OKR Planning: Everything You Should Know

An OKR planning session occurs at the beginning of each OKR cycle, once every quarter, and involves brainstorming across the company, departments, or teams. OKR planning, also known as the OKR cycle or OKR setting, should be personalized across several levels: the entire company, departments, and individual teams. 

OKRs, or objectives and key results, are a framework for businesses and teams to set and reach goals while tracking measurable progress. There are three main elements:

1. Objectives: What to achieve

2. Key Results: How to know if the goal has been achieved

3. Initiatives: How to achieve the goal

Objectives and key results are rarely static and should be updated based on the market, the company’s business model, leadership decisions, and stakeholder input from individuals on the team to keep OKRs realistic. The OKR cycle should ensure strategic relevance, organizational focus, and execution velocity with a predictable rhythm of review and recalibration.​

Before an OKR Planning Session

It sounds cliché, but leaders must plan ahead for the planning session. Here are the steps managers and company officers should take ahead of the OKR brainstorming meeting:

1. Inform the participants at least one month in advance about when the session will take place.

2. Make sure all participants know the company’s mission, vision, and current priorities ahead of time.

3. Send the meeting agenda to the participants at least two weeks prior to the brainstorming session.

4. Participants should think of possible objectives.

5. Give participants questions to think about regarding what’s working, what's not working, and where the company can improve.

6. Show examples of OKRs to the participants.

How Does an OKR Planning Session Work in Practice?

Plan on five to six hours for the brainstorming session. Consider having the meeting off-site, or use virtual meetings with breaks if your company has a remote working environment.

Think about having five sections for an OKR planning session with plenty of space for breaks and a meal.

1. Introduce Everyone With an Icebreaker (30 min)

Start with a round of introductions and an icebreaker activity to set the tone. The goal here is to give people a safe space where conversation is encouraged and rewarded. Make sure all members of the team are present, including the managers.

2. Discuss the Company’s Mission, Values, Strategy, and Initiative (30-45 min)

The person running the meeting then starts with a discussion of the company’s core mission, values, strategic vision, and current initiatives. This will serve as the overarching theme of OKR planning.

3. Agree on Company Objectives (30-60 min)

Leaders should go over recent wins and challenges and discuss why they're having an OKR planning session. 

• Is the company facing market headwinds? 

• What is currently not working or blocking progress?

• Have disruptions caused a drop in revenue or clients? 

• Should the company expand? 

• What options do we have to solve our problems?

• Are we still aligned with our vision?

• Do our goals align with current company priorities?

• Are the goals realistically achievable? Ambitious? Clear and easy to understand?

• Do our competitors offer something we don't offer yet?

• What does success look like?

• How does each team member's work contribute to success?

• What interdependencies do we need to consider?

• What are the important tradeoffs or bets we are purposely making?

There are many reasons that leadership wants to have regular brainstorming sessions for planning for the future.

Next, come up with a system to organize people’s ideas for objectives such as sticky notes, Google Slides, or a FigJam board. Every stakeholder should contribute, and ideas should be grouped by themes or similarities. 

Decide on a way to narrow down the objectives to two to four final choices. You can choose to have people vote or have the leaders in the group decide which objectives make the most sense. Make sure the objectives are achievable within the next quarter. Understand who will be responsible for making each objective come to pass.

Consider taking a 30-minute break at this point.

4. Define Key Results (60-120 min)

Have the group select three to five key results for each objective. Participants must consider how to measure achievements through the key results and whether previously creative objectives were reached. Choosing the high-level k​ey result metrics should be done first before filling in the concrete, precise key results later. 

For example:

• Objective: Increase monthly recurring revenue (MRR) for the next quarter by 30%

  • Key Result 1: Increase new client​s by 20%

  • Key Result 2: Increase revenue per client by 15%

  • Key Result 3: Reduce client churn by 10%

5. Create Action Plans (30-60 min)

Finally, have people in the group come up with projects that lead to accomplishing the key results. Break the group into smaller teams so they can outline challenges, criteria for success, who owns the key result, and the deadline for achieving a key result.

Using the example of adding MRR, managers may decide that they need to invest in new customer success managers to reduce churn and increase revenue or hire new salespeople to increase the number of new clients.

Post-OKR Planning Session Reviews​

Leaders must monitor OKRs weekly to see how teams are progressing. 

• Are there any obstacles? 

• What tradeoffs are happening? 

• What resources need to be shifted?

Toward the end of the quarter, and before the next OKR planning session begins, leaders need to assess whether the OKRs will be achieved within the three-month timeline and what happened during this quarter. 

• Did anything need to change? 

• What OKRs should the company focus on for the next cycle? 

• What can be improved?

• What had the largest impact?

• What prevented progress?

• Where did our systems fail?

• How do we refine our goals for the next quarter?

Why Do Teams Need OKR Planning?

OKR planning sessions help teams draft OKRs based on realistic timelines. The goal is to strategically move the company through the upcoming quarter until the next planning session, in three months, when OKRs will be re-evaluated.

Top Down vs Bottoms Up Planning

Top down planning is when senior management defines specific objectives and strategies that are dictated down to the individual teams and contributors at a company. However, in bottoms up planning, specific plans and goals start at the team level, which are then aggregated to create the overall strategy across the organization. 

Why Does OKR Planning Happen Quarterly?

OKR planning serves as a continuous process of improvement used to check the progress of the previous OKRs. Adjusting or resetting OKRs will happen in the next quarterly session.

Other reasons to have OKR brainstorming every quarter include:

• Maintaining relevance as markets evolve and your business model needs to keep up

• Building organizational focus so that stakeholders keep working towards objectives

• Driving execution velocity through predictable meetings every three months

• Giving leaders regular clarity, alignment, and accountability for their teams

• Shortening the time between strategy and action

• Reducing misalignment between teams and objectives

• Focusing on facts rather than assumptions

• Surfacing problems early to correct quickly

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