The Secret to Successful One-on-One Meetings

Whether you don't know how to lead a 1:1 meeting or if you're an experienced pro, you'll benefit from this how-to-guide.

People have many different opinions about one-on-one meetings. Some think one-on-ones are painful and describe them as a dreaded part of their day. Yet, others see them as the key to their effectiveness. Regardless of which side of the spectrum you reside on, one-on-one’s, which consist of sharing information, committing to the best course of action, and building connections with your team members, are a vital practice necessary to help achieve your organization’s goals. The opportunity to improve one-on-one meetings requires adjusting how they’re run and what is discussed. Your one-on-one meetings can be fun, energizing, and uplifting with the right tweaks and technological support.

The 3 C’s to improving how your one-on-one’s are run.


Improving one-on-one meetings starts with consistency. Increasing consistency begins with choosing a meeting cadence that best aligns with the needs of the participant. Several factors determine needs level of the team member and the meeting frequency you should choose:

  • How well do you know the team member you’re working with?
  • How complex is the project the team member is working on?
  • What’s the behavioral style of the team member?

The answers to those questions will determine if a weekly, bi-weekly, or monthly one-on-one cadence is best.

Next, once you establish a cadence, do everything in your power to prevent cancelling and rescheduling. By not cancelling or rescheduling you demonstrate that the meeting is a priority. When you prioritize one-on-one meetings you show that the meeting is important and ultimately that you care about the person, their well-being, and their personal growth and development.

Collaborative (agendas)

Collaboration fosters engagement. When your team members have a say in the content and agenda items of the meeting, they are more likely to come with a positive mindset and be more involved. The more involved your team members are the richer the exchange, new perspectives and information will be shared. Additionally, commitment to the process will increase as well as enthusiasm.  

Capture (sentiment and stress levels)

Leader's aren't mind readers, and neither are your team members. Sharing sentiment and stress levels help communicate unexpressed emotions and feelings. Now, you no longer have to guess nor look for clues regarding what a person might be experiencing. You'll be able to quickly identify where both you and your team member need additional support. Plus, sharing your sentiment and stress levels creates psychological safety and empathy with your team member.

C.A.R.E.™, the framework that helps you facilitate successful one-on-one's.

"Without a good question, a good answer has no place to go." - Clay Christensen

C.A.R.E.™ is an acronym that stands for Coaching, Appreciation,Rapport and Evaluation. Each component of the acronym represents a category of questions that help guide your one-on-one discussions to connect to the whole person. This powerful strategy allows you to develop deeper connections, improve collaboration, and uncover understandings that traditional approaches leave undiscovered. When you use the C.A.R.E.™ approach, you’ll become a more effective manager and your team will reach their goals like never before.


In his article “Leadership that Gets Results” Psychologist Daniel Goleman remarks that coaching as a leadership style is one of the most impactful approaches influencing performance, culture and financial results. Coaching as a leadership style is all about asking the right questions to help your team member discover their own solution. Our natural tendency as leaders is to "fix it, solve it and offer solutions." However, by asking questions you'll reduce over-dependence, guard against being overwhelmed, and help your team members do more of the work that has impact and meaning.

We recommend asking one question from each category during your one-on-one. Some of the coaching questions you’ll find within our platform are:

  • What obstacles have you run into since we last met that you'd like to troubleshoot?
  • What can I hold you accountable for the next time we talk?
  • What tasks are you stuck on?

Each of the coaching questions are designed to help your team member get unstuck or up-skill.


Team members rely on appreciation, more commonly referred to as praise and recognition, to know if their manager and organization value their work.  Today’s modern worker attributes a lack of praise and recognition as being akin to being ignored. There’s no better time to show that you're aware of your team member's contributions than by sharing praise and recognition during one-on-one’s. Why? A study by Gallup found that “one of the most memorable types of recognition was private from a boss, peer or customer.”

Here are some example prompts we provide to facilitate appreciation discussions:

  • What's the best thing about working with them?
  • What have they done for you that you appreciate?
  • What’s better today because of them?


Organizations move at the speed of trust. The same is true from teams. Without trust your team cannot reach its full potential. Getting to know and genuinely connect with your teammates by building rapport is the fastest way to increase trust. Building enduring relationships will make your days more pleasant, which will make it easier to do your job. The best and most effective time to develop relationships is during your one-on-one.

Here are some example prompts we provide to build rapport:

  • What personal goals do you have?
  • What is your favorite quote?
  • What had the biggest impact on the person you’ve become?


Evaluation questions are designed to help you identify if your teammates goals and objectives have been met. Many managers struggle with asking evaluation questions because they are concerned that the team member will respond negatively (eg. The person may get discouraged, may quit or shutdown). The key is to balance “what needs improvement” questions, with questions that surface “Yes that!” moments. "Yes that!" moments are all about you actively looking for excellence and calling it out when you see it.

Here are some example prompts we provide to evaluate performance:

  • What's something you did well recently, and what qualities and skills enabled you to do this?
  • Who is doing a great job on the team? What have they done?
  • What's something we do well as a team?

Using the 3 C’s and the C.A.R.E.™ framework during your one-on-one’s will enhance the experience your team members have at your organization. When your team member’s experience improves, you’ll find that they'll be more involved in their work, committed to the organization and enthusiastic in their recommendations about working on your team and your workplace.