The Difficulty of Delegation

Many entrepreneurs have a tough time with delegation, particularly at the beginning. When you’ve been doing it all alone for so long, it can be really difficult to bring someone else in to help you. But if you want to scale and grow your business, it is an essential part of growth!

When you hire someone, you are hopefully hiring them because they know something or can provide a service that you cannot. Maybe you just don’t have time to do it any more, or you struggle with one aspect of it, so you want it off your plate. That’s totally fine and normal, but I’m seeing a LOT of people struggle with the step after someone has been hired and mostly integrated into the fold.

There’s always going to be an imbalance at the beginning- you’re bringing someone new into your business, your world, and you need to show them around, let them get a feel for what you’re trying to achieve, and perhaps you have to give them their day to day duties. You are in charge. But at some point, the relationship should transition and the person that you’ve hired should become someone to whom you listen and exchange with. This transition has been a pain point for a couple clients in my history and I wanted to share my observations.

When I come into a new contract, I spend a few days reading the client’s pages and profiles, asking questions, and filling out my own guideline sheet of how to handle the duties I have been set. Then I start making suggestions, small changes, and maintaining simple tasks like inviting people to like the page or following relevant profiles. These things never really cause a stir. But when I start to write posts, answer messages, or take over other, larger duties, the troubles begin. What I ask for from my clients is feedback: if they don’t like something they can talk to me about it and we can decide what needs to be done differently next time. Most of the time, I don’t get these conversations. This can very quickly make the business relationship untenable to one side or the other, and it stems from three major problems:

·         Being unable/unwilling to communicate

·         Being unable/unwilling to let go of control

·         Being unable/unwilling to trust

Notice that I have marked them all as unable OR unwilling- because I know that the people I am dealing with are not trying to be rude or uncooperative- sometimes they genuinely don’t have the skills needed to work with another person on their business or project.

So how do we identify if we are struggling with any of the above problems? And how do we solve them? I have a few suggestions:


Identifying the problem: Are you and your new hire communicating at least once a week? Do you ask any questions of them? Do you talk to them about what you liked or didn’t like in their recent work? If you answered no to any of these questions, you may have a communication problem.

Solutions: Schedule time to talk with your new hire, even just once a week for a few minutes. During this time, make sure to ask them if they have all the information they need, and what they are currently working on for you. Try to fit in one piece of feedback, be it positive or constructive. HINT: Positive and constructive are your only two options for a reason!


Identifying the problem: Do you correct or change your new hires work on a regular basis without talking to them about it, or before the task is complete? Do you find that they execute a task in a way that makes you anxious? Do you tell yourself “it’s just easier if I do it”? If you answered yes to any of these, you may have a problem letting go of control.

Solutions: Ask your new hire to tell you why they execute tasks the way they do and really listen to their response. Walk away when you can and let them handle the task. Resist the urge to correct work immediately, rather think of what you want to be different about the same task in the future and find a way to communicate that to your new hire.


Identifying the problem: Do you feel like you have to tiptoe around your new hires, or behave in a particular way so they won’t know that you’re observing them? Do you feel the need to hide information or thoughts from them? Do you feel that your business cannot possibly do without you helming the tasks you previously decided you could hire out? If you answered yes to any of these, you may have a problem with trust.

I must clarify that if you don’t trust someone because you feel they are stealing from you or something equally significant, you should NOT be working with that person. But does the trust issue lie with them, or with you? An easy way to identify if it’s about them is to think if you have these feelings about other people in your life and business regularly. If it’s a one off, it could be a sign that this person is in fact NOT trustworthy. But if you feel this way about multiple people, regularly, with no big reason, then you may indeed have a problem with trust.

Solutions: Try to get to know your new hire- ask them questions about what they want from working with you, what they see for the future of the business, and what they want from their own life. If you form a bond with them, you are more likely to trust them.

The bottom line is that the person you hire won’t stick around unless you accept what they want to contribute to your business. And their potential contributions are why you hired them in the first place! My mission may be to help people, but it’s not to teach those around me to respect me. That should be where we all start from- respect. Respect your new hires and expect their respect in return!