Pivotal Moments in Leadership

What financial role does your growing business actually need?
As a business grows, the financial questions change. A bookkeeper, accountant, controller, and CFO may all work with numbers—but they do very different jobs.
In this conversation on Lead with Possibility, Tana Plewes sits down with Rod Evanenko of Profit Edge Insights to unpack the differences between these financial roles and, more importantly, when a growing business needs each one.
They explore why hiring the wrong financial role can create confusion, why profit may not tell the whole story, and how better financial information can change the way a business owner sees the business itself.
You’ll discover:
• Why bookkeeping is the foundation of reliable financial information• The difference between an accountant, controller, and CFO• Why a CFO is not simply the next level above a controller• Whether a growing CEO needs a CFO or COO first• What financial insight a CFO can bring to major business decisions• What five days can mean for a $5 million business• How to recognize the right financial person for your business• Why profit can sometimes be a misleading number• Rod’s perspective on the design flaw in the cash flow statement• Where Profit Edge Insights fits on the finance-role spectrum• How good financial information can help leaders see their business differently
The bigger question is not simply, Who should I hire?
It’s: What does my business need to see, understand, and act on next?
When the right information reaches the right person at the right time, financial numbers become more than reports. They become a way to understand the business, make better decisions, and see possibilities that may otherwise remain hidden.

Why do so many business loan applications get turned down?
In this conversation, Andrew D. Gregson shares what lenders are really looking for, the common mistakes business owners make, and the simple steps that can improve your chances of getting approved.
From choosing the right lender to preparing your financials, managing cash flow, and building a strong borrowing strategy, this episode is packed with practical advice you can use before you apply for funding.
If you're planning to grow your business or apply for financing, this conversation will help you avoid costly mistakes and approach lenders with confidence.

How much profit are you leaving on the table because of your pricing?
Most business owners focus on increasing sales or cutting costs when profitability starts to decline. But what if the fastest path to higher profits isn't selling more—it's pricing better?
In this episode of Lead with Possibility, Tana Plewes sits down with pricing expert Andrew Gregson to unpack one of the most overlooked drivers of business success: your pricing strategy.
Drawing from decades of business ownership and consulting experience, Andrew explains why pricing is one of the most powerful tools available to entrepreneurs—and why so many businesses still rely on guesswork instead of strategy.
You'll discover:
Why pricing has a greater impact on profitability than most owners realize.
The hidden cost of copying competitors' prices.
Why raising prices isn't always the answer.
How a strong Unique Selling Proposition (USP) creates pricing power.
The Goldilocks Pricing Strategy—finding the price that's not too high and not too low.
Practical examples that challenge conventional thinking about pricing.
If you're a business owner, entrepreneur, consultant, or leader looking to improve profitability without simply working harder, this conversation will help you rethink how you price your products and services.

Most family businesses don’t fail overnight.
They slowly drift into dysfunction through avoided conversations, unclear expectations, unresolved tension, weak systems, and emotional blind spots that quietly build over time.
In this podcast, Tana Plewes breaks down the 10 biggest warning signs that your family business may be at risk — and what leaders can do before small issues become expensive crises.
From poor communication and unresolved family conflict to succession planning, financial transparency, accountability, and resistance to change, this conversation explores the hidden systems issues that impact trust, culture, leadership, and long-term sustainability in family-owned businesses.
You’ll also learn why many operational problems are actually alignment problems — and how emotionally intelligent leadership creates healthier businesses, stronger teams, and more resilient organizations.
If you’re navigating family business dynamics, succession challenges, leadership conflict, or operational stress, this video will help you recognize the warning signs before they escalate.
Download 10 Warning Signs PDF: https://possibility.ca/10-warning-signs-guide

Favoritism in the workplace rarely begins with bad intentions.
It usually begins with fear.
Fear of conflict. Fear of disappointing people. Fear of losing loyalty. Fear of uncomfortable conversations.
In this podcast, Tana Plewes explores how workplace favoritism quietly damages trust, accountability, leadership credibility, and organizational culture — especially in family businesses and founder-led companies.
You’ll learn why favoritism is not simply a personality problem, but a systems problem rooted in unclear expectations, weak accountability structures, emotional decision-making, and leadership avoidance.
Through powerful leadership insights, real-world business dynamics, and emotionally intelligent systems thinking, Tana explains how favoritism creates resentment, political behavior, poor communication, and declining performance across teams.
If you’re struggling with workplace fairness, family business conflict, leadership inconsistency, employee resentment, or accountability challenges, this conversation will help you identify the hidden patterns damaging your culture.
Download 10 Warning Signs PDF: https://possibility.ca/10-warning-signs-guide

What happens when loyalty replaces accountability inside a family business?
Hiring family members can feel natural, trusted, and emotionally safe. But without clear expectations, defined roles, and strong systems, even the best intentions can quietly create tension, resentment, and operational strain.
In this podcast, Tana Plewes explores one of the most emotionally complex challenges in family business leadership: promoting family over merit. Through practical leadership insight, personal reflection, and systems thinking, you’ll discover why many family businesses struggle not because people don’t care — but because they care so deeply they avoid difficult conversations.
You’ll learn:• Why hiring family without systems creates hidden risks• How unclear expectations damage trust and culture• The emotional cost of favoritism in family businesses• Why tolerated problems quietly grow over time• The difference between love and leadership• How strong systems protect important relationships• Why external experience strengthens family leadership• How role clarity improves performance and reduces resentment• Why process prevents politics inside growing businesses
This conversation is especially valuable for founders, family business owners, leadership teams, second-generation leaders, and entrepreneurs navigating succession, accountability, team dynamics, and organizational growth.
Because sometimes the greatest act of leadership is creating systems strong enough to protect the relationships that matter most.
Download 10 Warning Signs PDF: https://possibility.ca/10-warning-signs-guide

Why do so many family businesses struggle or fail across generations?
Most don’t collapse overnight. They decline slowly through hidden operational risks, unclear roles, undocumented processes, and unresolved conflict.
In this video, we break down 10 warning signs your family business may be at risk, including overdependence on one person, emotional decision-making, lack of financial transparency, disengaged employees, and outdated systems.
Recognizing these patterns early can help protect both your business operations and your family relationships.
Download 10 Warning Signs PDF: https://possibility.ca/10-warning-signs-guide

Most business owners think they’re the reason their company survives.But what if the real problem is that the business can’t function without them?
In this video, Tana Plewes breaks down why founders become the operating system of their business — and how unclear systems, undocumented processes, and constant decision dependency quietly create burnout, bottlenecks, and operational chaos.
Using powerful real-world stories and systems-thinking metaphors, you’ll discover how to move from founder dependency to scalable leadership by building processes that empower your team to think independently and operate with clarity.
If you’ve ever said:• “No one can do it like I can”• “I have to check everything”• “If I step away, things fall apart”
…this conversation may completely change how you see leadership, systems, and growth.
Whether you run a family business, lead a growing company, or want operational excellence without constant overwhelm, this video will help you identify the hidden patterns keeping your business stuck in survival mode.
Download 10 Warning Signs PDF: https://possibility.ca/10-warning-signs-guide