The Trusty Oak Blog

This Leadership Skill Can Predict Success

Entrepreneurs and business owners are driven people who aren’t scared to work hard, burn the midnight oil, and sacrifice to make their dreams a reality. They’re skilled and ambitious, and frankly, they’re our favorite kind of people to work with. On the other hand, entrepreneurs often share the same Achilles heel: their greatest strength has a flip side that can be their greatest vulnerability. This strength is a work ethic that doesn’t quit; this vulnerability is the tendency to do it all alone.

Does this describe you? The drive that has taken you this far is becoming a liability as your organization grows; you can’t do everything anymore. You’ve reached the point where your workload is too much, and it’s a good thing—you’ve probably been dreaming of the day your company expanded beyond your ability to manage it alone. But now that you’re here, you’re finding it difficult to hand over the reins.

Ironically, many people don’t make the time to delegate. Carol Walker, president of consulting firm Prepared to Lead, says, “Most people will tell you they are too busy to delegate—that it’s more efficient for them to just do it themselves.” Of course, the clear problem with this mindset is that it’s a fallacy: it isn’t more efficient to handle everything yourself. Delegation frees up time, empowers team members to invest in their work, and improves outcomes. So why aren’t you doing it?

Delegation Made Simple

We understand—it can be hard to hand over the helm when you built the ship from scratch. Here are some tips to get you started.

1. Start Small

You don’t have to hand over the keys to the kingdom tomorrow to begin delegating. Identify someone you’d like to start delegating to and start developing a sense of trust. Hand off a small project to your assistant or volunteer, and truly let go. Let them take the lead and present their work for your feedback. Delegation is a skill like any other; it’ll take some practice before you’re good at it. Start small and work your way up.

2. Identify Your Strengths, Delegate Your Weaknesses

You’re good at what you do, and it’s gotten you this far. But you have areas where you’re not as adept—maybe it’s bookkeeping, marketing, writing, or answering the phones. Sit down and identify the areas you know you’re weakest in, and develop a plan for delegating them. Once you’ve handed these areas off, try to step back. It’s easy to micromanage when you’re invested in the final product, but it only creates workflow bottlenecks. Imagine following an electrician around while they wire your house—if you’re not a certified electrician, your feedback and management will only gum up the process.

3. Develop a Smart Workflow

Delegation shouldn’t be stuck on your to-do list; it should be part of your workflow. Develop a workflow with your assistant that includes procedures for handing off work and checking in on projects. An effective delegation workflow will free up time for business-critical tasks that you should be focusing on.

4. Let Go

The final and most important step of delegating effectively? Let go. As your business grows and you move from one-man-show to the head of a developing company, you’ll have to let go of tasks you once did yourself. It’s the hardest and most critical part of delegating, but mastering this art can predict your future success.

If you’re ready to delegate, give us a call. We’d love to chat about pairing you with a skilled virtual assistant who can take work off your plate. 

How it Works

Emily Fisk

Emily Fisk began her career in marketing after graduating from Boise State University with her B.A. in English, Rhetoric and Composition. Emily started freelancing as a writer and found Trusty Oak in 2016. Emily spent three years as a virtual assistant, helping clients build their digital marketing efforts, while taking on more responsibility as an account manager and marketing manager as Trusty Oak grew. In 2019, Emily took on the role of Marketing Director, and in 2020, she began serving as Trusty Oak's Vice President of Operations. Emily’s passion for clear communication, vibrant teamwork, and helping others find meaningful careers has made her a key part of Trusty Oak’s growth. She gets a kick out bringing Trusty Oak’s story alive and watching clients succeed. Under her leadership, the Trusty Oak marketing team has accomplished large-scale projects and numerous successful campaigns, undertaken new brand identity initiatives and launched innovative content. When she’s not working, Emily loves digging into a good book, cooking a delicious meal, and getting outside with her two daughters and husband. She lives in beautiful Boise, Idaho and is a founding member of a (totally cool, not at all nerdy) writing group.


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