Most agency owners don’t think they have a leadership problem. They think they have a delegation problem.
Too many decisions still come to them. Too many escalations. Too much context switching. Time away requires over-preparing—and even then, they’re still checking in.
The usual response is to hire more leaders, clarify responsibilities, or “get better at delegating.”
Those things can help. But they rarely solve the real issue.
The deeper problem is that the agency still depends on the owner in ways that haven’t been designed out of the system. Until that changes, both scale and exit-readiness remain fragile.
The real constraint most owners misdiagnose
In Work Less, Earn More, I describe a continuum of day-to-day involvement:
- Mandatory – the business cannot function without you
- Necessary – things work, but with friction
- Needed – you’re involved by design, not necessity
- Optional – the business runs without you, and you choose when to engage
Most owners want to move rightward on that continuum. Fewer decisions. More leverage. More space to think.
Where many get stuck is focusing on reducing their workload, instead of reducing the business’s dependence on them.
If your absence—even briefly—creates hesitation, confusion, or risk, you’re not optional. And if you’re not optional, your agency will struggle to scale smoothly or stand up to serious scrutiny from buyers or investors.
- You can have a leadership team and still be the fail-safe.
- You can delegate heavily and still be the bottleneck.
- You can step out of delivery and still be indispensable.
That’s the trap.
Why leadership teams don’t automatically create independence
At a certain size, most agencies have leadership: department heads, directors, sometimes a COO or Managing Director.
And yet, key decisions still roll uphill. That’s because not all leadership structures reduce owner dependence in the same way.
Broadly, I see three patterns.
Functional leaders
These leaders own parts of the business: delivery, operations, sales, accounts.
They’re essential, as department or division leaders. But by design, they don’t carry the whole. When something crosses functions or requires enterprise-level judgment, it escalates… usually to you.
Deputized leaders
These leaders act with authority—but within guardrails. They manage well, keep things moving, and execute plans, but still look to the owner for confirmation when stakes rise or ambiguity appears.
Escalation is built-in… and frequent. They’re doing their best—but they can’t fully do your job.
The independent #2
This is different. An independent #2 is someone who can take on whatever the owner is currently doing, even as that work evolves over time.
This isn’t about replacing the owner. It isn’t about acting without alignment. And it isn’t about a specific title.
What matters is capacity. In commercial aviation, they’re the first officer—a fully qualified pilot who can fly on their own if needed. Indeed, the copilot usually flies half the trips, with the captain serving as “pilot monitoring.”
Your true #2 has Desire, Competence, and Capacity to do the job.
What an “independent #2” actually means (and doesn’t)
By independent, I don’t mean unchecked or unaccountable. And I don’t mean someone who permanently takes over the business.
I mean someone who can take over. An independent #2 is a leader who can carry the owner’s current scope of work—strategy, prioritization, decision-making, tradeoffs—without constant escalation.
Not forever. Not perfectly. But well enough that the business doesn’t wobble under stress. They’re a full copilot, not a student pilot.
Think about critical moments like:
- Illness or family crisis
- Prolonged distraction
- Extended leave
- Buyer diligence
- A transition period before an exit
There isn’t a fixed “owner role.” What owners do changes over time. Early on, it’s delivery and sales. Later, it’s leadership, capital allocation, and judgment.
The sooner someone else can handle whatever you’re doing right now, the more resilient—and valuable—the agency becomes.
What happens when you don’t have one
Many agencies look stable—until the owner steps back even slightly. Without an independent #2, the costs show up quickly.
Operational drag
Decisions slow because no one is sure who can decide. Leaders hedge. Meetings multiply. The owner becomes the safety net—not because they insist on it, but because the system quietly requires it.
Human cost
Owners burn out from being the default. Senior leaders grow frustrated by fuzzy authority. Strong people leave—not because they’re unhappy, but because they don’t see a path to real ownership.
Strategic fragility
Scale stalls. Complexity increases dependence. Exit-readiness remains theoretical. Buyers see risk even when historic and day-to-day performance looks strong.
The business works—but only with you present.
The leverage unlocked by an independent #2
When an agency has an independent #2, three paths open up.
Path 1: You can step back
You move into a Founder, Chair, or Vision role. You’re still involved—but by choice, not necessity. You focus on direction, not throughput.
Path 2: You can exit
The agency becomes meaningfully sellable. Buyers acquire continuity, not just revenue. The #2 stays to run the business, reducing transition risk.
Path 3: You can keep your options open
You also don’t have to do the other paths—you can keep your options open.
Here’s the key insight: All three paths require the same prerequisite. Someone else must be able to carry the work you’re currently doing without you.
That’s why the independent #2 is the hinge point between founder-dependence and exit-readiness.
What’s the right job title for your #2?
Titles matter more than owners like to admit—but less than they often think. The right job title:
- Attracts the right candidates
- Leaves room for growth
- Supports your ramp-up plan
- And signals authority internally and externally
In my work across hundreds of agencies, common titles for an independent #2 include:
- President
- Chief Operating Officer (COO)
- Managing Director (MD)
- General Manager (GM)
- Vice President (at mid-sized agencies)
- Director of Operations (occasionally, at smaller agencies)
Which one fits depends largely on your current title. Here’s a rough guide:
- If you want to become Founder/Chair, they may be President (and eventually CEO)
- If you’re the CEO, they might be President, COO, or Managing Director
- If you’re the President, they might be COO, VP, GM, or Managing Director
- If you’re a Principal or Partner, they might start as VP or GM
Think about where your #2 will start, and where you want them to end up. For example, someone might start as VP, hit defined milestones, and be promoted to COO. Later, they could become President—or even CEO.
This is also a good moment to reassess your own title. President or Partner may have worked in the past—but if you’re functioning as CEO, it’s reasonable to reflect that. If you’re hiring a formal #2, you almost certainly deserve a C-level title yourself.
Realistic ramp-up plan: An example
Independence doesn’t happen on day one. You build it deliberately.
One client wanted to delegate most of their CEO workload. They planned to retain ownership of growth (sales and marketing) while handing off delivery and internal operations.
They had an internal senior leader with potential—but not yet the full scope. Working together, we:
- Defined the future COO role
- Worked backward to create an interim role
- Set clear, KPI-based milestones
Each time the employee hit milestones, their role—and compensation—expanded. They kept moving up.
The result: the CEO gained space to focus on growth and strategy, and the agency reinforced a culture of internal advancement.
Trying to skip this ramp-up almost always backfires—because you promote someone beyond their level of competence.
How much should you budget for an independent #2?
The short answer: a lot. Expect:
- A six-figure base salary
- Profit-sharing or performance incentives
- Possibly equity or long-term upside, especially if exit is on the table
If that feels uncomfortable, it’s worth asking whether you are actually ready for this role.
Beyond the finances, you’ll also externally and internally describe them as your second-in-command. For some of my clients, this is easy—but for others, it’s a shift in mindset around how they view themselves, and it’s a harder transition.
Whatever you do, don’t cheap out. Your agency is likely your largest financial asset. This isn’t the moment to look for a bargain to manage it.
A cautionary tale: the “bargain” #2
At a conference, an owner said they wanted to go from Mandatory to Optional within a year.
They didn’t have an internal candidate, so they planned to hire a “rising star” at up to $90K—when the market rate was closer to $150–200K+. No equity. Maybe profit-sharing. Minimal contact—they wanted to talk with the employee maybe “three times a year.”
I told them their strategy was unlikely to achieve their goals. A strong #2 knows their value. They expect compensation and incentives aligned with responsibility.
Someone willing to take $90K for that level of responsibility isn’t likely capable of needing you only a few times a year. That salary is more appropriate for a senior Executive Assistant or Chief of Staff—roles that still require frequent owner involvement.
What concerned me most was their mindset. The owner didn’t enjoy running the agency, yet underestimated how hard the job actually was. That wasn’t delegation—it was abdication.
I declined to work with them.
Why most attempts fail
Most failures here aren’t personal. They’re structural. Common mistakes include:
- Promoting your best department leader to run the business, without having a plan to shift their prior work to others
- Avoiding real authority conversations
- Hiring “help” instead of coverage
- Confusing loyalty with readiness
These are design errors—not moral failures.
Delegation alone doesn’t create independence. Coverage—and real ownership of results—does.
What comes next
This article is the foundation. From here, the practical questions follow:
- What an independent #2 truly needs to own
- How to evaluate readiness
- How to hire or develop someone into that role
I’ll go deeper on those topics in related articles, including:
- Defining a second-in-command role that truly reduces owner dependence
- Reference-check questions that reveal independence, not just competence
- Hiring externally vs. promotion from within
And if you want an experienced outside view on where your agency stands today—and what would need to change to finally make you truly optional—that’s exactly what my Exit-Readiness Audit is designed to surface.
Optionality isn’t about disappearing. It’s about building a business that doesn’t depend on you to work.
Question: What’s your next step to hire—or empower—an independent #2 at your agency?
