How To Find Out If Your Prospective Boss Is Worth Working For?

A good boss can make or break your career.

But it is not easy to find out if your boss is a leader or a typical manager, during the interview process.

A smart way to go about it is to identify the person you want to work with, and then try and find ways to work with her. This is more efficient than analyzing someone you met during the course of the interview and don’t have much info about it.

If you are reading this piece at a point, when you are already in the middle of an interview process then you can use some parameters to identify a leader or a good boss.

How To Identify A Good Boss

A good boss may not be a charismatic leader and still help you while you are in a job. But it helps if she is a leader.

So who is a leader? Someone who has followers. My pal and co-author Derek Sivers gave a short but insightful TED talk about this.

This out of our way, let’s look at some indicators that you can use to find out about your prospective boss.


Listen to your gut. See if your prospective boss is someone you’d like to follow. Do you like her energy when you meet her? Even before you meet look at her LinkedIn profile and see if she inspires you. See if she has had some success of the kind you want for yourself. A person’s success is not make or break but someone who is not successful will not be confident in her ability to achieve. And, such a person usually will not be self-secured enough to motivate others. Someone who is not secure in their abilities and experience will be scared of you taking their turf if hired. Be wary of this if you are ambitious and are reasonably smart.


See if she is a good communicator and if she shares her thoughts in public in some form. Notice if she openly shares what is expected of you, and about the support that is available and what you’ll have to figure out yourself. Try’n notice the passion they have about their work and industry. When you ask her a question about the role and responsibilities see if she offers a logical answer or a vague one.


Has she done something unique even if it was as a volunteer? Daniel Goleman has said that true leaders are driven to achieve beyond expectations, their own and of everyone else. So look for people who have challenged themselves in some way in the past, either by doing what they were not supposed to (in jobs they have been). Find out if they are open to talk with peers and other colleagues in the industry. You can ask a friend to write to them for help. Trust but check. You can do this by looking at their social profiles and by asking those who worked with them in the past. On Glassdoor, you can find the title of a person and what employees think of them. This is rare but can help if you are looking to work for a company which is not too big.


If you want to be even more methodical about it then make a list of traits you’ll want in your future boss and weigh those you meet based on those parameters.


If you come close to being hired, ask the person hiring you about her work style. Ask if she believes in delegation or if she is someone who is more hands-on. The extremes of both approaches are not good. You want someone who delegates but is there to hold your hand in the beginning and delegates more as her trust and your comfort level with work increase.


If you are interviewing for a small company, you’ll usually be interviewing in the office of your prospective boss. Look around to see how organized and relaxed she is. This is the sign of a productive person. If they are taking calls in the middle of the interview, then you’ll want to avoid working for her. If interviewing for a large company, see if your interviewer comes by to greet you as you arrive or she is open and forthcoming when entering a conference room (or location of the interview).


Look if the person interviewing you asks questions about your passions at some point during the interview. This is a sign of a person who takes a genuine interest in other humans and will also make sure that you don’t choose to work for a task machine. 


When interviewing you want someone who asks you about work and your skillsets and does not hire you just based on the fact that she likes you as a person. Such an interview may be pleasant but you’ll want to be judged on merit (along with likability) and not on likability only because in such a situation you may suddenly go out of favor without any logical explanation.

So, that’s a brief list of points you can consider to understand the kind of person your boss is. This is not a definitive list but I hope it helps you in some way in finding a good boss.

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