From Chaos to Structure: Agency Evolution

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Do your employees have a clear path for growth within your agency? Do they feel supported, empowered, and fulfilled in their role? Today's featured guest shares insights from his journey transforming his agency team structure that resulted in thriving for the business, his team, and himself.

After years of struggle, this agency CEO took ownership of his role and developed a strategic approach to employee motivation and development. By reimagining annual reviews and creating meaningful growth opportunities, he shifted from an environment of stagnation to one of continuous improvement. In this interview, learn the benefits of offering a clear path for growth within your agency, and how to improve your team’s experience during annual reviews. He also shares how to get yourself out of sales — if that’s something you want — and why you need to keep doing what you love.

Warren Wilansky is the president and founder of Plank, a Montreal-based digital agency specializing in arts and culture, nonprofit, and higher education projects. He shares his agency ownership journey and discusses the challenges of navigating the early days of the agency, including the learning curve of running a business and the evolution of his role as a sole owner.

In this episode, we’ll discuss:

• The mindset shift that allowed for team retention and growth.

• Redefining employee reviews and how to have them review you.

• Maintaining purpose as your agency grows.

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Sponsors and Resources

E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.

A Traditional Story of Accidental Agency Ownership

Warren’s journey is a pretty traditional accidental agency owner story. Starting with a communications degree, he transitioned from freelance website design to founding an agency with two partners. However, the partnership proved unstable—one left after six months, and the other departed after five years, ultimately leaving Warren as the sole owner for years, until his first employee became his current partner.

Initially, Warren viewed his agency more as a collaborative collective among friends rather than a structured business. This perception shifted dramatically when his second partner departed, forcing him to fully embrace his role as a CEO. For the first time, he recognized the need to take complete responsibility for every aspect of the agency.

While continuing to engage in website design—his original passion—Warren realized that his most critical project was the company itself and its strategic development.

A Mindset Shifts that Allows for Employee Retention and Growth

As he navigated the early stages of his agency, Warren quickly recognized the importance of hiring people who could outshine him in their respective roles. For instance, the agency hired its first creative director once he discovered someone who was a better designer than he’d ever be. This realization marked a turning point in his business strategy. Instead of attempting to be the best at every task, Warren embraced the idea that the success of his agency depended on assembling a team of skilled professionals who could bring their expertise to the table.

Another important milestone in his hiring structure was the introduction of director-level positions. Initially, Warren adopted a model where all team members were viewed as equals, believing this would promote collaboration and creativity. However, he soon realized that this lack of hierarchy left employees with limited opportunities for advancement. Without clear pathways to grow within the organization, talented individuals often felt stagnant, leading to disengagement and, ultimately, turnover.

A structured hierarchy with a path for career progression allows individuals who excelled in their roles to take on new challenges and responsibilities. It also serves as a chance for team members to figure out whether they liked the feeling of running a company, fostering a sense of ownership and accountability among team members.

Redefining Employee Reviews - and Having Them Review You

Most employees have a love-hate relationship with the annual review. On the one hand, they fear the feedback but on the other they also await the meeting in order to discuss a raise. At Warren’s agency, the team conducts annual and quarterly reviews for more regular check-ins.

Although they’re still called “reviews” at Warren’s agency, Jason’s advice is to change the term to something that doesn’t evoke feelings of judgment and scrutiny, redefining this process by labeling it as a "coaching session." This emphasizes the supportive nature of the interaction, framing it as an opportunity for development rather than an evaluation of past performance.

Overall, the biggest challenge is finding the right balance of positivity while still offering areas of improvement without demotivating employees in the process. As Warren points out, traditional reviews often begin with critiques, which can overshadow positive feedback. By reorienting the conversation to highlight accomplishments first, followed by constructive suggestions for improvement, employees are more likely to retain and act upon the feedback provided. In addition to reviewing your team, as a CEO or founder you should also want to know your areas of improvement. It can be hard getting that information out of employees, who might feel intimidated. A good framing to get the information you want is to ask "What do you want me to start doing?" "What do you want me to keep doing?" and "What do you want me to stop doing?" In this way, you will get provide enough context for valuable insights without putting your team in the awkward position of formally reviewing you.

Agency Sales: Freeing the Founder & Empowering the Team

As CEO, Warren’s current role is mostly looking for ways to support his strategy team, tapping into his network to bring more opportunities for the agency, and being the face of the agency. The CEO is also the person who has all the relationships and all the stories that shape an agency’s identity and are a great tool to converting a new client.

Having all the stories can lead a CEO to believe no one could possibly replace them in sales, after all, only they have the necessary narratives to engage clients. However, then the agency would fall apart if the founder ever decided to retire. Instead, if you can share those stories with your team to use on different case scenarios, you will free up your time to focus on the agency’s growth and empower your team to  share their own client success stories.

In the end, are the stories from 10 or 20 years ago the only ones worth telling in your agency? For Warren, the stories being created today are just as important and even more so. Instead of romanticizing old stories, give your team the chance to use them to engage clients as they gain experience instead of just selling on features. Eventually, they’ll have stories of their own and they will take full ownership of sales, which in turn will free you up as agency owner to dedicate to the business’ growth.

How to Maintain Purpose as Your Agency Grows

As CEO you should do what you love and delegate or eliminate the things you don’t. In Marc’s case, he enjoys sales, which he views as relationship building rather than a transactional process. He advocates for founders to carefully distinguish between tasks they love and those they want to delegate.

Completely removing yourself from sales can lead to professional dissatisfaction, so Marc recommends creating processes flexible enough to allow strategic involvement. While the team should be capable of handling most sales independently, founders can still contribute by joining initial or final calls to add depth and personal connection.

Just be mindful of the things you hate doing and want to delegate and the things that really bring you joy and wish to keep doing. Only with that clarity you’ll be able to prioritize and choose a path that won’t kill your love of the work.

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