Annual Planning Tips for Startups


Annual Planning is an important part of any startup’s operations, and without the right plan, your company may struggle to reach its full potential. To explore the topic of Annual Planning for early-stage companies, we hosted a Workshop with Jeff Martin. The session covered creating and maintaining team alignment, focus, and accountability in a high-growth, changing environment. It recommended tools and resources to build a clear, unified team vision and plan leveraging OKRs and KPIs.


Planning is an important part of running a company at any stage, but is even more critical for a startup given the constant changes and shifts that Founders navigate at the early stage of their business. Even if you sometimes feel like you don’t know what’s going to happen tomorrow, your employees, customers, investors, and other stakeholders will want to know where your company is headed in the future. This is why planning and revisiting your vision on a recurring basis can be helpful.

Successful planning starts with:

  • Creating organizational alignment

  • Developing focus

  • Implementing a cadence to stay on course

This is accomplished by:

  • Pre-planning

  • Following a planning methodology

  • Implementing a weekly meeting focused on solving problems

Learn more about OKRs

Pre-Planning Meeting

To equip your team to succeed in planning, it is important to have a pre-planning meeting to share the planning methodology and agenda and execute on planning pre-work. Pre-work consists of live discussions and/or individual or team assignments that allow the leadership team to unpack their thoughts before the planning sessions. During pre-work, you and your team should gather feedback, data, and information from internal teams to inform bottoms-up and top-down planning during the session. This may include issuing a Team Survey that assesses the organization's health. Survey results can be reviewed in the pre-planning meeting and discussed in more detail during the Annual Planning session.

It is also advised to share Best Practices and Expectations for the Planning Meeting during your pre-planning session. This helps prep your team on what they can expect during the meeting and keeps them on track to get the best outcomes. Encourage all team members to be open, equal, and transparent and allow them to share their expectations for what they hope to achieve in the planning sessions.

Annual Planning Meeting Agenda

A framework and agenda for what to cover during the Annual Planning Meeting is essential to success. Each meeting may have new topics to explore, given what is going on at that stage in your business, but the following topics are helpful to cover during each meeting.

  • Review Expectations & Planning Goals. Kick off the session by reviewing the expectations the group discussed during the pre-planning meeting. This will help define what you want to accomplish in the planning process and you will measure against this list at the end of the session to define if your planning goals were met.

  • Discuss the Team Survey Results. A team annual and quarterly survey helps provide a feedback cadence as the team reviews where they are and assesses the organization's overall health. The Survey should explore both strengths and opportunities that can be leveraged in the planning process.

  • Review Current Roles and Responsibilities. As teams grow, people's roles and responsibilities will change. This often creates operating challenges if not addressed regularly. This can be solved by using the Annual Planning Meeting as an opportunity for executives to revisit and review their company roles and responsibilities and make any adjustments as needed.

  • Define (or Re-visit) Your Three Year Vision. In order to organize a team to be successful, they must have a vision of where they are going. Using the analogy of climbing a mountain, the peak is your three-year vision. For all businesses, it is important to put a flag in the ground for where you want to go so that your employees, customers, partners, and investors know what they are working toward. Make sure your three-year vision captures all elements of the business.

  • Define (or Re-visit) Your One Year Plan. Once you have defined your three-year vision, discuss where you want to be within the next year - keeping in mind the end goals you defined for your three-year vision. Build your one-year plan by developing objectives in each functional area of the business. These objectives are a mix of Key Performance Indicators (KPIs), metric-based objectives (MBOs), and non-metric-based objectives.

  • Set Quarterly Team OKRs (Objectives and Key Results). Leveraging your one-year plan and KPIs, define your Q1 OKRs. At the leadership or core team level (depending upon size) it is recommended to define five objectives and associated key results. For startups specifically, it is important to focus OKRs on developing capabilities within your organization to accomplish your KPIs - unlike some methodologies where OKRs are just measuring output. Having OKRs focused on building capabilities aligns cross-functional teams on what matters most - repeatable growth. Assign only one owner to each OKR to help with accountability.

  • Set Functional Team Objectives. Similar to Team OKRs Peak Teams also build a layer of OKRs at each functional level of the business. This is done to maximize the team's capacity and hone focus for each area of the business. As mentioned above, assign only one owner to each OKR to help with accountability.

Define and Schedule Your Weekly Meeting Cadence

The completion of your Planning Meeting does not mean your work is complete. It’s important to follow up with your team to ensure that everyone is aligned on the outcome of the meeting and that they are on track to achieve the goals outlined during the session.

As important as the planning meeting itself is the execution of the planning. Immediately after the initial planning meeting, schedule your recurring Weekly Camp Meetings, which should focus on maintaining alignment, team focus, and accountability every week. In an ever-changing environment, it is important to have a meeting cadence of reviewing your OKRs and KPIs to stay on course - or course-correct as needed.

It is helpful to start each of your Weekly Camp Meetings with a “human-first” approach. You can do this by asking everyone to share:

  • One “Best” - best thing that has happened for them this week (can be work or personal).

  • One “Thanks” - thank one team member for something they did or helped with.

Doing general team updates during these calls is not recommended as these can take up a lot of time and often take the meeting off-track. Instead, focus on 3 topics/problems you want to solve that you identify based on 1) what’s urgent and 2) what’s important. The owner of the topic should start and facilitate the discussion.

Regarding the length of your meetings:
  • Annual Planning Meeting - recommended to block out two full days for the session - not including the Pre-planning Meeting.

  • Quarterly Planning Meetings - recommended to block out one day per quarter. This can also be broken into two half-days.

  • Weekly Camp Meetings - block out about one hour each week.


Leveraging Annual Planning can help set your organization up for short- and long-term success. By implementing a process of pre-planning, structured annual meetings, and frequent follow-up you and your team can achieve more over your calendar year.

Big thank you to Jeff for sharing his tips! If you are interested in the Collective Genius Peak Teams program visit

Watch the video recording from the Annual Planning Workshop.

Learn more about building OKRs



Jeff Martin has founded, sold, and played multiple roles at venture-backed technology companies. Jeff has worked with hundreds of venture-backed leadership teams and investors across the US and worldwide. In 2004, Jeff founded Collective Genius to assist CEOs, founders, and investors in building high-performing teams. Collective Genius combines decades of experience in venture-backed organizations to uplift teams and help them exceed their potential.