Development Through One-on-One Meetings

During a recent walk in urban Durham, NC, I couldn’t help but notice the number of raised beds consuming most of the lawn in front of each bungalow home. As my son and I walked down the street, we saw how the city gardens varied in size, configuration and order. Some of the gardens were woven into and between the existing landscaping. Others were thriving in meticulously maintained raised beds, with automatic watering systems and labels on each row showing the variety of produce being grown. I thought about the different ways each of these landowners was providing healthy food for their family, friends and community, while following their individual passions to grow at home.

As I took in these sights, I was struck by the similarities between gardening and growing great leaders. For many leaders, leadership development is either woven into the existing structures of their work or fostered in well planned and prepared processes. As I’ve thought more about organizations that excel at growing people and teams, I’ve become convinced that the foundation of great team leadership is the creation of a good “raised bed” for leaders. And that raised bed structure begins with a properly focused approach to one-on-one meetings.

Leading Effective One-on-Ones

Creating a healthy one-on-one process provides the soil for our future leaders to grow. The nutrients, attention and focus a leader gives his or her direct reports can collectively grow them into a thriving group ready to withstand anything the environment throws at them. Conversely, without the proper care, individuals can’t blossom or mature to their fullest.

One-on-one meetings are based on the relationship between supervisors and their direct reports. Like the gardener and the plant, the employee must grow for the supervisor and organization to harvest the full fruits of the relationship. Additionally, the employee needs to feel that the supervisor is both interested and invested in his or her well-being, growth and support.

Scope and Schedule

One-on-one meetings should be held at least once a month, and as frequently as necessary. A best practice is to schedule the meetings for an hour, so you can be unhurried and productive. These meetings shouldn’t include discussions about a direct report’s projects or initiatives; those meetings are most appropriate as project or status updates. Instead, plan to focus on how the employee is doing, both personally and professionally, as well as with their individual development and growth in leading and managing others.


These discussions should be held in a spirit of continuous improvement between two team members. It’s in both of your best interests that you create a stronger relationship and an understanding of how to get the most out of your overall organization. You won’t always totally agree, but the goal is to create an honest dialogue about what’s best for you and your team.


Two days prior to each one-on-one, the supervisor and direct report should agree on an agenda. Once the agenda is finalized, keep it in a shared location for easy reference as a best practice.

Focus your one-on-one meetings on how you’re functioning together. Try to identify areas of stress, confusion or disconnection. Some common questions are:

  • How are we both personally doing outside of the work environment?
  • How’s communication going between the two of us?
  • How’s the team performing overall?
  • Are the goals and strategies that we’re working on clear?
  • Are the responsibilities and strategies understood?
  • What are your shared observations about areas that might need attention?
  • Do both of us have the tools and resources we need to be successful?
  • Can you discuss specific examples of where you’re excelling, feeling supported and having confidence?
  • Can you also discuss areas where you’re needing support or guidance?

Get our list of 30+ Powerful Coaching Questions.

These discussions can help both you and your team members clarify opportunities to improve engagement and performance. They are analogous to the gardener filling the raised bed with well tilled, rich soil.

However, the most important and often overlooked aspect of a successful one-on-one meeting is the agreed-upon actions from the discussion, which are the seeds to a continuous development discussion.

As you wrap up the meeting, ask yourselves: is there a way to leverage the clear successes you’re feeling across the challenges that are being discussed?  What kind of assistance and support can be established for a better outcome?


As a result of this discussion, it’s important that appropriate “actions” be identified for both the supervisor and the direct report. Try to incorporate actions that can take place in between one-on-ones where the direct report can observe, experience or be exposed to others in the organization who can provide a positive influence in the areas you have agreed to develop. Consider exposing them to other managers who are excellent mentors or role models to develop these skillsets. Think creatively about how to coach, guide, teach and train your direct reports. Walk alongside them in their development so you can encourage and support them.

With each one-on-one meeting, you’re germinating the seeds and growing a higher-producing leader and direct report. In time, they’ll be strong and able to take on new challenges with courage and clarity because of your tending.

Occasionally, look to both your human resource department or your own mentors and coaches for stories, examples and tools to support your employee. However, there’s no better learning resource than a personal experience you’ve had during your development as a leader or manager. Sharing your challenges and successes will provide a deeper connection and continue to build trust with your direct report.

By setting a healthy example on performance one-on-ones with your direct reports, you provide a model to deploy to their direct reports as well. Holding them accountable for these same meetings provides a culture in your organization of growing, developing, and communicating with your team about performance on a monthly basis.

Developing Your People One-on-One

In both gardening and leadership, consistency is the key. By providing the right amount of attention, care and resources to those under your watch and protection, your teams will be able to withstand any and all pressures the outside world throws at you. This will grow an engaged workforce that’s focused on balancing the needs of the organization with their individual performance and development.

For more ideas on how to use coaching to develop vibrant and engaged teams, check out Becoming a Coaching Leader by Building Champions CEO Daniel Harkavy.


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