Holding Effective 1-1's Enhanced with AI

3 Keys to Success

Introduction

One of the most important skills for any leader is the ability to hold effective one-on-one meetings with their direct reports. These meetings are an opportunity to build trust, provide feedback, align on goals, and support the development of your team members. However, many leaders struggle with how to make the most of these meetings and avoid common pitfalls such as lack of preparation, poor listening, or vague follow-up. 

In this blog, I will share with you how I use AI to help me hold effective one-on-one meetings with my direct reports. AI can be a powerful tool to enhance your communication, coaching, and collaboration skills, and to make your meetings more productive and engaging. Here are the three keys to success that I follow: 

1. Prepare

Preparation is the foundation of any successful meeting. Before each one-on-one, I do the following: 

• Review the last 1-1 meeting’s action items and check the progress and status of each one. 
• Draft an agenda with the topics that I want to discuss with my direct report, such as their goals, challenges, feedback, and development needs. I also ask them to do the same and share their agenda with me in advance. 
• Use AI to help me respond to virtual conversations, such as chats and messaging, that my direct report may have initiated or participated in since our last meeting. This helps me to stay updated on their work, issues, and achievements, and to acknowledge their contributions. 
• Use AI to request coaching advice based on the current situations as well as their personality type (such as DISC) with my direct report. For example, if they are facing a difficult client, a conflict with a colleague, or a personal challenge, I can ask AI to suggest some questions or tips to help me coach them effectively based on their DISC type. 
• Confirm that my direct report is ok with recording our meeting and if so, enable recording and transcription for our meeting. This allows me to focus on the conversation and not worry about taking notes or missing any details. 

2. Listen and Coach 

During the meeting, I follow these steps: 

• Review the last meeting’s action items, celebrate the achievements and address the challenges. 
• Ask the employee to review and discuss their agenda items first before I discuss anything on my portion of the agenda. This shows that I value their input and perspective, and that I am there to support them. 
• Listen carefully for context and pay attention to emotions. Try to analyze the tone, sentiment, and emotion of the conversation, and be aware if there are any signs of stress, frustration, or dissatisfaction.  If so, state that it sounds like they may be frustrated and ask for further clarification. 
• Confirm what I heard and ask if they would like direction and/or support. I use AI coaching advice in the preparation step to help me paraphrase and summarize the key points and action items, and to check for understanding and agreement. 
• Ask questions about progress and potential challenges on each of their goals. I use AI in the preparation step to help me generate relevant and open-ended questions that encourage them to think critically and creatively, and to share their insights and ideas. 
• Pursue mutual agreement on development level for each goal by discussing the competence and confidence for each of their goals. 

• Match their development level with the appropriate leadership style.  

• • For example:

• • • if they are highly competent and confident, I use a delegating style 
    • if they are moderately competent and confident, I use a supporting style 
    • if they are moderately competent but less confident, I use a coaching style 
    • if they are less competent and confident, I use a directing style. 

3. Follow Up

After the meeting, I do the following: 

• Review the transcript and AI-generated recap of the meeting. This helps me to refresh my memory, identify any gaps or errors, and extract the key takeaways and action items. 
• Review and develop a plan to address the action items. I use AI to help me prioritize, delegate, and track the action items, and to remind me and my direct report of the deadlines and deliverables. 
• Confirm recurring appointments are set up and stub out time to prepare for the next 1-1 meeting. I use AI to help me schedule and manage my calendar, and to notify me and my direct report of the upcoming meetings and preparation steps. 

Holding 1-1’s with Inspire Software and Microsoft Copilot 
With Inspire, you can: 

• Set agendas for your 1-1 meetings and share them with your direct reports in advance, so that both of you have clear expectations and objectives for the meeting. 
• Assess the development levels of your direct reports and tailor your coaching style accordingly, using Inspire's situational leadership framework. 
• Send messages between direct reports and leaders before the meeting, to remind them of the agenda, ask for feedback, or acknowledge their achievements while AI provides response suggestions based on the situation and DISC type of the direct report. 
• Receive coaching advice from Inspire prior to the meeting, based on the agenda items, DISC personality type and the development levels of your direct reports. Inspire will suggest questions, topics, and techniques that can help you listen and coach effectively. 
• Use video conferencing tools like MS Teams or Zoom to conduct your 1-1 meetings virtually, especially if you have a hybrid or remote workforce. These tools can transcribe the discussions and provide you with a record of the meeting. 
• Use AI tools like Microsoft's Copilot to summarize and track any commitments or action items that arise from the meeting. Copilot can also help you prioritize, delegate, and follow-up on the action items, and remind you and your direct reports of the deadlines and deliverables. 
• Store meeting summaries and action items in Inspire, to ensure accountability and transparency. Inspire will also provide you with rich data and insights on the performance and development of your direct reports, which can help you draft your performance evaluations at the end of the performance cycle. 

By using Inspire and other AI tools, you can make your one-on-one meetings more productive, engaging, and rewarding for both you and your team members. You can leverage the power of AI to enhance your communication, coaching, and collaboration skills, and to achieve your goals and objectives. Inspire is your ally in holding effective one-on-one meetings with your direct reports. 

Conclusion
Holding effective one-on-one meetings with your direct reports is a key skill for any leader. By using AI to help you prepare, listen and coach, and follow-up, you can make your meetings more efficient, productive, engaging, and rewarding for both you and your team members. AI can be your ally in enhancing your communication, coaching, and collaboration skills, and in achieving your goals and objectives.