Your Guide to One-On-Ones

One-on-ones take an informal approach to regularly scheduled meetings and instead take time to engage in conversation and focus on the employee.

One-on-ones (or 1:1s, simplified), are regularly scheduled time for managers to check in with their people. One-on-ones may carry a negative connotation for many. After all, stereotypical 1:1s are an obligatory meeting with a manager you probably don’t have face time with in an average day. There are rapid fire questions, and then you walk away feeling like you fell short of having a five-year plan in place.

According to Harvard Business Review, research shows that the main complaints and challenges employees have with their managers stem from simply not enough communication. Specifically, receiving constructive feedback, setting expectations, and failure to set aside time in the first place. Luckily, refining the way 1:1s are done is becoming more of a priority in the workplace.

One-on-ones are taking on a more informal approach. One where the manager plays a support role — simply listening to challenges, focusing on finding solutions, and developing strategies alongside the employee. These regular meetings serve as on ongoing feedback strategy to keep both managers and employees updated on their progress, identify opportunities to develop skills, and allows for room to discuss any challenges along the way.

When planning a 1:1, keep in mind:

1. Cadence
2. Expectations
3. Setting
4. Intentions
5. Follow up

Wisetail LMS employees engage in a one-on-one in the Wisetail office.


Regular, effective communication is necessary in any workplace. However, it’s easy for communication to fall by the wayside with the usual day-to-day frenzy. Steer clear of calling on an employee only when you need something. This is a damaging approach and can affect the relationship in the long run.

In an ideal world, a manager would sit down with their employees individually on a daily basis. Of course, this isn’t practical after your team reaches a given size. The key to a 1:1 is cadence. Weekly meetings are a great goal, but you can also start off on a biweekly or monthly basis.

What’s the best way to find time? Carve it out in advance. When managing your own work schedule, save time for your employees weeks or even months ahead. For instance, use the Google calendar. Choose to make 1:1 meetings on a consistent weekly, monthly, or a customized basis. Invite your employee to the calendar event as well. The small gesture shows that the employee’s development is part of your job and that you’re invested in their growth.

Also consider the consequences of cancelling a 1:1 meeting last minute. When you’ve already invested so much into blocking out times for your employee, they could be frustrated when you don’t follow through.


When it comes to a 1:1, the employee should run the show. They prioritize the content of the conversation and share the responsibility of setting the agenda. Make sure they know they’re in the driver’s seat.

For example, ask one of the following questions at least a day before the one-on-one meeting, ideally in person:

• Do you have anything you’d like to discuss in our next meeting?
• Are you facing any difficulties in your day-to-day workflow?
• What is something that went well or that you’re proud of?

Wisetail LMS employees engage in a one-on-one in the Wisetail office.


Don’t hesitate to switch up the setting of these meetings — grab a coffee, sit down over lunch, take an office dog for a walk, or simply get some fresh air somewhere outdoors. A little variety is good and shows creative intention from you. It also helps establish a more informal, relationship-based meeting.

Pro tip:
To help track an employee’s progress on the go, take running notes during these meetings. These notes can be used to reference their progress in the future to illustrate their growth. This tiny detail proves you’re committed to their professional development and that you’re actually listening.

We recommend utilizing resources like Google Calendar and Dropbox to help establish a consistent cadence and encourage collaboration.


The goals of these 1:1 meetings should be employee-oriented and relationship-driven. It’s your chance to focus on the employee’s needs and how they benefit the company.

Using these 1:1s, track progress toward long-term goals and the employee’s happiness as a management strategy to help keep them happy and maximize their output.

Some employee-oriented questions you can consider asking include:

• What have you been focusing on?
• What are your upcoming plans and priorities?
• What challenges or roadblocks do you need help with?

Follow Up

If you’re running a successful 1:1, then each week you’ll uncover different challenges and opportunities. Maybe it’s a desire to grow a new skill or why they’re stuck on a particular project. When issues do crop up, it’s essential to follow up and see that they’re resolved. This shows the employees that you truly care about their concerns because you took the time (and remembered) to address their needs.

Ultimately, the way you integrate 1:1s into your management style is up to you. One-on-ones give employees the time to provide status updates on their projects to managers. But with a little extra intention, these conversations can be great opportunities to discuss longer-term vision such as career development and job satisfaction. All very important things to consider when trying to retain talented, loyal employees and grow a successful company.

Wisetail LMS Learning and Development Lead, Courtney Fitzpatrick.

Courtney Fitzpatrick

Learning and Development

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