “always on” in a virtual environment?

Leadership and Development:

  • What are some approaches to effectively lead a hybrid team with diverse work styles and preferences?
  • What are ways to empower remote employees and encourage ownership of their work?
  • What opportunities for professional development and training should I offer to both remote and in-office employees?
  • How do I stay connected and provide support to remote employees who may feel less visible?
  • What are some ways to ensure fair and equitable opportunities for growth and advancement for all team members?
Personal and Time Management

Personal and Time Management

Personal Effectiveness:

  • How can I stay focused and avoid distractions in a demanding work environment?
  • What are approaches I can use to prioritize tasks effectively and manage my workload efficiently?
  • How can I establish healthy work-life boundaries and prevent burnout?
  • What are approaches to maintain my energy and well-being throughout the workday?
  • What strategies can I use to delegate tasks effectively and empower my team?

Team Productivity:

  • How can I foster a culture of accountability and responsibility within my team?
  • How do I motivate and engage my team to achieve peak performance?
  • How should I identify and address time management challenges faced by individual team members?
  • What tools and techniques can I use to improve team communication and collaboration?
  • How do I develop an approach in support of a flexible work environment that supports different work styles and schedules?

Managing Meetings and Communication:

  • What are the best approaches to conduct effective and efficient meetings that produce actionable results?
  • How can I minimize the number of meetings and ensure they are only held when necessary?
  • How can I encourage clear and concise communication within my team to avoid misunderstandings?
  • How do I create a system for managing emails and instant messages effectively?
  • How can I utilize technology to streamline communication and collaboration within my team?

Personal Development and Learning:

  • How can I identify and prioritize areas for my own personal and professional development?
  • What resources and learning opportunities are available to help me improve my management skills?
  • How do I make time for learning and development amidst a busy schedule?
  • How can I encourage a culture of continuous learning and development within my team?
  • How can I stay up-to-date on the latest trends and best practices in management and productivity?
Communicating Ideas and Creating Presentations

Communicating Ideas and Creating Presentations

Crafting the Message:

  • How do I determine the key message I want to convey? How can I make it clear, concise, and impactful?
  • How do I identify my audience’s needs, interests, and prior knowledge? How can I tailor my message to resonate with them?
  • How do I use data and evidence to support my key message? What are some approaches that I can use to present my information compellingly and concisely?
  • What are some examples that I can learn from to build a story that I tell to engage my audience and make the information memorable?

Visual Storytelling:

  • What are some examples of visuals that managers use to support their message and capture attention? (slides, infographics, videos, etc.)
  • Are there tips and tricks for creating visually appealing and professional-looking presentations?
  • What is the best practice around the number of slides to create and how much information to include on each slide?

Delivery and Impact:

  • How do I learn to deliver my presentation with confidence and clarity?
  • What are some approaches that are used to overcome nervousness and stage fright?
  • How do the best presenters engage with their audience and answer questions effectively?
  • Are there recommendations for how to use my voice and body language to emphasize key points?
  • How can I measure the impact of my presentation and assess if it achieved its goals?


  • What technology and tools should I use for my presentation?
  • How can I ensure my presentation is accessible to everyone in the audience?
  • What are ways that presenter practice and rehearse their presentations?
  • How should I handle unexpected situations during the presentation?
  • How can I continuously learn and improve my presentation skills?
Staying Current and Leveraging Technology

Staying Current and Leveraging Technology

Understanding the Landscape:

  • How do I determine the most significant emerging technologies that could impact my industry?
  • How can I find out if these technologies are being used by competitors and leading organizations?
  • How can I identify and evaluate potential technology solutions for my specific needs?
  • How do I identify the resources I should use to stay informed about the latest technological trends?

Implementation and Integration:

  • How can I effectively integrate new technologies into our existing systems and processes?
  • What are the potential challenges and risks associated with technology implementation?
  • How can I ensure that new technologies are adopted and used effectively by employees?
  • What training and support are needed for employees to adapt to new technologies?
  • How can I measure the return on investment (ROI) of technology investments?

Security and Data Management:

  • How do I learn about the key cybersecurity threats and vulnerabilities facing our organization?
  • How can we implement effective data security measures to protect sensitive information?
  • How can we develop a culture of cybersecurity awareness within the organization?

Budgeting and Resource Allocation:

  • How do I determine how much should we invest in technology each year?
  • How do I determine the appropriate allocation of resources effectively to support our technology needs?
  • How do I measure the value of technology investments beyond just the cost?

Leadership and Change Management:

  • How should I lead my team through technological change effectively?
  • How can I overcome resistance to change and build buy-in for new technologies?
  • How do I create a culture of innovation and continuous learning within my team?
  • What skills and capabilities do I need to develop to be an effective technology leader?
  • How do I stay ahead of the curve and prepare for future technological disruptions?

Creating Your Own Prompts

As you can see from the list of prompts above, it is not hard to create your own. Here are some simple steps to get you started.

  • Think about the area that you are interested in or questions that you have.
  • Describe your interest or ask your question in full sentences as if you are asking another manager or mentor.
  • Consider including context. If you think about talking to a manager or mentor, they likely have a good deal of context. They may know the company well, have history with you, and/or know about the topic area. The chatbot does not. In order to get the best response, providing context relevant to the topic or question will be helpful.
  • If you do not get the response that you were looking for, try asking the question again in a different way, with more details, and with more context.

That is all there is to it. As you use chatbots – you will get better and better at writing prompts.

Chatting with Chatbots

Chatting with Chatbots

There is a reason that they call them chatbots (rather than something like answering machines). It is because you can chat with them. Interact. Have a discussion.

Here is how I typically chat with a chatbot.

  • I first provide a good deal of context that is relevant to the area that I want to chat about.
    • For example, before I ask questions about developing a strategy, I would provide the chatbot with information about my company, organization, and projects that we have underway. I would provide some background on what we have done related to strategy in the past.
  • Then I describe my problem, ask my question, etc.
  • I then review the response that I receive from the chatbot.
    • If it happened to provide me with exactly what I needed, great, I am done.
    • It is more likely that I didn’t get exactly what I needed.
  • I then refine my question or ask a follow-up question.
    • For example, if I asked about developing a strategy and the response started with evaluating the competition, I would restate the question making it clear what aspect of developing strategy I was looking and not looking for.
  • There are times when I get a response that triggers more questions. This is perfect, the chatbot now has context and I can ask these additional questions.

Most of the chatbots allow for separate threads. These threads allow you to keep a conversation alive so that you can go back and review the responses later, or more importantly, you can continue the conversation where you left off.

I can’t overemphasize how valuable this is. I constantly go back to previous threads to continue the conversation, drill down, get clarity, or ask more questions.


Chatbots are well-trained to provide help for managers across the many aspects of your job. Pick one and start using it. Give it a try with one of the prompts above or create your own.

As you get more comfortable, start having conversations (threads) in the areas most important to you. Go back when you need more information, clarity, or have additional questions.

See Also

Categories: Tools


Jeff Tarter · February 7, 2024 at 5:59 am

This is really well researched and pulled together. There are a lot of thought provoking questions.

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