3 Surprising Lessons Learned When Sharing a “Playing To Win” Mindset

Strategic thinking isn’t isolated to your strategy team. It’s shared.

Photo by Mark Fletcher-Brown on Unsplash

Thanks for the extensive write-up Anthony Murphy. At Littlepay, we had our leadership team construct their own ‘functional strategies’ per department in alignment with Company Goals and OKRS.

So, we followed most of what you described in your article and followed Robert L Martin’s Strategy framework to a tee 😜. It worked well, but there were a few things we learned in the process.

1. Shared OKRs exposed the need to collaborate more

Our teams often didn’t have specific strategies that were isolated to a department. We found some shared OKRs that needed to pairing/collaboration between departments. For example:

  • Product + Engineering = new product design of APIs that needed tighter engineering feedback loops
  • Ops + Engineering = bug fixes and resolutions that needed more context and investigations before working on a solution to fix the bugs raised
  • Pre-sales + Product = gaining more understanding of client objectives before responding to a feature request. Some feature requests didn’t really need to be requested if the pre-sales activities with clients were approached differently and the client knew about functionality that was already available.

So, if we scored low on these KRs, then we knew that we weren’t collaborating well across the organisation.

2. Some definitions of ‘How We’ll Win’ varied widely

Although we had shared company goals, “how we’ll win” was defined differently per department. For example:

  • For Sales, winning meant closing deals. For Product, the adoption of a specific feature with positive client feedback regardless of whether or not that feature made money in the short term was considered a win. In fact, some features helped client retention, which protected revenue loss.
  • For Operations, fulfilling a client request for bespoke reporting to help analyse a fraud issue may be of utmost importance to a strategic customer; however, to the Product team, creating a product that stopped fraud from happening across all clients was more important.

3. Management systems and processes to succeed need cross-functional discipline

When answering “5. What management systems are necessary to operate to build and maintain the key capabilities?”, some executive team members relied on some forum or joint meeting to be arranged to help cross-functional collaboration to maintain the key capabilities needed to pull off each of our functional strategies that had shared OKRs.

Before using shared OKRs, we would rely on another team to set up a meeting. With shared objectives and KRs that hold more than one team accountable and responsible to achieve results, this meant that both teams had an incentive and shared purpose to drive towards.

Written by

Head of Product @ Littlepay | Writing memos on Product, Leadership, Startups, and the Mind | andrewquan.net

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