You finally built a leadership team at your agency, by hiring (and promoting) key team members. You might have even added a Head of Operations, a COO, or a Managing Director.
And yet… you keep getting pulled into decisions. You’re still the tie-breaker, or the safety net when things are ambiguous or high-stakes.
Growth was supposed to give you freedom. Instead, growth bought you a bigger job.
This doesn’t mean your leaders are bad—but it’s a reminder that having a leadership team doesn’t automatically make you optional. Some types of leaders reduce delivery chaos, while others improve how the agency runs. But if your real constraint is owner dependence, you need a different kind of leadership coverage.
This article will help you identify what kind of leadership coverage you actually need next: delivery leadership, operating leadership, or true second-in-command coverage. Job titles are useful shorthand, but the title matters less than the level or scope of leadership coverage.
Optional is the goal—but first, identify the dependency
Most agency owners think they have a delegation problem:
- Too many escalations
- Too many decisions
- Too much context-switching
- Too many people (and tasks) waiting on them
But the deeper issue is usually founder dependency—a leadership coverage problem.
Where are you still mandatory or necessary? Where are you merely needed? And where are you actually optional?
The four stages of founder dependency
Here’s how I define the four stages, focused on Agency Optionality.
Stage 1: Mandatory
Without you, work stops. This is normal early in the agency’s life; when you start, you are the agency.
The problem is staying mandatory after you’ve built a team. You might be mandatory for sales calls, pricing, client strategy, hiring, reviewing deliverables, approving proposals, or handling every “important” client issue.
If people can’t take action without you, you’re not leading a company; you’re just keeping it from falling apart.
Stage 2: Necessary
Key decisions still require you. The agency can function for a few days without you. You might be able to take a long weekend—but longer than that, decisions pile up. Team members wait, meetings get rescheduled, clients don’t hear back, and internal priorities stall.
This is where many agency owners live for years. The agency looks successful from the outside. But internally—as your team is well aware—the owner is still involved in every key approval workflow.
Stage 3: Needed
Your team seeks your judgment, not your permission. This is a healthier place. Your leaders can make most decisions without you—but they still benefit from your perspective on bigger issues.
They’re not asking, “Can I do this?” They’re asking, “Here’s what I’m thinking. What am I missing?” This shift makes a big impact, for everyone involved.
The goal isn’t for your leaders to stop needing your judgment. The goal is for them to stop needing your permission.
Stage 4: Optional
Your involvement becomes a choice. Optional doesn’t mean “absent” or “abdicated.” And it doesn’t mean leaders operate with zero oversight.
It means the agency keeps moving when you’re unavailable. You’re involved because you choose to be—not because the business depends on you to function.
That’s a very different kind of freedom. And at this point, you might consider an exit—or step back to become founder and board chair.
Why building a leadership team can increase escalations
Adding leaders doesn’t automatically reduce owner dependency. In fact, it can make the bottleneck worse—at least at first.
As you add leaders, coordination paths multiply. More people own more pieces of the larger business. More decisions span multiple functions. More things become “gray area.” And all of this is normal.
What’s not ideal—but common—is what tends to happen next:
- Decision authority isn’t explicit.
- Leaders won’t commit to decisions.
- Ambiguity triggers escalation.
- Meetings multiply (and get longer and longer).
- You become the safety net for every major decision.
You aren’t the backup because you insist on it; you’re the backup because the system quietly requires it.
This is why two agencies can both have “a COO”—yet only one owner becomes more optional. It’s not about the job title; it’s about the scope, authority, and leadership coverage. And AI makes this gap even more obvious.
AI can help teams execute faster—but faster execution often exposes slower leadership. If every meaningful decision still waits on you, AI doesn’t remove the bottleneck. It just makes the bottleneck more visible, and more painful. Here’s more on scaling your agency with AI.
The bottleneck is often a pileup of hats
Before you decide which leadership role you need next, look at which “hats” you’re still wearing.
Every agency has six core roles:
- Specialist: doing the highly-billable client work (e.g., design, development, content)
- Delivery Leader: delivering work smoothly, profitably, and on time
- Account Leader: managing client relationships day to day, and growing their budgets
- Strategist: advising clients on how to get results based on the available budget
- Growth: marketing, sales, partnerships, and other “net new revenue” work
- Firm Leader: running business operations and setting the long-term vision
Early on, you probably wore all six hats. As you’ve grown, you likely handed off some of the hats—but probably not as many (or as quickly) as you’d like.
Over time, the goal is to recognize and take off poor-fit hats that contribute to owner dependence. This doesn’t require moving to “zero hats.” You may still choose to do client strategy, or growth—and you’ll still own vision as the firm leader.
But if you’re still reviewing every deliverable, solving every delivery issue, managing every client escalation, and approving every proposal, you don’t just have a workload problem. You have a leadership coverage problem.
The question isn’t, “Do I have leaders?” The question is: What am I still doing that someone else should own?
Here’s how to start fixing that at your agency.
Three levels of leadership coverage—and which one you actually need
This is where agency owners often get stuck in debates about job titles.
- “Do I need a COO?”
- “Should this person be President?”
- “Is a Managing Director the same as a General Manager?”
- “Is Head of Operations enough?”
Those are all reasonable questions—but they can distract you from the real issue: the title matters less than the leadership coverage.
A Managing Director might be an operating leader in one agency and a true second-in-command in another. A COO might be a process-focused operator in one agency and the owner’s full counterpart in another. A President might function like a COO, a CEO, or something else entirely.
So don’t start with the job title. Instead, start with the constraint you’re trying to solve.
1) Delivery leader: fixes delivery chaos
This is the role many agencies need first—because delivery chaos is expensive. A strong Delivery leader improves delivery consistency, resourcing visibility, project predictability, scope discipline, client communication, and gross profit margins.
Common titles include Head of Delivery, VP of Delivery, Director of Client Services, Head of Client Services, or VP of Client Services.
This role is especially useful when the agency is struggling with:
- Scope creep
- Client surprises
- Resourcing headaches
- Inconsistent follow-through
- Profit leaks from delivery execution
- Delivery teams feeling overloaded
A strong Delivery leader can make the agency feel much more stable. But here’s the limit: having a Delivery leader doesn’t automatically solve owner-level tradeoffs.
They may influence pricing vs. staffing decisions, sales promises vs. delivery capacity, full-agency prioritization, and cross-functional resource tradeoffs—but they usually don’t own the final call when leaders disagree. That doesn’t mean they’re failing—it’s just beyond the scope of their job.
If delivery chaos is the constraint, hire or strengthen delivery leadership. But they won’t remove you from every cross-functional decision. If that’s your goal, you’ll need broader leadership coverage—potentially an Operating leader (see the next section), and sometimes a true second-in-command (see the section after that.
2) Operating leader: improves how the agency runs
An Operating leader improves the agency’s operating system: cadence, meetings, metrics, process, accountability, and follow-through. They usually help your net profit margins, too—although they’re not solely responsible for that.
Common titles include VP of Operations, Head of Operations, VP (with no “of…” modifier), Managing Director, or COO (especially when the COO role is lighter or operations-focused).
This role is especially useful when:
- Leaders exist but aren’t aligned
- Meetings are frequent but decisions are fuzzy
- Accountability isn’t sticking
- Process is inconsistent
- Handoffs are messy
- Teams keep reinventing how work gets done
An Operating leader can reduce your context-switching, help leaders coordinate, and make the business feel less chaotic.
That’s valuable. But if their scope is primarily business operations—not full-agency leadership—the hardest decisions may still come to you.
For example, one of my clients was frustrated that they had to make so many decisions, even with a VP of Operations. As we dug deeper, the answer became clear: the VP was strong at business operations, but they didn’t want to run the entire agency. That wasn’t a problem with the VP; it was a mismatch between what the owner wanted—optionality—and what the role was designed to cover: operations.
An Operating leader can reduce chaos. But if you want to become optional, operating leadership may not be enough. Instead, you need a true second-in-command.
3) Second-in-command: reduces owner dependence
A true second-in-command reduces owner dependence. They don’t just make the agency run better; they help the agency run without depending on you.
Common titles include President, General Manager, Managing Director, COO in a heavier or full-agency scope, or CEO successor in some agencies. As before, the job title isn’t the point; it’s really about their level of leadership coverage.
A second-in-command can carry owner-level scope: prioritization, strategic tradeoffs, cross-functional authority, decision-making under ambiguity, leadership alignment, and continuity when you’re unavailable. This is the role you need when the constraint is owner dependence.
You’ll know owner dependence is the issue when:
- Your absence creates hesitation, confusion, or risk.
- Leaders hedge (or wait) because the stakes feel high.
- Cross-functional decisions still require you.
- People wait for your approval instead of using their own judgment.
- “We need you” shows up in areas where you don’t want to be involved.
A true second-in-command isn’t about unchecked autonomy, and (at least initially) it’s not about replacing the owner.
It’s someone who can take over much of the owner’s current scope without constant escalation. They’re a full copilot, not a student pilot.
The title trap: why giving someone an executive title doesn’t make you optional
Titles can create a false sense of progress. You name someone COO, Managing Director, President, or General Manager—and assume the dependency problem is solved.
But a job title doesn’t automatically give them decision-making authority, define escalation rules, backfill their previous role, or ensure they have Desire, Competence, and Capacity.
Here’s the test: If you disappeared for two weeks, what decisions would stall? If the answer is “most of them,” you don’t yet have the right leadership coverage.
And here’s an even higher-stakes version: If a family emergency pulled you away from the agency for 90 days, what would break first?
That answer tells you where the real dependency lives, and provides clues on how to fix the problem.
Problem example: C-level promotion, without VP-level backfill
Here’s an example I’ve seen, in similar forms, at several agencies: an owner promotes the Head of Accounts into a CEO-type role.
On paper, that looks like a big move toward owner optionality, and the owner is excited to step back. But if no one backfills (or restructures) account leadership, the new CEO is now doing two jobs: running the agency and still leading the Accounts team.
What happens next is predictable: the CEO gets stretched, the Accounts team is frustrated, and the owner gets pulled back in. The promotion wasn’t wrong, but the role design and execution were incomplete.
When the Accounts leadership role is properly backfilled, the CEO can actually function like a CEO—and the owner stops filling the gap. In this case, everyone is happier—thanks to intentional design and implementation.
How to turn the right role into optionality
We’ve established that proper leadership coverage can increase your owner optionality—but it won’t just fall into place. Here’s how to design for it.
Define authority
Create three “buckets” for decision-making authority:
- They decide
- You decide
- Joint decision (rare, with clear criteria)
If your leaders don’t know who can decide, they’ll escalate to the person with the most perceived authority… and that’s usually you. And if everything is a joint decision, you haven’t created leadership coverage; you’ve created leadership by committee.
Define escalation rules
Make it explicit what escalates—and what doesn’t. And define what a good escalation looks like.
A good escalation includes the issue, options considered, and a recommendation. If everything comes to you as an unstructured “heads up,” your leaders are still asking you to think for them. That keeps you overly involved.
Build a ramp-up plan
Independence doesn’t happen immediately. You expand scope based on milestones, demonstrated judgment, and trust. You need a ramp-up plan.
This protects both sides: the agency isn’t betting everything on a title change, and the leader isn’t set up to fail by inheriting too much too fast. It also protects you from the mistake I described earlier: moving someone up before you’ve covered their old responsibilities.
Confirm they have Desire, Competence, and Capacity
Someone wanting a promotion is important—but it isn’t enough for them to succeed.
Before you expand someone’s role, confirm they have three things:
- Desire: they actually want the broader role.
- Competence: they know how to do it—or can learn with training, coaching, and other support.
- Capacity: they have the time and space to succeed.
The missing piece is often capacity. A leader may want the role and be capable of doing it—but if they’re still carrying their old job (or if their new job is actually three jobs), the promotion becomes a trap.
And if they have competence and capacity but don’t want the role? That’s not your future #2; that’s a reluctant leader.
Align incentives with responsibility
If you want someone to run the entire agency for you, their compensation will likely be higher—and more incentive-based—than anyone else on your team.
A true second-in-command role usually requires meaningful upside potential: strong base compensation, performance incentives, and sometimes equity or phantom equity—especially if exit-readiness is part of the goal.
You don’t need to overpay—but if you want someone to carry owner-level responsibility, the compensation plan needs to match the weight of the role. Hiring executives on the cheap rarely ends well.
Hire for the constraint you actually have
So what do you need next? Start here:
- If delivery chaos is the constraint, you likely need a Delivery leader.
- If operating chaos is the constraint, you likely need an Operating leader.
- If owner dependence is the constraint, you likely need a Second-in-command.
Don’t hire for the title you wish would solve the problem. Instead, hire for the problem or constraint that keeps pulling you back in. Growth should create more freedom, not more dependence.
Does this problem sound familiar?
My hope is that this article empowers leaders to recognize and address what’s keeping them the bottleneck. If this article has resonated with you, there’s a chance you may feel overwhelmed, or would value outside guidance.
The most expensive leadership issues in agencies often come from things nobody formally designed: leadership coverage, role boundaries, escalation paths, decision authority, and what “good” looks like for each leader. That’s what the Agency Value Audit (AVA) is built to uncover.
The AVA gives you a clear, data-informed snapshot of where the agency is strong, where it’s underperforming, and where leadership alignment—or misalignment—is hurting the business. And you’ll get a custom roadmap for what to prioritize next, so that it doesn’t all fall to you.
After the 8–10 week project, many owners continue with ongoing support—either in-depth Executive Advisory or streamlined Agency Growth Coaching—to implement the changes and keep the leadership team aligned as you grow.
Want to fix this, so you can make your agency more valuable and less dependent on you? Please get in touch and I’ll confirm if we’re a match to work together.
QUESTION: What’s still landing on your desk that shouldn’t?
