What’s your endgame as an agency owner? You can’t work forever—and most people don’t want to. But the path between “still in charge” and “fully stepped away” isn’t always clear.
That’s where succession planning comes in.
Whether you’re preparing to sell—or you just want your agency to stop running through you—succession is about building a business that works without you in the middle. That takes more than a job title change. It takes leadership, communication, and a plan that doesn’t fall apart the moment you step away from the Slack or Teams thread.
I’ve helped agency founders make that transition. And when it works, it can change their life—and their family’s future. But I’ve also seen what happens when people wait too long—or pick the wrong strategy or the wrong successor—and it gets messy.
In my work advising hundreds of agency leaders, I’ve found that succession works best when it aligns the founder’s life goals, the team’s capabilities, and the market reality. Skip that alignment, and the best-case outcome is frustration. Worst case? A slow-motion implosion.
3 succession paths: Exit, Chair, or TBD
At the core, you have three succession paths:
- Grow toward an exit,
- Shift to a lifestyle model, or
- Keep your options open.
Succession planning doesn’t just mean “exit.” For agency founders, it means preparing your business to run without you—sooner or later—and ensuring it thrives, whether or not you sell.
Each path has tradeoffs, and each benefits from taking action early (yes, even if you want to keep your options open), especially when it comes to developing your internal leadership pipeline.
Why succession planning fails (and how to avoid that)
Many agency succession plans fail—or stall—because founders wait too long before preparing. They avoid the hard conversations, assume a successor or buyer will magically be ready, or have unrealistic expectations about how soon (and how profitably) they can step back.
The stakes are high: If you leave without a plan, the business may flounder. If you try to sell without a second-in-command, buyers may lose interest—or lower their offer.
But when you approach succession intentionally, the results can be life-changing.
Path 1: Grow toward an exit
You’re familiar with this classic play: scale the business, sell it, and move on to what’s next.
In this path, succession planning is about preparing someone (often internal) to run the business without you—either to help drive growth toward a sale, or to lead the team after the sale.
Some agency founders promote their #2 to COO or CEO before a deal, so that buyers see a strong leadership bench. Others make the successor part of the deal—where they continue to lead under the new ownership, or even become a new owner.
Don’t just promote someone because they’ve worked for you a long time. This is about competence, not just loyalty.
Example: Delegating to sell
The founder of a B2C marketing agency enlisted a past colleague as their #2. The employee became a minority owner in the agency, which created strong incentive alignment. While the founder oversaw strategy and bizdev, the junior partner led operations.
This worked out well—and the agency is about to exit.
Path 1 works well when:
- You want to sell the agency within the next 3-5 years.
- Your financial goals depend on an external buyer.
- You’re willing to invest in growing and mentoring a successor.
Watch out for:
- Your bandwidth: Beware becoming too busy to actually delegate.
- Unchecked assumptions: Don’t assume a successor is ready (or interested) without a conversation. Ultimately, it will probably involve many conversations.
- Dealbreakers: If your successor lacks incentives to stay after you sell, buyers will be concerned.
What helps you sell the agency:
- Coach your successor to grow into the role, including time for a ramp-up plan.
- Start exit planning early, to build-in flexibility.
- Create a clear division of responsibilities (e.g., EOS or a RACI chart).
- Pay for a valuation to learn how much the agency is worth today—for instance, from Punctuation or TobinLeff.
I’ve seen some founders treat leadership succession like a checkbox—putting someone in a leadership role because they think it looks good, or because the founder is tired and eager to stop running everything. Start the process early—when there’s still time to build real leadership trust and process continuity.
This path fits if you subscribe to the FIRE movement (Financial Independence, Retire Early).
Path 2: Shift to a lifestyle business model, with you as Chair
You may not want to sell, or not for the foreseeable future. Some founders want to keep the agency but reduce their involvement—to grow another business, volunteer, or just take more time off.
In the lifestyle approach, the agency supports your life, rather than the other way around. And you keep 100% of the profits (or perhaps 90%, after profit-sharing incentives to your #2).
Succession here means stepping back from day-to-day leadership—perhaps moving from CEO to Chair. You’ll still own the agency, but your team will run it.
Example: From CEO to Chair
The founder of a niche marketing agency promoted a long-time team member into a leadership role, with my support over several years. Eventually, that employee became CEO. The founder now works a few hours a week by choice, as Founder/Chair.
They didn’t sell, but they gained freedom—without dismantling what they built. They have time for new things, without losing the stream of steady profits. And their public “Founder” title extends their prior authority—without everyone expecting them to fulfill all (or any of) the work.
Path 2 works well when:
- You’re financially stable and don’t need a big exit.
- You trust your team and want to see them grow.
- You want to stay involved, but only on your terms.
Watch out for:
- Your expectations: This transition doesn’t happen overnight.
- Underestimating the emotional transition in addition to the logistics.
- Delegating authority without clarity or follow-through; look for Desire, Competence, and Capacity to lead (as well as good character).
What helps you move from CEO to Chair:
- Transition gradually, with defined milestones.
- Coach and train the new leaders.
- Define clear role boundaries (e.g., Chair vs. CEO), without swoop-and-poop.
Agency founders sometimes tell me, “I don’t want to sell—I just don’t want to run it anymore.” That’s the sweet spot of lifestyle succession: less stress, without giving up ownership. But it only works if your successor—the new CEO or President—has the authority (and the confidence) to actually run things.
This path can be a good match if you follow what I’ve seen described as the FILE lifestyle (Financial Independence, Live Early). Compared to FIRE, FILE is about shifting your work to enable travel and other pursuits now—rather than stopping work entirely. And if you do it right, your overall income continues—or might even grow.
Path 3: Keep your options open
Not ready to commit to selling or stepping back entirely? That’s OK—at least for now. (Eventually, you’ll need to make a decision.)
In this third path, your goal is optionality. By investing in succession planning (even if you don’t have a firm timeline), you protect your flexibility and create better options for the future.
You might not sell for another 10 years. But when you start building a leadership bench now, you gain time, leverage, and peace of mind.
Example: Preparing for what’s next
An agency founder wasn’t sure if they’d sell or stay… but they knew the business was too dependent on them. They began delegating to two senior team members, preparing them to eventually run things.
One of those team members will likely become CEO—with the other as COO—or the founder might choose to sell externally. Either way, they’re preparing now to have options in the future.
Path 3 works well when:
- You’re uncertain about your timeline.
- You want to reduce the agency’s dependency on you.
- You’re open to future possibilities, including an exit or step-back.
Watch out for:
- Letting indecision stall progress.
- Succession-by-default (hoping someone steps up eventually).
- Team confusion if you aren’t clear about direction, or if two people each think they’re your primary successor.
What helps you keep your options open:
- Delegate intentionally, not reactively.
- Coach your potential successors, ideally letting them know what you’re considering.
- Check in regularly with the team about your long-term vision.
Founders sometimes think “optional” means “later.” But real optionality is built now—by removing yourself as the bottleneck and giving someone else space to lead. If you wait until you need options, you may find you have no options.
Quiz: Which path might be right for you?
There’s no one-size-fits-all answer. But if you’re weighing your next chapter, do a gut-check:
- Do you want to eventually sell and move on? → Path 1 (exit, to eventually leave entirely)
- Do you want to stay involved but work less? → Path 2 (lifestyle, with a hired CEO running things and you as the chair)
- Are you undecided but want more flexibility? → Path 3 (keep your options open, while making the day-to-day easier)
Create clarity by coaching your successor
All three paths have one thing in common: you can’t do it alone.
Whether you’re stepping back, selling, or still figuring it out, someone will need to take on your old job. That’s not just a title change—it’s a leadership shift. The successor is usually the person leading delivery or client sevices—or occasionally the person leading business operations.
I often advise agency founders during this process, and sometimes also coach their #2. It’s not about ‘fixing’ people. It’s about giving both parties space, structure, and support to evolve.
The earlier you start succession planning, the more options you’ll have. That’s true whether you’re exiting in six months or six years. If you’re trying to decide what you even want to do, start with an Agency Growth Diagnostic. In the AGD, I usually create a custom roadmap to reach your goals—but I can adjust to focus on helping you choose your ideal destination.
Get your Exit Plan Template (free of charge)
Want a head start, especially if you’re leaning toward Path 1? Use my Exit Plan Template to help you:
- Define what “success” looks like.
- Consider your goals, timelines, and constraints—including the exit price you want (or need) to achieve.
- Avoid common traps that make succession harder than it needs to be.
Get your free copy and start filling it out. I bet you’ll be surprised by what you notice, even after the first three questions.
You might double down on Path 1—or decide you’re happy with Path 2 or Path 3.
Want to see what this looks like in practice?
Join me and agency M&A advisor Jonathan Baker for a behind-the-scenes fireside chat: Your Ideal Exit. We’ll each share real-world lessons on what works (and what doesn’t) when it comes to building your agency’s leadership bench. Sign up to get the recording here.
Succession isn’t a someday problem. It’s a right now opportunity. Even if you’re not ready to sell. Even if you’re not planning to disappear. Even if you haven’t found “the one” to replace you.
Because here’s the thing: you will leave your agency someday. The only question is—will it be on your terms? Start now. Start small. Start with the Exit Plan Template.
But whatever you do, don’t wait until you’re too burned out to care. I’ve seen what it looks like when founders wait too long. It’s not pretty—and it’s expensive. You deserve better.
Question: Which succession planning path will you take?
