Are you avoiding your boss? Pave the way to your next conversation

We often talk about the skills leaders need in conversations with their people. Another equally important conversation is when people need to talk with their leaders. These conversations can be quite intimidating. 

Have you ever avoided conversations about getting involved in a project, asking for personal development or career advancement, clarifying a misunderstanding or smoothing out some of the rough edges in the relationship? I have.

Conversations like these are not necessarily easy. We can come up with a million and one reasons not to have the conversation. We hope they will just figure it out. They are a leader, after all. Surely someone else will mention something to them and they will take notice. 

Truth is, you are busy and they are busy. Some important conversations that could create opportunity or synergy in working relationships are missed simply because we get too busy. Putting off important conversations means the seed of discontent can grow. Ruminating thoughts may circle around and fuel frustrations. Comments are dropped in casual conversations that reflect disappointments. When these things start happening, it’s time to engage the conversation even when it’s hard. So how do you begin? Here are a couple of thoughts.

Prepare yourself for the conversation.

Notice  where you might have some emotion or feel some urgency. Acknowledging that emotion is important so it doesn’t derail the conversation. Get clarity on the source of the emotion or urgency as well as describing what you hope for as an outcome for the conversation.

Think it through before you begin.

What is your goal? Where might your points of difference emerge? How can you be prepared to address concerns in advance? How can this be an opportunity for you to invest in their growth as a leader? Answering questions like this can provide clarity on the purpose for the conversation.

Facilitate the conversation.

Once your purpose is clear, you can create a plan for the conversation and facilitate the plan with some practical strategies that serve your purpose. Strategies such as:

  • Clearly state your purpose for the conversation and expected timeframe for it.
  • Watch the clock and keep the conversation moving forward and ending on time.
  • Notice when to pause and summarize the conversation to point toward your purpose.
  • Call out points of agreement and where you see shared goals
  • Rephrase their words to signal you have been listening
  • Notice points of divergence as well, while still pointing to how you are hopeful moving forward
  • End with concrete, agreed upon action steps — even if it’s simply planning the next conversation

It might take a series of conversations, so being patient in the process contributes to the long-term nature of both building the relationship and addressing the concerns. The key to unlocking these essential conversations is bringing an inviting attitude to the conversation that you would like to receive if the tables were turned.  Spend some time in the days ahead and see if you need to have any of these important conversations with your boss. Conversations fuel progress.

Next Steps

Check out the Side By Side Podcast episode, Influential Conversations with Your Leader for some great tips from a conversation with Mary Steiber-Reynhout. As you prepare the conversation you can also check out episodes Before You Say A Word Part 1 and Before You Say A Word Part 2 to help you prepare for the conversation.

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Annie Perdue Olson

Annie is founder of Leading Better Together, guiding leaders through the relationship and people challenges that sidetrack ministry. With 20+ years of experience in nonprofit management and pastoral ministry she equips people and teams to work better together. She holds a Master of Arts in Human Resources and Change Leadership from St. Thomas University and received her coaching certification from the Center for Coaching Excellence.

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