The Speculator’s Edge
Why adaptive leaders speculate, experiment, and seize what others miss.
Forget playing it safe.
The real edge in today’s world isn’t about flawless plans or polished strategies — it’s about daring to test bold hypotheses before the world knows they matter. Adaptive leaders aren’t waiting for perfect data or conditions; they’re stepping into uncertainty, running disciplined experiments, and building the muscle to adapt faster than the competition.
This backlog isn’t managed like a traditional project plan. It’s prioritized for learning, dynamically reshaped by live feedback, and ruthlessly focused on reducing the uncertainty that kills slow-moving competitors.
Ready to stop clinging to control and start leading the way into what’s next? Let’s go!
One thing we keep learning — usually the hard way — is that you can’t plan uncertainty away. Plans work when you’re dealing with what’s known, what you can control. But uncertainty, along with its messy cousins ambiguity and vagueness, doesn’t play by those rules. It defies the very idea of planning.
When I first introduced the Adaptive Life Cycle in Adaptive Software Development (2000), I laid out three phases: Speculate, Collaborate, and Learn (Figure below). I expanded in Agile Project Managemenet (2010). But through it all, one thing stayed constant — Speculate takes center stage.
The Shift: Planning says, “I know what’s coming, and here’s how it’s going to go.” Speculate says, “Here’s my best guess — let’s poke it and see what happens.” That difference matters because in complexity, the plan gets you what you intended — not what you need.
In old-school thinking, deviations from the plan are mistakes to fix. In adaptive thinking, they’re signals — clues pointing to better paths. When we speculate, we lay out a mission as best we can, but we stay humble. We know we’re probably wrong. Sure, “speculate” can sound like wild bets, but its real meaning is just “to form a hypothesis based on incomplete info.” I’ll be honest: some of my early banking clients squirmed when I told them we had a development phase called Speculate. But that discomfort is exactly the point.
Language Shapes Behavior Calling something a “requirement” implies finality; calling it a “story” invites evolution. Calling it a “plan” hardens expectations; calling it a “speculation” signals openness to change. The words we choose ripple through how we work.
Stefan Thomke, in his 2020 book Experimentation Works, and echoed by thinkers like Rita McGrath on discovery-driven planning. Amy Edmondson on psychological safety, hits it even harder:
“Leaders must abandon the illusion that they can predict the outcomes of innovations and focus instead on designing and running disciplined experiments.”
That’s the kicker. We say we want learning, but we organize around control. We need to stop pretending we can plan our way through uncertainty. We need to speculate, hypothesize, experiment — and do it with intent.
Here’s where wish-based planning creeps in. Under tremendous pressure — from markets, competitors, internal ambitions — product managers often shift from realistic assessment to wishful demands. It’s their job to push the envelope, sure, but when “must-have because I say so” replaces grounded planning, things spiral. First, we craft plans that wildly exceed capacity. Teams get pressured to accept, even if they don’t buy in. Then, inevitably, features slip and deadlines crumble. But instead of recognizing the flaw in the plan, leadership frames it as a performance failure. Development loses credibility. And so the next cycle begins: marketing and management ignore the people doing the work, demand even more, and trust erodes across the board.
Another trap? Using aggressive deadlines as a motivational whip. A nine-month project, carefully estimated, gets shaved to six months “to light a fire.” Maybe that works once. But across a portfolio, cooperation disintegrates, teams retreat into silos, and motivation turns toxic. Internally driven commitment matters; externally imposed pressure backfires.
This mismatch between demand and capacity leads to cascading dysfunctions: late-stage feature cuts, rushed testing, fragile code, rework disasters. Worst of all, as I discovered at one large client, when release plans finally collapse under their own weight, the wrong people get rewarded. Teams that quietly signed on to impossible promises are praised for their grit. Teams that raised red flags early get labeled obstructionist. Rewarding the wrong behavior sets the stage for even deeper dysfunction next time around.
That’s why shifting from plan to speculation isn’t cosmetic — it’s cultural surgery.
What Cultural Surgery Looks Like Imagine a leadership team that stops demanding rigid timelines and instead invites teams to surface their hardest truths, even the ugly ones. Or a product group that reshapes its roadmap mid-flight, not as failure, but as learning. Cultural surgery cuts old habits, reshapes trust, and stitches the system back together for resilience.
It’s about breaking cycles of mistrust, rebalancing capacity and demand, and building a system where teams can experiment, learn, and adapt without punishment. It asks leaders to embrace the discomfort of saying, “We’re learning as we go,” and to create the psychological safety their teams need to challenge assumptions and take smart risks.
Here’s the paradox at the heart of adaptive leadership: the more you try to control uncertainty, the more fragile you become. The more you loosen your grip, the stronger and more resilient you get.
So here’s the gut-check: where in your own leadership are you clinging to plans — not because they work, but because they soothe? Speculating isn’t just using better words. It’s rewiring how you handle uncertainty — in your mind, your team, your system. Every time you double down on detailed roadmaps and fixed deliverables, you might be trading away the very adaptability you claim to value. Where do you need to let go, form a bold hypothesis, and pull your team into the messy, exhilarating, slightly terrifying work of real experimentation?
Comfort feels safe. But comfort rarely sparks transformation.
What comfort are you willing to give up tomorrow? What uncomfortable conversation, bold hypothesis, or risky experiment will you dare to launch — not next quarter, but this week?
My AI Assistant Byron (ChatGPT-4o with Canvas) helped with drafts, idea development, editing, and visual images. Perplexity AI assisted with research.