In a recent leadership conversation, we discussed what separates a manager from a director. Beyond the title, the distinction wasn’t clear to any of us.
That’s a problem when people are asking to advance in their careers.
Someone wants a bigger title or more money. As an owner, you’re trying to determine whether their performance and responsibilities justify the change. You want to recognize people who have earned it. And always top of mind is the nagging reminder that you have a business to run and a payroll, if left unchecked, will grow wildly.
So what do you tell the person who wants to move up?
Like you, I expect advancement to be earned. Demonstrate stronger judgment, take greater ownership, produce consistently better results, and then we can talk about advancement. Those expectations seem reasonable from my side of the conversation.
From the employee’s perspective, they leave a lot of unanswered questions.
What does greater ownership mean? Which results matter? How consistently do I need to produce them? What separates the work I’m doing today from the work that would qualify me for the next level? How much more experience do I actually need? Do I need more education, more certifications, or something else to advance?
If we can’t answer those questions clearly, we’re asking employees to satisfy expectations that we have yet to define. That leaves them guessing.
The frustration runs in both directions. An owner can hear another request for a raise and wonder why the employee thinks they’ve earned it. The employee can hear “not now” and wonder whether there’s a future for them here.
Neither leaves with much confidence about what just happened and what will happen next.
One conversation that stood out involved an employee who was hesitant to demonstrate initiative because she was concerned about overstepping. Think about how easily that can become a performance issue. A supervisor wants someone to take more ownership. The employee is waiting to understand how much ownership she’s allowed to take. Both can walk away frustrated while believing they’re doing their part.
The same uncertainty shows up in titles. If we haven’t defined what a director owns, which decisions they make, and how that contribution differs from a manager’s, we haven’t given either person a standard. We’ve given them something to negotiate over.
Pay gets pulled into that negotiation, too. Without defined levels and compensation ranges, each request requires another individual explanation. It becomes harder to show someone how developing their capabilities connects to earning more.
Our communication around this has been terrible. That’s part of what we’re now trying to fix. We’re working through those issues right now.
I tasked our supervisors to define advancement requirements within their departments. They know the work better than anyone, and they need to explain what strong performance looks like and when someone is ready for more responsibility.
We’re establishing a consistent career ladder across Proxa while leaving department leaders responsible for the standards specific to their work. As an example, there will be junior, mid, and senior levels in all departments. That consistency will give us a common framework. But advancing in SEO will require different expertise than advancing in Finance.
I also required supervisors to share their proposed career paths with their employees before submitting them for approval. Employees need an opportunity to ask questions and point out what remains unclear. We won’t solve a communication problem by finishing a document that the people affected haven’t seen, discussed, or had any input into.
We’re still in the middle of this. We’ve yet to resolve every ambiguity and still have several individual raise and promotion conversations every week. People are still confused. The defined career paths is our attempt to clarify how to advance here, and we hope it will resolve these opposing tensions and confusion.
The work is forcing us to make decisions we had previously left undecided. When you’re building an agency, you spend years winning business, delivering work, hiring people, and keeping the company moving. If you’re lucky, you build a meaningful business, and often that happens well before you finally get around to fully defining how someone builds a career inside it.
If career conversations in your agency keep ending in frustration, reply directly to [email protected] and tell me which expectation has been hardest to define.
~ Erik
About
Erik J. Olson is the Founder and CEO of Proxa, where he builds and operates multiple marketing agencies focused on predictable, system-driven growth. He has scaled agencies across multiple markets by replacing fragmented execution with structured systems that drive consistent revenue. Erik is the author of Million Dollar Journey and writes The Business of Agency newsletter. He is building Proxa into a $100M platform with a planned private equity exit.
