Recently I had dinner with a friend that I had not seen in years and we had a lot of catching up to do. He shared with me some of his challenges and wins on the work front and I was struck by one story, in particular, that echoed circumstances that I have heard from many clients. My friend got a great job with a growing company, and he jumped in with much excitement. Unfortunately, he quickly realized that his boss, who was located on the other side of the country, was difficult to reach, had little understanding of my friend’s area of responsibility, and appeared to be pretty ineffective as a company leader.

My friend tried to make the best of a bad situation, keeping his boss in the loop as much as possible, being innovative in his work, and building relationships with key stakeholders. But when his boss started questioning his decisions and sent him an email outlining significant negative changes to his duties and compensation, he had had enough. Most of us have had those moments in our careers when we were angry, frustrated, unhappy and downright pissed off. What we do in those moments often sets us on a new course, for better or for worse.

I faced one of those moments early in my career when I was fed up with my manager giving me menial tasks and sending me on errands in the office building to “pick up this videotape” or “deliver this box.” Four months into the job, with my hands shaking from anger, I snatched the latest package from his hands and stormed off. Tears welling up in my eyes, I rushed to the restroom to hide – and cry. As I stood there, feeling like I wanted to quit and beating myself up for letting things get to this point, I decided it was time to take control. I did deliver the package and then I walked into my boss’s office and asked to meet with him – over coffee in the cafeteria instead of his office, where I was afraid I would be too nervous.

My friend made a similar decision to take control. In his case, he sent an email to his boss’s boss, the CEO, expressing his frustration with the turn of events, outlining his needs for changes in his reporting and compensation, and requesting an opportunity to meet. He knew that going over his boss’s head could be a big problem and outlining what could be perceived as demands for his job could get him fired. But, he was prepared to accept whatever came next.

Both my story and my friend’s story have great endings. I had a calm and productive conversation with my boss and learned that his abrupt and belittling manner was an outcome of the pressure and stress he was feeling. I helped him to see that I had the knowledge and experience to help him with substantive work if he would give me a chance. My friend received a call not long after hitting “send,” and ended up getting everything he asked for, including a new VP to report to. He has the support, autonomy, and resources he needs to really soar.

“Have the conversation you need to have,” is the guidance I give to many of my clients. If you are frustrated with someone or something, if you need a change in how you work, if you want more responsibility or a higher salary, you are guaranteed not to get it if no one but you knows what you want or need. Have the conversation, and before (during, and after) you do, here are a few tips to help make sure your conversation is a positive experience:

  • Outline what you want and what you’re willing to let go of
  • Consider meeting in neutral territory (like the cafeteria) if needed
  • Know that this is one of several conversations you will most likely need to have to reach an agreement
  • Think through possible questions, concerns and challenges and be prepared to respond
  • Challenge your assumptions about the situation, the other person(s), and even yourself
  • Breathe and center yourself to be calm and self-assured
  • Thank the person you speak with
  • Reward yourself for getting out of your comfort zone

Certainly not every conversation will go your way or have a happy ending. And while having a difficult conversation with someone at a higher level in your organization is never easy, if you weigh the consequences and potential outcomes, plan for the conversation, and step into it with confidence and clear intentions, then you can build trust and possibly get that thing that you have been hoping for.

What conversation do you need to have to get what you want at work?
Tell us your story about a tough conversation you had with your boss.

If you enjoyed this post, you can read more like it in our book, The Power of Thoughtful Leadership: 101 Minutes To Being the Leader You Want To Be, available on Amazon.

For support in preparing for the conversation you need to have, contact Robyn at

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