One-on-One Meeting Guide for Small Businesses [Remote]

What is a one-on-one meeting, how do you run one, and why is it important for growth and trust? Here’s everything you need to know about one-on-one meetings – including how Ninety’s One-on-One Meeting tool makes it easy to run one-on-ones, even remotely.

What is a One-on-One Meeting for Managers and Remote Teams?

This is a comprehensive action plan for small businesses on how to run a good one-on-one meeting.

If you want to:

• Establish two-way trust between a leader and each member of their team,
• Act on potential challenges faster,
• And build better teams…

Then you’ll love this guide, whether you work in a hybrid environment, in-person, or as a remote team. Let’s get started.

What’s Covered in This Guide

Click on each link to jump to that section.

• What is a One-on-One Meeting?
• What Do You Talk About in a 1-on-1 Meeting?
• How Often Should You Have 1-on-1s?
• What is the Purpose of a One-on-One Meeting? Why Have Them?
• How One-on-One Meetings Work
• How to Use Ninety to Run Your One-on-One Meetings
• How to Prepare for a One-on-One Meeting
• 1:1 Meeting Agenda Checklist
• 8 Ways to Make 1-on-1s More Meaningful

What is a One-on-One Meeting?

A 1-on-1 meeting is when two people in an organization meet regularly for mutual feedback and updates. Broad topics that are typically discussed can include work, performance, what motivates them, development opportunities, career growth, and more. It’s a platform for two people to build a stronger working relationship.

People refer to this type of meeting in different ways. You’ll hear people call it: 

• “One-on-one” 
• “1-on-1 meeting” 
• “One-on-one meeting” 
• “Face-to-face” 
• “1:1 meeting”
• And other similar variations of the term

No matter your preference, they all mean the same thing. 

One-on-ones are most often scheduled between a team leader and a team member as a way to connect and stay engaged with one another. They can also occur between a teammate and a mentor, a team member and an executive leader (called a “skip-level 1:1”), or a teammate and an intern.

A one-on-one meeting is unlike any other type of meeting. That’s because it’s a time dedicated to open-ended conversations, coaching, discussing, offering opinions, mentoring, and other communication that helps to keep each person informed, resolve issues, and give feedback that helps them grow in their roles.

“A one-on-one in Ninety is purely a performance conversation, not a pay conversation,” says Kris Snyder, Ninety coach and founder of Impact Architects. “We separate the two so leaders and direct reports can give and get better feedback on performance without being distracted by talk about compensation. This is critical for mutual growth.”

With Ninety’s One-on-One tool, build face-to-face conversations that also integrate with that employee’s goals, roles and responsibilities, and more — all inside one platform. Try it for free now.

What Do You Talk About in a 1-on-1 Meeting?

According to a recent survey on one-on-one meeting topics:

• 75% of leaders and team members talk about growth and development
• 73% discuss the status of specific projects
• 70% want to understand and eliminate roadblocks
• 61% get a pulse check on how they’re feeling about work right now
• 56% discuss employee performance
• 49% talk about the level and strength of their motivation
• 47% explore their connection to work and other people in the company
• 45% talk about things related to accountability and autonomy
• 23% want to know how they relate to the company’s vision and mission

Understanding how to run a good one-on-one meeting starts with laying the groundwork for trust between two people and forging a productive work relationship together. Rather than using a standardized formal approach, one-on-one conversations are personalized for the people having the meeting. Creating a custom agenda is the way to go. 

These simple guidelines can help:

1. Set a goal for every one-on-one meeting.

By collaborating on a goal that’s relevant to your relationship, both of you will get more value out of the meeting. A goal can be broad, like career growth. It can be personal, like a pulse check on how you’re feeling about things. Or it can be a check-in on work in general. Or a share session about what motivates you to pursue your passions. Once you determine the thing you’re going to talk about, you can create the meeting structure with agenda items around your goal.

2. Use conversation starters (called “Segues” in Ninety Meetings).

Start a 1:1 meeting in a way that keeps you both relaxed and receptive. It could start by asking a question about a mutual pastime, a new hobby, a long-held interest, or anything that helps create a psychologically safe environment. It means people can feel free to share meaningful personal information without fear of bad consequences to their self-image, role, or responsibilities. 

A conversation starter does not mean “small-talk” about the weather or the weekend. What works better to break the ice are discussions that help you learn more about each other and segue smoothly into the main goal of the meeting.

3. Avoid too much status update talk.

When updates on specific projects dominate a one-on-one meeting, there’s no time to develop a rapport that builds lasting trust. Use consistent feedback instead.

Recent research by Gallup on the global work environment finds that when people receive consistent feedback, it helps them connect emotionally and psychologically to their work and to their place of work. So including performance feedback as part of 1-on-1 agendas can inspire higher levels of productivity and higher quality outcomes.

“Meeting one-on-one helps establish a really good connection between a leader and a team member that simply can’t evolve during the course of daily work. You need that opportunity to be able to see how a team member is doing, a platform for them to bring any issues to the surface that they may not discuss otherwise. Ninety helps you do this.”

-Zack Swire, Founder & Coach, Top Teams

How Often Should You Have 1-on-1s?

How often to have a one-on-one meeting depends on what will work for both people on a regular basis. The frequency and length are really up to you, based on the relationship. The important thing is to get accustomed to meeting regularly for this purpose. 

Another consideration for scheduling is the number of people one leader needs to meet one-on-one. Everyone needs to be accommodated within a schedule you can live with.

Ninety recommends that a leader and a direct report schedule a one-on-one meeting at least once a quarter, frequent enough without losing a connection with someone. If monthly is a better frequency, make it a once-a-month occurrence. Increase the number of meet-ups if you need more.

Research from Google reveals that the frequency of 1-on-1 meetings can make a difference in performance. The more frequent one-on-ones are, the better the outcome. Leaders who were surveyed report that their sweet spot for 1:1 meeting frequency is every week. The preferred meeting length is 30 minutes.

Other things to consider when deciding on a 1:1 meeting schedule:

• Nurture a new relationship with more meetings and adjust the schedule when needed.
• Determine the number of topics you cover consistently during each meeting and how much time it takes to get through them. If the meetings run long or you stop them without getting through all agenda items, adjust the meeting schedule to accommodate meaningful discussion.
• Schedule one-on-ones at a frequency and length that allows you to discuss things that come up between meetings.

What is the Purpose of a One-on-One Meeting? Why Have Them?

The number one reason for one-on-one meetings is to build better relationships at work.

One-on-ones are an opportunity to get to know all of your team members personally. Setting aside a specific time to talk face-to-face gives insight into what motivates them to pursue their aspirations for a career and how the two of you can work together to achieve them.

Leaders can make a difference in their team members’ lives, which affects the health of the entire organization. Even though at least half of employees say they have left their seats because of toxic relationships with team leaders, a leader can affect an employee’s engagement by an advantage of 70%, according to Gallup. Leaders who meet regularly with their direct reports inspire them to be three times more engaged than those who don’t. Having consistent one-on-ones is one of the keys to making work better.

In a massive study on how to improve workplace happiness and loyalty, survey participants at all company levels say they are much more satisfied and happy at work – and in life; when the relationship they have with the person they report to is more like a partnership.

Good partnerships are one of the results of consistent 1:1 meetings. Partnerships can help:

• Create trust between two people.
• Resolve issues before they fester into problems.
• Identify expectations relating to roles and responsibilities.
• Guide a person’s career development.
• Coach someone with improving their personal skills.
• Keep productivity high.
• Improve team member retention.
• Learn how to improve in your own role.
• Keep people happy and satisfied at work.

Other reasons for conducting consistent one-on-one meetings include:

• Discovering potential problems faster.

There are bound to be issues that arise when working as a team. When people feel free to discuss them in a regular private conversation with no fear of retribution, team members can monitor situations and act quickly to shut down any negative consequences.

• Freely discussing and analyzing performance.

One-on-one meetings allow you to keep an eye on a team member’s performance in the context of daily responsibilities and their role in creating value for the company. When people meet weekly for 1-on-1 meetings, questions about performance are top-of-mind. Also, the information can fuel better annual performance reviews later on.

• Expressing thanks more often.

Regular one-on-ones allow people to easily recognize great work right when it’s happening. Common feedback among team members is that they don’t hear positive feedback often enough. One-on-one meetings are an ideal place to do more than pointing out places where a person could correct behavior or performance.

When people engage in regular one-on-one meetings, it benefits the company. Overall success and creating value are built on solid collaborative effort among leaders and team members. It builds a culture of trust, improves productivity, and keeps everyone invested in achieving growth for the organization.

“Making trust easier to see, understand, measure, and build is one of our primary objectives.”

-Mark Abbott, Founder and CEO of Ninety.io

How One-on-One Meetings Work

How do you conduct a one-on-one meeting? Here are six common attributes of a good 1:1 meeting:

1. They’re scheduled regularly.

They should appear as a recurring meeting on your calendar. Weekly, monthly, quarterly – the two of you decide.

2. There’s a 1:1 with everyone on a team.

Each member gets face time with the leader, which improves trust, accountability, engagement, and outcomes.

3. Typically they’re 30 minutes long.

Any shorter and there won’t be time for feedback. Any longer and they may become cumbersome, which is something no one looks forward to. But it’s not a hard length. Again, the two of you decide.

4. Their agendas are personalized.

They’re based on the relationship of the two people who meet. This allows for open discussions and honest feedback, every time.

5. They’re a place to ask questions, listen, and coach.

Each participant gets to absorb information like feedback so they can improve performance, be more productive, and grow within their roles.

6. There’s always time to take notes.

Documenting what gets discussed – including any solutions – and making it available 24/7 lets the participants review, remember, and retain action items that are critical to success.

How to Use Ninety to Run Your One-on-One Meetings

The Ninety platform helps users think of a 1:1 meeting as hour-long conversations rather than typical reviews. This is how Ninety walks small business leaders and team members through the 1:1 meeting process. “It opens the door for thoughtful comments around the context of work,” Kris Snyder says. “You can talk about it openly, honestly, and discuss the ‘whys’ in a more meaningful way.”

During 1:1 conversations in Ninety’s software, each participant selects their initial assessment from a multiple-choice menu. Then the two have time to comment more deeply on each response. A leader can explain their responses while a direct report can speak to their own behavior. Kris says, “This is one of the key ways Ninety helps leaders and team members give and get better feedback, which is critical for mutual growth.”

Participants have several types of conversations:

• About the company’s core values. Participants have instant access to core values within One-on-One Meetings via the Vision + Goals tool.
• About employee performance. This is based on goal completion over the quarter. Participants can review any type of priority or goal associated with the direct report’s seat in 90-Day Goals, available within One-on-Ones.
• About leadership performance. This is a 360 approach to solicit feedback from a direct report on a leader’s performance, based on five questions in two categories.

Compared to other 1-on-1 meeting template options, Ninety’s One-on-One meeting template tool not only saves time. “Having a predictable structure already built inside the operating system that both participants understand and anticipate, definitely frees up time,” Kris says. “It also allows each person to focus more energy on the comment section of each conversation, which is where they find the most value in terms of accountability and trust.” 

Keep all your one-on-one meeting notes accessible – and private – in the secure Ninety platform. Sign up for a 30-day trial now.

How to Prepare for a One-on-One Meeting

How should leaders conduct 1-on-1 meetings? How should team members view them? 

Research shows that nearly half of leaders agree that the responsibility of creating the meeting agenda should be shared between participants. However, 26% of leaders polled are solely responsible for how a one-on-one is conducted while about 20% of direct reports create the agenda on their own.

With one-on-one meetings in Ninety, a direct report is in the driver’s seat, setting the stage for the 1:1. They choose the timing and the data of the conversation and then offer their feedback first during the meeting.

Leaders and team members should prepare for different responsibilities during a 1:1 meeting.

The leader should make sure the meeting atmosphere is psychologically safe. Open communication is the goal. Thoughts, opinions, and feedback can be shared freely and without judgment. This should be the expectation of both participants.

• Set the tone for the conversation by sharing your own views honestly in a relaxed, relatable manner.
• Realize there’s a limit to challenging people with too much feedback, good and bad. Use your meeting agenda to focus on one or two aspects of the person’s role or responsibilities.
• Come to an agreement with your direct report by acknowledging feedback and committing to act on it in a way that leaves things better than they were before.

The team member should make the most of 1:1s by using the time to get to know their leader. Since you have their undivided attention, take charge of the conversation.

• Get to know your leader’s communication style and what they expect of you.
• Express how you’re feeling about work, team dynamics, what you’re passionate about, and how you’d like to move forward within the organization. 
• Tell leaders how and when they are helpful and effective.
• Identify the obstacles you’re facing and how you can collaborate to overcome them.

1-on-1 Meeting Agenda Checklist

Ninety’s One-on-One tool is a great 1-on-1 meeting template that walks you through the entire process. It provides:

• A detailed meeting agenda.
• A meeting checklist.
• Intuitive ways to give and get mutual feedback.
• A record of everything discussed during the meeting so both people can refer back to it, quarter-over-quarter and year-over-year.

Ninety’s One-on-One template initiates informal feedback sessions, which are one-hour, one-on-one meetings that occur every 90 days. They are an opportunity to share a conversation about what’s working and what’s not.

By keeping 1:1s purely performance conversations, Ninety’s One-on-One Meeting tool helps foster growth – for the leader, the direct report, the team, and the company overall.

Running a one-on-one within Ninety, leaders and their direct reports can easily analyze the data from the Roles & Responsibilities Chart every single meeting with an eye toward the future. “When people are crystal clear on expectations and conduct their work based on the right agreements, accountability increases,” Kris says.

Ninety’s quarterly feedback sessions are a way to improve trust within an organization. “We regularly talk about the components of trust,” Kris says. “Like character, which we explore through our core values conversation. Another is the depth, frequency, and duration of our connection. How deep do we go? How much are we interacting? Are we spending enough time talking about everything we need to talk about to achieve great outcomes? It’s a discipline we are developing that the Ninety software supports.”  

Participants can document meeting notes for any one-on-one meetings in the Ninety platform and have them available to review during the meeting. People can also prepare thoughts for this conversation by filling out forms and then bringing these notes to the meeting.

Another Way to Have a One-on-One Meeting in Ninety

When two people require a private setting to conduct a meeting one-on-one, they can set up Private Teams on Ninety. Having a 1:1 meeting through private teams ensures the privacy people need and still have access to the full suite of Ninety tools to help facilitate and support the discussion.

Private teams can access the same functionality within Ninety as other teams. The private team members can create 90-Day Goals, schedule Meetings, add Issues, and assign To-Dos that are not accessible to anyone else. This makes these one-on-one tool capabilities so desirable and effective for meetings meant to be private. Private teams also have access to public data and functionality within Ninety, such as Scorecard trends.

8 Ways to Make 1-on-1s More Meaningful

No matter what role you have in your company, you can get more from one-on-one meetings by doing these eight things:

1. Prepare before the meeting.

Help everyone understand the context of one-on-one meetings. Explain what they are and why they’re scheduled. Do it in a weekly meeting. Write a follow-up email or message to each team member that includes:

• A meeting invite.
• Schedule details moving forward.
• A review of the process.
• General meeting goals, such as a list of broad topics to collaborate on.
• How to personalize agenda items.
• Shared expectations. This can include starting on time, avoiding canceling or rescheduling, coming prepared to talk, etc.

2. Agree to be transparent.

Be open and honest as you communicate. People can usually tell if you’re holding something back. You both can learn from standard details and positive ideas as well as information that may be uncomfortable to hear. Think before you react. Show you’re open to criticism.

3. Prepare and share every agenda before each meeting.

Get three to five questions down as agenda items. Let people know what they are before they come to the meeting. This gives people time to think about solutions so they’re ready to discuss answers at meeting time. It also helps make the time you have together efficient and effective.

4. Choose the preferred way to meet. 

People like to meet in person. But if this isn’t always possible, such as with remote teams or in hybrid work environments, have a dedicated tool for meeting face-to-face with each team member. Consider video conferencing, phone calls, and other ways to have a private conversation where you can see and hear the other person.

5. Be ready, willing, and able to listen, most of the time.

Active listening is critical for communication that drives success in your workplace. Embrace moments of silence. They’re great for thinking. Experts say talking less than 50% of one on one meeting time is a good gauge. Ask questions that require more than a yes or no answer. Before answering yourself, wait for a response.

6. Ask questions on the fly.

New thoughts and insights are rarely scripted. When a question comes up naturally in the conversation, ask it! There’s no better time than during one-on-ones.

7. Make sure feedback is part of every meeting.

Learn something you didn’t know every time you meet. Make it a regular agenda item. Ask for and give thoughts, opinions, knowledge, or subject matter expertise. This supports the safe space you’re creating to build the trust and transparency necessary to make work better.

8. Keep everything in one place.

Use a cloud-based, integrated platform like Ninety to keep all agendas, notes, next steps, and summaries in one place and accessible only to the one-on-one participants. Not only will this help with the prep work, but it will also make your meetin