The best way to have difficult conversations with your manager is to have done the work upfront to build the trusting relationship necessary to have this or any kind of conversation in a way that is productive and successful.

To prepare, you need to understand how to best communicate with your manager and how you build an honest and trusting relationship.

The Best Way to Communicate with Your Manager

You will have a wide range of conversations with your manager. Work-related topics such as:

  • Progress updates
  • Challenges and opportunities
  • Ways to improve productivity
  • Thoughts and input on strategy

And topics that are more directly related to you.

  • How you are doing
  • What it takes to be promoted
  • Whether you are being paid enough

Some of these conversations will be simple and comfortable, while others will be more challenging. That is completely normal.

As you think about the different types of conversations that you have with your manager, you need to consider the right approach to achieve an optimal outcome. I strongly believe that communication is situational. You need to choose an approach that fits best with the topic, the urgency, complexity, and most importantly, the communication style of your manager.

My recommendation is to spend time watching, listening, and trying different forms of communication in order to find something that works for both you and your manager.

Example: How I Interact with My Manager

One thing to keep in mind, everyone is different, therefore there is no one size fits all. But in all cases, you need to find an effective and efficient way to communicate with your manager. Be flexible and don’t ever stop working on the best way to do this.

The Importance of an Honest and Trusting Relationship

One reason for having a wide range of conversations with your manager is to build a relationship. They provide an opportunity for you to get to know them and for them to get to know you. They also provide the opportunity to build trust. The more you work with someone, and the more you are open and honest, the better that relationship will be.

Here are the behaviors that I think are most important in building trust.

  • Be reliable, do what you say you will do
  • Be honest, say what needs to be said, be factual, not emotional
  • Be (mostly) positive, not the person who always complains or gossips
  • Be open to feedback
  • Trust your manager

If you are able to operate in this way, the interactions that you have will result in better outcomes. Much of this is the result of the trust that you have developed.

Making Sure You Have Regular and Ongoing Communication

You need to have regular and ongoing conversations with your boss. There will, of course, be times when you need to interact more frequently, but you should not let the interaction frequency die down too much in between. Keep the interaction going always.

I think that it is especially important that your boss always has a few things top of mind – that you have done lately. You can read my post about this to get more insight. (Keep 3 Important Things Top of Mind with Your Manager).

In addition to all of the positive reasons for having regular and ongoing conversations, it is incredibly important when you have a challenging topic to discuss. The relationship and trust that you have built will make the conversation easier. Your manager will start from a positive frame of mind and will be more willing to listen before reacting or jumping to conclusions.

Having Difficult Conversations

After you have worked through the best communication approach, build a trusting relationship, and ensure you are communicating on a regular basis – you are now ready for those difficult conversations!

Do your homework before the conversation. Make the conversation as factual as you can, minimizing emotion. Adhere to the behaviors that you have used to build trust, and trust your manager.

I firmly believe this will produce the best result.

Closing Thoughts

This all sounds simple and logical. It turns out that it is not that easy. You have to work at it. You have to build the kind of trusting relationship that you need to have a productive conversation about anything.

When you need to have a difficult conversation, you have to come in with the right attitude.  You need to:

  • Be prepared
  • Bring evidence
  • Keep your cool
  • Separate yourself from the emotion
  • Own up
  • Be a positive force
  • Ask for their feedback/perspective
  • Listen
  • Arrive at a path forward
  • Think hard about how to frame the problem to be constructive and not binary

This approach works amazingly well with your manager. It also works with other leaders. You will not be able to spend the same time and effort in understanding the best way to communicate with them, nor will you likely spend as much time building a trusting relationship. But even with less time, the same model applies. And with effort, you will get many of the same benefits.

Good luck, hope that was helpful. Please provide comments!

See Also

Keep 3 Important Things Top of Mind with Your Manager

How to Manage Your Manager

Kieran Desmond – Experienced Executive Seen Success Working Remotely from Headquarters

Categories: Communication


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