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Whatever You Do, Don't Not Delegate: 8 Tips for Cultivating Keen Employees Delegating is the second-hardest thing for an entrepreneur to do. The hardest is not delegating.

By Matthew Toren

Go Gardening Soil

You know the saying, "it's hard to find good help"? It's a copout, and here's why.

If you hire people simply to do your bidding, that's what they'll do. And, in the process, you'll constantly field their questions or problems if anything out of the ordinary happens. It's all well and good to have an open-door policy, but if it feels like a revolving door, you may never get to your own work. The secret to getting the best from employees is understanding when and how to delegate.

For fast-growing startups that are, say, hiring a first, second or even tenth employee the nut of delegating can be tough to crack. But if you ever want to get eight hours of sleep a night again, it'll behoove you to figure this out now.

Here are eight ways for improving your delegating skills as your business grows:

1. Hire team members, not order-takers. When you hire people, look for those who are willing to take initiative and work independently. You don't want someone who expects the same level of training available in a large corporation. Ask probing questions to help ferret out their capabilities, such as: "Give me an example of a time when you had a project to accomplish and didn't know where to start -- what did you do first?"

Related: Are You Taking More Than You Give? 3 Tips for More Balanced Relationships

2. Delegate in stages. Even an employee with initiative can be overwhelmed if you dump lots of duties on them and then close your office door. Have new employees shadow you as you demonstrate how to handle various aspects of the job. Start small and increase responsibilities as the employee shows the ability to handle it. Strive to challenge an employee without expecting too much too soon.

3. Delegate responsibilities, not just tasks. Rather than assigning work to someone, give them the responsibility of heading up an area. For example, instead of giving your employee a list of customers to bill, have he or she manage billing. With your employee developing systems that work and troubleshooting problems, you will have more free time to focus on your own concerns -- and they'll feel empowered.

Related: The 6 Best Entrepreneurial Habits for Rapid Growth

4. Encourage initiative. One way to do this is to let your employees know that if they feel comfortable making a decision they should make it. Over time, their comfort-zones will expand and they will need to ask for help less and less. If you are not confident in your employees' ability to make decisions on their own, you've hired the wrong employees.

5. Accept mistakes. No matter how good your employees are, they don't have the knowledge and expertise that you have. Mistakes will be made. What's important is having everyone learn from them and move on.

6. Avoid blame. The magic words here are, "I don't care about whose fault it is, I care about solving the problem." Once your staff realizes that attention is on solutions instead of who "caused" the problem, the pressure to use CYA behaviors will diminish and real responsibility will evolve.

Related: Not a Superhero Entrepreneur? You'll Still Need a Sidekick

7. People do things differently. No matter how good your employees are, they're not you. They will approach their business responsibilities in different ways. Sometimes those ways may not seem as good to you, but as long as the job gets done professionally and to your quality standards, let go of the process. It's the results you care about.

8. Be prepared for happy surprises. When you hire talented people and give them autonomy, you will find out that they often find better ways to do things than you did originally. Enjoy this. It's not a challenge to your capabilities. It's a gift for your business.

What delegating tips would you add to this list? Let us know in the comments section.

Matthew Toren

Serial Entrepreneur, Mentor and co-founder of

Matthew Toren is a serial entrepreneur, mentor, investor and co-founder of He is co-author, with his brother Adam, of Kidpreneurs and Small Business, BIG Vision: Lessons on How to Dominate Your Market from Self-Made Entrepreneurs Who Did it Right (Wiley). He's based in Vancouver, B.C.

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