If there’s one consistent regret founders share about OKRs, it’s this:
“We should have started earlier.”
Our 2025 Startup OKR Report found that nearly 9 in 10 founders wished they had implemented OKRs sooner. They delayed because they thought their team was “too small,” or they wanted to “stay scrappy” a little longer.
But by the time they felt the pain - scattered priorities, duplicate work, and accountability slipping - it was already expensive to fix.
This isn’t about billion-dollar companies or 500-person orgs. It’s about the messy middle: that 6–10 person stage where alignment debt quietly builds. The faster you’re growing, the faster it compounds.
In this post, I’ll unpack why waiting is such a costly mistake, the breaking point every startup hits, and - most importantly - how you can start small and simple so you never have to say “we should have done this earlier.”
Why Founders Delay (and Pay the Price)
When you’re early, OKRs feel like overkill. The team is small, everyone’s moving fast, and communication feels effortless. Why add structure?
Here’s the catch: alignment debt is invisible - until it’s not. Like technical debt, you don’t notice it until you’re tripping over it:
- Scattered priorities: The growth team is pushing one metric, product is focused on another, and no one’s sure what the “real” company goal is.
- Shadow work: Side projects absorb time without linking back to outcomes.
- Founder bottlenecks: Everyone looks to the founder for direction because there’s no shared source of truth.
Our research shows that 56% of startups began with spreadsheets or Notion to track goals. By the time they hit 8–10 people, those systems collapsed. And 89% of founders later said they should have implemented OKRs earlier.
The lesson is simple: waiting doesn’t protect your speed. It erodes it.
The 6–10 Person Breaking Point
The first five hires don’t need OKRs. You can sit around a table (or a Slack channel) and know what matters. But once you hit 6–10 people, everything changes.
Here’s what founders told us in the report:
- “We set too many goals and it was hard for people to connect them to their daily work.”
- “Check-ins were inconsistent, so OKRs lost momentum.”
- “Shadow work crept in - half our projects weren’t tied to OKRs.”
What’s happening here isn’t laziness. It’s math. With every new hire, the number of communication lines grows exponentially. Misalignment isn’t a people problem - it’s a systems problem.
And once you cross that threshold, shouting priorities in Slack isn’t enough. You need a framework to keep focus sharp and visible.
How to Start Small (and Avoid the Trap)
Here’s the real value: you don’t need a massive rollout or enterprise playbook.
You just need to start with a lightweight version that works for your team today. Over the last decade, I’ve seen this simple five-part framework work again and again.
1. One Company Objective
The biggest mistake first-time OKR users make is overstuffing the sheet. Five objectives, ten key results, endless sub-projects. It collapses under its own weight.
Instead, start with one company-level objective. That’s it.
Make it specific, time-bound, and inspiring. For example:
- “Improve activation from free trial to paid user.”
- “Get our first 50 paying customers.”
- “Hit $50k MRR with a stable core product.”
The key is to pick the outcome that matters most this quarter - not everything that matters. That focus forces clarity.
2. Three Key Results
Once you’ve picked your objective, define three measurable key results. Not outputs, not tasks - results.
Bad key results look like: “Redesign onboarding flow” or “Ship v2 of dashboard.” Those are tasks.
Good key results look like: “Increase trial-to-paid conversion from 20% → 35%.” That’s an outcome.
Three is the sweet spot. One is too narrow, five is too fuzzy. At three, you balance ambition with focus.
3. One Cycle
Don’t overthink cadence. Run a single 90-day cycle - one quarter. It’s long enough to make meaningful progress, short enough to adjust quickly if you overshoot or miss.
At the end of the cycle, hold a simple retro:
- What worked?
- What didn’t?
- What will we change next time?
That reflection is more important than perfection. Every cycle you run improves the next.
4. Weekly Touchpoint
OKRs die when they disappear into a spreadsheet. They live when they’re part of the rhythm of work.
The sweet spot: one weekly touchpoint.
That can be:
- A 10-minute async check-in (via Slack or your OKR software).
- A quick review in your Monday standup.
- A slide in the Friday all-hands.
It doesn’t matter how you do it - what matters is consistency. Skipped updates are the first sign OKRs are fading.
5. Visibility First
Don’t let your OKRs become a hidden file. Make them visible, simple, and accessible to everyone.
- Pin them in Slack.
- Share a dashboard link.
- Print them out and put them on the wall if you’re in-office.
The point is to keep them in sight, in mind. The more visible the goals, the harder they are to ignore.
Why Waiting Is the Real Mistake
Here’s the kicker: the startups in our report that reached $1M ARR fastest weren’t the ones with the fanciest frameworks. They were the ones who implemented OKRs early - before chaos set in.
They didn’t wait until they had 30 people and a tangled mess of priorities. They built the habit when they had 6–10, and it scaled with them.
Waiting doesn’t keep you nimble. It makes you reactive.
The Lightweight OKR Starter Kit: 5 Steps
Before we wrap up, here’s the 5-step OKR starter kit founders can use to get moving today - no consultants, no complexity, just the essentials.
This is the bare minimum structure you need to avoid the “we started too late” trap. Get this rhythm in place, then build from there.
Don’t Wait for Chaos to Start
OKRs aren’t bureaucracy. They’re a focus system. They give your team a shared definition of success, protect you from distraction, and build a rhythm that compounds over time.
If you’re running a 6–10 person startup without OKRs, you don’t need to wait until you “feel ready.” You’re ready now.
Start small: one objective, three key results, one cycle, one weekly touchpoint, full visibility. That’s it.
It won’t be perfect. It doesn’t need to be. But it will save you from the #1 mistake almost every founder admits: waiting too long.
