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The Art of the Turnaround
By Teasha Cable
Most executives think of restructuring as a spreadsheet problem: cut costs, protect margin, survive the quarter.
Most executives think of restructuring as a spreadsheet problem: cut costs, protect margin, survive the quarter.
Derrek Lennox, senior vice president of corporate development and CFO at DougallMedia, spent nearly two decades teaching a very different version of that story to MBA students at Schulich School of Business - York University.
On a recent episode of the Dynamic Decisions Podcast, he laid out a framework that treats restructuring as equal parts financial engineering, organizational psychology, and strategic honesty, and explained why some of the best turnarounds never involve a single layoff.
Derrek's day job puts him in an unusual position. He is the CFO of a legacy broadcast media company navigating digital transformation, a managing partner at his own consulting practice, and an advisor on Indigenous economic development projects across Canada.
Three very different worlds, but as he told host me, the same diagnostic questions apply to all of them.
Three Types of Broken, Not One
The first thing Derrek looks for when he walks into a struggling organization is which of three things is actually failing:
- Finances
- Operations
- Strategy
Most people jump straight to the financial statements, he said, because that is the visible symptom.
But a company can have a clean balance sheet and a broken strategy, or healthy revenue and a workflow that quietly bleeds margin every day. Diagnosing the wrong problem means fixing the wrong thing, no matter how good the spreadsheet work is.
At Dougall Media, that framework shows up in how Derrek thinks about the shrinking broadcast business. Rather than treating the decline as a restructuring problem to be managed down, he treats it as one part of a larger system that also includes growth.
If one area is shrinking, can the organization redirect its energy somewhere else? That is the question he asks, aiming the urgency of a declining segment toward digital growth rather than only defending what is disappearing.
The First Answer Is Never the Real Answer
Derrek's operating method, honed over 17 years of teaching restructuring, comes down to two moves repeated on a loop: ask questions, and do the math. The math part is intuitive. The questions part is where most people stop too early.
Financial statements rarely tell the whole story, especially in organizations that have not kept clean books. A bad account on paper might actually be a client relationship built on years of trust that a spreadsheet cannot capture. A discount that looks like a leak might be the only reason a key vendor still answers the phone.
Derrek's rule is that the first set of answers is never enough, whether people are withholding information on purpose or simply do not know what is buried in their own numbers. Getting to the truth requires going back, again and again, until the math and the story behind it actually line up.
Can Everyone Stay in the Room?
The most striking part of the conversation was how Derrek applies lessons from Indigenous economic development work to conventional corporate restructuring. In First Nation-owned organizations, keeping the community employed is often a non-negotiable starting condition, not a nice-to-have.
Derrek has started carrying that same question into private and semi-private restructuring engagements: can we fix this with everyone still here at the end of the day?
He described one arena complex owned by a First Nation community that was losing roughly half a million dollars a year. The instinct going in, from ownership and staff alike, was that layoffs were inevitable. Instead, Derrek's team found the losses came from mismanagement and a lack of sales motivation, not from having too many people on staff.
Through an employee engagement process built around opportunity rather than the threat of job loss, the organization turned that half-million-dollar loss into a million-dollar profit within a year, without cutting a single position.
Decisions Are a Process, Not a Moment
He also shared how he structures his own decision-making, a system built on a mix of monthly, weekly, and daily checkpoints. Monthly, he checks whether current work is on track to produce results by month's end.
Weekly, he plans across four lanes: personal, corporate, team, and client priorities, a habit borrowed from the Franklin Covey "first things first" method he adopted more than three decades ago. Daily, he reviews the night before what needs to happen the next morning.
Underlying all of it is a definition of decision-making that treats a decision as an ongoing process rather than a single event.
Making the call is the easy part, Derrek argued. The harder discipline is deciding how to hold that decision in place once new information, resistance, or fatigue starts pulling at it, and knowing when the evidence has genuinely shifted enough to justify changing course.
My Learnings
Whether the business is a shrinking broadcast network, a mismanaged arena, or a mid-sized manufacturer, Derrek's approach keeps returning to the same idea:
The numbers are a starting point, not the whole diagnosis, and the people in the room are often the fastest path to a real fix.
Before assuming a restructuring means cutting your way to health, it is worth asking his question first: can we get there with everyone still here?
Listen to our conversation where ever you get your podcasts.