One-on-One Meetings Toolkit:

Introduction

As a leader, the last thing you want an employee to think when you send an invite for a one-on-one meeting is “what have I done wrong.” Unfortunately, if you use your catch-up meetings as performance reviews or a report card of everything an employee has done right and wrong, the amazing potential of these meetings can vanish and instead be replaced by fear and anxiety. 

You want to ensure this does not happen and to do so, you need to prioritize your employees in your one-on-one’s together. Think about it as GrooveHQ did; “If an employee is having a bad day or week, or is unhappy in their role, or if just about anything else is wrong in their eyes, it’s easy to hide it. And that’s very scary. Cultures, where important things get left unsaid, are unproductive, unpleasant, and frankly toxic to the business. Without any encouragement or processes for pulling those important things out of people, we were in danger of building that kind of culture.” 

By hosting regular one-on-one meetings with each team member that encourages honest, two-way communication, you can build trust and a healthy working relationship. These are two things an employee needs if they are going to confide in you about such thoughts or feelings in time for you to fix or mitigate them. Not to mention, touching base with employees is a chance to receive progress updates, offer support or guidance, discuss career goals, and provide timely coaching.

In the following toolkit, you will find a checklist, template, and list of questions to ensure every one-on-one meeting you host as a manager, supervisor, or leader, has the best possible effect on the engagement, loyalty, and productivity of your employees. 

One-on-One Meeting Checklist for Before, During, and After

Hosting an effective one-on-one meeting with a direct report goes beyond the 30-minutes in the meeting itself. There are things as a leader you must do before, during, and after to ensure the meeting objectives are met and the employee feels it was a good use of time spent away from the job. The following one-on-one meeting checklist should help you along the way and over time will become second nature. 

• Ask yourself, “Is the meeting necessary? Or could this meeting be an email?”

• Define the meeting objective before doing anything else

• Review the notes from your last meeting so you can follow up on any action items

• Put together an agenda and ask your direct report for their input/additions prior to sending the meeting request

• Send a meeting request that highlights the purpose/objective of the meeting and agenda

• Manage expectations by telling your direct report things you want them to prepare, share, or research prior to the meeting

• Prepare your discussion points against the agenda prior to the meeting

• If you're hosting your one-on-one meeting virtually, agree to turn your cameras on so you feel more face-to-face

• Show up on time, follow the set agenda, and end on time

• Agree to mute phones and computers to minimize distractions or tangents

• Start off on a high note by offering a compliment on their recent work or spending some time getting to know them as a person with non-work-related questions

• Be mindful of yourself and know when it is time to listen versus speak

• Take notes, especially of action items you and your employee agree to

• Recap accountabilities and expectations, as well as clarify things like timelines and tactics

• End with words of encouragement or appreciation

• Send an email after the meeting reiterating the key points or action items, and schedule/remind your employee of your next one-on-one

One-on-One Meeting Agenda and Meeting Request Template

A one on one meeting agenda serves two purposes: it helps define the purpose of the meeting and sets the expectation of either party for the dedicated time together. Ideally, the agenda is put together in collaboration with your direct report, as one-on-one’s are a time to focus on them and their needs. Within a 30-60 minute window, you should be able to socialize, get a recap of their workload or current projects, provide feedback, answer questions, find out what support they need from you, and get commitment to the accountabilities discussed. 

Once you have collaborated on an agenda, send an email such as the one on one meeting template below that contains the one on one meeting agenda template and a calendar invite.

To: [Name of Your Employee]

Subject Line: Agenda and Invite For Our Next One-on-One

Hi [First Name],

In advance of our one-on-one meeting, here is an invite to our one-on-one on [Day] at [Time] and the agenda we will follow. I want this time to be as beneficial to you as possible, so please let me know anything you want to be added to the agenda as we lead up to our time together.

• Recap of your current projects and assignments

• Review [XYZ project]; please bring a copy of what you have so far and any feedback or support you need from me to continue and hit our deadline

• Confirm action items to be completed before our next meeting

Talk soon!

[Your Name] 

List of One-on-One Meeting Questions for Leaders

Running an effective one-on-one meeting as a manager or leader is all about asking the right questions and then listening to what your employee has to say (or not say). Based on their answer, you can determine what they need from you, if anything, whether it be feedback, resources, or support removing a roadblock. The following list of one-on-one meeting questions is quite extensive, so do not expect to cover them all. But over time and as your relationship builds, you can begin to dig a little deeper.

Questions to Build Your Relationship & Establish a Connection

As a leader, a one-on-one meeting might be your only chance all week to really connect with your employees. Since building a solid relationship and establishing trust is key to a healthy working relationship, always plan to take some time out of the agenda to get to know your employees better as people. This will help you see them as people who have passions, aspirations, and lives beyond what you see between 9 and 5. 

Questions Regarding Progress and Support Needed

This is a time to ask questions and listen; not for you to vent, discuss office politics, or share the annoyances of your own job. Questions like those below will make your employee feel that you are looking out for them and want to help as they need it.

• What is on your agenda to cover?
• What would be the best use of our time today?
• What has your week been like? Capacity?
• Where could you use my help?
• Are you running into any roadblocks?
• Are there any challenges you’re currently facing?
• Have any new priorities come up that may impact your accountabilities?
• How are you tracking against deadlines?
• What is your biggest worry right now? How is your work-life balance?

Questions to Encourage Feedback

Once you and your employee have what you need regarding the day-to-day, you can transition this part of the agenda of your one-on-one meeting to seek and encourage feedback. The key to success here is not making your employees feel like they are on the spot. Clarify that this is just a chance for you to get to know them better and identify ways to support them. People appreciate being asked their opinions, especially those on the frontlines, as it makes them feel you value their experience. Ask questions like:  

• Do you have any feedback for me? How can I better support you (in the short- or long-term)?
• Do you have any suggestions on how we can work together better?
• Do you feel like you leave these meetings with clear direction? Or with a degree of uncertainty?
• Do you feel empowered to do your best work? If not, is there anything in particular that makes you feel this way?
• What is the level of support you need from me to be successful?
• Do you feel aligned with the mission and culture of the company?
• Is the vision for our team and our contribution to the organization clear?
• Have you identified anything we should do to achieve our goals?

Questions to Support Their Professional Development

As a leader, you are more than likely the one who knows your employee's goals, strengths, areas for improvement, or preferences the best. This makes you the ideal person to coach and advocate for them as appropriate. By asking questions during your one-on-one meetings such as those below, you can play a vital role in keeping employees engaged and challenged.

• What do you like about your role and the organization?
• What inspires/engages you at work?
• Where do you see yourself in the next five years?
• What’s the best way for you to learn something new?
• Is there a skill or topic you would like to learn that would support your current role and your career trajectory?
• Would you find a mentor or coach beneficial?
• What are your professional goals?