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The Role that Leadership Buy-In Plays in OKR Adoption

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Wednesday, July 26, 2023

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6 min read
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Key takeaway: How do you ensure your entire organization’s priorities are aligned? Spoiler alert: It will almost certainly take more than compiling a single spreadsheet of everyone’s priorities, although that might be a solid starting point. 

To pursue true alignment, you must go beyond learning where everyone’s focus is — you’ll need to ensure everyone focuses on the right things.

This is what the team at Chargebee found in 2019 when it pursued company-wide visibility and transparency of priorities, as Lavanya Gopinath, Senior Director of Culture and Systems, shares. The simple solution of entering priorities somewhere was simply the first step. While articulating these priorities helped teams identify collaborators based on shared goals, true alignment required a larger framework. 

“We were all working on too many things, so now the question becomes, how do we focus on the right things?” Lavanya explains. “How do we map all of this out?” Adopting Objectives and Key Results (OKRs) was a clear solution — and over the past four years, OKRs have allowed the Chargebee team to accomplish more by clarifying what everyone is working toward.

On an episode of Dreams with Deadlines, Lavanya discusses what worked when adopting OKRs, how the Chargebee team set expectations and cadence for reviewing OKRs, and the wins and challenges they’ve found along the way.

The challenge of working backward

Adopting OKRs doesn’t happen overnight, and it certainly didn’t at Chargebee. The company took nearly three quarters to get into the right rhythm.

When starting from scratch with OKRs, the ultimate goals are to assess the value everyone should deliver, decide how to measure that value, and make a plan to deliver. Achieving these goals is easier said than done. The Chargebee team found that one of the biggest challenges was learning to have the right OKR conversations at the right stages.

Any given team will approach a conversation about priorities and goals through its own lens. Then, when they encounter others’ priorities, team members experience a natural temptation to simply map those goals onto their own — what Lavanya calls “plug[ging] them in together.”

To combat this tendency, leadership needs to work backward. The earliest conversations should address the value the organization delivers as a whole. Those high-level discussions can then transition into how that value becomes objectives and shared goals which, from there, disperse to the rest of the organization. 

That way, everyone can set OKRs that fit well into the bigger picture — not just the objectives representing their piece of the puzzle.

The voice of the CEO in OKR adoption

So how do you bring an entire organization to a new way of thinking? For Chargebee, this seemingly impossible task started at the highest level: with CEO Krish Subramanian.

If you’re selling the idea of OKRs to employees, you might meet some resistance. People may question how OKRs differ from SMART goals and other methodologies, for instance, or express skepticism about how OKRs will change their daily work.

The key is to respond to these questions with openness and honesty. Company leadership should acknowledge that the goal is to try something new and learn whether OKRs work for the organization. 

Start by hosting “Ask Me Anything” (AMA) sessions. For Chargebee, Krish served as the voice for these discussions.

CEOs (or other executives) should acknowledge the company’s direction — where it came from and where it’s going. Then, bring everyone back to the core values they live and breathe in their work and illustrate how having OKRs can help them better deliver on those values.

Krish reminded the team at Chargebee of the importance of the customer experience, empathy toward other employees, and continuous learning. While everyone felt connected to the mission and vision of the company, they agreed that having shared objectives for the quarter and the year would help them work together better and bring those values to life.

For Chargebee, the AMA sessions first gave the CEO the space to share why he thought they should work on OKRs and how he believed they would help the company grow. Over time, he shared more about company objectives for the year ahead and how OKRs would apply to each team individually. 

The conversations kept expanding to other aspects of OKRs to help everyone feel comfortable with the upcoming changes. Other executive team members added their perspectives, all in service of allowing employees to gain answers to their questions.

The teams received some elements better than others — they appreciated objectives early on, but learning to turn value into measurable key results took training and time. But the top-down approach eased the transition and helped with adoption overall.

Setting clear expectations for OKRs

Clear expectations are an important part of any OKR undertaking. They ensure everyone starts and stays on the same page about how OKR implementation should look. At Chargebee, the list of expectations wasn’t lengthy, but everyone needed to know what those expectations were.

First, senior leadership had to show investment in OKRs. Their responsibility was to talk about adoption within their roles and teams. Clear C-suite buy-in conveyed the importance of OKRs to individual team members and, in turn, fostered engagement. 

Next, Chargebee set clear structural constraints. To keep OKRs simple, leadership set an expectation that teams should not have more than four objectives — and that they set three to five key results per objective. Once again, working with leadership played an important role in bringing these expectations to life.

Finally, the operations team conducted efforts to communicate why OKRs matter. These included writing blog posts, starting Slack conversations, and designating appointed contacts. Chargebee brought in an OKR program manager who communicated with champions and leaders, answered questions, and guided everyone through setting up OKRs in a meaningful way. 

Establish your top priority for OKR adoption. (For Chargebee, keeping things simple for employees and building momentum from the top down were key.) From there, set clear expectations and targets to enable you to deliver those priorities and set up the entire company for success.

Finding the right OKR cadence

Chargebee sets OKRs at multiple levels, each with its own cadence.

In early Q4, leadership set company OKRs that operate on an annual cadence. They announce these OKRs in the first all-hands meeting of Q1, which drives excitement and alignment to kickstart the year. Executives revisit these OKRs on a monthly cadence.

Each function also has its own level of OKRs, which everyone revisits quarterly. Company goals cascade down to the functional level to drive these objectives.

Within each function, teams also set their own OKRs, with function-level OKRs cascading down. Chargebee leadership encourages each team to set its own cadence for revisiting OKRs. They recommend a bi-weekly rhythm, but some teams feel more comfortable reviewing every week. For both function and team levels, staff meetings serve as an ideal forum to discuss OKRs because leaders can set aside time for discussion, and the meeting cadence aligns with the rhythm for the review process.

At all three levels, regularly revisiting progress against OKRs throughout the year allows everyone to check their progress and assess the next steps for any lagging areas. Chargebee adopted OKRs to pursue greater visibility and priority alignment — the reviews keep organizational (and more local) goals front and center for all employees.

A daring OKR journey

Lavanya says Chargebee’s journey of adopting and implementing OKRs over the past four years involved “a bit of daring.” This has been clear through the company’s willingness to experiment and try things they’re uncertain about doing.

At one point, leadership tested having quarterly OKRs at the company level, which Lavanya describes as “exciting and slightly terrifying.” They determined that this effort only introduced complexity. Just a month in, leadership acknowledged that the experiment didn’t quite pan out.

But a failed experiment isn’t useless — especially when you choose to learn from the outcome. That’s exactly what Lavanya and the team at Chargebee have done. Although every experiment may not have staying power, the alignment OKRs brought to Chargebee will surely stick around for the long haul.


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.

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