These Leaders Get the Most Out of 1-on-1 Meetings

Establishing an agenda is only the first step.
Written by Remy Merritt
August 10, 2021Updated: August 12, 2021

One-on-one meetings can be daunting. The ability to cover important topics, provide useful feedback and share personal goals gets easier with time and practice, but just like all interpersonal skills, meeting the nuances of different settings and personalities can require some fine tuning.

With this in mind, we met with four local leaders to gather insight on how to get the most out of one-on-one meetings. And while the topics of conversation and personal style will always vary from one team to the next, there are two best practices that all respondents recommended. 

The first is an agenda — whether informal or structured, having a list of important discussion points helps keep team members and their managers on track. In Jared Jiron’s experience at Pie Insurance, keeping structure “sets a mutual expectation that these meetings are to work on development and building our relationship.” Aligning on goals from the outset of a meeting helps both parties stay on track and keep the discussion productive.

The second, which sets a general tone for the one-on-one, is an honest and transparent relationship. “It is essential to cultivate a relationship where both parties are comfortable expressing their opinions and ideas and are free to challenge one another,” said Tracy Lacewell, vice president of sales at Pax8. It is in these settings that creativity flows and individuals and their managers can feel at ease sharing goals and challenges.

 

 

Kyle McDerment
Customer Success Manager // Automox

 

In Kyle McDerment’s experience at Automox, a cloud-native solution for IT operations, successful one-on-one meetings build trust between managers and their team members. 

 

Do you have a structure to your one-on-one meetings?

Our meetings have a casual agenda to guide our discussion. One-on-one meetings are scheduled as a standing weekly with my manager. During our meetings, we review any topics from the prior week's meeting that required follow-up actions. We then dive into new topics of discussion and outline an action plan for how to tackle those topics.

From there, we discuss any company-wide news such as partnerships, funding and changes in leadership. We then narrow our focus to our team, which recently has revolved around growth. We discuss recent candidates’ interview performance, new-hire training, future hiring plans, and where I feel I fit into the team both now and in the future.

Lastly, my manager always leaves time at the end to ask if there is anything else — either professional or personal — that is on my mind and that I would like to discuss.

 

How has your manager helped to grow your career? What role did one-on-one meetings play in that process?

After starting my journey with Automox in sales, my manager, Ali, offered me a job on her team as the third customer success manager. Our initial one-on-ones started as coffee breaks and happy hours, and eventually led me to joining an amazing team and kick-starting my career in customer success.  

Now during our official one-on-ones, we often discuss the growth of our team and where I see myself in the future. As Automox continues to grow, so will our needs as a customer success team. Ali has been extremely proactive in preparing me to think about the next role I will grow into. Whether that be a senior role, or even a more technical role on our customer-facing engineering team, Ali is always ensuring the decision is mine to make.

Trust is the pillar on which my relationship with my manager is built.” 

Overall, how do you build a good relationship with your manager?

Trust is the pillar on which my relationship with my manager is built. She trusts that I am willing and able to accomplish the goals and tasks I’m faced with in my role, and I trust that my manager will support me in the day-to-day challenges that I face. You can’t have trust without being honest and open with one another.

This is why one-on-ones with your manager are so important. I find that young employees often struggle with being open with their managers when it comes to asking for help, and saying “no” to additional tasks when they’re already buried.  Your one-on-one is the time to share this with your manager and be proactive about the issue, rather than letting it snowball into a bigger problem.

 

 

 

Tracy Lacewell
Vice President of Sales // Pax8

 

As vice president of sales at Pax8 — a platform helping partners buy, sell and manage their cloud technology, Lacewell finds keeping one-on-one meetings structured and aligned with company goals delivers consistent success. 

 

Do you have a structure to your one-on-one meetings?

At Pax8, we believe structured one-on-ones ensure we hit important topics and have consistency across the organization. We have created templates for several different one-on-one meetings, including director to manager, manager to sales rep and sales rep to solution consultant. The topics are fairly general and intended to spark dialogue. 

We start every meeting by asking how the other person is doing, because we believe in the power of connection. We all lack the human interaction we were accustomed to before the pandemic, and we must be in tune with our employees and peers and understand their mental and emotional states. We genuinely care about each other at Pax8 and want to understand how we can better support one another. 

The second question we ask during the meeting is whether or not there’s anything important to discuss. This question creates a two-way dialogue as both individuals generally have pressing items to discuss, which we honor. 

Lastly, we encourage everyone to enter information into our one-on-one tool before their meetings, ensuring smooth and efficient conversations.

 

How have managers helped to grow your career? What role did one-on-one meetings play in that process?

I have been fortunate to have many phenomenal managers throughout my career, and my current one is no exception. He has been instrumental in guiding me in my journey at Pax8, progressing from manager to director and now to vice president in less than four years. I have never felt alone, and his encouragement and guidance helped me gain the confidence and skill set required for my current role. He has created an environment where I feel empowered, supported and safe to speak my truth.

We spend our one-on-ones brainstorming ideas to optimize sales operations, increase efficiencies and provide further education to elevate both myself and the sales team. Most importantly, he helps me prioritize tasks and initiatives to align with the company’s larger goals and vision. My manager also helped me through some personal challenges, always displaying compassion, empathy and encouragement.

I encourage people to be vulnerable and let their managers know how they are truly doing and where they could use help.”

Overall, how do you build a good relationship with your manager?

I believe building a strong connection comes down to openness and honesty. It is essential to cultivate a relationship where both parties are comfortable expressing their opinions and ideas and are free to challenge one another. Getting to know your manager and colleagues on a personal level can be extremely beneficial, and it creates a more enjoyable working environment. You want to understand what motivates them, what is important to them, and how to best communicate with them to collaborate effectively.

In addition, being receptive to my manager’s guidance and coaching has always served me well. I encourage people to be vulnerable and let their managers know how they are truly doing and where they could use help. One-on-one meetings are a great place to voice concerns, develop strong and productive relationships, and ensure you get the support needed to take your career in the direction you desire.

 

 

 

Allison Grenney
Senior Director of Customer Success // PAIRIN

In Allison Grenney’s experience at PAIRIN, a social enterprise company dedicated to unifying the workforce and education, one-on-one meetings have been the most impactful setting for growth.

 

Allison Grenney's 1:1 Must-Haves

  • Personal check-ins
  • Specific feedback
  • Brainstorming time
  • A prepared but flexible agenda

 

Do you have a structure to your one-on-one meetings?

My manager and I use a shared document to compile agenda items for our one-on-one meetings. We typically check in personally before diving into the prioritized list. The shared document allows us to be very flexible while ensuring we don’t forget to cover an important topic.

 

How has your manager helped to grow your career? What role did one-on-one meetings play in that process?

One-on-one meetings are where I have had the highest concentration of growth. During this time, my manager gives me very specific feedback, asks me questions to help me reflect and provides frameworks for me to think through my next area of skill development.

 

How do you build a good relationship with your manager?

I think the number one way I’ve built a good relationship with my manager is by valuing her as a whole person. Knowing the multiple roles she plays in her life, hearing about her past experiences and understanding what work she enjoys is key to building a strong working relationship.

 

 

 

Jared Jiron
Customer Success Team Lead // Pie Insurance

For Jared Jiron, customer success team lead at Pie Insurance, one-on-one meetings provide an opportunity to work on both business development and interpersonal relationships.

 

Do you have a structure to your one-on-one meetings?

I have always found it important to have structure to the one-on-ones I attend, but I have also found they hold more value when mostly unplanned. While having structure is important, I find it can also lead to a less enthusiastic conversation, so I work hard to find the middle ground between a formal meeting and a more relaxed chat.

I believe one-on-one meetings have the most value if action plans are the outcome. I go into these meetings with a clear understanding of the expectations, so by the end we both have an understanding that I am here to help meet the goals we set and provide assistance in any way possible.

I also ensure one-on-ones are used as an opportunity to build on our relationship. Having free-flowing conversations and communicating in a more informal fashion develops a safe environment to get to know each other on a personal level.

 

Querying the Solution

Jared Jiron recommends the “seek to understand” method, wherein participants ask questions to reveal the root cause of a given problem.

 

How has your manager helped to grow your career? What role did one-on-one meetings play in that process?

As a young professional, there have been many times my manager has helped me grow not only at work, but as a person as well. One example that continues to help me is the ability to ask questions and never assume what the cause of an action is. My manager has taught me the “seek to understand” method, which empowers me to ask questions to reveal the root cause of a concern.

Using this method allows me to be successful with any item brought to my attention, and gives us confidence to work together and find solutions. My manager and I used our one-on-ones to role-play conversations — this gave me a chance to practice this method until it became second nature. I believe this has helped me communicate with individuals in my day-to-day life and to encourage others to work on this skill as much as possible.

 

How do you build a good relationship with your manager?

Building a relationship with your manager is extremely important, and to have a successful one takes time and consideration. Some of the most important things to work on while building this relationship are honesty and transparency. I have always been honest with my manager, telling him how I am doing, explaining what I think is not going well at work, and advocating for my peers if they are struggling. Doing this encourages both of us to build a trusting relationship that will last a lifetime.

Since I began leading my team, I ensure they have every opportunity to build a great relationship with me. I do this by first being very honest and transparent with them as my manager was before me — this shows I am happy to converse and help with any topic they bring. I also make sure to provide feedback to help them build their knowledge and give them the chance to become very successful in what they do.

 

 

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