EP 274 - Growing Managers: From “Best Boss” Moments to Self-Awareness Breakthroughs - Freedom by Design, Pt 12 with Michael Walsh

Meet the guest. Michael Walsh is a Vancouver-based business strategist, author of Business Growth by Design, and founder of Walsh Business Growth Institute, the international consultancy he’s run since 1995 to help owners scale sustainably and earn the “freedom dividend” they started their companies for.  

In Part 12 of our ongoing Freedom by Design series, Michael brings a deceptively simple napkin scribble: 

“Grow Managers – Best Boss / Worst Boss. Do bad bosses know they’re bad?” 

Those three lines crack open one of the biggest constraints to growth: the gulf between technical excellence and people leadership. As Michael tells me: 

“The truth is that being a middle manager is probably the toughest job in any company.” 

“The skills it takes to deliver a result are very different from the skills it takes to support somebody else to generate the result.” 

Why “Best Boss / Worst Boss” is More Than a Fun Ice-Breaker 

When Michael runs this exercise with leadership teams, he first asks everyone to list the best boss they’ve ever had and what made that person great. Patterns emerge fast: clear communication, mentorship, celebrating wins, “walking the talk,” and structuring roles for success. 

Then he flips it: list the worst boss and why. Out pour traits like micromanagement, credit-stealing, indecision, and absenteeism. The power is in the contrast. Leaders suddenly see that greatness isn’t mysterious—nor is mediocrity accidental. 

But the kicker is Michael’s final question: “Do bad bosses know they’re bad?” Most don’t. Self-awareness—bolstered by data, feedback loops, and intentional development—is the lever that turns average managers into growth multipliers. 

The Hidden Cost of Un-Trained Managers 

Promoting a rock-star individual contributor without equipping them to lead is like handing a talented chef a chainsaw and saying, “Now go build the restaurant.” Skill transfer fails, engagement drops, and A-players walk. Michael argues that 21st-century growth depends on deliberately growing managers who can translate talent into performance: 

“Your deliverable as a manager is the expertise of your people.” 

That means shifting from “command and control” to coaching, designing feedback systems that surface truth quickly, and rewarding leaders who create more leaders—not just more output. 

5 Key Takeaways & Action Steps (no tables, just straight talk) 

1. Manager is a distinct profession, not a reward. Take Action: Before promoting, map the new role’s core leadership competencies and assess candidates against them—don’t rely on technical prowess alone. 

2. Self-awareness is the first management skill. Take Action: Implement 360-degree feedback for every manager, paired with coaching to interpret and act on the data. 

3. Celebrate “best boss” behaviors publicly. Take Action: At monthly all-hands, spotlight one manager story that exemplifies clarity, mentorship, or walking the talk. Make it contagious. 

4. Diagnose “worst boss” traits early. Take Action: Use stay-interviews (not exit-interviews) to surface micromanagement, lack of recognition, or indecision—then coach or course-correct quickly. 

5. Grow managers to grow the business. Take Action: Carve out 10 percent of every manager’s workload for leadership development—courses, peer groups, or coaching—so growth is baked into the job, not bolted on. 

 

Your Turn: Write It on a Napkin 

Who was your best boss? What’s one behavior you can model today? Grab a napkin, jot it down, snap a pic, and post with #PaperNapkinWisdom. Let’s crowd-source a playbook for growing managers everywhere. 

(Connect with Michael at walshbusinessgrowth.com and let him know your biggest insight from Part 12 of the series.)