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How to Conduct an OKR Planning Process

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In “Measure What Matters,” John Doerr draws an interesting analogy between team OKRs and a Swiss Army knife. Like that handy tool, OKRs are versatile, adaptable, and key to navigating any organization’s complexities. 

Whether you’re in a startup focusing on survival or part of a large company breaking down silos, OKRs are your ultimate guide. However, effective OKR planning goes beyond merely setting goals; it’s about creating a dynamic process. This process sharpens clarity, aligns your leadership team, and generates fresh ideas to reach measurable objectives.

Let’s explore how to go about planning company OKRs successfully. We’ll also examine how they relate to SMART goals and contribute to achieving your organization’s critical aims. 

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What Is OKR Planning?

OKRs, or Objectives and Key Results, offer a straightforward yet flexible way to set goals, define objectives, and measure outcomes. With OKRs, you can align individual, team, and organizational goals while keeping track of your progress. 

Though this framework dates back to the 1980s, it has recently gained traction among startups and major tech companies. This popularity stems from its ability to foster alignment and ensure that all team members are focused on the same priorities.

When employees perceive their jobs as high in task significance, they display higher job performance.

The Significance of Task Significance: Job Performance Effects, Relational Mechanisms, and Boundary Conditions

While your team can tailor your OKRs to fit your needs, the most effective ones usually share certain traits:

  • Objectives: Objectives represent what you aim to achieve. The best objectives are specific, measurable, and time-bound. Avoid vague, aspirational goals; instead, opt for concrete targets your team can strive for
  • Key Results: Key results are the indicators that measure your progress toward these objectives. They should be quantifiable, allowing employees to clearly see whether they’ve succeeded or missed the mark. Adding time constraints to these results can enhance their effectiveness

Importance of OKR Strategic Planning Sessions

OKR meetings provide a platform for the entire team to discuss and refine their goals, ensuring everyone understands their roles and responsibilities. Integrating these sessions into your goal-setting strategies can enhance team collaboration and commitment. 

Here’s what makes OKR planning sessions so crucial to organizations:

  • Collaboration: Teams can work together, fostering stronger relationships and shared understanding. For instance, when the product development team collaborates with customer support during an OKR planning session, they can align on objectives related to improving customer satisfaction, which can lead to better product features and more effective support strategies
  • Adaptability: Regular planning allows for adjustments based on the changing landscape, keeping goals relevant. For example, if a sudden market shift requires a new product launch, an OKR planning session can help the team quickly redefine their goals to respond effectively, ensuring they remain relevant and impactful
  • Clarity: They provide an opportunity to clarify objectives and key results, reducing confusion. During an OKR planning session, a team might clarify their objective of “improving user engagement” by specifying key results like “increasing daily active users by 20%,” making the goal much clearer
  • Focus: Planning sessions enhance focus on what truly matters. That is, instead of spreading themselves thin by tackling multiple projects, a team might focus solely on increasing customer retention, ensuring their efforts lead to measurable success
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How to Structure Effective OKRs

An effective OKR structure starts with a clear, inspiring objective that sets the overall direction. This is followed by two to four key results that are specific, measurable, and time-bound. 

Using this structure, you instill a sense of purpose and ensure that your team’s efforts are aligned toward achieving their objective.

Setting ambitious objectives

Objectives should be motivating, memorable, and qualitative. When crafting objectives, consider whether they resonate emotionally. You want your team to feel excited and think, “Yes, I want to be part of that!”

Typically, objectives are set monthly or quarterly. Don’t have more than one to three objectives per team each quarter, though this can vary depending on your organization’s needs. 

The goal is to avoid having so many priorities that you end up prioritizing none. Keeping objectives short, punchy, and concise makes them easier for everyone to understand.

💡 Pro Tip: When formulating objectives, ask yourself why achieving them is important.

Defining key results

Setting quantitative key results—clearly defined metrics—is crucial for tracking progress toward objectives. Using numbers for your key results allows straightforward and meaningful communication about progress.

Additionally, ensure that key results focus on outcomes rather than specific tasks. They should describe the ideal results needed to achieve the objective without dictating how they should be reached.

You may limit key results to three to five per objective, but this can depend on your business context. The good news is that you can always revise these statements later, and it takes practice to find a good rhythm for defining both objectives and key results.

📌 Now, let’s look at good OKR examples

A simple yet effective objective could be to “Lower your carbon footprint.” Your key results might include converting to 100% renewable energy within six months or using 100% recycled materials within three months.

On a broader scale, you might want to “make customers happy.” You could support this with key results like achieving a specific Net Promoter Score (NPS), reducing customer churn to a certain percentage, or gathering a set amount of customer feedback each month.

OKRs can serve various purposes, whether it’s driving company-wide goals or enhancing personal productivity. Regardless of their scope, their true strength lies in creating consensus, clarifying actions, and motivating individuals to achieve meaningful strategic goals.

Lastly, when you want to track OKRs, keep in mind that regular reviews and updates will help maintain alignment and momentum toward those crucial objectives.

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How to Run an OKR Planning Process

OKRs provide a clear framework for setting measurable objectives, helping teams stay focused and track progress. 

But to truly implement and unlock the power of OKRs, you need more than just well-defined objectives—you need a structured approach that fosters collaboration, prioritization, and ongoing communication.

Start with strategy alignment

The first step to running a successful OKR planning process is to ensure your OKRs are directly aligned with the company’s strategic goals. 

📌 For example, if a company’s long-term strategy is to expand into new markets, an OKR for the marketing team might be: Increase brand awareness in Southeast Asia by Q2. 

This objective aligns with the company’s strategy and ensures everyone contributes to the bigger picture. Without this alignment, teams may end up working in silos, pursuing goals that don’t directly support the organization’s direction.

Aligning your OKRs with the company’s strategic goals keeps everyone on the same page and ensures that efforts are focused where they matter most.

Facilitate brainstorming sessions

After ensuring the objective aligns with your company’s strategy, the next step is to gather your key team members to brainstorm potential ways to achieve it. Invite participants from marketing, sales, and product teams to contribute ideas. 

📌 In a brainstorming session, the marketing team may suggest ideas like launching region-specific ad campaigns or creating localized content. The product team might suggest offering regionalized features to capture the audience’s attention, and the sales team could explore partnerships with influencers or local businesses.

By encouraging different teams to share their insights, you generate diverse ideas and foster collaboration, ensuring the objectives have broad input and buy-in from across the organization.

Prioritize and finalize OKRs

Once you’ve gathered ideas from your brainstorming session, it’s time to prioritize which key results will make the most impact. 

📌 You might have several proposed key results to increase brand awareness, but you should focus on those that will have the highest reach and are realistic within the time frame. 

For example, you may decide to prioritize key results, such as: 

  • Launching three targeted ad campaigns
  • Partnering with five local influencers with a reach of over 150,000 followers each
  • Increasing social media engagement in Southeast Asia by 15% 

These key results are clear, actionable, and measurable, making it easier to track progress.

At this stage, it’s crucial to avoid spreading your resources too thin by choosing too many key results. Stick to those that directly align with the objective and your company vision and that your team can realistically achieve within the given timeframe.

Communicate and implement OKRs

After defining your OKRs, clear communication is essential. Ensure the marketing, product, and sales teams know the objective and key results. 

ClickUp Interface: OKR Planning
Align OKR planning with work management and achieve ambitious goals faster with ClickUp 

Using project management platforms such as ClickUp, you can ensure that each team knows their role and has visibility on progress. 

Review progress regularly

Lastly, the OKR process is not complete without regular check-ins. Schedule biweekly or monthly reviews to assess your team’s progress toward the goal. 

During these reviews, check if your key results are being met. For example, if you’ve already launched one of the ad campaigns but haven’t seen the expected rise in engagement, this would be the perfect time to adjust the approach. 

Or, if influencer partnerships are yielding great results, you might want to double down on that tactic.

Regular reviews keep the team on track, and adjustments can be made quickly if any challenges arise. They also provide a chance to celebrate wins, such as hitting your engagement targets early, which keeps morale high and focus sharp.

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Tools for OKR Planning

Having the right tools can make all the difference between ineffective and effective OKR planning, and ClickUp can be the Watson to your Sherlock here. 

As an all-in-one project management platform, ClickUp enables you to achieve complete visibility over your planned OKRs, from goal setting and task assignment to measuring outcomes.

Tools and resources for setting OKRs

To start, create a dedicated Space or Folder for your OKRs in ClickUp. Define your high-level objectives, which should be ambitious but realistic, and tie them to specific, measurable key results. 

ClickUp Goals

ClickUp Goals provides a fantastic virtual space to establish your objectives and keep everything organized, making it easier to set, track, and achieve your team goals—all in one place. Plus, it has a structured framework that helps you break down big goals into actionable plans, which you can set up as tasks for smooth monitoring.

ClickUp Goals: OKR Planning
Create, measure, and achieve your team’s goals with ClickUp Goals

To ensure your goals are measurable, you can incorporate Targets. These Targets are super helpful for tracking success metrics and keeping you focused on what matters. 

For instance, you might track:

  • A number: Like how many e-books were downloaded during your last marketing push
  • True/False: Checking if your new onboarding flow is bug-free and ready to launch
  • A percentage: Such as the increase in revenue you’ve seen over the past quarter
  • Currency: For example, your target savings from automation this quarter

You can also organize your goals by creating folders for your OKRs, tracking sprint cycles, viewing progress scorecards, and comparing results over different time frames.

ClickUp’s Custom Fields and goal-tracking templates allow you to link these key results to real-time data. This setup provides a clear view of how well your goals align with broader company objectives.

If you’re just getting started, these goal-setting templates are here to help guide you:

The ClickUp OKRs Template

Enable precise tracking and alignment of objectives with the ClickUp OKRs Template, facilitating organized goal-setting and helping you measure your progress effectively

Starting with the ClickUp OKRs Template is a fantastic way to dive into OKRs. With this template, you can:

  • Get a well-defined framework along with workspaces, making it simpler to begin planning your objectives
  • Find customizable OKR templates, a handy goal-setting guide, and even sample OKRs to inspire you
  • Access an OKR checklist and playbook that outlines best practices for implementing OKRs within your organization 

All these components work together seamlessly to help you get started with OKRs without hassle.

To execute OKRs successfully, understanding your team’s specific framework is crucial. This template helps you set up and customize OKRs that cater to your team’s unique requirements. With all the visual tools, workspaces, and resources included, everyone will understand their objectives and know how to work towards them effectively.

The ClickUp OKRs Framework Template

Help your team focus on priority goals and measure progress systematically with the ClickUp OKR Framework Template

The ClickUp OKR Framework Template is an awesome resource for kicking off your OKR journey quickly and smoothly. It includes ready-made OKR frameworks, customizable templates, helpful guides, and practical examples to make planning a breeze. You’ll also find a dedicated OKR checklist and playbook, which provide valuable insights for integrating OKRs into your business strategy.

Here’s how managers can leverage this OKR template to set and monitor their objectives and key results:

  • Begin by using the Global OKR View to create and track your overall company goals and objectives
  • Next, get insights into how each team is doing with the OKR Progress Board View
  • Finally, plan and monitor the timelines for each goal through the Timeline View

💡 Pro Tip: Use these SMART goal templates to set specific, measurable, attainable, relevant, and time-bound goals or SMART goals, track progress, and review them occasionally.

Tools and resources for achieving OKRs

Achieving OKRs is crucial for aligning team efforts and driving measurable outcomes. ClickUp simplifies the process through easy-to-use features that help teams set, track, and adjust their OKRs. 

Here’s a breakdown of how you can achieve OKRs effectively using ClickUp.

ClickUp Tasks

Once OKRs are in place, break them down into actionable tasks and milestones for each team member. ClickUp Tasks allow you to do this by assigning responsibilities, setting deadlines, and establishing dependencies. Assign each key result to specific owners, ensuring accountability. 

The intuitive drag-and-drop interface makes it easy to manage tasks, and you can choose from 15+ ClickUp Views—List, Table, Calendar, Kanban board, Gantt chart, and more—for clearer visibility into your workflow.

ClickUp Tasks: OKR Planning
Use ClickUp Tasks to outline key results and initiatives without messy spreadsheets

Here are some additional factors to consider when assessing the success of your OKR implementation process:

  • Timelines: Use ClickUp Time Tracking to compare estimated time with the actual time taken to achieve goals
  • Dependencies: Track dependencies that either sped up results or held your team back using ClickUp Dependencies
  • Milestones: Capture key moments in the project and celebrate wins with ClickUp Milestones, such as reaching 50% of your original goal

ClickUp also provides a range of automations, recurring tasks, and similar features that reduce manual work, allowing you to spend more time on decision-making.

Tools and resources for tracking OKRs

With the ClickUp Goal Tracking Feature, you can easily make edits as needed and notify everyone about the changes, which enhances transparency in the OKR cycle.

ClickUp Goal Tracking Feature
Create a clear order of operations by adding “blocking” or “waiting on” dependencies between tasks to keep your team on track to know what to work on first with the ClickUp Goal Tracking Feature

You can also establish task dependencies, assign team members, set timelines, and automate progress tracking.

With OKRs, you’ll evaluate success on key results. 

ClickUp Dashboards

ClickUp Dashboards are ideal for tracking and enhancing organizational performance across different goals and metrics. Build customizable dashboards and add widgets for the goals that matter most to you.

ClickUp Dashboard
Get instant insights from the OKR dashboard

ClickUp also offers a predefined OKR dashboard, making it easy to visualize your performance, identify bottlenecks, and spot risks early.

Now, OKRs are typically set every quarter at the team level. On the organizational side, they run in cycles and can be somewhat iterative. This means team managers can re-map their OKRs every quarter.

ClickUp Docs

At this point, it’s important to ask if everyone on your team can access the data you’ve gathered. Do they know what worked well and what didn’t?

Documenting successes and challenges is essential. You want to improve your OKR tracking process by relying on real-time data instead of guesswork or intuition.

ClickUp Docs serve as a centralized hub where team members, project managers, leaders, and C-suite executives can store all information related to OKRs. This can include insights from previous OKR cycles, reasons behind successes and failures, standard operating procedures, and tracking methods.

ClickUp Docs
Easily format and collaborate on Docs alongside the team without overlap in ClickUp

ClickUp Docs feature real-time editing and rich formatting options. This ensures documents stay intuitive and are always updated with the latest information.

You can also use threaded comments and discussions within tasks to connect with your team, share updates, and tackle any challenges.

Bonus tip: Regularly reviewing and adjusting goals

OKRs require ongoing attention, so it’s important to review progress regularly. 

Using the ClickUp Goals Dashboard, you can review your overall achievement of goals, paying special attention to any that fell behind. Schedule recurring check-ins or sprints to review and adjust your OKRs as needed. 

❗️If you notice that a key result is off track, reallocate resources, adjust timelines, or modify the OKR if necessary. 

ClickUp also offers goal widgets, making it easy to visualize progress and course-correct in real-time.

By setting clear OKRs, breaking them into manageable tasks, and regularly reviewing them in ClickUp, teams can stay aligned, focused, and adaptive—driving the outcomes that matter most.

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Best Practices for OKR Planning Sessions

If you want your OKR planning session to hit the mark, it’s essential to approach it with a thoughtful strategy. Consider these best practices to make the session more effective and keep everyone on track:

Encourage participation

Involve your team in the conversation. Everyone’s input matters and it helps create a sense of ownership. 

When people feel they’ve contributed, they’re more invested in achieving the objectives. Plus, having diverse perspectives can lead to more well-rounded and realistic goals.

Keep objectives attainable and measurable

While it’s great to aim high, make sure the objectives are within reach and can be clearly measured. 

By sticking to SMART goals (Specific, Measurable, Achievable, Relevant, and Time-bound), you avoid setting objectives that are either too vague or too ambitious.

Keep a balance

A good balance between bold, inspiring goals and more achievable ones can keep the team motivated. 

While some objectives should push boundaries, others need to be within easy reach to maintain morale and encourage progress.

Check-in regularly

Frequent progress reviews are key to keeping things on track. 

Regularly monitoring the key results lets you make timely adjustments and gives everyone a chance to discuss any challenges they’ve encountered.

Use tech to your advantage

Lastly, technology can make all the difference in tracking progress. Project management tools (like ClickUp 🤩) help you keep an eye on key results in real time and allow the team to stay accountable. 

By weaving these practices into your OKR planning sessions, you’ll not only set clear and achievable goals but also foster a more engaged and aligned team ready to drive results.

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Do Better OKR Planning and Achieve More With ClickUp

Achieving better OKR planning is all about setting clear, actionable goals and keeping everyone on the same page throughout the process. And when executed well, OKRs can connect ambition with actual results. 

Even if your team doesn’t meet every lofty goal, setting high aspirations can inspire them to achieve more than they originally believed possible.

ClickUp can accelerate your OKR implementation with its unique features, such as ClickUp Goals, ready-made templates, and customizable Dashboards. These tools help you establish a transparent, structured framework for developing clear OKRs and tracking team objectives at every stage on your path to success.

Sign up for a free ClickUp account and start working on your OKRs today!

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