How To Avoid (Another) Horrible Boss

A version of this article previously appeared on Inc.

Someone on Quora recently asked me to answer the following question: How can I avoid repeating the big job disappointments of my past? This caused me to ponder some of my career choices. As I thought about my past career missteps, I had to admit to myself that in each case there were clear warning signs that I chose to either discount or ignore entirely.

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It's Not Me, It's You

Nearly everyone ends up with one or two bad bosses during their careers. However, if you are repeatedly working for miscreant managers, you should stop blaming your bosses and examine your boss selection methodology.

Below are a five suggestions that may help you avoid another unhealthy career move.

1. Try Before You Buy - If possible, perform ad hoc projects for your prospective employer part time during the weekends and evenings. I did this twice in my career and it allowed me to assess the people, culture and veracity of the company's value proposition before I joined full time. Although this tactic is not practical for everyone, it is a highly effective way to minimize career mistakes.

2. Boss Reference - Your potential boss will check your references. You should do the same. Although it is clearly inappropriate to ask your new boss for a list of referrals, you can readily devise such a list on your own via LinkedIn.

Speak with people who formerly worked with or for your potential boss. Even if the reference did not work directly with your future manager, they may still have valuable insights that would otherwise be impossible for you to uncover during the interview process.

You should also have coffee or lunch with one or more employees of your prospective employer. Ostensibly, your purpose is to learn general information about the company, its culture, etc. However, use this opportunity to discover as much about your potential boss as possible, without appearing creepy.

3. Bad Hires - Ask your potential boss about former employees who were not compatible with her work style. Assess the manner in which your would-be manager describes the process by which she fired these employees. If she is sympathetic and takes ownership of the employees' failures, then she will likely be empathetic with you as well. If she becomes defensive and/or demeans the terminated employees, you should expect a similarly negative reaction should she subsequently find fault with your performance.

This conversation might also make it easier for you to identify and speak with some of the terminated employees. Although you may have to filter their input through a prism of bitterness, their feedback will no doubt be additive to your overall decision process.

4. Matching Patterns- As discussed in Is Your Startup More Like Russell Brand Or Bruce Willis? institutional investors utilize pattern matching to minimize their mistakes. You should also identify patterns when assessing a new job opportunity. For instance, consider your past incompetent supervisors. How did these horrible bosses mask their personality flaws during the recruitment process? Were there signs that should have alerted you to the trouble ahead?

5. Make A Job - The only way to ensure you will never encounter another bad boss is to call upon your inner entrepreneur and make a job, rather than take one. Although you will not have a formal boss at your startup, you will remain accountable to investors, partners, customers and your employees. The pressure from these stakeholders may cause you to wish that your biggest problem was a difficult boss.

Silver Lining

Although bad bosses suck, you can learn a great deal from them. In fact, my managerial skills were greatly enhanced after working with one particularly horrible boss, as he reinforced what not to do when attempting to motivate and manage people.

Even though a bad-boss experience can be enlightening, it is best to avoid incompetent managers by doing your research, having the courage to ask awkward questions and speaking with people who have first-hand experience working with your prospective boss.

Ultimately, as described more fully in Advice For Emerging Entrepreneurs (And Anyone Else With A Boss), if you have a problem with your boss, you have a problem, not your boss. You can either attempt to resolve the issues or move on in your career. Assuming your boss will accommodate you is an unrealistic, losing strategy. Thus, if you currently find yourself in the clutches of yet another dreadful boss, force yourself to honestly answer this question: "Why did I agree to work for this cretin when I could be working for an awesome boss?"

Follow my startup-oriented Twitter feed here: @johngreathouse. I promise I will never tweet about butterflies, kittens or that killer burrito I just ate.

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John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.


Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.





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