There is a moment in every leader’s journey when the very habits that once fueled our success begin to hold us back.
We don’t always recognize it right away. In fact, we often celebrate those habits—our grit, our independence, our willingness to do whatever it takes. We tell ourselves stories about how no one can do it quite like we can. How being deeply involved proves we care. How control equals quality.
And for a while, those stories are true.
But eventually, the business grows. The demands multiply. The inbox fills faster than it empties. The nights stretch longer. The weekends disappear. And suddenly, we’re spending more time running the business than growing it.
That’s where this conversation begins with Cathy Baillargeon —not with tactics or tools, but with a truth many executives quietly wrestle with:
Delegation isn’t a task. It’s a transformation.
The Post‑COVID Shift No One Could Ignore
The way we work fundamentally changed when the world slowed down.
COVID didn’t just disrupt supply chains and office space—it forced leaders into reflection. Business owners who had spent years grinding suddenly found themselves asking deeper questions:
- Why am I doing all of this myself?
- What am I actually good at?
- Is this business serving my life, or consuming it?
For many, that reflection opened the door to a new way of thinking about support—particularly virtual and fractional support. Not as a luxury. Not as a sign of weakness. But as a strategic lever.
Virtual assistants and remote teams moved from “nice to have” to “how did I ever operate without this?”
And yet, despite the logic, the resistance remained.
Why Delegation Is So Much Harder Than It Looks
Delegation is often framed as a productivity skill. In reality, it’s an emotional one.
Some leaders come from corporate environments where delegation was built into the hierarchy. Others are pure entrepreneurs—builders who have never managed a team, never handed off work, never trusted someone else with their vision.
But regardless of background, something changes when it’s your business.
Your business isn’t just an entity. It’s your identity. Your reputation. Your livelihood. Your baby.
Handing pieces of it to someone else—especially someone you may never meet in person—can feel terrifying.
There’s pride involved. There’s guilt. There’s fear. There’s vulnerability.
And there’s the quiet question many leaders won’t say out loud:
If someone else can do this better than me… what does that say about me?
Here’s the answer, plainly and powerfully:
It says you’re evolving.
The First Hand‑Off: When Vulnerability Meets Freedom
Almost every leader remembers the first thing they delegated—and the emotions that came with it.
For many, that moment centers around email.
Email is the nervous system of modern leadership. It holds decisions, relationships, confidential information, opportunities, frustrations, and far too much spam. Giving someone else access feels exposing. Intimate. Risky.
And yet, it’s often the most liberating step a leader ever takes.
Imagine opening your inbox and seeing only what truly requires your attention. No newsletters you meant to unsubscribe from. No promotional clutter.
No hours lost triaging messages that don’t move the business forward.
Just clarity.
That single shift can return hours each week—and even more importantly, mental bandwidth.
And mental bandwidth is where leadership lives.
Time: The One Resource You Can’t Scale
I often say this to fellow business owners:
You can make more money. You can hire more people. You can build better systems.
But you cannot make more time.
Every hour spent on low‑value administrative work is an hour not spent on strategy, relationships, innovation, or rest. And while hustle culture loves to glorify exhaustion, seasoned leaders know better.
Burnout is not a badge of honor. It’s a warning sign.
One of the most powerful stories I’ve heard involved a business owner who loved her craft—but was drowning in administration. Her passion had become a prison. Her evenings were consumed by paperwork. Her growth stalled. Her personal life suffered.
After bringing in virtual support and implementing systems, something remarkable happened.
For the first time in years, she took an evening off.
Not because the work disappeared—but because it was finally handled.
She spent time with her spouse. She breathed. She remembered why she started the business in the first place.
That is not a small win. That is leadership reclaimed.
Delegation as Empowerment—Not Abdication
One of the most misunderstood aspects of delegation is the idea that it diminishes the leader’s role.
In reality, delegation expands it.
When you delegate thoughtfully, you don’t just offload tasks—you create opportunity. You give someone else the chance to grow, to learn, to anticipate needs, to become proactive rather than reactive.
But that growth requires trust. And trust requires practice.
No one becomes great at delegation overnight. It’s built through communication, feedback, patience, and intention. And yes—sometimes mistakes.
But without that first task handed over, nothing changes.
The Cultural Cost of Ignoring Delegation
There’s another layer many leaders overlook: culture.
Even in small, fully remote teams, culture matters. Especially in remote teams.
When leaders are stretched thin, communication suffers. Connection weakens. Team members feel isolated. Work becomes transactional rather than relational.
Culture doesn’t happen by accident—it’s modeled.
And when leaders invest in clarity, inclusion, and shared purpose, even a two‑person team can feel aligned and energized.
Remote doesn’t mean disconnected. But it does mean intentional.
Numbers Don’t Lie—Even When We Avoid Them
Let’s talk about the lesson many entrepreneurs learn the hard way.
You can love your people. You can believe in your mission. You can feel busy and successful.
But if you don’t know your numbers, you’re flying blind.
Avoiding financial visibility is common—especially among leaders who don’t identify as “numbers people.” But growth demands clarity. And clarity demands data.
Understanding revenue, margins, capacity, and staffing levels isn’t cold or impersonal—it’s responsible leadership.
Sometimes, the numbers reveal hard truths: Overstaffing. Unprofitable services. Misaligned effort.
And sometimes, they force decisions no leader wants to make.
Those moments are painful. They’re human. And they’re unavoidable.
But leaders who face them early, with eyes open, protect the long‑term health of their organizations—and the people within them.
What Leaders Must Unlearn to Scale
Scaling doesn’t require doing more. It requires doing fewer of the wrong things.
That means unlearning beliefs like:
- “If I don’t do it myself, it won’t be done right.”
- “I should be able to handle this.”
- “Delegation slows me down.”
- “I’ll give it up later, when things calm down.”
Spoiler alert: things don’t calm down on their own.
You don’t delegate because you’re overwhelmed. You delegate so you don’t become overwhelmed.
The Executive Takeaway
If you are a business owner, executive, or founder reading this, here’s what I want you to hear clearly:
- Delegation is not a loss of control—it’s a refinement of focus.
- Virtual support is not a compromise—it’s a strategic advantage.
- Vulnerability is not weakness—it’s leadership maturity.
- Time is your most valuable asset—protect it relentlessly.
You started your business because you were passionate about something. Don’t let administrative noise bury that passion.
Let others handle what they do best. So you can do what only you can do.
That’s how real growth happens. That’s how leaders stay in the game. And that’s how businesses scale—without losing their soul.
Listen to the full episode on C-Suite Radio: Disrupt & Innovate | C-Suite Network
Watch the episode: DI 136 Delegate to Elevate: Building Freedom with Virtual Cathy.
This article was drafted with the assistance of an AI writing assistant (Abacus.AI’s ChatLLM Teams) and edited by Lisa L. Levy for accuracy, tone, and final content.
