Ways to Strategize Successful 1 on 1 Meetings for Leaders

by Editorial Team on March 16, 2022

Frequent and effective communication with your staff is one of the most important things a leader can do. It keeps you aware of how projects are going, allows you to build a relationship with everyone on your team, and gives you the chance to get ahead of problems before they arise. 

However, there’s currently a gap in how effective these one-on-ones seem to be. While 94% of leaders report having regular one-on-ones, 67% of employees complain that meetings keep them from being productive. Additionally, leaders report ‘providing value during these meetings’ as their number one challenge when talking about their one-on-one strategies. 

So the question becomes how to strategize ways to make these one-on-one meetings successful for both leaders and employees. Let’s break it down into 4 core components of a successful one on one strategy:

  • Setting Expectations (Why are these one-on-one meetings important?)
  • Identifying Bandwidth (How do you determine who you should have one-on-ones with?)
  • Creating Appropriate Plans (What’s the best cadence for these meetings?)
  • Prioritizing High-Value Content (What agenda or goal should each one on one have?)

1: Setting Expectations

There are many benefits to including regular one on ones for both parties. It gives you insight into activities, team engagement, project statuses, and personal concerns or issues. It gives them the opportunity to bring up concerns, questions, or issues they may have. It also allows them a chance to engage in some mentorship, career advice, or coaching.

Ultimately the goal is employee performance. Having regular direct report meetings helps you understand how your team is doing and how each individual is contributing. As well as sharing feedback, asking questions one-on-one, or catching up on goal progress. So make sure you are clear (and clearly communicating) expectations and purpose of your one on one meetings for staff.

Coaching Question: Here are some helpful questions to ask yourself when determining your expectations and purpose of a one-on-one meeting.

  • What is your vision for these meetings? What is the employees?
  • What do you like about this employee's performance? What don't you like?
  • What changes would you like to see in the employee's performance? How can you help support those changes?
  • What do you know about the employee's career goals and aspirations? How can you help support those ambitions?

2: Identifying Bandwidth

As a busy leader in your business - you may be looking at your calendar thinking ‘there’s just no way’. And your staff may be so overwhelmed with projects that the idea of an hour a week feels like too much time away from work.

Oftentimes when you are a smaller company you can have direct relationships with everyone organically; but at 100, 200, or 1,000 employees you can’t have that same level of relationship with everyone.

So it’s important to be strategic and thoughtful when deciding who to have these regular meetings with. Your direct reports are the most obvious, as you need to stay in close communication with them regularly.  But who else do you want to have regular one-on-one meetings with and why?

Coaching Question: What does your perfect week look like? What are your top priorities? What can you delegate or remove to allocate more time to your priorities?  Who do you need to stay in contact with to support your priorities?

3: Creating Appropriate Plans

To maintain ongoing communication with your direct reports, you’ll want to schedule frequent meetings. But there is not a once size fits all plan. Every team and company, as well as management style and employee relationship will have a different frequency. So don’t feel required to fit any certain mold or routine that you may have tried in the past. You know your team and company environment best.

Coaching Question: Here are some helpful questions to ask yourself when determining the cadence for meetings:

  • Are you (or the employee) new?
  • How many people do you need to prioritize time for?
  • Is the employee working on a big project or goal?
  • Are there opportunities for informal conversations and relationship-building moments to replace or supplement one-on-one meetings?

4: Prioritizing High-Value Content

With time spent strategically identifying the previous steps - the last part is the actual meeting! Spend time ensuring that both parties receive value from the time together. While we recommend meetings always have flexibility in topics, a loose agenda will help get both parties warmed up on what they want to discuss. There is a variety of formats these meetings can have, and each one will depend on you, your team, and your goals. Some ideas to try include:

  • Keep up with the status of ongoing projects
  • Coach their career development
  • Addressing any issues or concerns
  • Handling difficult conversations privately
  • Getting to know and building positive relationships

Coaching Question: Here are some helpful questions for you to begin to identify high-value content for these meetings.

  • What is the employee's biggest project right now? What challenges are they facing?
  • What does the employee need the most right now?
  • What agenda feels most valuable to you and your employee?
  • What's the most important thing you want to accomplish during the meeting?


As a leader, you’re no stranger to one-on-one meetings. But now is the time to revisit, rethink, and re-identify ways to make sure they become high-value, successful communication points for both parties. This ensures better performance and more effective relationships within your business.

Topics: Effective Leadership