One of the most difficult challenges for any entrepreneur is learning how and when to delegate tasks. In the beginning, there was no one to hand tasks off to. You were the head cook and bottle washer. The buck literally stopped here. As your entity grew, you convinced others to join you on this merry quest because you knew the work could no longer be handled by one person. Unfortunately, no one told you how difficult the act of handing over tasks was going to be. Why is it so hard to delegate?

As entrepreneurs, we are used to burning the midnight oil in order to get things just right. Time is not relevant as we are driven by the outcome. Once a reliable conclusion is reached, why would we go back and do it again? Many of us are perfectionists and cringe when a task is altered in some fashion.

By the way, "perfectionist" is just a really nice synonym for control freak. I've come to realize that control is a sizable barrier to doling out tasks. I would also suggest that there is a great deal of fear involved. What if they do it wrong? Even worse, what if their way is better?

The title of this article comes from a lightning rod moment I experienced when reviewing a Brian Tracy video on YouTube.As some of you know, Brian Tracy is productivity expert made famous by his book, Eat That Frog: 21 Ways to Quit Procrastinating and Get Things Done! I have made a couple of references to him in past articles on management and working with employees. If you haven’t been exposed to his work, I highly encourage you to look him up. This concept was explained during a segment on prioritizing tasks.

When determining what tasks to delegate, you have to ask yourself if the activity is below your pay grade. If you are a manager making $35 per hour, why are you doing $10-dollar-an-hour work? Isn’t it really cheating your employer out of 25 bucks an hour? Ouch. That stings a bit.

Although many of us don’t have a boss, per say, there are plenty of people we are accountable to. In some cases, there are shareholders or financing partners. In most cases, it is as simple as accountability to a spouse or family. We owe it to all of them to be focused on high level work versus taking a mental holiday on the lower pay tasks.

Trust me, I am not being disrespectful to those who should be completing these tasks. On the contrary, they are the backbone of any working entity. And someday they will be the one’s struggling to delegate tasks.

Beyond the control aspect, there is a perceived time barrier to handing over tasks. How many times have we heard this: “By the time I get done explaining it, I could have done it myself.” This is probably true. It will take longer to teach someone else how to perform the task than to just do it yourself. You know how to do it; they don’t.

If you can’t be burdened with teaching a task, then you will be shackled to the activity forever. Hope you like spending weekends at the office.The real reward comes down the line once your team member has the ability to take ownership of their task. Now time is on your side.

Gaining time to work on more meaningful projects is a positive outcome, but that isn’t the only benefit of effective delegation. By handing more and more work over to those in your employ, you can actually improve morale. It hardly seems possible that giving someone more work would improve their sense of well-being, but it can do just that.

When a person is given responsibility for a task, there is conveyance of trust associated with the hand off. If the person can improve upon the execution of the task, then a building of confidence will follow. As we delegate increasingly complex tasks, the person’s skill set is broadened. Exposure and execution of tasks once thought to be the work of management can ultimately lead to a promotable individual. Isn’t that what we want for all members of our team?

In order to delegate effectively, you first have to take a critical look at your daily task list. What is taking your time? If you haven’t done this in a while, it will probably be enlightening. Review the tasks and prioritize. Which activities will have the most meaningful impact on your organization? Obviously, these are the ones we need to focus on. As managers, or owners, these are the ones we are paid to tackle.

Conversely, what tasks could easily be handled by others? Go a little deeper. With a little coaching, what additional tasks could I hand off? Now you are ready to buy some time.

Who, what, why and how are critical elements of delegation. We have already tackled the what and why, but the other questions are equally important. Choosing the right person will help make the handoff easier. If you need to have someone create some spreadsheets for data analysis, a sales-minded individual is your best pick. Make sure the task is in alignment with your candidate’s ability. Otherwise, you will get the task right back and wreck a perfectly good team member in the process.

Start with smaller tasks and match them up to your newer folks. As each task is mastered, you can start adding more complex tasks. Don’t be afraid to test them a bit. Go ahead and challenge them. Some of these seemingly green recruits will surprise you. Make sure that you delegate the whole task. Giving the employee bits and pieces will just force you to come in and complete the project. Nobody wins in that scenario. Many of your newer employees are a vast untapped resource of creativity. Let them find the logical conclusion.

Finally, learn to be a good teacher. Remember, knowing and teaching are two completely different actions. Patience is the key to building confidence in your newer folks. Are they going to make mistakes? Sure. I don’t know about you, but I tend to learn better with a few bumps and bruises.

Clarity is critical to controlling the outcome. Be clear in your direction and don’t be afraid to create a checklist for more complex tasks. Be sure to check in, but don’t micro manage. Consistent feedback will help folks understand your expectations.

Learning to delegate is one of the most difficult things any owner, manager or entrepreneur will face. Mastery of this skill will prepare your team for the next logical step – empowerment. I’ll leave that discussion for another day. If you need help, I am always here to listen.