1. Unclear Message
Instructions need to be clear. I think all of us have been in the situation where we have performed a task, only to find that we misunderstood the instructions and the job had to be redone. In any communication both parties are responsible - the sender of the message must ensure that the recipient received the message, and the recipient should make sure he understood the intended instruction. It takes time, but the sender needs to ask the other to repeat the message, to see if he grasped it. If he does not, the recipient could repeat the message, and ask if he has heard it correctly.
2. Message Overload
It is probably a good idea to write down a list of tasks, or at least to divide them up into some logical order, or half the message will most probably be forgotten. Association is a good way to help ensure that the message is heard. For example, "I would like you to contact Bob, Jill, Greg, Sue and Dave as I need them to come to the meeting on career planning on Tuesday; then if you could arrange for me to be booked on a flight as early as possible on Monday morning - for the Conference at Cabana Beach. I also need to discuss the budget with Mark, Steve, Ray and Alan, so would you please set up a meeting with them before year end." This is a lot of information to remember, but has been broken up into three categories, and made easier to remember because of the association attached to each task.
On the contrary, the shorter sentence "Please get hold of Bob, Jill, Greg, Sue, Dave, Mark, Steve, Ray, Alan and the travel agent for me" is more likely to result in someone being left out.
3. Bad Timing
If the message is not received, there was no point in sending it. So, choose your moment, and make sure you have undivided attention.