Episode 32

How to Do OKRs Right

With Deidre Paknad, CEO & Co-Founder at WorkBoard

By Ashu Garg


This episode goes deep on a topic that many founders, especially first-time founders, obsess over but usually get wrong: OKRs, objectives and key results. And there’s literally no greater authority on this topic than our guest Deidre Paknad, CEO and cofounder of Workboard, the enterprise standard in OKR software and expertise. Deidre is one of the most methodical, systematic, and gutsy leaders we’ve ever had on the show. Many CEOs overdo or underdo OKRs. Listen to Deidre and she’ll tell you how to do OKRs right.

I. The Recap

What is WorkBoard?

WorkBoard is a SaaS company that helps organizations get aligned on their strategic priorities, adjust them as the market changes, and drives ownership and transparency on their progress towards those goals. Some call them OKRs, but WorkBoard is about more than just OKRs. WorkBoard helps drive alignment across the entire organization.

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Why do early-stage founders/CEOs struggle with goal alignment?

  • When they’re leading the pack, they can lose sight of who is running behind them.

  • They change their minds quickly and frequently in the early stages of growth.

  • They might be new to the experience of leadership and have yet to learn how to communicate with their team.

  • Founders spend 24/7 thinking about their company and often forget to articulate their ideas and bring their team along with them.

Best practices for companies with…

0-10 employees:

  • Spend your time iterating, focusing, and aligning on your strategic priorities

10-25 employees:

  • Structure your OKRs at a team/company level only. Individuals should not have OKRs.

  • Spend some time defining the onboarding journey and operating rhythm for new hires at this stage.

100+ employees:

  • Create a common framework across every business function for your rising managers to follow. This allows alignment across all departments.

  • At this level you need a platform to manage your OKRs. Deidre recommends WorkBoard.

Helpful advice from a CEO that has hired 82 people in the last year:

  • Communication breakdown — Once your team has reached 200+, you’ve likely increased your executive staff. These people are measurement driven because they understand their obligation to provide results or “outcome” to the board. But the operating staff remains activity driven, focused solely on output. This presents a “tearing in the fabric,” as Deidre puts it, leading to a breakdown in communication among the staff. Maintaining a consistent, company-wide framework will help keep you aligned as your company grows and teams become more siloed.

  • If you don’t implement a process for aligning on outcomes below your board and leadership team, your company will suffer.

  • One-on-one meetings and skip-level meetings are crucial to maintain alignment with your team. You should make yourself accessible.

Published on 06.28.21
Written by Ashu Garg

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