5 Things Sh*tty Bosses Taught Me

E.J. Zain
3 min readMar 10, 2021

I’ve had a range of jobs. Some good, some bad. Then I became a boss.

I’ll get right to it, I’m not the best employer. I’m also not going to win the employee of the year award. In my youth, I was a terrible employee. I got better in my twenties. I’ve also had some shitty bosses who would make any employee want to quit.

I’ve taken emotionally brief notes to myself over the course of each job I’ve come away with 5 things I feel are the most important for small biz employees, but it’s applicable on a larger scale.

  1. Check-in with them regularly. No communication leaves room for anxious minds to go astray. You don’t need anxiety in your business. Be honest about your business, but also ask them how they’re doing. Then, this is the hardest part: LISTEN UP.
  2. Support them in education. If there are things they want to learn, that they’ve expressed interest in, see where you can meet those needs. Employees have dreams too. They’re not all self-starters. For many, it may be the first time they’ve ever had ACCESS to talking to a business owner. You heard me right. Many kids, especially, don’t have ACCESS to people like YOU. You may have that business mind to share expertise or know a corporate accountant who can do an hour of pro bono to help your employee grow their own business in confidence on the side. Don’t be greedy, encourage their hustles! Many re-entering the workforce could use some help to navigate too. Take the time to show them some tools or arrange for dedicated time if everything else in their resume is up to snuff. I’ve preferred teachable applicants over experience.
  3. Don’t make them lie for you. I once had a boss who made me lie to people, and it really threw me for a moral dilemma loop. I also discovered that I was expected to lie when I said I didn’t feel comfortable doing it and then discovered the story he told me about a contractor was false — he was withholding payment just because he knew they wanted the business associated with his family name. Looking back, it reeks of ol’ boy tactics. I don’t prescribe to ol’ boy tactics.
  4. Don’t pressure them about their “outside of work” lives. Don’t expect them to put aside their time with their kids just to shoot 200 emails for you. No one reads emails on a Saturday, anyway. (well, I still do) Respect their time or do your own work. You’re never too good to do that
  5. Just don’t be shitty. Period. If you can’t look your kid in the face and say “Son, this happened today at work,” or “this is the decision we made as a board,” then maybe you need to rethink what the hell you’re doing. I realize these may be lofty reaches for some, if they are, don’t expect people to work well for you, continue to be shitty. I once had a project I was in charge of and a new Chief Architect came in. He told the CEO, who was his friend, basically that he did not want to be debriefed by a subordinate woman. I wish I was joking.

When all’s said and done, it’s profits, I know, but what I’m saying is, profits suffer along with your employees. You won’t make them all happy or we’d not have disgruntled ones. And when and if you do (if you’re in business long enough, this is inevitable) you can at least rest knowing that you tried. Ultimately, that’s what matters most, putting in the effort whether it pays out. Know that you’re teaching directly or indirectly good or bad things to potentially transitory people in your life who may give you a side-eye to your face but an angry emoji in their mind. They may also give you a forced smile, but be so let down you wouldn’t know it because they need to pay their bills. It all reverberates into the rest of the world whether you see it with your own eyes. In such a transactional society, be better and rise above the expectation that because you sign their checks, you own them.



E.J. Zain

Entrepreneur and writer based down South. Spinner of tales and learning addict. Always got time to talk biz, art, life and love.