Why Engineering Leaders Should Weigh Decisions by the Stories They Create
Why Engineering Leaders Should Weigh Decisions by the Stories They Create

Rethinking Decision-Making: The Power of Story in Engineering Leadership
As engineering leaders, we’re taught to scrutinize every decision through the lens of risk, cost, and timeline. Those numbers, those projections—they’re the guardrails of every technical plan I’ve ever built. But if I’m honest, there’s a powerful dimension that often gets left behind. And after enough late nights and tough calls, I’ve come to see it as every bit as important as the spreadsheets.
That missing lens is story. More specifically, engineering leadership decision storytelling. Amjad Masad, CEO of Replit, summed it up with a line that’s stuck with me: “When I hit a fork in the road, I choose the one that will make the better story.” At first, it might sound poetic—maybe even naive next to the cold comfort of data. But I’ve lived through moments where the narrative we crafted through our choices changed outcomes, lifted morale, and shaped culture in ways no metric could capture.
I lean on a mental model here: ‘narrative capital.’ Teams build up a bank of shared stories—assets that guide behavior and define what’s possible. When we consciously create and share these stories, we’re not just hopping from project to project. We’re accumulating narrative capital we can draw on during pivotal moments or rough transitions.
Don’t get me wrong—traditional frameworks are non-negotiable. They keep us from flying blind or betting the farm on a hunch. But think back on your own experience. The stories your team retells at kickoffs or retros? They rarely come from playing it safe. They’re born from times when you stretched further than was comfortable or prudent. Let’s look at why—and how—story deserves a real place at your decision-making table.
Treating Story as Real ROI
If you’re anything like most engineering leaders I know (I’ve definitely been there), narrative can feel like an afterthought—a bit of polish added after the real work is done. Yet the most effective teams treat story not as “fluff,” but as leverage. When two options are neck-and-neck on paper, I ask myself: which path leaves us with a story worth telling if it works?
A compelling story builds trust inside and outside your org. It shows your team is willing to take thoughtful risks—to aspire beyond checklists. This narrative becomes a magnet when you’re hiring; talented people want to work with teams known for courage and innovation. And let’s be honest: ideas stick when they’re woven into a story—far more than when they’re buried in another slide deck.
Take Atlassian’s origin story—launching Jira as a side project while still supporting paying customers. That scrappy spirit became foundational to their brand. It’s still referenced in recruiting and onboarding today. It’s proof that intentional storytelling can support business goals for years.
Internal PR isn’t just about numbers; it’s about giving people something to believe in. The legend of “the project where we took a swing” will outlast any quarterly win. Especially during uncertainty or big transitions, stories become anchors—a way to remind ourselves (and our teams) why bold moves matter.
Storytelling might feel out of place in a data-driven world. But research shows storytelling isn’t just a communication tool—it’s a critical leadership asset. It boosts collaboration, ignites creativity, and cultivates empathy across teams—the kind of qualities that drive impact beyond raw metrics.
For more on how leaders use story to inspire clarity and buy-in, explore the power of storytelling in leadership.
Stretching Beyond the Checklist: Choosing Growth Over Safety
Let’s slow down here for a moment. Engineering leadership isn’t just about minimizing risk; it’s about maximizing growth. I’ve shipped my fair share of releases that checked every box—another ticket closed, another deadline met. But those moments? They don’t galvanize a team or redefine what we think is possible.
The decisions that get remembered—the ones that live on as stories—are the ones that stretch us. They demand courage and creativity, especially when success isn’t guaranteed. These moments become defining stories—told at all-hands meetings or during recruiting long after technical details fade from memory.
Teams don’t rally around “safest choice wins.” Morale surges when people see themselves as part of something bigger—a group willing to stretch, innovate, and sometimes defy expectations. This isn’t about being reckless; it’s about deliberately choosing growth when the opportunity calls.
I’ve found the ‘comfort zone vs. growth zone’ framework helps teams visualize these choices: staying in the comfort zone keeps things safe but caps learning; stepping into the growth zone—though uncertain—yields stories that spark development and cultural change.
Satya Nadella distilled Microsoft’s culture shift into three words: “empathy, empowerment, and innovation.” That story changed everything for them.
Microsoft’s transformation under his leadership shows how embracing a growth-centered narrative can reshape outcomes—and collective purpose—for an entire organization.
Here’s where you often see the divide: Senior engineers set themselves apart by seeing how each decision fits into a broader narrative—not just knocking out what’s next on the list (Amjad Masad on taste and leadership). This systems-thinking mindset is what separates true leaders from checklist followers.
Leaders are architects of culture—there’s no shortcut around it. Their actions and attitudes set the tone for company values and beliefs. A leader’s influence can accelerate or stall culture change, as shown in these successful organizational culture change case studies. When you use story-driven approaches to frame decisions, you clarify what matters—and inspire others to follow suit.
For engineers interested in unlocking their own communication advantage, storytelling: the engineer’s hidden superpower offers practical examples and insights.
Crafting a Resilient Narrative: Learning from Bold Misses
Here’s something I’ve had to learn firsthand: not every bold move pays off right away—or at all. Some of your most valuable stories will be born from misses, if you approach them with honesty and reflection.
Adopting a ‘failure postmortem’ mindset—one that focuses on extracting lessons and reinforcing values—can turn setbacks into real institutional learning. This doesn’t just normalize intelligent risk-taking; it helps build a culture where psychological safety fuels innovation.
In my experience, teams grow more from well-intentioned failures than from routine wins. When leaders own the story—sharing not just what went wrong but what was learned—they create psychological safety and nurture a growth mindset. A transparent postmortem isn’t just damage control; it reinforces values like resilience, curiosity, and adaptability.
Culture gets shaped in these moments more than any other. A story of bold effort followed by thoughtful reflection becomes a touchstone for future decisions—a reminder that trying matters as much as succeeding. Over time, this makes teams less afraid to reach higher, knowing even setbacks have lasting value.
I won’t sugarcoat it: you’ll feel resistance here. Owning misses publicly is uncomfortable—I still feel that pinch every time I do it. But modeling this kind of vulnerability is one of the most powerful ways to build trust and foster learning across your organization.
If you’re looking for actionable ways to help teams rebound after setbacks, see 4 ways engineering leaders rally teams after a project fails.
Making Story the Tiebreaker: When Logic Isn’t Enough
Sometimes logic reaches its limit—when risk and reward are balanced, or data alone doesn’t move people forward. In those moments, story becomes more than nice-to-have; it often breaks the deadlock and gets teams unstuck.
Numbers bring rigor but rarely spark action on their own. What tips the scale is a well-framed “why”—a narrative that connects your choice to purpose. When teams are hesitant or divided, sharing the potential story (“Imagine if we could say we were the first to…”) transforms doubt into energy.
Story gives decisions emotional weight. It turns risky bets into rallying points. When people believe they’re part of something worth talking about—a story they’ll be proud to retell—they commit with genuine enthusiasm.
One practical tool I’ve used is borrowing from the ‘Hero’s Journey’ when framing decisions: define the challenge, highlight your team’s quest, anticipate obstacles, and articulate what transformation is at stake. It brings abstract choices down to earth for everyone involved.
A study of over 700 international executives found that 60% identified poor problem formulation as one of the top two barriers to effective problem-solving. That underscores why story-centric decision-making matters: stories help leaders reframe problems so they inspire action—not just analysis paralysis.
Putting It Into Practice: Your Move as an Engineering Leader
So how do you put this into practice? Here are some steps I’ve seen make a difference:
- Make story part of your evaluation criteria
When weighing options with your team, ask explicitly: “If both succeed, which path gives us the better story?” Give this question real weight alongside risk and ROI—it deserves its own seat at the table. - Encourage courageous proposals
Foster an environment where team members feel empowered to pitch bold ideas—especially those that stretch skills or redefine norms. Remind them that memorable stories rarely start with “we did what everyone expected.” - Debrief with narrative in mind
After major projects—wins or losses—reflect not just on technical outcomes but on the story you’ll tell next. What did you learn? What values were demonstrated? How will this experience shape your team’s culture? - Share pivotal stories openly
Don’t wait for annual reviews or company all-hands to surface defining stories. Make storytelling a regular habit—in retrospectives, onboarding sessions, even Slack threads. The more you share these narratives, the more your team will internalize their importance. - Model vulnerability and honesty
When sharing stories of bold bets that didn’t pan out, go first—be transparent yourself. Frame setbacks as opportunities for growth rather than failures to hide away.
Additionally, I recommend keeping a running ‘story log’—a simple document where key moments, risks taken, and lessons learned get captured in real time. Over time, this log becomes a rich resource for onboarding newcomers, coaching future leaders, and celebrating progress as a team.
To see how leaders can transform everyday routines into meaningful rituals for alignment and engagement, check out transform standup meetings: engage and align your team.
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Conclusion: The Right Story Turns a Risky Bet Into a Rallying Point
Let me bring this home. In engineering leadership, decision-making will always involve balancing risk, cost, and timelines—I wouldn’t have it any other way. But if you want your plans to do more than survive scrutiny—if you want them to inspire belief, attract talent, and build lasting culture—you need to ask one more question: What story will this choice allow us to tell?
The right story doesn’t replace sound planning; it amplifies it. It transforms ordinary choices into defining moments—and binds teams through shared meaning and pride. As you face your next fork in the road, remember: sometimes, the bolder path isn’t just riskier—it’s also the one you’ll be proudest to retell at your next kickoff or all-hands meeting.
Ultimately, your choices as a leader shape more than project outcomes—they become part of your organization’s living story. As you navigate future crossroads, remember every decision is an opportunity to inspire belief and create meaning for those around you.
I’ve wrestled with these questions myself—and seen how much power there is in choosing not just what’s safest or fastest, but what will be most meaningful down the line.
Don’t just manage for today—lead so your team will be proud to remember and retell.
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