What Are Your Biggest Frustrations Working for an Entrepreneur?

Our previous blog shared part of the results of a focus group we held for support team across the country in a giant attempt to figure out where the disconnect lies between the boss and the team when trying to reach a common goal within a small business.  We shared in this blog what team member’s greatest joy was in their job.  Many business owners were surprised to see what really meant the most and connected to their support team.

In this blog, we are sharing with you the greatest frustration team shared.  We want to share our findings with you, not to scare you, but to inspire you.  We are hopeful you will hear the commitment of team with an honest, while respectful, cry for you to allow them to help you grow your business with joy and ease.  Team members and bosses speak two distinctly different languages, which often leads to disconnect even though both sides want to achieve the same goal.  Our hope with this blog series is to allow you an inside look into the thought process and voices of support team so you can better understand and communicate with yours. 

Are you surprised when you hear what team members think?  What we hope you notice is the massive about of “CARING” for the business, and your success, behind each of these frustrations.  Team members who are just collecting a paycheck typically don’t care if clients are mad or things aren’t done.  These team members care – intrapreneurs in an entrepreneur’s world.

What is Your Greatest Frustration Working for an Entrepreneur?
a. When I stop believing in my boss because I don’t have faith/trust that they will get it done.  I would not hire my own boss as a client. And I don’t like feeling that way, it is disheartening.
b. The entrepreneur won’t just let go and trust the key people in the company.  If he would I think things would run much smoother.  I realize it’s his baby and hard to do that, but crucial at some point in time for the best of the business.  That’s my biggest frustration. 
c. The business owner won’t get out of my way. I expressed my frustrations to him in the moment and received encouragement … then all downhill from there…things go back to the same.  I really am at a loss to get his attention and I really don’t think he would miss me if I left.  I can’t seem to communicate that to him without sounding “entitled” or risk being told “I’m a less than stellar performer”.  I say these words as a tear rolls down my cheek and I hate myself for that.  Those contradicting words from how I felt 6 months ago to now haunt me on a daily basis, every time I open the door here.  I am working a “job” right now because I’ve told myself I’m doing this for my family and to get my daughter through college.  It’s the only thing that eases the pain.  But, when she’s done with college and the BIGGEST reason is gone….. I’m afraid my heart will be more broken than usable as I look for the spark of passion every day. 
d. We are known as the “Last Minute Larry’s” and now we’ve all gotten in the “HABIT” of making that the standard/norm.
e. Letting the boss hire family; when the boss hires the wife, kids, extended family, etc. and there is no accountability in the business.  The team doesn’t respect them and will never say anything because they are afraid they will be out of a job. And it sucks for the spouse because they become the buffer because people will go “WHINE” to them hoping they will do something about it at home. Then the circular cycle begins.
f. Getting interrupted.  I am preparing documents, answering phones and keeping the calendar and everything else.  I will be in middle of drafting and the boss is always “shouting” out things to me and I lose track and mistakes happen. I don’t have 4 walls or a door around me so I am in the constant firing line and if something comes into his mind he has to interrupt me to tell me at that very moment, and everything goes downhill.
g. Lack of responsibility on entrepreneur’s part.
h. Getting my boss to focus on the top pressing cases.  I present the TOP 3 Gotta’s for the day, he will agree to it but then he will go hide out in email and not do what he said he would. Then sometimes things will linger out there for 2-3 weeks and the clients will be frustrated and screaming at me. At first I was hopeful that things would happen and now I just feel blown off, disrespected and don’t ever believe that he is going to follow through.  Then I have to lie and make excuses for clients.  I don’t lie. It is not o.k. with me to lie.
i. False Agreement. No matter how many times we remind them that they have priorities and they agree they have absolutely no commitment to it. They are just “YESSING” us to get us out of their office but they are going to go and do what they want anyways.
j. The Hero Complex. I am so excited at the start of the week when we have our TOP things identified that we are going to knock out of the ballpark this week. Then we have a sick or emergency client.  We will over care for them and over compensate to help them and drop all the other things, and everything else goes out the window. It’s a new distraction for the entrepreneur so they get to come out as a hero without any understanding of how they just wrecked the world of the assistants and other clients. Not to say we are not going to tend to our clients in need but the business owner will make it into a big social worker ordeal to do so they don’t have to “work” on the things they don’t like, They thrive in chaos and crisis.
k. Nothing is ever as easy as the entrepreneur thinks when they initially commit, and it is insulting to our intelligence. I feel like she thinks what I do and the value I bring is tasks that are simply “quick and easy”.
l. Trying to manage my schedule but I feel like I always need to go back to my boss to get stuff from them and I have to stand there until they finish it because I have no faith that he will ever complete it unless I hound and pounce, or eventually break down in tears.  Then I am appearing emotionally unstable vs. committed to the business.
m. They destroy their weekly calendar which in fact destroys ours.
n. Time management with the boss.  They are very unorganized and it’s very frustrating when they throw a curve ball into everyone else’s day.
o. Trying to close the loop on open items.  When you are trying to pin down the business owner and I have a deadlines.  I submitted the same thing four times and it keeps getting “lost” in her priorities and now I am in the red and can’t move this off my list and it looks like I am not getting MY job done. I don’t like feeling like I am not doing my job.

Are you surprised at what team members think?  What we hope you noticed is the massive about of “CARING” for the business behind each of these frustrations.  Team members who are just collecting a paycheck don’t care if clients are mad or things aren’t done.  These team members care – and that is invaluable.

Stay tuned for the 3rd, and final, series of this blog, “If there is one thing you could change in your business, what would it be?”

If you have a team you want to be honest, while respectful, with you about what isn’t working in your business consider enrolling them in the Don’t Be a Yes Chick tele-training series to participate in conversations such as these.  Next series begins September 4th – contact info@yeschick.com to register or with questions. 

To read Part 1 of this series – click here.

Champions of your continued success,

Molly and Laney

employee playbook


Everything you need to turn around your people, processes, productivity and profitability is right here in this free e-Book.


Feel like your people—and their productivity—are a mess? Don’t worry, this book has your back! Download this book for free and follow our advice about how to empower your employees to step up and lead!

You have Successfully Subscribed!