The Small Business Owner’s Guide to Annual Team Meetings

Brittany Burke
Office Accomplice
Published in
4 min readMay 28, 2019

Life as a small business owner is busy, exciting, unpredictable, and occasionally chaotic. The sometimes-frenetic pace of life leads most small business owners to the same realization: launching a business alone is much simpler than running a business alone. Enter: your team. This group of professionals will keep your business growing and running smoothly and keep you sane. They will become your organization’s biggest strength and can provide valuable insight and suggestions as you set long-term goals — if you make the time to have big picture discussions.

As a small business owner — and the head of a remote team- I can’t say enough good things about setting aside time solely dedicated to face to face communication in the form of an annual full team meeting. In fact, the Office Accomplice annual meeting is right around the corner, and preparations are well underway. While valuable, team meetings have a high price tag — in both time and money. So take the time to set clear goals for your event well in advance. Heading into the meeting with well-defined goals ensures that every minute of your time together is used wisely.

In my case, I have three main goals for my annual team meetings: communicating annual goals and changes, developing and improving group dynamics, and dedicating time to client relationships and appreciation.

Internal Communications

In my experience, it’s best to set goals and announce major changes when you have everybody in the same room. I come prepared with specific ideas that I want to discuss, but I make sure to leave plenty of room for conversation. To be clear — the conversation isn’t about whether or not changes will happen. If I’m bringing them up at an annual meeting, then the changes are set in stone. The conversation is about the details and giving my team time to process the changes and provide feedback.

My role is to listen to their feedback. I’m not interested in delivering an edict from on high. I want to give my team a say in where the company is going. The in-person dialogue surrounding organizational changes and goals is always productive and improves the organization as a whole.

Group Dynamics

Serious, goal-setting conversations are important — but they can also be draining. Which is why I think dedicating time to fun, team-building activities is equally valuable. Make this activity fun, light, and preferably active. Get your team moving, thinking, and communicating in a low-stakes way. At the end of the activity, you and your team should have laughed together and developed a common bond. If time is tight, you might be tempted to cut non-business-related activities. I would caution you against that course of action. After we have a retreat, the way people communicate and work together is always better. That moment — and the connection it creates — is valuable.

Client Relationships

Clients are people too, and they will appreciate the opportunity to get some face time with your team. We try to make the client-facing portion of our annual meeting casual and fun. Our clients have already spent time with us in a professional environment, and it’s nice to enjoy one another’s company without focusing on work tasks. I’ve found that events centered around activities, like sporting events, are the best way to get my team and our clients together and having fun. Plus, a special and fun event is a great avenue to show our clients how much we appreciate them! At the end of the day, my hope is that we all leave feeling like we’re on the same team.

Planning a team meeting takes time and focus — both resources that can be in short supply for small business owners. The Office Accomplice team is here to take office management tasks off your plate, and leave you with the time you need to focus on tasks that will improve your business. Contact us today, and learn more about how we can support you.

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