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How to Get Started with OKRs (Free OKR Playbook)

Getting started with OKRs doesn’t have to be a mess. This guide breaks it down step-by-step - plus a free OKR playbook to help you roll it out in 90 days

Steven Macdonald
5 Mins read
July 11, 2025
How to Get Started with OKRs (Free OKR Playbook)

Getting started with OKRs felt like overkill.

When I first looked into it, OKRs seemed like something built for big org charts, layers of managers, and quarterly planning retreats - not scrappy startup teams like mine juggling a hundred priorities with one whiteboard and Slack.

But the deeper I got into building, hiring, and trying to scale with clarity - the more I realized how badly we needed focus. A shared direction. Real, measurable progress.

OKRs gave us that.

Not in some bloated enterprise way. But in a lightweight, fast-moving, “let’s actually ship and learn” way.

In this article, I’ll share exactly how we got started with OKRs - what worked, what didn’t, and how you can use them to align your team and move faster with less chaos.

Let’s break it down.

Why OKRs Matter for Your Startup

As a startup, you’re often juggling multiple tasks, facing challenges, and trying to scale quickly. In such an environment, aligning your team with clear and measurable goals is critical. 

OKRs offer a structured framework that allows you to prioritize efforts, stay focused on what matters most, and track progress toward your most important objectives. 

They ensure everyone in your startup is aligned, committed, and moving in the same direction - helping your team achieve more in less time.

OKRs don’t just help with goal-setting; they help drive focus, motivate your team, and make data-driven decisions based on the outcomes that matter most.

1. Brainstorm Your Stretch Goals

Before diving into OKRs, take a step back and think big. 

As a startup, it’s important to set stretch goals - the ambitious, bold objectives that will drive your business forward.

Start by brainstorming the goals that will have the most significant impact on your growth. 

Whether it’s increasing your user base, launching a new product, or expanding into a new market, these stretch goals should challenge your team and give them something big to work toward. 

Think of these goals as the North Star for your startup - guiding your decisions and aligning your team’s efforts.

2. Discuss and Align as a Team

Once you’ve identified your stretch goals, it’s time to align your team around them. 

OKRs are most effective when everyone is on the same page, so you need to have an open discussion about these goals with your team members.

Hold a meeting (or multiple if necessary) to discuss and refine your goals. 

Be sure to explain the reasoning behind each objective and make sure everyone understands their role in achieving it. Encourage feedback and make adjustments as needed to ensure that the goals resonate with everyone. 

This open dialogue will help you get buy-in and keep your team engaged.

Remember, it’s not just about setting the goals - it’s about making sure everyone is clear on the purpose behind them.

3. Break Down Your Goals into Actionable Key Results

Now that you have your stretch goals in place, it’s time to break them down into Key Results. 

These are the specific, measurable outcomes that will show you whether you’ve achieved your objective. Key Results should be clear, actionable, and quantifiable.

For example, if your objective is to increase customer acquisition, your Key Results could be:

  • Acquire 200 new customers by the end of the quarter.
  • Increase the conversion rate by 15%.
  • Reduce customer churn by 10%.

These Key Results give you specific metrics to track, ensuring that everyone knows exactly what they’re working toward and how to measure success.

4. Test It Out on a Small Scale

Don’t feel like you need to implement OKRs across your entire team right away.

Instead, test the system on a small scale. Start by applying OKRs to one team or department to iron out any issues before rolling them out more widely.

By piloting OKRs with a smaller group, you’ll be able to identify challenges and adjust your approach. This gives you a chance to learn and refine your strategy before expanding it to your whole team.

5. Review and Agree on OKRs Regularly

OKRs are most effective when they’re regularly reviewed and updated. 

Schedule periodic check-ins to assess your team’s progress. These meetings should focus on tracking progress, identifying blockers, and adjusting goals as needed.

During these reviews, ensure that everyone is aligned on the next steps and agrees on what actions need to be taken. Regular reviews help ensure that your team stays focused on the most important goals and can adjust quickly if things aren’t going as planned.

6. Find the Right OKR Platform

With your OKRs defined, it’s time to find the right OKR platform to track them. 

As your startup grows, manually tracking OKRs can become a daunting task. The best OKR software simplifies the process, offers real-time progress tracking, and allows your team to stay aligned.

Look for a platform that’s easy to use, integrates with the tools your team already uses (such as Slack or Google Workspace), and can grow with your startup as your team expands.

OKR software will help you streamline goal-setting, tracking, and collaboration, saving time and keeping everyone focused on your most important objectives.

Track progress in OKRs Tooll

📋 Not sure if you're ready for OKRs? Use this quick checklist.

OKRs work best when you’re clear on what you want to change and have the bandwidth to follow through. If most of these sound like you — you're ready to give OKRs a shot.

Statement Ready?
We have 1–3 big priorities this quarter we need to nail
We’re not aligned on what success looks like
Team members want more clarity and direction
We want to track outcomes, not just tasks
We're ready to check in weekly or biweekly
We don’t need OKRs yet — just keeping the lights on for now

3 Common OKR Pitfalls to Avoid

Even though OKRs are incredibly helpful, startups often face challenges when implementing them. Here are some of the reasons why OKRs fail in startups:

1. Setting Too Many OKRs

While it's tempting to set OKRs across the board, overloading your team with too many OKRs can cause confusion and reduce focus. 

Stick to 1-2 objectives per OKR cycle for clarity and effectiveness.

2. Lack of Regular Check-Ins

OKRs need to be reviewed regularly to stay on track. 

Waiting until the end of the cycle to see if goals are met may lead to missed opportunities for adjustments. 

Schedule regular weekly or bi-weekly check-ins to keep things on course.

3. Vague Key Results

Your Key Results should be specific and measurable

Avoid ambiguity by making sure each Key Result has a clear, actionable metric tied to it. Instead of saying "Increase customer satisfaction," go for something like "Increase customer satisfaction score by 15%."

By avoiding these pitfalls, you'll ensure that your OKRs are more effective, focused, and achievable.

Conclusion

Getting started with OKRs doesn’t have to be overwhelming. 

By brainstorming stretch goals, aligning your team, setting measurable Key Results, and regularly reviewing progress, you can start using OKRs to propel your startup forward.

Start small, test your approach, and refine it as you go. And with the right OKR platform, you’ll be able to track, align, and achieve your startup’s goals with ease.

📥 Free Download: The Lean Startup’s OKR Playbook

Kickstart your OKR journey with a proven roadmap designed for small, fast-moving teams.

  • ✅ 90-day OKR rollout checklist
  • ✅ Templates to plan, write, and review OKRs
  • ✅ Crawl → Walk → Run stages for real startup momentum
Download the Playbook →
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Founder

Steven Macdonald│LinkedInX

Steven is the founder of OKRs Tool and has 4+ years of experience helping startups and scaleups put OKRs into practice. After advising dozens of teams, he built an OKR platform to make setting objectives, tracking progress, and staying aligned simple for small teams.