Team Member Meetings
Use the new year to revisit one-on-one team meetings
Happy Thursday, 👋
We begin January 1st no different than the start of any other month, except January 1st is the one day we can make changes without causing those around us to question if we are ok as we decide to try something different. The new year provides a free pass to try a new process or revise how we interact with our teams.
Email Management
It has been a few years since the shift toward remote or hybrid work impacted all industries so a few bad habits are starting to emerge. One we see most often is management by email, or any form of electronic communication, which tends to increase as teams expand. A 2019 study found more than half of managers use digital communications to handle work conflicts, a number which is almost certainly much higher in the post-Covid remote work environment.
A few times over the past year we have worked with companies operating on a hybrid model but default to using email for major announcements or changes within a team. More than one company has hosted an in-person discussion only to follow up a few hours later with an email outlining a change in strategy. If leadership is no longer comfortable discussing change with their team, it is often a sign there are greater areas of concern within the team dynamic.
The new year is a time to reconsider how managers and their teams interact. Electronic leadership may be the easy option but long term it is not an ideal way to build a cohesive team focused on achieving goals in the new year. As companies grow beyond the start-up stage, team management becomes increasingly important, reinforcing the need for active advisory boards to provide external perspectives.
Managing Takes Time
Leading a team requires building trust and engagement so as companies grow it becomes important to maintain a continued focus on developing management skillsets. A powerful tool for fostering team engagement is a cadence of one-on-one meetings. The objective is for managers and their teams to establish a set time to review goals, challenges, and address specific questions. Building a professional relationship with each team member through recurring meetings mitigates managers turning to email for difficult conversations and increases the potential for achieving greater goals in the new year.
Meeting One-on-One
Developing a one-on-one meeting schedule can be a powerful tool but takes time to develop the right approach and process. We have used the following suggestions to help several companies develop their internal meeting procedures.
👂 Focus on the needs, concerns, and ambitions of the team member. The meetings should not be a forum for managers to implement drastic change, but instead a time for them to listen and learn.
📅 Scheduling weekly one-on-one meetings is ideal followed by monthly. We realize weekly meetings can crowd schedules so experiment with different timeframes. Over time some teams move to monthly meetings but anything longer tends to result in lost momentum.
🚷 Canceling meetings happens but should be minimized as it signals team members are not important. An alternative is reducing the meeting time as even a few minutes of conversation can be helpful.
📝 Let team members establish the agenda as this removes the anxiety over uncertainty of the discussion and maintains a focused conversation.
🔚 Close the meetings with a summary and clarify key takeaways, as these become the basis for the next meeting.
💭 During the meeting we suggest managers keep in mind at least two questions:
What can I do to help or provide better support for my team members?
Do I completely understand the other person’s perspective or concerns?
Implementation Challenges and Company Stories
Implementing concepts such as one-on-one meetings can be a powerful tool but is only one component of managing a growing company. We often meet business leaders attempting to try new ideas but become frustrated when the change does not generate the results they expected. Most often the failure results from lacking a complete picture of the ideal outcome, so as activity slows down into year-end, take time to write your company story for the new year.
Write out an ideal vision for how the company should be organized, imagine free flowing conversations among departments and team members. Consider how an ideal meeting would function. Envision a team environment capable of overcoming challenges and achieving the 2023 goals.
Once this story is written, start on January 1st to reverse engineer the process. Work backwards with the team and build the systems and procedures needed to achieve the ideal outcome. Use one-on-one meetings as the basis for the process of understanding challenges and reviewing strategies.
Making The Change
Making changes to team operations often raises concerns, so use the new year as a great excuse for trying something different. Developing one-on-one meetings provides an opportunity for input from all team members instead of just those who are more open to expressing opinions. Often our basic level of individual communication can bring some of the most powerful results.
Early stage venture investments frequently require more than just investing capital into a company as often we become advisors to founders as companies transition into more complex organizations. Achieving some corporate goals is possible through building better technology or products, but developing a culture of one-on-one conversations can accelerate all areas of corporate growth.
Thank You and Happy New Years
We appreciate everyone who joined us this year and those who have been with us since our first discussions in 2021.
If you know someone who might be interested in our discussions, let them know about us as we always enjoy having more smart readers join us every few weeks.
Wishing everyone a great weekend.
-The Caymont Team.
Let us know how we can help as our focus is on Seed through Series A venture investments along with providing financial and strategic advisory to companies big and small.

