Master the Art of Tough Conversations

About time you call a spade a spade.

Dipesh Jain
5 min readSep 6, 2021
Photo by Roland Samuel on Unsplash

Humans have a natural tendency to avoid (or at least procrastinate) tough conversations. It triggers our reptilian brains and evokes a fight or flight response.

As a result, we continue harboring ill feelings, dragging out toxic relationships, working horrible jobs, and even suppressing some of our most volatile emotions. We continue with things that need to end.

Things can reach a point wherein these issues take a toll on your mental health and impact your quality of life. More often than not, it does the same to the other person as well.

I had a strong inclination to avoid these talks and sweep things under the rug both personally and professionally. Things got to a point wherein debris from under this proverbial rug came out at the most inappropriate times in the most noncontextual way possible. Phrases like “You should have told this before!” or “Why did I hear this from someone else and not from you?” became very common.

Not only that, in my quest to keep everyone happy and avoid breaking bad news to them, my personal goals and achievements suffered. That’s when I realized the need to have direct talks. I had those to restore some sanity in my life.

Uncomfortable straight talks are an integral part of strong communication and form the basis of many successful human endeavors. So let’s look at what happens when you have tough conversations at the right times.

  1. Improved relationships: By far, the biggest benefit of straight tough talks. It helps you clear the air, understand other’s points of view and even set the right expectations.
  2. Better situational understanding: Tough conversations almost always get others sharing their viewpoints. It can help you see some aspects that were completely hidden from you or things that you ignored.
  3. It helps others see things holistically: You are not the only one who benefits from these conversations. It provides the other parties a peek into your thought process. This can make things clearer for them and even make them aware of their mistakes or shortcomings (if any).
  4. Enhanced mental health and well-being: When you continue to harbor negative feelings or views towards something or someone, it is not that they disappear magically. They remain in your subconscious and have high chances of erupting at a completely inappropriate time in the most ‘out of context’ way possible. All it does is wreaks havoc on your mental health.

Whenever in doubt whether you should or should not have the hard talk, go for the former. Err on the side of early communication to avoid late repercussions.

So how do we get there? How do we go from being an ever-pleasing everyone kind of a person to someone who’s direct and isn’t afraid to call a spade a spade?

The below points may not hold all the answers but could be a good way to get started.

#1 Acknowledge the need for tough conversations

What are the conversations that you’ve been holding out on? What gossip do you love spreading? We have answers to all these questions, and somewhere deep down, we also know the discussions we need to have and actions we need to take. Bring them out in front of people that matter. Acknowledge the need to take action and communicate them. If need be, write all of these down to ensure that you don’t miss anything.

#2 Approach the person and set up some time

Yes, YOU have to approach the person you hold grudges against and set up some dedicated in-person (preferably) or virtual time. Don’t let your ego get in the way of this. Also, avoid having these conversations in a group or with others around. No matter how reasonable your points are, a conversation like this in a group will always be seen as a personal attack and raise the other person’s defenses. You’d make matters worse.

#3 Get to the point quickly

I see the ‘sandwich approach’ widely prevalent. It’s basically a form of feedback that wraps negative feedback in praise. Start with a positive statement or praise the other person before breaking the bad news and then end with something positive. Not only is it a complete waste of your time but (and more importantly), it is hardly ever effective. Chuck the small talks and weather discussions and get straight to the point. Trust me, the other person will appreciate it.

#4 Differentiate facts from opinions

This is probably the toughest thing to do. Especially if you’ve been harboring negative feelings for a while (Hence, don’t!). We are emotional beings and not logical beings and will mix facts and opinions in no time. Acknowledge that and be self-aware.

There’s absolutely no harm in stating opinions and your feelings about a situation. However, keep in mind that the other person is entitled to feelings or opinions of their own. When it comes to facts, though, there are no ‘your facts’ vs. ‘my facts.’

Your colleague kept your manager and your manager’s manager in the cc is a fact. Your getting offended about it is an emotion and thinking of it as inappropriate is an opinion. It’s perfectly fine to communicate those but remember that there will be a different perspective from the other side.

#5 Shut up and listen

Listening to the other person is the least you can do to respect their time and effort. After you’re done talking and sharing your thoughts, please let the other person a) express their thoughts and b) respond to your statements.

Don’t be that verbal bully who goes into a conversation with the sole intent of hijacking it and making it all about their agenda.

#6 Conclude or agree to disagree

At this point, two things would happen. a) You’d have concluded and agreed on the next steps or b) continued to hold to your opinions and not find a resolution. Either way, it is important to move on.

It is great to have some agreement and discuss the next steps to avoid the behavior or action that led to this situation in the first place. However, that won’t always happen. There will be times when your discussions won’t go anywhere. In that case, agree to disagree and move on. At least you’d have understood their point of view and learned your lessons.

If this difference of opinion is a deal-breaker, well, you have other problems to solve.

One of the biggest fears that keep prevents some of us from holding our thoughts back is — This will spoil our relationship. Yes, the other person will resent the straight talk initially. That’s not their fault, it is our natural defensive instinct making them do that.

However, if done well, these conversations will not only enhance your relationships but also have a major positive impact on your happiness and quality of life in the long run.

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Dipesh Jain

Musings About Sales, Productivity & Behavioral Science