How to handle difficult conversations

4 min readSep 17, 2021

None likes it but everyone needs it.

As a project management professional, your role is undefined. It’s a lonely role, so you need friends. Apart from writing code (of course, you can do that as well), you are responsible for everything else. It’s not that you need to do it all by yourself, but rather get the job done.

In that journey, there’ll be a lot of discussions that will be smooth and straightforward. Compared to that there will be a select few which are difficult in nature and you will be hesitant to take them up!

With the passage of time, some problems will go away so you don't have to deal with difficult conversations. For other times, read on.

Below are the key facets to focus on when having a difficult conversation -

1. What’s your objective ✨

Be focused on the end goal. What is your ultimate objective? Don’t tell me that it’s to blast someone during a difficult conversation. Be clear on your objective and the outcome you are trying to achieve.

Example:

“I want to delay your production rollout to allow more testing to complete to achieve better quality”

So, delaying your production rollout may seem to be a difficult conversation, but the outcome is different. Once that’s clearly explained, the conversation becomes rather easy.

2. Preparation is key 🔑

Be well prepared. Rather over-prepared. With supporting data and facts and figures. One thing is clear — data never lies.

The most difficult conversations are misunderstandings. To make it straight, it’s easier to have the data right.

3. Listen to the other part 👂

If there is one part that is most difficult is to implement is to listen to the other part. Start the part with “listen”.You might have come prepared with data/facts, but don't show your cards at the beginning. Once the other part has vented his/her frustration, you’ll realise that the conversation becomes a lot easy.

Let me tell you two example scenario from my today’s experience.

a. This meeting was to align on a common understanding of a difficult situation. To achieve this, selected people were brought in together to share their position. I started to talk after 10mins and started by listening to a few problems. As I went via preparation, I started covering the problems in my slide as answers. So, when I actually started talking after 10mins, I knew the problems and also have a mental map of how my data would shape a solution.

b. Another difficult discussion started by explaining a solution itself when I allow the first few minutes to get the talk going. Then I presented my contradictory viewpoint by justification, which was readily accepted.

The key to both the above situation is to listen first. Like a test match batting, give the first hour to the bowler and then the rest of the day is all your’s for batting.

4. Respect and be under control 😎

Be respectful of others and keep yourself under control. Under pressure, composure is the first thing to fall apart. Watch your body language, tone and selected words. For such meetings, my go-to position is “emotionless”.

Tell a line like a newspaper reader. There is absolute professionalism but no emotion at all. If it gets tense, it’s better to take a break respectfully and rejoin later.

5. Negotiate to make a win-win situation 🏆

All difficult conversations will not be in your favour. That’s not expected as well. What’s expected is to have a win-win situation. A classic mistake is to get out of the meeting with one thinking as “win” and the other thinking as “loss”. The best is to summarise the common understanding.

Be the more intelligent dumb-ass of the room. Ask the other party what they want. If that’s better than your’s, keep quiet. If not, allow the discussion to move towards your solution but let that come from the other. In that way, they will be committed to that as it’s their winning position. It’s a win-win situation.