The OKR Check-in Dilemma: How Often Should You Track Progress?

So, you’ve set your OKRs. Great! You’ve aligned your objectives, key results, and teams. Now comes the tricky part: how often should you check in on them?

TL;DR

The ideal frequency for OKR check-ins is bi-weekly. Weekly check-ins often feel repetitive, create meeting fatigue, and lead to fake updates. Monthly check-ins are too infrequent, causing delays in spotting issues and missed opportunities for course correction. Bi-weekly check-ins strike the balance: frequent enough to maintain accountability and focus, but spaced enough to show real progress. Alongside progress updates, check-ins should include confidence tracking—low, medium, or high confidence—so teams can identify risks early, address blockers, and adjust priorities. Done right, check-ins build habits of execution without becoming a burden.

So, you’ve set your OKRs. Great! You’ve aligned your objectives, key results, and teams. Now comes the tricky part: how often should you check in on them?

Too often, and your team starts rolling their eyes every time OKRs are mentioned. Not often enough, and, well…nothing happens.

Ben Lamorte, OKR coach to over 2,000 business leaders, has seen it all from companies that never check in (the “set it and forget it” crowd) to those that check-in so often it becomes counterproductive.

His advice? The sweet spot is bi-weekly check-ins.

“When I started, companies thought weekly check-ins were the way to go. But for most teams, it’s too much. And monthly check-ins? Not enough. Bi-weekly? That’s the Goldilocks zone.” – Ben Lamorte.

So, let’s talk about why bi-weekly check-ins are the best rhythm for keeping teams engaged, ensuring accountability, and driving results.

Why Weekly Check-ins Can Feel Like Overkill.

OKRs are meant to be a strategy execution tool, not a micromanagement exercise. Yet, many companies have thought weekly check-ins are the best way to keep momentum. The logic makes sense: OKRs are essential, so let’s talk about them every single week.

But here’s the problem:

“When you check in every week, there’s usually little to say. Most key results don’t move every week, and teams start feeling like these meetings are just another box to check.” – Ben Lamorte.

Sound familiar?

Weekly check-ins often lead to:

• Repetitive conversations – “Yep, still working on that.”
• Meeting fatigue – Teams start tuning out because there’s nothing new to report.
• Fake updates – People start updating numbers to make it look like things are happening.

If your team dreads OKR check-ins, you’re probably doing them too often.

Why Monthly Check-ins Aren’t Enough

On the flip side, some companies go too far in the other direction. They assume, “Well, we track KPIs monthly, so let’s just do OKRs the same way.”

That’s a huge mistake. “Monthly check-ins are too slow. If you only check in once a month, by the time you realize a key result is off-track, it’s already too late to fix it.” – Ben Lamorte.

Monthly check-ins lead to:

• Lack of urgency – No one feels the pressure to take action.
• Delayed course correction – Issues aren’t spotted early enough.
• Scramble mode at the end of the quarter – Teams realize too late that they’re off track.

If OKRs are about focus and execution, you can’t afford to wait 30 days before checking progress.

Bi-Weekly Check-ins: The “Just Right” Approach

This is why bi-weekly check-ins have become the gold standard for most teams.

• Frequent enough to stay on track
• Not so frequent that it feels excessive
• It gives teams enough time to make real progress between updates

“For most companies, bi-weekly check-ins are ideal. They give teams time to progress while maintaining high momentum and accountability.” – Ben Lamorte. A bi-weekly cadence ensures that OKRs stay front and center without overwhelming the team. And the best part? If you miss one, it’s not the end of the world.

“I worked with a large bank that was doing weekly check-ins. The team hated it. When we switched them to bi-weekly, engagement shot up because now, the meetings felt useful.” Ben Lamorte.

OKR Confidence Tracking: More Than Just Updating Numbers

One of the biggest mistakes teams make during check-ins? They focus only on numbers.

Check-ins shouldn’t be about “Where are we on this key result?” They should also answer:

1. How confident are we that we’ll achieve this OKR?
2. What’s preventing progress?
3. Do we need to adjust priorities or remove blockers?

Ben emphasizes OKR confidence tracking as a key part of check-ins:

“If I’m an executive, I don’t just want to know the current number I want to know if my team believes they can hit the goal.” – Ben Lamorte.

That’s why confidence scores are so powerful. Instead of just tracking numbers, teams assess:

• Low Confidence (0-40%) – “We’re off track, and we’re not sure we can hit this.”
• Medium Confidence (50-70%) – “We’re making progress, but there’s a risk.”
• High Confidence (80-100%) – “We’ve got this.”

This helps teams spot problems early and shift priorities before it’s too late.

OKRs Should Be a Habit, Not a Burden. The goal of check-ins isn’t to add another meeting for the sake of meetings. It’s to make sure OKRs are helping teams focus and execute.

That’s why bi-weekly check-ins are the best rhythm for most companies.

So before your next check-in, ask yourself:

“Are we just going through the motions or driving results?”