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What 180+ Startups Wish They Knew Before Their First OKR Cycle

180+ founders share what changed after their first OKR cycle - clarity, focus, engagement, and process. Skip the mistakes, get to results faster.

Steven Macdonald
5 Mins read
September 12, 2025
What 180+ Startups Wish They Knew Before Their First OKR Cycle

If you’re about to run your first OKR cycle, here’s the hard truth: 

It’s probably going to be messy. 

Most teams overload on goals, write vague results, and skip check-ins. It’s so common that founders often finish cycle one wondering if OKRs even work.

But here’s the part most don’t realize - cycle one isn’t the real test. It’s practice. The real learning happens in cycles two and three, when the mistakes are behind you and the system starts to click.

That’s why we asked 180+ founders to share what changed the most after their first OKR cycle. Their lessons are the playbook you wish you had before you started. 

Here are the five takeaways you can steal right now.

This article is a preview of our upcoming 2025 OKR Benchmark Report. We’re sharing early insights from 200+ teams so you can see what separates average results from top performance.

1. From Chaos to Clarity

The most common shift was moving from bloated, scattershot OKRs to tighter, sharper goals.

One founder admitted:

“We have started to set less goals. We were a little too disorderly originally and it was hard to track. Once we scaled back, people could actually connect OKRs to their day-to-day work.”

Another said:

“We got better at making them more simple. We were able to define more measurable results, and more realistic goals.”

A third pointed to the impact on confidence:

“We became much better at setting clear, measurable key results, which has improved alignment and confidence.”

What it means: Early OKRs tend to read like wish lists. Over time, teams learn that clarity matters more than ambition. Fewer goals, tied to real outcomes, are easier to execute and measure.

Your move: Start with 3–5 company-level OKRs max. Cut anything extra into a “parking lot” for later. Focus turns OKRs from theory into traction.

2. Engagement Builds Over Time

Many founders reported that engagement was shaky at first. Teams saw OKRs as “management’s framework” rather than something that helped their work. But once results showed up, buy-in grew fast.

One founder explained:

“The team’s engagement was low at first, but once everyone saw the effectiveness and high efficiency it brought not just to the corporation but for each individual, the engagement grew drastically.”

Another echoed the shift:

“People are way more engaged with the process now compared to back then.”

And a third noted the cultural impact:

“All individuals had a greater sense of teamwork and higher morale.”

What it means: Engagement doesn’t come from demanding updates. It comes when teams see OKRs making their work easier, more meaningful, and better aligned with company priorities.

Your move: Don’t add new meetings. Instead, build OKR updates into existing cadences (standups, all-hands, retros). Make progress visible, and celebrate wins in public.

3. Streamlined Process Beats Heavy Process

The first cycle often felt clunky - too many meetings, too much admin. Later cycles worked because they were lighter and more consistent.

One founder described the shift:

Check-ins are better organized and more regular, which helps everyone stay on the same page. Everyone knows what their top priorities are, which has made things go more smoothly.”

Another said:

“We’ve gotten more streamlined in adaptation.”

And a third added:

“Everything’s a bit more standardized now with clear responsibilities.”

What it means: Cycle one usually drowns in over-engineering. Cycle two works better because teams strip it back. The sweet spot is short, predictable rhythms - 10–15 minutes per week, async if possible.

Your move: Pick one lightweight rhythm (weekly updates, monthly reviews) and stick to it. Consistency matters more than complexity.

4. Productivity and Speed Increase

Founders consistently noticed that execution got faster once OKRs clicked. Teams stopped scattering effort and focused on what mattered.

One shared:

“An increase in execution speeds and employees’ efficiency.”

Another said:

“What changed the most is our efficiency. We have been way more efficient with OKRs. It was tough at first, but we toughed it out.”

A third put it simply:

“Productivity skyrocketed.”

What it means: OKRs don’t magically make teams faster - they make teams choose. By forcing prioritization and cutting distractions, execution speeds up naturally.

Your move: Pair every OKR cycle with a cut list - what you won’t do this quarter. That’s where the real speed comes from.

5. Tools Help, But Habits Come First

Several founders shared how their tools evolved - from spreadsheets, to project management tools, to OKR software. But the common lesson was clear: tools only help once the team has built good OKR habits.

One said:

“We started using software to keep track.”

Another shared:

“Hosting team and individual dashboards on our OKR tool increased clarity and made it easier to use OKRs in meetings.”

And a third added:

“We started to implement AI into our software.”

What it means: Tools don’t fix broken OKR processes. They amplify what’s already working. Without habits, even the best platform turns into another abandoned dashboard.

Your move: Start simple with spreadsheets or free OKR tools. Once the rhythm sticks, invest in software that reduces friction and scales with you.

5 Biggest Shifts After Cycle One

If there’s one clear takeaway from these 180+ founders, it’s that OKRs evolve in predictable ways. The messy first cycle always gives way to sharper goals, stronger engagement, and simpler processes - if you stick with it.

Lesson What Changed for Founders Your Move
Clarity Fewer goals, sharper key results, clearer focus Limit to 3–5 OKRs, tie them to measurable outcomes
Engagement Teams bought in once they saw OKRs drive progress Make OKRs visible in standups, all-hands, retros
Process From heavy, confusing cycles to simple, repeatable ones Adopt a 10–15 min weekly update rhythm
Productivity Execution sped up as teams made trade-offs Create a “cut list” of what won’t get done
Tools Shift from spreadsheets to software and dashboards Build habits first, then invest in tools


Treat this as your roadmap for cycle two.
If you can nail these five lessons early, you’ll avoid most of the pitfalls that trip up first-time OKR teams and start compounding the benefits much sooner.

Final Thoughts

The biggest lesson from 180+ founders is simple: 

The first OKR cycle is not a verdict, it’s a rehearsal. 

It exposes weak spots in clarity, focus, and process - but that’s exactly what it’s meant to do.

By cycle two, the noise drops. By cycle three, the benefits compound. Goals sharpen. Teams engage. Processes streamline. Execution speeds up. And the right tools amplify what’s already working.

Too many startups abandon OKRs right before this shift happens. If you push through the messy first round, you’ll find the system starts working for you - not against you.

These are the five takeaways 180+ founders wish they knew before their first OKR cycle. Now you can use them before you even start.

📘 Free Resource: OKR Planning Template Pack

What’s inside:

  • Company & team OKR templates
  • 60-minute planning agenda & alignment checklist
  • Weekly check-in format to keep progress visible
Download the pack (PDF) →
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Founder

Steven Macdonald│LinkedInX

Steven is the founder of OKRs Tool and has helped 500+ startup and scale-up teams start their OKR journey through the platform. With 4+ years of experience in OKR management, he built OKRs Tool to make setting objectives, tracking progress, and staying aligned simple for small teams.