Essential Readings :

Context

In a world of increasing uncertainty, we face a thorny dilemma: as the stakes of a decision get higher and higher, we crave more and more certainty in order to make our choice. But increasing our level of certainty takes time, and in an increasingly uncertain and fast-paced world time is exactly the resource we don’t have. Clarity thus remains frustratingly out of reach, or else arrives far too late to be useful.

This keynote explores how successful organizations and leaders take action in these circumstances. Often, action precedes certainty, as they move quickly. But what’s more surprising is that these organizations actually use that action to generate the confidence they’re seeking, in a way that “more consulting and analysis” simply can’t. By calibrating decisions to your level of confidence—rather than waiting for certainty—you can create strategic advantages while competitors get bogged down in slower and slower decision-making.

Content

Let's explore six pieces that further illuminate this perspective.

The Hidden Risks of Thinking Through Decisions

Forthcoming in the Globe & Mail, co-authored with Julia Chung

Here we examine the hidden dangers of our quest for certainty in rapidly changing environments. Julia and I argue that excessive consultation and information-gathering often creates an avalanche of conflicting data, making clarity harder to achieve. And the longer we take, the more out-of-date our earlier inputs become. Counterintuitively, the "safe" option of waiting and seeing frequently increases risk, as businesses that hold back during downturns find themselves unprepared when cycles change. This perspective provides a foundation for the keynote's focus on avoiding decision paralysis and identifying the hidden risks in maintaining current trajectories.

🔗Strategy In A VUCA World: The Importance Of Coherence And Clarity

Originally published in Forbes, co-authored with Karl Moore

This article examines how strategy-crafting must evolve to foster agility and clarity amid chaos. We argue that in a volatile, uncertain, complex, and ambiguous (VUCA) world, strategy is less about predicting the future with precision and more about creating a framework that enables coordinated autonomy. We challenge the notion that rapid change makes strategy obsolete, instead proposing that effective strategy processes actually enhance organizational agility. This perspective aligns perfectly with the keynote's emphasis on moving forward despite incomplete information, using frameworks that enable action while maintaining strategic coherence.

🔗When TO Do Strategy

Originally published on Linkedin

This piece tackles the critical question of timing in strategic decision-making. I propose that the right time to do strategy is "when your current path is leading you toward outcomes that are no longer acceptable". I also show how organizations retain control over their "acceptability criteria" even when they can't control all outcomes. The article distinguishes between proactive and reactive approaches to change, noting that leaders who proactively decide the status quo isn't acceptable tend to build bolder, more differentiated strategies. This connects directly to the keynote's discussion of assessing status-quo dangers and the hidden risks in maintaining current trajectories.

🔗Soldiers and Scouts with Julia Galef

Originally appeared on The Decision Lab podcast

In this fascinating conversation, Julia Galef and I explore two cognitive mindsets that influence how we process information and make decisions. The "scout mindset" approaches uncertainty with genuine curiosity and accuracy-motivation, while the "soldier mindset" defends predetermined conclusions. Galef argues that these mindsets fluctuate situationally and are both valuable in different contexts. Her insights on developing "emotional regulation around uncertainty" directly support the keynote's focus on building confidence in un-knowing and transforming uncertainty from paralyzing to energizing.

🔗Screw Up Less When It Matters Most with Olivier Sibony

Originally appeared on The Decision Lab podcast

Olivier and I discuss the systemic biases that affect strategic decision-making at organizational levels. He highlights the paradoxical tendency of organizations to be simultaneously risk-averse with small decisions and surprisingly risk-seeking with large ones, creating an upside-down approach to risk management. His practical advice on building better decision systems through "dialogue, divergence, and dynamics" offers valuable frameworks for the keynote's goal of enabling forward movement with appropriate safeguards. Sibony's emphasis on creating processes that challenge decision-makers provides concrete methods for avoiding the decision paralysis addressed in the keynote.

🔗Mental Models for Business Decisions with Roger Martin

Originally appeared on The Decision Lab podcast

Roger and I explore how executives use mental models to navigate complex decision environments and what happens when these models break down. He advocates for explicit articulation of assumptions and testing criteria, arguing that writing down "what would have to be true" for a decision to succeed creates accountability and learning opportunities. This approach creates what Roger calls "the canary in the coal mine"—early warning signals that monitor when conditions change enough to require adapting our approach. These practical frameworks directly complement the keynote's focus on leveraging decisiveness while maintaining appropriate risk awareness.

Coherence: How It All Comes Together

Looking across these diverse explorations, a consistent thread emerges.

Decision-making amid uncertainty is not about eliminating ambiguity. The object of the exercise is to start using approaches that embrace it productively. Some of those approaches include scenario planning, assumption testing, or cultivating a scout mindset. This body of knowledge all points toward a fundamental shift in how we approach uncertainty. Rather than treating uncertainty as an obstacle to be overcome before action, they position uncertainty as a constant feature to be navigated through action. By building appropriate guardrails, explicit assumptions, and learning-oriented processes, we can move forward with confidence even when certainty remains elusive.

Connection: Personal Growth

My advocacy for this approach isn't merely theoretical. It's deeply personal.

Launching my own business at Converge has been the second-biggest opportunity for learning and personal growth of my lifetime (second only to building a family). In my professional life, nothing has ever come close to the uncertainty and range of potential pathways that I encounter on the daily in running Converge, which is equal parts thrilling and potentially paralyzing. I had previously encountered these ideas, techniques and approaches in writing. I’d even written about them myself. But Converge is what lets me understand what they feel like from the inside.

Two major insights have come out of that. The first is that “uncertainty” seems clear on paper but it isn’t always obvious to recognize it in real life when you’re staring it in the face. The second is that the feeling of “pacing” (how quickly to act, in order to provoke clarity to emerge) is very much a sensibility that gets built through experience. I’ve become a better leader and facilitator as a result, with personal experience helping me to guide others in encountering these realities as well and learning to calibrate their own decisions to their confidence levels.

Carrying Insight Into Action: Next Steps

Is your organization struggling with any of these challenges:

• Endless loops, where you don’t reach a decision before the situation changes again and you feel you need to go back to the beginning
• Missed opportunities, where the most impactful moments for a course of action have passed by the time you get there
• Low team energy, drained by decisions that are constantly reopened for the same debate, and lingering anxiety about the path taken

This keynote provides practical frameworks for calibrating decisions to confidence, enabling confident forward movement even amidst uncertainty. By learning to assess status-quo dangers, manage risk appropriately, and leverage action as a discovery tool, your team can develop competitive advantages that emerge specifically during periods of change and disruption.

If so, this talk can help you take some immediate steps to get change underway or contribute momentum to ongoing initiatives. Contact me to discuss how I can help.

Looking for an even bigger boost? Consider the Extended Session option, which pairs this keynote with an interactive workshop component, offered to help your team apply these frameworks to current strategic decisions, for an immediate boost to your strategic focus as well as your ability to act decisively.