The Dreams with Deadlines community brought together some of Austin’s most passionate strategy execution leaders and OKR advocates on June 21st. They gathered to share some of their top OKR best practices on launching, scaling, and improving OKR programs.
Our panel featured experienced OKR veterans, including John Henry, CEO of LOOP, Renae Fisher, OKR Practice Lead at Adobe, and Aaron Velek, Founder & OKR Coach at Square 1 Strategies. They discussed candid insights from their roles in startup and enterprise organizations, reflecting on their successes and challenges while offering universal advice for OKR programs of all sizes.
In this blog post, we’ll cover some key takeaways from the panel discussion, providing actionable tips and OKR best practices to inspire your OKR journey.
Key takeaway #1: Introduce OKRs through pilot programs and early adopters
Introducing pilot programs and engaging early adopters can be a great way to implement OKRs within your organization. These allow teams to experiment with OKRs, provide feedback, and align their efforts.
Aaron recommended running OKR pilot programs with a few cross-departmental teams for two quarters to assess OKR scalability. Renae encouraged involving OKR enthusiasts as early ‘OKR adopters’ to cultivate advocates and supporters within the organization. These early adopters not only promote the OKR method but also share their experiences and OKR best practices to help others understand the value of OKRs.
"For anybody that is in a position to be the sole champion of OKRs, you're going to have a lot of pressure to get it right when you're still figuring out this framework yourself… We would constantly level set with the team and say ‘we're figuring this out together’."
— John Henry
OKR best practice: Initiate team-based OKR pilot programs, engage early adopters to trial the OKR method, and create excitement around OKRs across your business.
Key takeaway #2: Consider the fit of OKRs with your company culture
The panelists agreed that OKRs are effective for aligning teams, embracing experimentation, and focusing on common goals. However, it’s important to assess whether your company culture is suitable for OKRs.
Leaders need to take an honest look at their culture and ask: Is there a general resistance to change? Are we genuinely supportive of collaboration and transparency? Do we trust our employees to make decisions aligned with our company priorities? If the answer to any of these questions is no, OKR implementation will be challenging.
Generally, OKRs work best in companies with a culture of growth, innovation, and intense ambition. Leaders must also be prepared to allocate plenty of resources for OKR program implementation and iteration.
OKR best practice: Before adopting OKRs, assess your company’s culture to ensure it embraces collaboration, transparency, ambition, and trust — OKR implementation may fail otherwise.
Key takeaway #3: Guide top-down leadership in OKR adoption
Successful OKR adoption requires strong top-down leadership. When leaders role model expected behaviors, such as learning, taking risks, and setting stretch goals, it boosts OKR adoption by encouraging others to follow suit.
Aaron also found that being prescriptive with executives by offering straightforward to-dos and assets makes OKR adoption easier. Busy executives often request clear instructions on what they need to do, so OKR program owners should be ready to provide actionable guidance.
"Having leaders role model what’s expected is critical. Because if that doesn’t trickle down, adoption is going to be really poor. We got super prescriptive… this is what a good check-in looks like, this is what your agenda looks like for a planning meeting."
— Aaron Velek
OKR best practice: Encourage leaders to role model desired behaviors and provide them with clear and actionable assets to support their OKR learning and adoption.
Key takeaway #4: Maintain the OKR spirit with ongoing training
With over three years of experience scaling OKRs within Adobe, Renae recommends hosting refresh workshops and relaunching OKRs for teams that need renewed energy. These workshops help maintain momentum while providing continuous education for team members.
She compares the role of an OKR implementer to that of a business therapist — they help uncover challenges and overcome resistance along the way. To succeed, she advises maintaining resilience and surrounding oneself with driven individuals who share the same vision.
OKR best practice: Sustain momentum by hosting periodic OKR workshops to continuously educate teams, reinforce their commitment to OKRs, and foster a supportive network of like-minded individuals who share the same drive for goal attainment.
Key takeaway #5: Focus on practice rather than perfection
The panelists stressed the importance of having grace, patience, and vulnerability during OKR implementation. Recognizing that everyone is learning together can create a powerful shift in momentum and increase buy-in from all team members.
While it may take multiple OKR cycles to identify the right key results, even imperfect key results can align the company and complete a cycle. Over time, with plenty of refinement and iteration, these imperfections can help nurture alignment and uncover inefficiencies.
“It took time, it took top-down leadership... and an army of people who were just as bought in as me."
— Renae Fisher
OKR best practice: Create a supportive environment where team members feel comfortable sharing their progress, challenges, and learning experiences during OKR implementation to nurture continuous improvement and learning.
In a nutshell
This panel emphasized critical truths about finding OKR success. The insights and OKR best practices shared during our community event included initiating team-based pilot programs and engaging early adopters, assessing the company’s OKR-culture fit, guiding top-down leadership during OKR implementation, facilitating ongoing OKR training, and fostering a culture of continuous improvement. Implementing these OKR best practices can unlock the true potential of OKRs for your organization, driving effective goal-setting and strategy execution.
Dreams with Deadlines is the one and only strategy meets execution community. We’re a global network of ambitious leaders who are passionate about using OKRs and agile practices to achieve audacious goals and build a better future.
Whether you’re new to OKRs or a seasoned pro, the Dreams with Deadlines community is where you’ll find the knowledge, connections, and resources you need to achieve your goals with greater confidence, efficiency, and impact.
About the speakers
John Henry - John is co-founder and co-CEO, at LOOP, an insurance startup committed to giving back and being a force for good. Influenced by mentors at Twitter and Google Ventures, John was adamant about using OKRs to execute LOOP’s strategy. But it wasn't a home run right off the bat. He admits they have “gone through the wringer in implementing OKRs and has a lot to share on the topic.”
Renae Fisher - Renae is the Practice Lead for OKRs at Adobe, where she has spent the last three years helping to solve the puzzle of how to make a company's mission, strategy, and daily activities align. Now, she’s on a mission to bring the power of OKRs to more areas of Adobe’s business.
Aaron Velek - Aaron is the founder and OKR coach at Square 1 Strategies. Previously OKR coach at SVB and head of strategy at Omega Engineering, where he came across OKRs. Aaron has been using the OKR framework to execute strategy ever since, and he finds it effective due to its simplicity, transparency, and accountability.