I recently had the pleasure of grappling with the complex challenge of crafting a critical strategy for my team. It was a genuinely engaging experience to understand how to pull on the right levers within large people systems, clarifying what strategy is truly all about for me. This article outlines the practical tools and approaches I rely on, focusing specifically on software delivery, or tactical strategy, which ideally cascades from a larger organizational or group strategy. I've taken some liberties, breaking from conventional wisdom by defining strategy not as answering the "why," but as establishing "a way of being" – an approach far more valuable for fostering true alignment and channeling high-performing individuals' energy in a world of high ambiguity and high complexity. In essence, my recipe provides a robust framework for action that empowers autonomy while ensuring every effort drives measurable value for software teams.
Strategy: The Strategic Choice Cascade
A recent and valuable addition to my strategy toolkit is the Strategic Choice Cascade, a framework popularized by A.G. Lafley and Roger L. Martin in their book "Playing to Win" (you can read my review of it here: A Book Review: Why Strategy is Important for Devs).
This is how I've taken to constructing my Choice Cascade: It involves genuinely listening and synthesizing insights from leaders and engineers into a coherent vision. I leverage frameworks like the Strategic Choice Cascade not as prescriptive exercises, but as structured approaches to incorporate diverse perspectives. This demands significant effort and a willingness to truly allow others' insights to shape my understanding of the problem and desired outcomes. By carefully gathering their key phrases and ideas, and thoughtfully mapping them into components like winning aspirations, where to play, how to win, unique capabilities, and those needing development, I ensure the strategy reflects our collective intelligence. While my intuition guides the overarching direction, the nuanced "how" emerges from deep engagement with a diverse team.
Values: Social Contracts
Well-understood values underpin any robust strategy. More than static platitudes, they are dynamic social contracts governing individual conduct. We often underestimate their contextual nature.
Consider "respect," for instance. An exceptional engineer, interpreting it as "Respect Leaders," constantly deferred to me, inadvertently undermining a new tech lead. We clarified that not seeking my direct approval wasn't disrespect, freeing her to collaborate with the new lead. This highlights why precise value definition is critical.
Similarly, in large, regulated companies, achieving goals might demand engineers adopt a higher-risk approach than previously accustomed. This requires explicitly establishing new social contracts and a values system to give them the 'go-ahead' for this shift.
It's just as important to declare what values are not as it is to state what they are. For instance, "be bold" does not automatically translate to "be cowboys," nor does "accountability" translate to "heads must roll" when something goes wrong.
Understanding the difference between espoused values (what we say we believe) and enacted values (how we actually behave) is critical. The entire company, especially its leaders, must practice what we preach. I distinctly recall an incident where a junior engineer deleted a huge amount of customers from our DB, after I insisted that he be given broader access to a production DB to get what he needed done in accordance with our values. I will never forget the words of the CEO on the call that morning: "Gio, we can't penalize the guy for trying." Both the CEO and I went to great extent to enact our company value despite the risk which in this case while recoverable was significant. Instead of ostracizing him, we re-examined our 'be bold' value and implemented checks and balances to help anyone, including a junior, make better decisions in enacting their boldness.
Goals: Signals
Finally, there are the highly measurable goals, with OKRs as my preferred tool for this. These are not just targets, but critical feedback loops. They indicate whether your strategy is hitting the mark and, crucially, how well your emergent strategy and defined value system are supporting desired outcomes. While these metrics provide the quantitative truth, understanding the full picture often requires qualitative insights into team behavior and operational flow. For me, conversations and surveys are my go-to methods here, allowing me to keep a finger on the pulse. Falling short of measures should never translate simply to failure. Instead, it should inform which components of your value system or strategic framework need to be re-examined, reframed, or adjusted. These measures are the objective lens through which the "living" nature of your strategy and values is truly tested and refined.
Conclusion: Planning is Important, The Plan Isn't
This dynamic interplay – a constantly flowing process where different parts of the business contribute to a living strategy, a value system drives the right behavior, and a robust OKR system signals when and how things need to change – allows us to continuously refine our path to success.
To start, don't try to get it perfect the first time around and be prepared to get it wrong. No body would let me get past 1st setences of my 1st, 2nd and 3rd attempt at a choice cascade. A good approach is to try gather 3-4 key perspectives that reflect wide groups. Trust your gut as you organize these insights into a Choice Cascade, a clear value system, and measurable goals. Present this initial draft to your stakeholders and closely monitor where you get allergic reactions and endorsements for the first round of iteration. Gradually, rinse and repeat this process as you socialize the strategy among the larger group.
Your strategy is always emerging because our environment is always changing. "Planning is important, the plan isn't." This encapsulates the core truth: the real value lies not in a static document, but in the ongoing, adaptive process of strategic alignment that empowers your high-performing teams.