Episode 13 — Leading Through Change and Uncertainty | The Prospecting Show with Dr Connor Robertson
Change isn’t the enemy of leadership; it’s the proof of it.
That’s how Dr Connor Robertson opens Episode 13 — Leading Through Change and Uncertainty.
After covering topics like systems, metrics, performance, and retention in prior episodes, this one shifts the focus to the intangible but essential trait every great leader must master: adaptability.
Dr Connor begins by acknowledging the reality many founders and managers avoid: stability is temporary. Markets shift, technology evolves, and people move on. The leaders who survive and, more importantly, grow are those who can make decisions amid ambiguity. “Uncertainty doesn’t destroy momentum,” he says. “Inaction does.”
The Psychology of Change
Before diving into frameworks, Dr Connor unpacks the psychology of change. Humans resist it not because they dislike new things, but because they fear losing control. Drawing from behavioral science research by Harvard Business Review and McKinsey & Company, he explains that the brain perceives uncertainty as a threat rather than an opportunity.
“Your team doesn’t need guarantees,” he says. “They need guidance.”
He shares a story from one of his businesses that faced a rapid pivot during market turbulence. Revenue dropped, and the instinct was to tighten control. Instead, he increased transparency through daily updates, open Slack channels, and clear metrics. The effect was counterintuitive: morale improved, not declined. People felt seen, not scared.
The takeaway: in times of uncertainty, information becomes reassurance.
The Framework: The C.A.L.M. Leadership Model
Dr Connor introduces the C.A.L.M. Model, his blueprint for leading through change.
- C — Clarity:
Ambiguity breeds anxiety. The first step is stating the truth clearly. Even bad news lands softer when it’s honest. Dr Connor encourages leaders to “communicate early, even when you don’t have all the answers.” He references Forbes Leadership research showing transparency boosts trust by 33%. - A — Alignment:
After clarity comes collective direction. Align decisions with the organization’s core values and mission. If strategy changes, explain how it supports the bigger “why.” Alignment keeps teams moving together even when the map changes. - L — Listening:
In uncertain times, feedback becomes a lifeline. Leaders must over-listen. Dr Connor encourages structured listening surveys, town halls, and one-on-ones to capture ground truth. “People who feel heard can handle almost anything,” he says. - M — Momentum:
Finally, small wins sustain morale. Keep projects moving, celebrate progress, and create visible forward motion. Momentum transforms fear into focus.
Together, these four elements form an operating system for steady leadership amid chaos.
Adaptive Decision-Making
Dr Connor then explores how to make decisions when data is incomplete. “In stable times, analysis leads action. In volatile times, action leads analysis.” He shares a story of a client company that postponed key decisions waiting for perfect data, losing both speed and opportunity.
His method: Decide small, decide fast, decide again. Break decisions into reversible micro-steps. This creates feedback loops that allow agility without recklessness.
He connects this principle to Episode 11 — Metrics That Matter, where continuous review cycles were discussed. “Data should shorten uncertainty, not stall it,” he reminds listeners.
Communication as the Anchor
Communication becomes the anchor in uncertain seasons. Dr Connor outlines three communication rules that protect trust when change feels overwhelming:
- Frequency beats perfection. Regular updates matter more than flawless ones.
- Context equals comfort. Always explain the “why” behind a decision.
- Consistency creates confidence. Deliver messages in predictable rhythms weekly, monthly, and quarterly.
He recalls instituting a “Monday Map” email during a major pivot every Monday, where leadership summarized priorities, challenges, and wins. It took 10 minutes to read, but it created immense clarity.
He references Gallup Workplace Studies proving that consistent communication improves engagement by 23% during organizational change.
The Emotional Equation of Leadership
“Your team’s anxiety mirrors your energy,” Dr Connor explains. Leaders must manage their own emotional state before managing others’. He uses an analogy: “You’re the thermostat, not the thermometer.”
He encourages journaling, coaching, or reflection time to process fear privately. Teams deserve a composed leader. “Stability,” he says, “isn’t pretending you’re fearless, it’s showing you can function through fear.”
Reframing Uncertainty as Innovation
Dr Connor reframes uncertainty as the birthplace of creativity. Many innovations from Airbnb’s early pivot to Apple’s product evolution emerged from constraint. He urges entrepreneurs to ask, “What opportunity is hiding inside this problem?”
He references HBR’s innovation-in-crisis studies, which show that companies maintaining R&D and creative investment during downturns outperform competitors long-term. “Don’t cut creativity when you need it most,” he warns.
Building Team Resilience
Resilience, Dr Connor notes, is not toughness; it’s elasticity. Teams bounce back faster when they understand that struggle is temporary and shared. He describes how to operationalize resilience through rituals:
- Weekly Reset Meetings to recap learnings from setbacks.
- Fail Forward Forums, where mistakes are discussed without blame.
- Recognition Moments highlighting adaptive behavior.
He emphasizes psychological safety again, referencing Episode 12 — Building a Performance Culture That Lasts. Resilient teams talk openly about what’s not working.
Leading Clients and Stakeholders
Dr Connor reminds listeners that uncertainty isn’t just internal; clients and partners feel it too. Leadership extends outward. He recommends transparent client communication: acknowledge challenges, reaffirm commitments, and outline solutions. This turns uncertainty into differentiation while competitors hide, communicators rise.
He shares a story where one of his portfolio companies called every client during an industry downturn to proactively discuss contingency plans. Not one client left. “Certainty of care,” he says, “outweighs certainty of outcome.”
Practical Tools for Navigating Change
To give listeners tactical grounding, Dr Connor lists his top five tools for steering teams through uncertainty:
- Change Maps: Visual summaries of what’s changing, why, and when.
- Risk Registers: Track threats and assign ownership.
- Scenario Planning: Build three models: best case, base case, worst case.
- Feedback Loops: Schedule listening checkpoints every 30 days.
- Narrative Documents: Update and share “The Story So Far” to reinforce progress.
He emphasizes that leaders are storytellers during transformation. People follow the story more than the spreadsheet.
Case Study: Transformation in Real Time
To illustrate, Dr Connor shares a case where a healthcare technology company he advised needed to pivot from B2C to B2B mid-year. The CEO applied the C.A.L.M. Model, aligning the team around a new mission, running weekly stand-ups, and celebrating small client wins. Within six months, morale rebounded and revenue returned to pre-pivot levels.
“Change doesn’t kill companies,” Dr Connor says. “Lack of clarity does.”
The Long Game
As the episode winds down, he emphasizes that great leadership is measured not by calm seas but by storms survived. The test of culture is continuity. Can your people maintain standards under stress?
He urges leaders to revisit their mission quarterly, document lessons learned, and keep leading even when unsure. “Courage,” he concludes, “isn’t certainty, it’s consistency.”