50 Things Keeping You From Scaling Your Agency

50 Things Keeping You From Scaling Your Agency

Having been an agency owner for over fifteen years, I occasionally reflect on the past and relive situations and scenarios, asking myself: what if I had made a different decision or what if I had behaved differently?

I do this not to dwell on missed opportunities or to fill myself up with regret (although there are twangs of pain) but to remind myself that looking ahead, it's firmly in my hands to do things better and to avoid making the same mistakes again.

It's in this spirit that I decided to jot down a list of 50 items that I felt have been blockers in helping me scale our agency. Where available, I've linked to blog posts I've written on some of these topics.

Without further delay, let's jump to it:

The List

  1. Your time management skills are lacking.
  2. You have unresolved issues with your co-founders and/or partners.
  3. You’re quick to blame others when things go wrong.
  4. You’ve not yet built a system to properly qualify clients. You don’t say “no” to enough poor fit prospects.
  5. You don’t have well-documented and repeatable processes. You end up “reinventing the wheel” on similar projects.
  6. You don’t know how to manage scope creep and give away too many freebies.
  7. You are afraid to provide clear feedback to your team members.
  8. You are afraid to ask your employees for feedback.
  9. You are afraid to ask clients for feedback on your agency’s performance.
  10. You don’t have a streamlined process for recruiting and hiring talent.
  11. You don’t have a proper onboarding process for new hires.
  12. You don’t have a clear vision or mission and/or these have not been clearly articulated to the team.
  13. You have not defined key metrics to track the performance of your business.
  14. You don’t have regularly scheduled, well-planned meetings with team leaders and only meet on an ad hoc basis.
  15. You don’t have a clearly defined org chart with roles, responsibilities, and direct reports mapped out.
  16. You don’t have a performance management process to evaluate and develop your employees.
  17. You don’t proactively invest in your team’s professional development.
  18. You don’t have a system for helping employees navigate career paths and career development at your company.
  19. You don’t have a clear way to measure profitability on your projects.
  20. You don’t have clearly defined statement of work with your clients.
  21. You don’t have clearly defined end dates on projects with your clients and allow projects to drag on without consequence.
  22. You don’t have a finance system that allows you to understand your company’s financial health and cash flow situation.
  23. You, as the owner, are essential for client engagements to succeed. You haven’t found a way to step away from day-to-day work.
  24. You don’t have a clear sense of your target audience and/or specialty and are prone to trying to be “everything to everyone”.
  25. You don’t keep a centralized database of business contacts and deals in a CRM.
  26. You don’t engage in any marketing for your agency.
  27. You haven't invested time or resources into growing existing client relationships and instead are always looking for the next new client who has a new project.
  28. You haven’t learned to let go and trust your employees with key responsibilities.
  29. You don’t make time for yourself to think and write about the long-term vision for your business.
  30. You’re afraid to have conversations about money with clients.
  31. You’re afraid to have conversations about salary and compensation with employees.
  32. You're afraid to make tough personnel moves even though you know it's the right thing to do.
  33. You embrace the mentality of "if it ain't broke, don't fix it" when it comes to processes and upgrading to new technologies.
  34. You have numerous pet "internal" projects that suck up the team's time
  35. You don't have a great post-project debrief process that lets the team discuss and document lessons.
  36. You haven't put in the effort or invested resources to expand your services offering.
  37. Your personal energy level is volatile and often running low.
  38. You have a lot of distractions and drama outside of work.
  39. You’re not much of a book reader and seldom read books on business.
  40. You've told yourself that you don't want the company to get bigger and have to deal with more people.
  41. You're afraid the quality of your agency's work will decline if you get bigger.
  42. You don't invest in marketing your agency as an attractive employer to potential recruits.
  43. You haven’t set up or secured funding sources to help with growth (e.g. line of credit, other forms of debt, cash reserves, investments, etc.).
  44. You’re hesitant to seek mentorship and advice from others who’ve scaled their businesses.
  45. You make hiring decisions based on short-term need rather than carefully considered growth plans supported by new business.
  46. You’re always complaining about being in too many meetings and not having enough time to think.
  47. You believe your personal involvement is essential in order to win new business for the agency and you can only win new business that comes from your personal network.
  48. You skimp out on software licenses and other essential tools for team members in order to keep costs down, often creating friction for your employees’ productivity.
  49. You haven’t set up clear policies and don’t have a central document that address employment topics ranging from paid time off to workplace behavior and other HR matters.
  50. You don’t think you have it in you to scale an agency business.

The Themes

If I were to tease out the primary themes from this list, they would be the following:


The unwillingness to confront and face tough decisions and difficult conversations (with clients, business partners, employees) may help avoid short-term pain but will stunt progress in the long run. Fear of confrontation, fear of being wrong, fear of failure – these are all emotions that nudge us to find evasive maneuvers, but deep down, we all know that for true progress, we have to face the pain.

The other fear that is prevalent is the fear of letting go and the fear that trusting someone else will lead to failure. This fear, which is wrapped up with one's sense of ego–that only the owner is qualified or capable of doing something right–is a major obstacle when it comes to scaling. The fear leads to constant micro-managing, which in turn prevents the growth and development of employees, and which ultimately leads to a vicious cycle of underperformance and attrition due to frustration and mutual distrust.

Lack of Discipline

It wasn't until I was nearly a decade into running my agency that I truly grasped the importance of discipline in being able to lead a company. I used to rely on big last-minute pushes spurred on by deadlines or the adrenaline of crisis situations to get things done. Day-to-day, I paid little attention to sleep, my energy levels, diet, and other behaviors. This led to volatile moods, lack of followthrough on important but non-urgent matters, and a general sense of inertia unless things absolutely needed my attention. 

Embracing discipline through deliberate habit-building, reliable routines, and consciousness around diet, fitness, sleep, and reading helped turn things around in a big way. My sense of time and what felt "feasible" as weekly to-do's completely changed – I had the energy to do the hard things right away and to feel good after a long and intense week of work. There was no need to self-medicate with alcohol or mindless TV. Working on myself has been one of the best ways to work on the business.

Lack of Systems & Processes

Operating in fear leads to being in a reactive mindset, which makes it hard for an agency owner to focus the mind on designing and building out processes for the company. This is deep thinking work that requires patience, communication, experiments, and adjustments to get right. But if most of the day is spent on reacting to unexpected fires, micro-managing employees, or unnecessary meetings, it'll feel near impossible to "find time" for systems and process work. 

The adage "work ON your business and not IN your business" is all about creating a collection of systems and processes that work together to reduce mental load throughout the organization and to streamline decision-making processes. An organization that can continue to optimize its systems and processes will have an easier time scaling up.

Start With Yourself First

The most important lesson I've learned in my 15 years of running an agency business is this: focus on becoming your very best self before all else.

Your health, your energy, your relationships, your belief in your abilities, your vision, your skills, and your confidence are what ultimately influence the decisions you make and the path you set for your business.

Good luck.