The word “boss” is terrifying, isn’t it? It exudes power and authority, making you quiver at the sound of the word alone. It is a terrifying word until you become a boss yourself, and then the ‘aha’ moment sets in. It’s then you say, “I don’t want to be a regular boss, I want to be a cool boss,” and you vow to be different. Of course, that is until your employees start treating you like the boss.

Then, it all gets weird again.

You notice them being “chipper” when they see you early in the day or quickly exiting out of social media as you walk into their office… and they’re always so positive! Why? (But don’t judge because you were them at one point, too) The best way to handle a new boss? Treat them like they’re a person, too. Of course, there are professional boundaries, but overall, keep in mind that your boss is a human, with complex emotions and feelings, with dreams and ambitions, with struggles and challenges just like you. They really are people, too.

Sure they can fire you, but only if you give them a reason. It amazes me how we ask bosses (leaders) to invest so much in their employees yet we rarely ask employees to do the same? What could it hurt for an employee to take an invested interest in the well-being of their boss? I’ve had my share of job shifts and changes. In a former experience, there was such a high turnover rate that I was one of five of the longest standing employees going into my second year of employment — I had been there longer than any boss within a direct line or even a grade above me… and I’d only been there a year.

Though challenging, I now see how my biases as an employee with little to no invested interest in my superiors, or rather, a short threshold for tolerance of their humanness (mistakes), lead me quickly out the door. I wouldn’t change that experience for the world, but it did shed light on how to deal with and approach ‘new’ in an organization, especially ‘new’ bosses. Now, five years removed from that experience and living out a professional experience I had only dreamed of at one point, and in being the boss myself, I can see the power in approaching bosses as people and doing these three things to ensure the relationship lasts:

  • 1. Interview your new boss: Ask them who they are and what they’re about. Seek to understand their motivations, their hopes and what they do outside of the office. What do you have in common? How are you polar opposites? Ask good questions.
  • 2. Ask your new boss to get together outside of the office: Once you feel them out in your interview, see if there is an activity or way to engage them outside of the walls of the organization. Top tips? Grab a coffee, meet for a fitness class or even grab lunch one day as a treat (we all gotta eat, right?).
  • 3: Be upfront — actually give your boss the things they ask for: Chances are there will be a point where your new boss asks for your advice or your feedback and chances are they actually do want or need it. Since they’re human, — you were asked for a reason (and no you don’t have to know the reason why) — share how you really feel or what you feel they should know.

Transition and change are difficult for any employee or organization; however, it is the most telling sign of overall personal satisfaction in a role if you can withstand and move through the transition into the resettling and deeper relationships with the new kid (a.k.a. your new boss).

Remember, a lot is learned in the first few months. I recommend setting a “checkpoint” date within three to six months following a major transition to evaluate the health of you and the organization from your lens. Know that it does take time for everyone to settle in and make the adjustment work, one bad day does not mean it’s a bad job or a bad boss. Seeing the newcomer, though, as a person more than a boss helps you to visualize your future: Will you work to be on their level or will you make an exit? Whatever comes of the transition, just know that taking the time to learn what you can about your boss, the person, will be a beneficial use of energy and learning as a professional.


  • Katelyn Pfeffer

    People Developer | Small Business Manager

    A warrior for wellness, Katelyn lives for the moments where the true soul shines. A non-profit consultant turned corporate public affairs specialist turned fitness professional and small business manager, she strives to be the light for others and herself. Her life's work revolves around her belief in the power of people. She coaches others to live true to themselves and live aligned in work + life. Follow, love and enjoy this messy millennial's ride.