Annual Planning for Remote Teams

Set an annual planning schedule

According to a study from McKinsey, 51 percent of employees whose companies had no formal annual planning process weren’t satisfied with the development of their strategies. Clarity and transparency begins with this first step.

The first step in any annual business planning process involves creating a schedule of events and milestones to begin planning for next year. Remote teams require a greater level of communication to ensure all angles are captured and no team is left behind.

Schedule recurring meetings weekly or semi-weekly to provide you and your organization ample time to pull together necessary resources and information to make the best decisions. Set clear goals and agendas for each meeting in advance to set expectations and hold responsible parties accountable.

While planning for next year, your goals are simple:

1. Walk away with a well-documented plan of action for how to achieve your goals for next year, and
2. Give your team the space to relax during the holiday season

Gather year-end reports

In many ways, annual planning for remote teams begins as usual. Work with your leadership team and department heads to gather as much information as possible about the prior year. You want the best picture available of where you’re at and what got you there.

A year-end financial report is a natural first step. Work with your finance team and analyze your previous budget against your actuals. Pull together your P&L statement, EBITDA numbers, revenue, depreciation, gross margins, operating expenses, and the like. You need to understand your capacity for all new initiatives.

Beyond the basics, look at ongoing market trends and your field of competitors. Where are they going? What moves are they making? Talk to your sales and customer success teams regarding customer satisfaction, retention, and feedback they’re hearing. They need to be conducting quarterly business reviews with top customers.

This may also be an excellent opportunity to hold annual performance reviews with employees and staff to gauge engagement and ground-floor processes.

Analyze the year objectively

Don’t leave qualitative research off the table. Collecting this feedback doesn’t need to be painstaking. A quick questionnaire or series of short interviews will allow you to gather vital feedback and help provide an idea of where you’re winning and where you need to catch up.

• What were some of your favorite projects?
• Where did the team succeed?
• Rank our biggest wins
• Rank our biggest flops
• Where can we do better?
• What would you like to do more of?
• What would you like to do differently?
• What does next year look like from your perspective?

Bring your leaders together

For teams conducting strategic planning in virtual environments, it can be tremendously helpful to provide a structured annual planning template for facilitating all annual planning process steps. At the top, bringing your leaders together for a virtual planning session requires forethought and discipline.

Share a clear meeting agenda with specific asks from each contributor. During your initial meetings with your leadership team, you should seek to realign on vision and your organization’s long-term strategic plan. If adjustments need to be made, make them clear, and document them transparently.

Once the company’s direction is secured, you need to agree on targets and set the budget. As with setting any goal, specificity, measurability, and realism are paramount. Annual planning for remote teams leaves little room for miscommunication, so be upfront when decisions are made and pause for a moment of confirmation from your team before moving on. Schedule follow-ups and assign action items to individuals for follow-through.

Kickoff the planning season with a company All-Hands Meeting

The next step in annual planning is to expand the field. One of the best ways to take the top-level decisions from your initial leadership meetings back to the team is through a company all-hands meeting.

Update the team on goals, targets, projections, and priorities. Reaffirm your mission statement. Renew the company vision. Remind the team of your organization’s core values–even for those who have been with you for a while. Cover pertinent financial information, including the budget for resource allocation, and highlight key problems and issues you expect the team to tackle in the coming year.

Use this time to answer questions–even the tough ones–and invite honest feedback from the team. Your goal here is buy-in. Coming out of this gathering, you want to have encouraged participation in the remainder of the planning process. Generate genuine excitement and anticipation for the year ahead.

Celebrate wins!

An often overlooked aspect of company culture is genuine recognition of team and employee achievement. Celebrating wins with your team makes the success worthwhile and can boost employee engagement and morale. That momentum is valuable as you move into the next year.

Highlight top achievements, targets hit, and quotas earned. To be really on the ball, ask beforehand how your team members like to be recognized (publically, privately, in small groups, etc.).

To build off of that last point, making your all-hands gathering a fun virtual event can feel like an unnecessary effort. Remote teams around the world will urge you otherwise. Sure, virtual happy hours may be tired, so spice them up with a costume theme or a contest. (Lip-sync video, anyone?!) Several businesses have pivoted to helping remote teams build teamwork. While everyone logs on from home, participate in a remote mixology class, a virtual escape room, or a group cooking class from your own kitchen! 

Lastly, small gifts are always appreciated. What are you doing with that extra event swag you didn’t use this year?

Brainstorm ideas and solidify the plan

With all context on the table, it’s time to develop an action plan for next year. Brainstorming sessions of this nature require intense preparation to be effective. Your team is likely made up of a mix of personality types that thrive in different creative environments. Lean into that by asking individuals to spend dedicated time on their own to solve some of the problems given. Ask them to write down questions they have, assumptions they hold, and take note of ideas they have individually.

Once you’ve gathered all of that from each team member, share it with the broader team a day or two ahead of a live brainstorming session. This gives everyone a chance to consider everything on the table and develop new combinations of ideas and come up with new threads that can lead to some truly incredible results.

Coming out of this step of annual planning, you should know how each department will maximize their efforts and achieve next year’s goals.

Publish the plan

The last step in annual planning is a particularly crucial one for remote teams. Publishing the plan with the organization clearly and transparently will help to start the year in alignment. When teams are aligned, they’re empowered to make minor adjustments or on-the-fly decisions to smooth the kickoff process in a direction consistent with the overall strategy.

The published plan should include everything uncovered in pre-planning, items highlighted during the all-hands meeting, and each department’s action plan with callouts for important milestones and checkpoints. Be clear about expectations and responsibilities and include significant tentpole dates like events and product launches.

• Goals
• Budget
• Milestones
• Projects
• Responsibilities

Execute with excellence

On the surface, annual planning can feel like a daunting endeavor. In large organizations, pulling everyone onto the same page can feel like steering a giant tanker through treacherous waters.

As you begin to execute your annual plan, your remote or hybrid team will inevitably require more discussions, additional decision points, and possible pivots. This is OK! Because you’ve been documenting your decisions transparently from the start, you can return to the planning process notes and remember why you made a particular decision or the reasons for choosing one path over another. Continue to take notes on the how and the why as you kick off the next year of success, and maintain the alignment with your remote team you spent time developing.