Running a larger agency can make your decisions harder… and more expensive.
You have more resources, but you also have more at stake. Leadership decisions impact dozens of people. Losing a client requires major changes. Shifting your own role takes months or years of preparation, instead of a couple delegation meetings.
As you scale, decisions also become more interconnected. Your growth goals affect your leadership team’s structure and roles. Your leadership team affects how optional you can become. Owner dependence directly impacts agency value—and your choices and outcomes if you eventually want to sell the business.
Here are 10 of the biggest decisions I see in my work as an agency advisor, along with how I’d help an agency owner think through each one. Click the question to jump to my answer.
- Should I grow to make myself optional, or specifically grow toward an exit?
- What should my role as owner and CEO look like three years from now?
- Do I need a stronger #2, or a new leadership structure entirely?
- Can my current leadership team get us to the next stage?
- Should I promote an internal leader, or hire an experienced outsider?
- Should I keep a large but problematic client, or accept the revenue hit?
- Should I coach an underperforming senior leader, or replace them?
- Should we prioritize growth, profitability, or risk-reduction right now?
- Which investments will increase agency value, and which are just adding overhead?
- What if the decision I’m wrestling with isn’t the real problem?
But first, let’s review a key tool to help you make any major decision.
Use an Advance Retrospective to think through consequential decisions
When the stakes are high, I often use an Advance Retrospective: writing about the future as if it’s already happened.
Like a standard retrospective that looks backward (at what happened, what worked, what didn’t, and what you’d do differently), an Advance Retrospective asks you to imagine you’ve already made the decision and enough time has passed to see the consequences.
Suppose you’re considering whether to hire a strong #2. Imagine it’s two years from now and the decision worked well. What does your role look like? What does your #2 own? Which decisions no longer reach you? What got easier? What new problems appeared?
Then do the same for the other realistic path.
This isn’t positive visualization (although you will frame things assuming they went well). The point is to get past today’s frustration—and the immediate relief a decision might provide—so you can think about second-order consequences.
When I’m helping an agency owner with a consequential decision, the Advance Retrospective process usually looks like this:
- Clarify the real decision. The presenting problem may not be the underlying problem.
- Narrow the realistic options. Usually two or three are enough.
- Look backward from the future. Pressure-test each realistic path.
- Compare the consequences. What does each option make easier, harder, possible, or impossible?
- Decide what happens next. Once you choose, what needs to happen in the next 90 days?
The right time horizon depends on the decision. Six months may be plenty for one issue; another may require looking 3–5 years ahead.
Sometimes, you realize you’re choosing between fundamentally different futures for the agency. That’s useful information; the strategic question is broader than you thought.
With that in mind, here are 10 decisions I see repeatedly.
1. Should I grow to make myself optional, or specifically grow toward an exit?
These goals overlap so much that owners often treat them as the same thing, but they aren’t.
If you want to double or triple the agency while reducing how much it depends on you, you’ll probably need stronger leadership, resilient client relationships, more predictable new business, and fewer situations where you’re the day-to-day safety net.
Those are also things a future buyer tends to value. But that doesn’t mean you need to run the company as if a sale is inevitable.
If you’re actively preparing for an exit, some priorities move up the list: concentration risk, financial quality, transferability of key relationships, and documenting what currently lives in people’s heads. Timing matters, too. “I might sell someday” is very different from “I want the option to sell within X years.”
I suggest looking 3–5 years into the future. What do you want your relationship with the agency to be? If you knew you were selling, what would you change now? Which of those changes would still be smart if you never sold?
If you’re genuinely torn between several futures, don’t force a narrow answer. You may need to choose the broader path first.
2. What should my role as owner and CEO look like three years from now?
When you first started or joined your agency, you did whatever needed to happen. That can work for a long time—until the business outgrows it.
Once your agency is established, “What do I want to stop doing?” is too narrow. A better question is: “What does the business need from its CEO, and which parts of that job should still be mine?”
You might remain the operating CEO, but spend far less time troubleshooting. You might focus on strategy, leadership, and a small number of high-value relationships. Or you might eventually become the Founder/Chair while someone else runs the day-to-day for you.
There’s no universal answer.
Picture an ordinary Tuesday two or three years from now. Not a vacation day. What are you doing? Who reports to you? Which decisions still reach you? What happens when a major client problem appears?
Your future calendar is often a better org-chart clue than your current title.
3. Do I need a stronger #2, or a new leadership structure entirely?
“I need a COO” sounds like a diagnosis. Usually, it’s a proposed solution—but it may not be solving the right problem.
Start with why decisions keep reaching you. Is it because no one else has the authority to make them? Because your current leaders aren’t capable of making them? Because roles overlap? Because people don’t hold each other accountable? Or because you keep jumping back in?
Those are different problems, so they need different fixes.
You may need an experienced #2 who can integrate the leadership team and run the agency day to day. Or you may already have the right people—but need clearer roles, decision rules, and accountability structure.
Hiring another executive won’t automatically fix ambiguity. Sometimes it makes things worse, by creating leadership misalignment.
Define the outcome before you hire anyone. When it’s 18–36 months from now, what should happen without you? What should a #2 own? Which decisions should other executives own without going through your #2?
Start with the work that needs to happen. Then decide what team structure supports it.
4. Can my current leadership team get us to the next stage?
This is hard because it’s easy to focus on past contributions. Your current leaders understand the clients, culture, and people in ways an outside hire won’t on Day 1. But the job and the industry keep changing.
Someone who was excellent at running a five-person department may struggle when it becomes a 20-person department with managers underneath them. A strong functional expert doesn’t automatically become a strong executive because you increased the title.
At the same time, don’t assume you need to “upgrade” someone simply because your growth has stalled.
I look at whether someone has the Desire, Competence, and Capacity to succeed in the role you need next. For senior leaders, I add another question: Have you actually given them the authority to show you?
If you routinely override their decisions, go around them, or solve problems before they get a chance, you don’t have a true perspective on their leadership capabilities when you’re not there.
Now imagine the agency is twice its current size. What would each leadership role require? Where would your current leaders thrive? Where would they need significant development? And where are you mostly relying on hope?
5. Should I promote an internal leader, or hire an experienced outsider?
Should you promote from within?
- An internal candidate brings context, relationships, cultural credibility, and a track record you’ve actually seen.
- An outside hire may bring something your agency doesn’t have yet: experience doing the job at a larger scale.
Neither path is automatically “safer.”
Internal promotions fail when owners confuse loyalty or functional expertise with executive potential. And external hires fail when you fall in love with a resume and don’t test whether the person’s approach fits the agency.
You may also inadvertently make an unfair comparison: the real internal candidate (whose weaknesses you know), versus the imaginary perfect outsider (whose weaknesses you haven’t met yet).
Compare real alternatives. What would have to be true for the internal candidate to succeed? What coaching would they need? If you hire externally, what will that person need to learn—and which relationships will they need to earn?
6. Should I keep a large but problematic client, or accept the revenue hit?
At an established agency, a difficult client may represent hundreds of thousands—or millions—of dollars in annual revenue. Their work may support an entire team.
This is especially dangerous if you have a client concentration problem. So the answer isn’t always “Fire the client tomorrow.”
But “keep tolerating it indefinitely” isn’t a solid option, either. When you keep toxic clients, you’re telling your team, “This revenue is more important than your happiness.”
Don’t make this only about whether you like the client. Look at what the account is doing to profitability, employee retention, leadership attention, your ability to serve other clients, your reputation, and your concentration risk.
Then ask the question owners often avoid: What happens if they fire us first?
- If losing the account unexpectedly would create layoffs or a cash-flow crisis, the problem already exists. Keeping the client doesn’t remove the risk; it just delays when you have to deal with it.
- Over the next six to 12 months, your realistic options might include repairing the relationship, renegotiating the engagement, intentionally reducing the account, replacing the revenue before exiting, or deciding the economics justify continuing.
The important part is choosing intentionally instead of letting the status quo choose for you.
7. Should I coach an underperforming senior leader, or replace them?
The hardest people decisions usually aren’t about someone who is obviously terrible. Those are easier; they need to go.
The difficult cases involve someone who has contributed a lot, has strong internal relationships, and may have succeeded for years—yet they aren’t succeeding in the role the agency needs now.
Before you decide the person is the problem, diagnose what’s actually happening. I usually separate four possibilities:
- Person problem: They don’t have the skills or behaviors the role requires.
- Role problem: You’ve created a job that doesn’t fit their strengths.
- Management problem: You (or their direct manager) have been unclear about expectations, feedback, or accountability.
- Stage-of-company problem: The role changed materially as the agency grew. For instance, you now need specialists instead of generalists.
If they can realistically improve, make the goalposts explicit. What needs to change? What support will they get? How will you measure progress? By when? And what happens if they don’t get there?
That might be a formal Performance Improvement Plan (PIP). For a senior leader, it may be a more tailored written plan with clear expectations, checkpoints, and consequences. Either way, “I need you to step up more” is not a plan.
Then look 6–18 months ahead. What happens if nothing changes? What’s the realistic upside if you invest in helping the person improve?
Past contribution matters, but it doesn’t automatically determine future responsibility. And if you’re going to replace someone, make sure you’ve diagnosed the problem before you solve the wrong one with a termination.
In some cases, you might skip the PIP, and opt to terminate them with severance. That’s especially relevant if there’s no way to constructively prove they’ve improved. This can happen when the role changes dramatically, or you just don’t trust them anymore. Don’t make them go through the indignity of taking a test they’re guaranteed to fail.
8. Should we prioritize growth, profitability, or risk-reduction right now?
You probably want all three. The problem is sequencing.
Aggressive growth often requires investment before the revenue arrives. Maximizing near-term profit may mean saying “not yet” to investments that could accelerate future growth. Reducing risk may require replacing revenue, adding leadership capacity, or making other moves whose payoff isn’t immediately visible on the P&L.
The important phrase is “right now.”
Maybe you have a rare market opportunity and it makes sense to invest aggressively for 18 months. Maybe you’ve grown quickly and need to integrate that growth. Or maybe the agency looks profitable on paper, but you have owner-dependence risks that limit your future options.
Start with the longer-term goal, then ask: What’s the biggest constraint between here and there?
If you want to double or triple the agency, the constraint may be sales capacity or leadership. If you want greater owner optionality, the constraint may be that too much still depends on you.
Your current constraint should drive your current priority.
9. Which investments will increase agency value, and which are just adding overhead?
As your agency grows, mistakes get more expensive.
A senior executive may cost hundreds of thousands of dollars once you include compensation, benefits, recruiting, and ramp-up time. A new sales function can take months to become productive. New systems can consume a surprising amount of leadership attention before they create leverage.
Some of those investments are worth it. Some are just expensive.
The question I care about is: “What capability are we ‘buying’ that we don’t have today?” Then ask: “Will that capability work without the owner personally holding it together?”
A stronger finance function can improve visibility and decision-making. A stronger leadership team can reduce key-person dependence. A repeatable sales engine can reduce dependence on the owner’s network. Those capabilities may increase agency value before they increase revenue.
But adding management layers because “companies our size have a COO” doesn’t automatically add value. Neither is buying technology—or changing software platforms—without changing the processes around it.
Look 2–4 years out and imagine the investment worked. What became possible? What changed financially or operationally? What became less dependent on you?
If you can’t name the capability you’re buying, reconsider whether you’re investing—or merely spending.
10. What if the decision I’m wrestling with isn’t the real problem?
This happens constantly. Owners come to me with questions like:
- Do I need a COO?
- Should I replace this executive?
- How do I get my team to take more ownership?
Those are legitimate questions. But as I touched on earlier, these are often solution-shaped questions, and you haven’t finished the diagnosis yet.
Maybe too many decisions reach you, so you assume you need a COO. But after looking more closely, you discover your existing executives are capable—yet their responsibilities overlap, and you routinely override their decisions.
Hiring a COO won’t automatically fix that. You may simply end up with one more expensive person whose decisions you override.
Before you move from problem to solution, ask one question: “If I solve this exactly as I’ve defined it, what happens next?”
If you’d still have essentially the same frustration six months later, keep digging.
Common traps as you make strategic decisions
The specifics vary, but I see the same patterns repeatedly:
- Solving the presenting problem instead of the underlying one. If you start with the obvious problem, you may miss the real problem. A hiring problem may actually be an org-design problem. An accountability problem may be unclear authority.
- Optimizing one variable while ignoring the second-order effects. For instance, increasing profitability may slow your growth. Pursuing growth can increase risk. Reducing your workload without building leadership capacity can shift the bottleneck somewhere else.
- Making a long-term decision because you’re frustrated right now. A terrible quarter can make an exit suddenly sound appealing. A great quarter can make aggressive expansion feel safer than it might really be.
- Treating every decision as permanent. Many decisions are reversible—or you can approach them iteratively. You can test, learn, and adjust before making the bigger commitment.
- Avoiding a hard conversation by making an organizational change. A reorg is an expensive substitute for clear feedback. Compared to other decisions, reorgs are hard to reverse.
- Confusing “I can do this” with “I should do this.” Your ability to rescue something personally doesn’t mean rescuing it is the best use of the CEO.
- Waiting for certainty. You rarely get 100% certainty on a consequential decision. The goal is to understand the risks, make the best call with the information available, and know what evidence would cause you to change course.
To repeat a final time: the bigger your agency gets, the more expensive these traps become.
Make the decision—and protect your future options
You don’t need outside help for every strategic decision. Some are cheap enough to test and reverse… and others aren’t.
That’s especially true when you’re deciding about your own role, a senior leader, the leadership structure, a major client, a significant investment, or the future direction of the agency.
You’re close to the situation—and sometimes you’re part of the problem.
- An outside perspective can help you figure out what’s actually going on, pressure-test your assumptions, and decide what deserves attention first.
- Sometimes that means resolving one consequential decision. Other times, it means stepping back and comparing several strategic paths before you commit to one.
This isn’t about getting a fancy report. Your goal is to make the right call—and then know what to do about it.
If you’re facing a consequential decision at your agency, reach out to start a conversation. Tell me what you’re wrestling with, and I’ll recommend what kind of help makes sense. There’s no obligation, and your inquiry is confidential.
