Get Started Today
Back to Blog

Venture Partner Presentation: Annual Planning Tips for Startups written by Allie Klun of Sierra Ventures

annual planning ceo early stage facilitation kpis planning session venture capital weekly camp meeting

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 how to create and maintain team alignment, focus, and accountability in a high-growth changing environment as well as recommended tools and resources to build a clear unified team vision and plan leveraging OKRs and KPIs.

Here are Jeff’s tips for Annual Planning.

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 sometimes you 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

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, 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 prior to the planning sessions. During pre-work, you and your team should gather feedback, data, and information from internal teams that will inform bottoms up as well as top down planning during the actual session. This may include issuing a Team Survey that assesses the health of the organization. Survey results can be reviewed in the pre-planning meeting and then discussed in more detail during the actual 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 your team on track to get the best outcomes. Encourage all team members to be open, equal, and transparent and give them an opportunity to share their expectations for what they hope to achieve in the planning sessions.

Annual Planning Meeting Agenda

Having 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 going over 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 overall health of the organization. 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 on a recurring basis. 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 it is imperative for them to 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 methodology 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 capacity of the team and to 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 on a weekly basis. 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 person on the team for something they did or helped with.

It is not recommended to do general team updates during these calls 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 success in the short and long-term. By implementing a process of pre-planning, structured annual meetings, and frequent follow-up you and your team can achieve more over the course of your calendar year. 

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



Allie joined Sierra Ventures in 2019 to lead Marketing efforts for the firm and partner with portfolio companies to drive awareness and provide insights on their marketing strategy. Allie has a background in business and marketing strategy, working with early-stage startups, agencies, venture firms, nonprofits, and political campaigns. Her experience includes forming and running a nonprofit, working as VP of Marketing at a Blockchain company, working in the Entertainment Industry, and managing Fortune 500 business accounts in the gaming and entertainment space. Allie holds a BA in Communication Studies from UCLA and is also a certified Yoga and Meditation teacher. Outside of work she enjoys traveling, hiking, cooking, and reading.


Join the Collective Genius community

Get the Collective Genius Newsletter to stay at the forefront of building high-performing, venture-backed growth teams. Unlock exclusive access to best practices, essential tools, and valuable resources delivered right to your inbox.