Roadmapping OKRs

Benny Wong

CTO at Spin



It generally takes a while for people to understand what OKRs are for and how to use them. We started out small without OKR’s, using sticky notes on a board to make sure things were getting done from top to bottom. Although the founding team had 10+ years of experience in the industry, implementing OKRs still came with a lot of challenges.

Initially, we set really ambitious OKRs and almost never hit any of them. We tried making changes and ended up hitting too many of them. We weren’t really following what OKRs should be and couldn’t figure out why. What we ended up realizing was that we were missing a roadmap. We had been making OKRs without following a roadmap and were unable to translate these high-level OKRs to completion.

Actions taken

We did a complete flip and started with only a few company-level OKRs to develop the team OKRs and roadmaps after. We now work on roadmaps and OKRs as the same entity to make sure resource planning gets done and to understand capabilities and cross-functional needs.

Originally, we began this process solely with the executive team and have since included people with expertise in their respective areas from other organizations.

Lessons learned

  • To be able to do an OKR, you need to have some understanding of your team’s capabilities. Most young businesses do not really know that. Everybody is working as hard as they can and you aren’t really sure of what is attainable or not. You become blindsided by the gaps until you try to do something.
  • Working on OKRs and roadmaps hand in hand allowed for more team alignment than ever before in terms of coordination and communication. In this way, organizations are more comfortable committing to OKRs because they know exactly what needs to get done and can better plan as a business.

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Benny Wong

CTO at Spin

Leadership DevelopmentCommunicationOrganizational StrategyTeam & Project Management

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