Embracing Digital Transformation

Episode #312: Leading Through Uncertainty — How Digital Transformation, AI, and Fit Organizations Drive Innovation

Host: Dr. Darren Pulsipher
Guest: Jeff McQueen, CEO of Accelo
Date: December 11, 2025

Episode Overview

In this episode, Dr. Darren Pulsipher sits down with Jeff McQueen, serial entrepreneur and CEO of Accelo, to unpack how leaders and organizations can effectively navigate the current era of pervasive uncertainty. They explore the intersection of people, process, and technology, emphasizing how digital transformation, AI, and organizational “fitness” are pivotal to thriving in disruption. The conversation ranges from strategies to handle uncertainty, organizational restructuring, leveraging AI, and the enduring elements of business that leaders should anchor to amid change.

Key Discussion Points & Insights

1. The Entrepreneur’s Mindset: Thriving in Uncertainty

• Risk vs. Uncertainty: Jeff challenges the stereotype of entrepreneurs as “daredevils” (00:00–01:30), noting:

  “The deeper truth is entrepreneurs are individuals who are comfortable with uncertainty, and most of us as people are not comfortable with uncertainty.” — Jeff McQueen (06:24)

• Adapting to Uncertainty: The conversation centers on how adaptability, not just risk tolerance, distinguishes effective leaders and organizations. Entrepreneurs rely on skills, experience, and inventiveness when the future can't be predicted (06:24–07:44).

2. Organizational Paralysis and the Need for Offense

• Corporate 'Freeze': Both speakers note large corporations’ tendency to “freeze” in the face of uncertainty, adopting defensive postures rather than progressing with confidence (03:02–03:32).
• Offense with Confidence: Being proactive is good, but wild, fear-driven offense fails; true progress requires offensive strategies rooted in grounded confidence and openness to change:

  “If you are on offense because you've centered yourself and you've got a plan, and you're also constantly prepared to live in the uncertainty… you're in a much better position.” — Jeff McQueen (08:00)

3. The Scale of Today’s Digital Disruption

• AI vs. The Internet: The new wave of technology, especially AI, is likened to the internet boom, but with even greater, more unpredictable impact.

  “This transition for sort of universal intelligence is like nothing any of us have ever thought of before.” — Jeff McQueen (09:55)

• The psychological adjustment is profound; the mental framework for understanding AI's implications is still developing (09:55–11:10).

4. From Pontificating to Action: Advice for Startups & Enterprises

• Let Go of Old Limitations: Leaders must shed outdated constraints, as technology now enables far greater speed and efficiency with leaner teams (11:31–13:52).
• Organizational Fitness Metaphor:
  • Losing Weight vs. Building Strength: Laying off employees isn’t enough; organizations must invest in reskilling, upskilling, and building cohesion.
  • “Fitness” is ongoing — not a one-time transformation (13:52–21:01).
• Special Forces Teams: Drawing on military analogies, Jeff recommends creating empowered “special forces” units within organizations to drive internal disruption and spearhead innovation (15:01–18:40).

  “You want that special forces play, but then you actually need to be able to protect them and allow them to do things that are uncomfortable.” — Jeff McQueen (15:01)

• The Good Bank/Bad Bank Model: Sometimes, isolating future-focused teams from legacy operations prevents innovation from being stifled by old processes or cultures (17:06–18:40).

5. People: Self-Selection and Passion

• Not everyone is suited (or desires) to join these high-intensity teams. Organizations should foster self-selection and assign roles based on passion, accountability, and willingness to embrace risk (18:40–19:39).

  “It's about the passion.” — Jeff McQueen (19:39)

• Equity, Not Equality: Recognize variations in skill, engagement, and appetite for change within the workforce (19:00–19:39).

6. Continuous Process and Culture Evolution

• Beyond Structure: Streamlining isn’t just about reducing headcount but eliminating unnecessary processes that impede speed and innovation (20:50–21:01).
• Building Routine Fitness: Ongoing training and cultural change are needed; crash “diets” (massive, one-off reorgs) are less effective than incremental, sustainable improvements (21:01–21:07).

7. Staying Focused on the Unchanging

• Leaders must periodically identify and anchor to aspects of their business that are unlikely to change — customer needs, core purpose, and fundamental value propositions — despite the evolving tech landscape (22:36–24:53).

  “Bezos said… people are going to like to have more selection. They're going to like stuff cheaper and they're going to like it faster. Those three things seem pretty universally like, that's not going to change.” — Jeff McQueen (23:15)

8. Human Intuition in the Age of AI

• The Limits of AI Decision-Making: AI can augment human judgment but cannot replace the intuitive, gut-driven decisions that characterize great leaders (24:53–25:56).

  “AI will never be able to run a whole business because AI doesn't have that intuition, that gut feeling.” — Dr. Darren Pulsipher (24:53)

• AI as a Thought Partner:
  • Both men attest to AI accelerating brainstorming and decision-making—providing diverse perspectives at unprecedented speed (25:56–27:46).
  • AI prompts richer conversations and can help uncover contrarian viewpoints, but ultimate responsibility and judgment lie with humans (27:46–28:25).

9. Diversity of Thought & AI’s Team Role

• AI for Team Creativity: With careful prompting, AI can bring in new angles and challenge groupthink without the complexities of hiring additional people.
  • Still, AI’s integration into team practice poses challenges regarding context sharing and relationship building (28:25–30:33).
• AI Enhancing Human Connection: Contrary to fears, GenAI may actually deepen human-to-human interaction by helping individuals express and refine their ideas before team discussions (30:33–31:15).

Notable Quotes & Memorable Moments

• On Uncertainty & Offense:

  “I think what these current times are really providing a massive opportunity for is a lot more entrepreneurship… we really need to change our attitude from being defensive to more offensive.”
  — Jeff McQueen (06:24)

• On Organizational Fitness:

  “…the defining characteristic of success, whether you're a startup or a big company in the transition we're going through, is actually mostly going to come down to your performance and your fitness.”
  — Jeff McQueen (13:31)

• On Special Forces Teams:

  “You want that special forces play, but then you actually need to be able to protect them and allow them to do things that are uncomfortable.”
  — Jeff McQueen (15:01)

• On What Won’t Change:

  “People are going to like to have more selection. They're going to like stuff cheaper and they're going to like it faster. Those three things seem pretty universally like, that's not going to change…”
  — Jeff McQueen (23:15)

• On Human Judgment vs. AI:

  “AI will never be able to run a whole business because AI doesn't have that intuition, that gut feeling.”
  — Dr. Darren Pulsipher (24:53)

• On AI as co-founder:

  “I found to be incredibly valuable, building my latest company, being able to use AI as a thought partner… managed to do more in 90 minutes than I would have done pre-AI in a whole week.”
  — Jeff McQueen (25:56)

Timestamps for Key Segments

• Entrepreneurial Mindset & Comfort with Uncertainty: 00:00–06:24
• Big Companies & Defensive Posture: 03:02–03:32
• Proactive vs. Fear-driven Offense: 07:44–09:11
• Scope of Today’s Disruption (AI vs. Internet): 09:17–11:10
• Tactical Steps for Startups: 11:31–13:52
• Organizational Fitness & Special Teams: 13:52–18:40
• People, Passion & Self-selection: 18:40–19:39
• Continuous Fitness & Process Evolution: 20:36–21:07
• Anchoring to the Unchanging: 22:36–24:53
• Intuition, Judgment & AI’s Limits: 24:53–25:56
• Experiences Using AI as a Thought Partner: 25:56–27:46
• AI’s Role in Team Dynamics: 28:25–30:33
• AI Deepening Human-to-Human Connection: 30:33–31:15

Resources & Contact

• Jeff McQueen: TeamScore.io | LinkedIn
• Team Score: Free and paid tiers; designed to provide managers with insight into distributed team productivity without invasive surveillance (31:25–32:20)

This detailed summary captures the rich insights, practical advice, and engaging dialogue of this episode, making it accessible to those who didn’t catch the full episode. The conversation balances optimism about new technology with pragmatic strategies for building resilient, innovative teams equipped to lead through uncertainty.