Cadence, culture, and clarity: making OKRs a living framework

Dean Swan, Vice President and General Manager of monday.com in APJ, says that’s what separates organisations who treat OKRs as a reporting exercise from those who use them as a catalyst for change.

“OKRs shine a light on progress, or the lack of it,” Dean Swan says. “That level of accountability can feel like a double-edged sword. The challenge for leaders is creating an environment where teams feel comfortable talking about what’s holding them back, and leaning into those problems together.”

Building ownership and ambition

For Dean Swan, the framework isn’t just about tracking results; instead, it’s about sparking ambition. Too often, he says, organisations play it safe with goals they already know they can achieve.

“When you’re setting OKRs, it’s easy to shy away from bold objectives,” Dean Swan explains. “That’s just metric setting. The real value comes when you set objectives that move your organisation forward in a meaningful way.”

He points to monday.com’s own journey: “In our retrospectives, we admitted we weren’t setting ambitious enough goals. So we reset our OKRs to think two years out, to challenge ourselves to aim higher.”

Rhythm of results

Cadence and rituals, Dean Swan says, are what sustain that ambition. Quarterly reviews might track overall objectives, but it’s the monthly conversations where teams discuss bottlenecks, resource gaps, and dependencies, and where executive sponsors can step in to unblock progress.

“You can’t just set OKRs and update the scoreboard every quarter,” Dean Swan says. “It’s not a living, breathing framework if that’s all you do. The cadence is where alignment happens, where you keep momentum and avoid surprises.”

Structure with agility

Dean Swan also stresses the need for balance. OKRs provide structure from the top, but empower teams to shape the “how” from the bottom up. That combination, he says, creates both alignment and agility.

“At monday.com, we set objectives at the leadership level, but then teams across the organisation design the initiatives to get there,” he says. “That gives teams ownership, but also ensures we’re all driving towards the same outcomes.”

Flexibility, he adds, is critical in today’s dynamic environment. “OKRs aren’t meant to be rigid. Best practice is reviewing and adjusting regularly, but with governance in place so changes are deliberate and for the right reasons.”

For Dean Swan, it comes down to creating clarity without killing adaptability. “OKRs are most powerful when they’re not just a framework for measurement, but a framework for conversation, cadence, and culture.”

To learn more please visit https://monday.com/enterprise-agile