The Top 6 Critical Conversations You Should Have With Your Boss

 In Career Tips

The Top 6 Critical Conversations You Should Have With Your BossCommunication seems to be the most under-rated, yet most critical thing we do as humans.  There are all too many things we should be discussing and communicating about, yet for some reason, we don’t.  Call it lazy, busy or reluctant; we don’t communicate enough about the right things in the most effective way.  Think of just how much better all your undertakings would be if all you did were improve this one critical capability.

In the workplace, almost all of us have a boss or someone we must be responsible to.  That means the place to focus your communication as your highest priority is the boss.  When you work well with the person in charge, chances are exceptionally high that you will like your job.  As a place to start, use this as a checklist for your communication plan with your boss:

Work or project.  You should be finding a variety of ways to keep your boss in the loop on what you are working on.  Don’t just go silent and hunker down in your office.  If you do that, you will force them to come extract information from you.  Consider sending short emails, hallway conversations or sound bites in staff meetings.  You can also consider preparing a monthly report that covers highlights, status and challenges–all the things the boss really wants to know.

Discuss problems you encounter.  Some people are reluctant to let anyone know they are encountering a problem.  Problems are why we were hired.  Consider discussing Situation-Action-Response or S-A-R.  Don’t just take a problem to the boss without offering at least one possible solution.  When you do the S-A-R approach you first outline the situation, and then outline what action you either did take or propose to take, followed by what result you expect.  This way the boss isn’t solving your problems, but is being given a “heads-up” on an issue and the opportunity to validate your approach.

Clarity.  If ever the boss gives you direction or communicates something you don’t understand or think you agree with, it’s time to seek clarity.  It only takes a few minutes to catch the boss to ask a few questions.  Keep in mind, their only ability to get their job done well is if you do; so don’t think of your questions as an interruption.

Your career goals.  Every boss wants to think they have hired real go-getters.  You can show that you are in a number of ways, and central to that is to engage your boss with your career goals.  If you discuss your goals and create development plans that mesh with both of you, you have a built-in advocate.  Your boss can’t guess what you want next; you have to let them know.

Your performance.  You need to start every new job by gaining an understanding of exactly what their expectations of you will be and how they will go about assessing you.  Once you know those details, take it upon yourself to seek ongoing feedback about how you are doing.  If you do this, you will avoid running your job off into the ditch.  If you need skill building, make your request when you have your performance discussion.

When it’s time to go.  Hopefully, you work for a boss and company where you can have open, honest discussions about things like leaving.  Many of us don’t.  If you do work in an environment where you can, let the boss know when you have reached your professional “expiration date.”  Keeping them in the loop and being a transparent professional will help their planning tremendously.  They will also respect you for doing so.

It’s not possible to over communicate with the boss or most people you work closely with.  Look for opportunities to share what’s going on with you every time you can.  You will find you work better with others when you do and you will be sought out as someone great to work with.

For more career tips and advice – FREE newsletter and eworkbook:  From Dorothy Tannahill-Moran – Your Career Change Agent from and  And check out Dorothy’s new book, “Career Mapping for Climbing Managers – Planning Your Career On Purpose”. You can find the book in print or Kindle on Amazon.



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