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Mastering the Art of Delegation

Delegation isn’t something that comes naturally to everyone.

Like other crucial leadership skills, delegation requires practice and strategy, and it’s not something entrepreneurs excel at overnight.

It can be especially challenging when you begin delegating for the first time. Perhaps you’ve been a solopreneur for a while, diligently building your company and doing everything yourself.

When your business grows and it’s time to start delegating, it can be difficult to let go—after all, you’ve built the ship from scratch, and handing over the helm sounds risky.

With some practice and the right techniques, however, you can be delegating in no time. Here are some tips to get the most out of your working relationships with assistants and employees to set yourself up for success as you continue to scale and grow your business.

1. Communicate Your Expectations Right Away

Before you start on any project or begin a relationship with an assistant, it’s vital to begin by setting expectations. There are several areas you’ll want to focus on while setting expectations.

  • Availability: How many hours a week do you expect your assistant or employee to be available? What hours do you want them to work? It’s especially important if you’re working with a remote worker or someone you won’t be seeing on a daily basis to make these availability expectations clear from the very beginning. Having this conversation early on will also help you ensure you’re not wasting anyone’s time: if their availability doesn’t meet up with your needs, it’s not a good fit.
  • Turnaround time: How quickly do you expect responses to emails, Slack messages, or phone calls? Some tasks may require quick turnaround times, while others can be completed within a window of time. Make sure your assistant knows what your expectations are here, and be sure to ask what they’re able to provide, as well.
  • Quality: The third thing you want to communicate clearly is your expectations for quality of work. Of course, quality can be a subjective thing to measure and expectations can vary widely. However, it’s best if you take the time to show examples of the kind of product you’d like to see. Some projects may require a high level of detail, accuracy, and attention, while others will be lower-priority tasks. Be clear, and when in doubt, over-communicate what you’d like to see rather than leave it up to interpretation.

2. Establish Guidelines for Communication

The second technique for efficient delegation is to set up communication guidelines with a tiered system. In other words, let your assistant know how you’d like to be communicated with based on the importance of the information.

You’re probably going to be communicating often by email. However, there are dozens of other communication options like Slack, text messages, phone calls, project management software notifications, and more. Establish early on your preferred tiers of escalation for communication. For instance, email may be what you choose for day-to-day communication and matters of typical urgency. However, if an important issue comes up that requires a fast response, you may ask your assistant to respond or use Slack, text messages, or phone calls.

You might tell your assistant, for example, “Let’s use email and Slack for day-to-day communication, and you can tag me in Trello to keep me updated on our ongoing projects. If a client needs immediate assistance, however, text me and then call me if I don’t respond within an hour.” Make sure your assistant also knows what to expect from you: will you call to shoot the breeze, or will you reserve phone calls for time-sensitive communication? Whatever system you set in place, make sure it’s mutually agreed-upon and clear.

3. Be Willing to Collaborate

Finally, one of the most important things to do to ensure smooth delegation is to maintain a willingness to collaborate. I cannot stress enough the importance of this.

When you hire an assistant, it’s really easy to think, “I’ve arrived! Time to start offloading things from my plate—delegation is so amazing, I don’t have to do these tasks anymore.” The truth is far more complicated than that. Collaboration is the key ingredient that makes delegation work.

Collaboration is important on an ongoing basis, but it’s essential when you’re first getting started. I recommend going into the relationship knowing you’ll need to collaborate and setting aside time to do just that. There’s always a learning curve with new team members, but clearly set expectations and collaboration will make the transition easier!

Collaboration Tools: Loom, Zoom, and Google Apps

Collaboration can be made more efficient with a few tools, particularly if you’re working with a remote assistant. I recommend using Loom, a free screen recording app, to make collaborating easier. You can record training videos, give feedback, or share important information straight from your browser with Loom. Loom lets you work like you’re sitting in the same room with someone and makes it easy to up your collaboration game. You can also use video conferencing tools for meetings such as Zoom, making it easier to share screens and work together on projects.

Google apps such as Google Docs and Google Sheets are also ideal collaboration tools. Shared documents like this allow you to track changes, share comments, and tackle projects together, no matter where you are in the world.



Need Help Delegating? We’re Here.

Delegation is hard, but we’re in this together. With the right techniques and strategies, you’ll become a delegation pro over time.
Are you ready to get some work off your plate?

Amber Gray

Amber Gray is the founder and CEO of Trusty Oak, an Austin-based virtual assistant company providing administrative and marketing support to small business leaders, authors, and creative teams. A people-first approach to hiring, along with a scalable growth model have positioned Trusty Oak as a flexible, dependable, and affordable alternative to hiring administrative and marketing employees. In 2021 and 2022, Trusty Oak was named Freelancer Hiring Platform of the Year, and in 2021 Amber was recognized as Austin Business Woman of the Year.

Before founding Trusty Oak, Amber spent five years at a rapidly growing digital agency based in Austin, TX. Four of those years, she was responsible for hiring and leading both local and virtual teams while working closely with clients ranging from CEOs to bestselling authors to build their brand online. As VP of Operations, Amber helped lead the company’s growth to #15 on Austin Business Journal’s Fast50 List in 2014.

As a female founder and leader of a company that has quickly established a recognizably special culture within a non-traditional workforce, Amber has energized and empowered women from diverse professional and personal backgrounds to go against the grain of historically standard female roles in business, technology, and leadership. Trusty Oak provides an opportunity for experienced admin and marketing professionals to work independently as freelancers, but with a supportive internal network consisting of other ambitious and resourceful remote workers.

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