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Five Key Conversations to Have With Your Boss

If you’ve just been promoted, this is obviously for you. If you have been in your role for a while, but your relationship and communication with your boss/supervisor/leader isn’t perfect, this will be of great help to you too. If you lead others and your relationships and communication with those you lead isn’t where you would like it to be, this will help you also.

The advice that follows is most effective, and probably easiest, if done from the beginning – right after you have been promoted or starting a new job.

If you are past the first weeks or months, this list may help you identify the gaps that could improve your relationship and communication with others.

The Five Conversations

  1. Getting to Know Them.
    Some people reading this are cringing, saying something like, “business is business, I don’t need to know everything about my boss and vice versa.” That’s true at some level; however, the reality is that relationships drive all sorts of organizational success. Different people have different relationship needs, and desire a different depth of relationship at work, but relationships always matter. Your job is to do what you can to figure out the relationship needs of the other person, and work to build it. This isn’t necessarily a conversation in itself, meaning you might not want to say “hey boss, can we have a getting to know each other conversation?” Rather it may be a part of all the other conversations you have, now and in the future.
  2. Clarifying Expectations.
    We all know job descriptions (when they exist) don’t tell the full job story. If you want to be successful you need to know what your boss expects of you and what success looks like to him/her. This is a critically important conversation that often doesn’t happen or is assumed. Ask them these questions and write down their answers. Then be willing to share with them what you expect and need. This doesn’t want to sound like (or be) a list of demands, rather an exploration and mutual agreement on what success looks like.
  3. Understanding Goals.
    Goals likely go beyond expectations. Let your boss know what your goals are – both personally and professionally. As a strong working relationship is formed your boss may help you reach those goals more quickly than you realize. But she can’t if she doesn’t know what they are. The reverse is also true. If you know what his goals are for your department, region or organization as a whole, you are in a much better position to help him achieve them, right? If you know a bit about his career goals, you can support that too.
  4. Setting the Stage for Help.
    In a new job you might want or need help and assistance. However, many like to put on the John Wayne, “I-can-do-it-myself” hat, assuming asking for help shows weakness. While you don’t want to go external to solve everything, you will be more productive more quickly if you have a coach. Your boss is in a perfect position to be your coach, and while this might be one of your expectations, it is important to set some explicit agreements about how much coaching you might want, when you might want it and how to receive it.
  5. Agreeing on Communication Strategies.
    Both of you need to know what, how, when and how frequently you need to communicate. While the answers to these questions may evolve as you grow in your role and trust builds with your boss, these agreements are critical. Does your boss prefer email? How often do they want face to face meetings? How will you handle informal exchanges? These three questions give you a sense of the scope of this topic. The more you can build common ground here, the more successful you will be. A huge percentage of workplace conflicts and challenges stem from a lack of agreement on communication needs and the misunderstandings that stem from this lack of agreement. Having this conversation will alleviate or eliminate those challenges.

All five of these topics might be handled in one conversation, but more likely they will evolve over a (hopefully short) period of time. If you have been in your role for a while, perhaps this will help you find areas for new or deeper conversations. Either way, success in these five conversations will lead to greater productivity, less stress and a better working relationship with your boss. Who wouldn’t want that?

The best preparation for good work tomorrow is to do good work today.

Elbert Hubbard
Adapted from Remarkable Learning, Kevin Eikenberry Group