From Task Manager to Succession Thinker: A New Perspective on Delegation
Chicago, 2008: "I'd like to introduce Alan, who will be co-managing the team with me."
Hearing this sparked a mix of surprise, curiosity, and skepticism. This was Day One of a new contract, and this was how I was being introduced. The gig was just six months, helping an IT service management team jumpstart.
“Co-manager?” That wasn't in my contract. But that word would change the trajectory of my career.
My new boss, Brendan, positioned me as an equal partner to a room full of my new clients and team. I wasn't immediately bought in but, as a young, bullish professional, I went with it.
Later that week, Brendan elaborated over lunch. He wasn't just handing me tasks; he was painting a picture of what was possible. He shared his aspirations to massively grow our company’s newest division, winning bigger contracts, and building something substantial. He saw potential in me that I hadn't recognized, and he was willing to invest in that potential despite having no guarantee I'd stay beyond my six-month commitment.
Over the following months, something remarkable happened. I stopped questioning the "co-manager" title and started embodying it. I didn't just complete assignments—I took ownership of outcomes, built relationships with the client and team, and began thinking strategically about the business. What Brendan had done wasn't traditional delegation. He wasn't delegating tasks; he was delegating his job.
The experience became the foundation for the leader I’d soon become. Brendan introduced me to what I now call "succession thinking"—the practice of building leaders not just to handle today's work, but to take over tomorrow's responsibilities.
When Succession Thinking Becomes Second Nature
After learning this approach from Brendan, I found myself naturally replicating it everywhere I led. I identify emerging leaders on my teams and begin positioning them for roles they could grow into, months before those roles become officially available.
My signature approach became making promotions feel inevitable to everyone involved. By the time I announced that someone was officially taking on a new title, the team and clients tended to respond, "Oh! Cool. I thought we were already operating that way, but - hell yea! Congratulations!" No surprises. No concerns, because they'd been watching that person demonstrate leadership capabilities for months.
This methodology multiplies leadership capacity across the entire organization. I'd focus on developing the next level of leaders, they'd do the same with their teams, setting up a leadership pipeline. Before long, we had built what felt like an unstoppable growth engine. Over five years, we scaled that initial team from about 12 people to 75, expanding revenue five-fold in the process.
The approach worked so consistently that I developed what I called the "vacation test." I would tell leaders: "You should be able to go on vacation for two weeks, never check your email or phone, and when you come back, the organization should be stronger than when you left."
When I got married, I put this principle to the ultimate test.
The Wedding Night Crisis
I returned from a three-week honeymoon, completely disconnected from work—no email, no calls, total radio silence. While debriefing with my successor, he shared something that made us both laugh about the awkward coincidences life delivers.
On my wedding night—not the reception, my actual wedding night—the client's payroll went down. The same type of mission-critical crisis that had tested me years earlier when I was growing into Brendan's role.
My successor told me his first thought: "We are NOT calling Alan." He pulled out the comprehensive troubleshooting guide I had created in anticipation for my vacation. That guide captured every ounce of my specialized knowledge on the system. Within hours, my team resolved the crisis.
Reflecting on this now, I recognize the beautiful irony. Before I officially filled Brendan’s shoes, he’d regularly travel on weekends. And invariably, some Priority 1 emergency would occur, forcing me to step up, and swing above my perceived weight class. History was repeating itself.
Just as I had, my successor handled the crisis, built his confidence, earned the client’s trust, and we passed the Vacation Test.
This is what succession thinking looks like when fully implemented: building people and systems that don't sink in your absence—they elevate.
Why Small Business Stakes Feel Different
Now, as a small business owner myself, I understand why delegation feels more daunting than it does in large company. When delegation works out poorly in a large organization, it might affect a process or a project. In a small business, it can affect entire business functions, client relationships, or your company's reputation.
The psychological weight is different. In my corporate days, I had backup systems, processes, and other team members who could absorb mistakes and cover gaps. As a small business owner, we often feel we are the backup system. Every delegation decision carries more concentrated responsibility because we have fewer people to share the load.
But here's what I've learned: this heightened sense of stakes makes succession thinking even more critical, not less. The very challenges that make small business owners hesitant to delegate are exactly why you need to build a business that works without you - so that you can actually take a real vacation, focus on growth instead of daily operations, and create the independence you started the business to achieve.
A Framework for Small Business Succession Thinking
Despite these different stakes, the core principles I learned from Brendan remain the same. Here's a framework for applying this thinking in your small business:
1. Start with Succession Thinking Ask yourself: Where do you want to be in your business 18 months from now? Paint that picture clearly. Are you focusing more on strategic growth while others handle operations? Are you developing new markets while your team manages existing clients? Like Brendan did with me, make your next level inevitable by clearly envisioning it.
2. Identify the Roles That Need to Exist Think beyond task lists to business functions. What jobs need to be done to achieve your vision? This might mean a part-time virtual assistant growing into an operations coordinator, or a contractor evolving into a business development partner. Don't limit yourself to traditional hiring—consider how technology can play a role too.
3. Begin Delegating Toward Those Roles Position your people for growth, not task completion. Instead of saying, "Can you handle these invoices?" try "I'd like you to take ownership of billing." Give them the context, authority, and support to grow into that expanded responsibility.
Don't limit yourself to traditional hiring—consider how technology can expand your delegation capacity. Many small business owners think they can't apply succession thinking because they lack a large team. But generative AI can handle everything from customer service responses to content creation and process documentation, effectively expanding your 'team' overnight. Mastering communication with AI has the added benefit of improving your interactions with human team members. AI augments human development by freeing your people to focus on the strategic, relationship-building work that develops them into your future leaders.
4. Apply the Vacation Test Regularly test whether your business can function without you. Start small—can you take a long weekend without checking in? Find the leaks and plug ‘em. Then build toward longer periods. Create detailed documentation, establish clear decision-making authority, and build systems that operate independently.
Building Business Value Through Independence
This approach does more than free up your time—it creates transferable intellectual capital, which is exactly what buyers look for when evaluating businesses. Companies that depend entirely on their owner-operators have limited (if any) value because the business isn't transferable.
Every system you document, every person you develop, every process you systematize adds to your company's enterprise value. You're building a business that works without you and one that creates true wealth.
The choice every small business owner faces is clear: remain indispensable or liberate your value.
Succession thinking is the path to liberation.
Your Next Step
Brendan took a chance on me when he had no guarantee I'd stay beyond six months. His investment in succession thinking paid off for him, me, and countless other leaders who stepped up over the years to be part of what we built.
The same multiplication of success is possible for you. It starts with shifting from task delegation to succession thinking. It requires seeing every delegation opportunity as an investment in your business's future.
Ready to explore how succession thinking could transform your business? Let's talk about what this looks like in your specific situation and how you can start building the independent, valuable business you've always envisioned.
About the Author
As a Success Architect at Liberated Leaders, Alan leverages 20 years of experience in technology leadership and consulting to help businesses optimize their technology strategies, gain an edge, and scale their operations. He is a twice certified executive and leadership coach who firmly believes that true business transformation can only occur with mindful investment in people and technology. Find out more about Alan on our About page.
Note: This article was 85% human generated and 15% machine (AI) generated.
Citations:
Drotter, Stephen J. and Charan, Ram. Ivey Business Journal (2001). Building Leaders at Every Level: A Leadership Pipeline
