delegation struggles

Delegation Struggles: Working with a Team

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Ryan Cassin

delegation struggles

Leaders understand the power of delegation.  It catalyzes business growth and provides space for personal freedom.  Even so, many entrepreneurs struggle with delegation.

Why? Three main factors lead to delegation struggles:

Let’s discuss teamwork. Do teamwork struggles prevent you from successful delegation? 

Challenges of Working with a Team


Working with others can be complicated, and the process can inhibit delegation:



Many leaders understand that delegation, when implemented effectively, can accelerate growth.  But the less-than-ideal experiences they have with delegation leave them disillusioned.

The power of delegation is not in IF you delegate, it is in HOW you delegate. 

Delegate with structure and intentionality.  You or your Superpowers Assistant can design a simple template to provide your team when you delegate a project.  The form should address:

  • The purpose of the project
  • Success criteria for the project
  • Any deadline expectations

In addition to an explanation form, clearly late out communication expectations for delegation.  Open lines of communication alleviate stress when delegating important tasks.  When your team knows your expectations for what and when to communicate, they can seamlessly keep you informed about progress and the choices they are making.

When you set your guidelines, delineate:

  • What details you want to know
  • How often (or at what points) you want updates

Rethinking Teamwork


I just need to hammer it out. It’ll take more time and effort to explain things than just to do them, and I can handle it myself.

Initially, this may be true. But as your company grows, you cannot do everything. Don’t be a bottleneck to growth.

Pro tip: When you need to delegate a task, record a video of yourself going through the process once, explaining any necessary details.  Have your assistant process the video and provide it to any future delegates.


I have a hard time communicating what I want to my team.  I ask for something, and it doesn’t match what my vision was.

Increases in efficiency are worth the initial struggle. Once you build your system for streamlining communication about expectations, the process will pick up and the rewards will begin rolling in.


Everything moves slower when I delegate things. They get stuck, I don’t know where things are at, and it just gets way too complicated.


Remember that your time is limited. You may do some tasks more efficiently than others for now, but if you do not delegate, your organization’s growth cannot outpace your time constraints.  If you put in place your communication protocols and set your team free to do their best work, unprecedented growth will come.



Is it time to strengthen or begin your delegation journey?  It is time to start building your team? We have something helpful for you!

At Superpowers, we want to connect you with an Executive Assistant who is a custom-tailored fit for you—your number one delegate.  Book a Discovery Call today to learn more about your Superpowers Assistant.


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