How to Prepare For and Have Difficult Discussions

Author By Jim Lara

Is there a difficult discussion or conversation that you’re dreading? Maybe you’re putting off meeting with your aviation reporting executive to discuss the budget?

Flight department budget discussions are never easy. Even the idea of a budgetary meeting can conjure up the scariest of scenarios. And it’s easy to focus on the potential of a negative outcome.

If you already know that your boss is looking for a “win,” it’s likely he or she will be looking for a weakness and exploit it.

The key is to come prepared and keep emotions out of the discussion.

Having a process for the preparation and constructing the meeting agenda will take the emotion out of the equation.


Let me illustrate the use of this process with the following scene:

The flight department, which you lead, is over budget. Corporate has unexpectedly increased executive use of the business aircraft fleet.

Now you need to meet with your reporting executive to discuss the budget moving forward.

Additionally, you learn that there are a couple of important programs that need to be funded for the morale and safety of the flight department that will require a budget variance approval.

Your reporting executive has been reluctant to approve these “extra'” programs in the past. What do you do?

Let’s start by prepping for the meeting.


Step I: Meeting Prep

When preparing for a difficult discussion, my colleague Jim Lara always turns to two essential reads in his library: “The Ten Commandments for Business Failure” by Donald Keough and “Crucial Conversations: Tools for Talking when Stakes are High” by Kerry Patterson.

However, if your eReader is already at maximum capacity and/or you just want the “Cliff Notes” version, here’s what you should consider.

Start by thinking positively. Then do some soul-searching on your part.

Ask yourself:

Do I have command of all the relevant facts from everyone’s perspective?

Do I have any personal styles or mannerisms that my reporting executive (or his/her boss) finds troublesome?

Has my boss shared repetitive concerns that I haven’t addressed? (If so, take note and fix them!)

Remember to “stack the deck” in your favor. Do so by scheduling the meeting at a mutually neutral venue if at all possible. This helps to create an even playing field.

Step II: The Meeting

During your face-to-face, start by creating alignment. Find some common ground.

What are the facts that you can agree upon?

You might start with a little small talk, but being too subservient creates a tone of weakness. Be strong and respectful.

Remember, YOU are the subject matter expert.

Now it’s time to present your ideas. Clearly define your proposal, the goals, the investment and the return on that investment.

Clear communication is vital to getting the results you want, so listen intently. Re-phrase what you hear. And don’t be afraid to ask clarifying, but not argumentative, questions.

This will ensure that you both remain aligned.

The golden rule is to always be positive and honest! And, again, it’s crucial to not show emotion or get defensive.

There’s no doubt that keeping your emotions in check is key to the outcome of any meeting.

When we allow our emotions to influence the discussions, chances are we’ll walk away from a meeting not achieving our objectives. And possibly even feeling ineffective.

Do we blame it on the unapproachable boss? Or, is it that we’ve allowed our feelings to obscure the facts during the meeting?

Step III: The Closing

So, how do you conclude the working session with the best win-win situation?

Chances are you won’t agree on everything. And, it’s okay to agree to disagree.

Be supportive and offer alternatives. If you’d like to reflect on the meeting discussion, request the opportunity to provide some additional thoughts following the meeting.

Take some time after the meeting to re-visit the content of the meeting.

How did it go? What areas were troublesome? These sessions always present opportunities for your growth. Ending such discussions on a good note is critical to keeping the doors open for future interactions.

These three steps offer some insight into preparing for challenging discussions, whether it is with your boss or a colleague.

Remember, it’s always productive to reflect first on the man/woman in the mirror. That’s YOU!

Ask yourself:

What am I bringing to the table that could be contributing to the success or failure to achieving my objectives?

Is there anything I can do to positively influence the outcomes of these interactions?

Then, a little investigation into your boss’s or colleague’s drivers and motivating factors can shed light on possible courses of action that will yield positive results.


Your Turn

Most of us have had an instance (maybe a few?) of conflict where we have walked away from a meeting feeling like we had failed in our mission.

How did you cope with the situation?

What insights can you offer to help other people who struggle with this challenge on a regular basis?

Please share your thoughts with us! We all wish we had sage advice at these times!

Remember the quote from Olivier,”Experience is what you don’t get until just after you needed it!”