30 Conversations | Conversation #4 | Getting Punched in the Face

Everyone has a plan until they get punched in the face.

Mike Tyson was talking about boxing, but the same might be true of strategy, careers, and life.

This week, I had the privilege of sitting down with Derek Deacon-Rogers, Managing Director, Strategy & Growth, supporting BCV Financial at ATB Financial, as part of my 30 Conversations project—a personal research initiative exploring the intersection of finance, strategy, venture capital, commercial law, innovation, and leadership.

I was particularly excited for this conversation because I’ve always known Derek to be challenging—not difficult, but genuinely willing to question the status quo. He brings a level of realness that is balanced by self-awareness and humility. I wanted to understand how those qualities have shaped his experience in strategy.

A little about Derek

Derek’s career rules are simple:

Go where the problems are. Never solve the same problem twice.

He began his career in PR and communications before moving into entrepreneurship and eventually strategy. Throughout each transition, he was drawn to solving the next problem rather than repeatedly solving the same one.

Early in his career, he felt disconnected from the core of the business and frustrated by the repetition of solving the same problems over and over again. He eventually realized that his experiences across communications, PR, and entrepreneurship had given him something valuable: the ability to see problems from different angles and connect the dots.

Today, as a Managing Director of Strategy & Growth, one of his greatest assets isn’t knowing everything.

It’s knowing which questions to ask.

Three ideas that challenged my thinking

💡 1. How do we add value without adding noise?

I’ve been thinking a lot about thought leadership and personal branding lately. With platforms like LinkedIn making it easier than ever to share ideas, we’re also living in a world where everyone has something to say.

The challenge isn’t simply having a perspective. It’s knowing when and how that perspective adds value.

Derek reframed thought leadership for me. Rather than always trying to be the expert with the answer, there is value in being the person who facilitates the conversation, asks the question that gets everyone thinking, or sparks an idea someone else can build on.

Reflection: Maybe thought leadership isn’t about having the loudest voice. It’s about asking questions that make the room think differently.

💡 2. The answer is often in the question.

Before strategists are analysts, storytellers, or problem-solvers, they are curious.

Strategy isn’t simply collecting data and presenting conclusions. Its real value comes from understanding what the information means, connecting seemingly unrelated dots, and communicating the why behind the numbers.

That requires asking better questions.

Curiosity can sometimes look like overthinking or analysis paralysis, but when channelled well, it becomes a powerful strategic tool.

Reflection: The quality of the answer is often limited by the quality of the question we were willing to ask.

💡 3. Getting punched in the face.

“Everyone has a plan until they get punched in the face.” — Mike Tyson

This might be my favourite lesson from the conversation.

Derek highlighted three common ways strategists can struggle when reality doesn’t cooperate with the plan: cognitive dissonance, inflexibility in the face of opposition, and confirmation bias.

We naturally create plans based on what we believe will happen. Then reality has a funny way of reminding us that it wasn’t consulted.

Like a boxer preparing for a fight, strategists use frameworks, experience, and preparation to develop a game plan. But once they’re in the ring, they have to respond to what is actually happening—not what they expected to happen.

The best boxers and strategists share something important: discipline without rigidity.

Reflection: A good strategy isn’t one that survives unchanged. It’s one that knows how to adapt when reality throws the first punch.

My Biggest Takeaway

One idea stayed with me long after our conversation:

“The punches aren’t interruptions to the strategy. They’re part of how the strategy gets better.”

Pushback, mistakes, failures, and unexpected obstacles give us information. They expose assumptions, reveal blind spots, and force us to adapt.

It changed the way I think about the “messy middle”—that uncomfortable space between where we started and where we’re trying to go, where the plan feels unclear, and nothing seems to be going according to schedule.

Maybe that’s where the real work happens.

The messy middle is where we test our assumptions, develop judgment, build resilience, and learn how to respond when the plan inevitably gets punched in the face.

How I’m applying this

Because of this conversation, I’m going to:

• Find more ways to facilitate conversations and spark new ideas.
• Practice asking better questions before rushing toward answers.
• Pay closer attention to how my experiences shape the lens through which I form perspectives and conclusions.
• Become more comfortable treating unexpected obstacles as information rather than failure.

I’m excited to see how these small changes shape my own career journey.

A Thank You

Thank you, Derek, for your generosity, openness, and willingness to challenge conventional thinking. I truly appreciate your time and the perspective you shared.

Conversations like these remind me how valuable it is to learn from people who are willing to challenge not just what we think, but how we think.

Help Me Reach 30 Conversations

This is Conversation #4 of 30.

My goal is to speak with professionals across:

• M&A & Commercial Law
  • Venture Capital
  • Investment Banking
  • Corporate Development
  • Corporate Strategy
  • Innovation & Entrepreneurship
  • Family Offices
  • Economic Development

If you work in one of these areas—or know someone whose perspective would add to this project—I would love an introduction.

Every conversation is helping me better understand how organizations create value through capital, strategy, governance, and innovation. I hope these reflections provide value to others exploring similar career questions.

Who do you think I should speak with next?

#30Conversations #CareerDevelopment #Leadership #CommercialLaw #MandA #VentureCapital #CorporateStrategy #Finance #Innovation #Mentorship

Four conversations down. Twenty-six more opportunities to learn.