Author’s Note: I learned the lessons in this article in the school of hard knocks. May those “knocks” make your life easier and your leadership more effective!

In the early stages of building a company, owners wear every hat. From sales and marketing to pricing, scheduling, and recruiting, they become the engine behind every function. This all-hands-on-deck approach is often necessary—but it’s not sustainable. As the business grows, so does the complexity of leadership. The real shift happens when owners move beyond delegating tasks and begin delegating roles—freeing themselves not just from doing, but from deciding what needs to be done in the first place.

At this stage, the owner performs many tasks and fills many roles. Approving payroll, signing checks, and creating estimates are tasks. Creating and executing the marketing and sales plans, being the financial leader (pricing model, reporting, profit margin optimization), and creating and executing the crew recruiting strategy are examples of roles. Tasks are well defined; roles usually require analysis, creativity, planning, and leadership.
As leadership expert John C. Maxwell put it, “If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.”

Delegating tasks is an important first step. However, the real value in delegating comes from delegating roles. When delegating a task, an owner is free from doing. When delegating a role, an owner is free from both thinking and doing because the person in the delegated role determines the tasks that need to be done to achieve a desired result.

Delegating in Five Steps
Here are five practical steps to help make this transition:

1. Inventory Your Tasks and Roles. Determining tasks is easy; create a list as you perform them. For roles, you might want to think about what executives and managers work at a $50 million landscape company. It is easy to see those roles by reviewing a company’s website or looking on Linked In. Small companies have the same roles; the difference is that people, including the owner, are attempting to fill multiple roles.
2. Begin to Delegate. Determine tasks and roles to delegate to existing employees.
3. Focus on High-Value Activities. Determine what you enjoy and where you excel – areas that have the biggest impact on growth or profit. Prioritize those roles and let go of the rest. You can also think five years ahead. How do you want to spend your time? That envisioned future helps identify what to delegate.
4. Your Next Hire. Determine what role(s) you would like the next management level hire to fill.
5. Outsource Strategically. Determine what roles can be outsourced to a specialized firm or a freelancer (contractor) through a marketplace like Upwork.

Outsourcing
Peter Drucker put it simply: “Do what you do best and outsource the rest.” That statement is true at the personal level as well as for the company. Outsourcing is the most overlooked opportunity for delegation.

When outsourcing roles, you will want to find people who are masters of their craft. Many owners have decided to outsource marketing and IT services. Clients of The Herring Group decided to outsource portions of their financial leadership (pricing, operational reporting, incentive plans and business strategy). The key to the successful outsourcing of roles is to make sure responsibilities and expected results are communicated clearly. When done well, the return on investment will be significant.

Marketplaces like Upwork provide opportunities to find freelancers for virtually any type of task and even some roles. Just post your project, review freelancer proposals, and choose the best fit based on profiles and ratings. Collaborate and pay securely through the platform by the hour or by the project. At The Herring Group, we have used many freelancers with great success. By leveraging freelance platforms, even a small company can tap into a vast network of professionals.

Ultimately, owners have a choice: they can delegate roles and grow, or they can keep their current roles and stop growing. What is your choice?

~ The author is the CEO of The Herring Group, a professional services and data analytics firm providing data and outsourced financial leadership to the landscape industry. We are on a mission to improve the profit margin of companies, the life margin of owners and executives, and the autonomy of employees.