Top 5 Reasons You Should Know How to Have Difficult Conversations

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By definition, people look to avoid having difficult conversations. That is what makes them difficult.

It is natural for us humans to shy away from having conversations that can induce conflict or friction with others.

A difficult conversation for one individual may be a comfortable conversation for another. Regardless of what may or may not be difficult for you, there is always room to improve your confidence and ability in managing these difficulties.

Through personal experience, I have found great benefits from going towards discomfort and not running away from it.

Tough conversations can happen at home, in your social life, on your university campus, and in the workplace.

This is a skill that can be learned and practiced and will help separate you from your peers.




  • Asking a professor for additional help/flexibility
  • Confronting a group member about their lack of contribution
  • Asserting your voice in clubs and organizations you are a part of

Personal and Social Life

  • Breaking up with someone
  • Telling your significant other you don’t like something they do
  • Cutting off leeching friends
  • Speaking with a disruptive neighbor
  • Telling a family member you can’t make it to an event they looked forward to

The underlying thread that connects all these examples is the potential for conflict involved. Conflict can be intimidating for individuals.

Either you want to avoid the conflict altogether or do not want to be perceived a certain way by creating conflict.

You might think you’re coming off as…

  • Bossy
  • Disrespectful
  • Close-minded
  • Selfish

Depending on how you go about managing difficult conversations, you can avoid these perceptions and be seen in a positive light.

I believe the ability to have difficult conversations provides 5 major benefits to one’s life.

Let’s dive into them.

5 Reasons Why You Should Know How to Have Difficult Conversations


When you avoid difficult conversations, your thoughts and feelings are never expressed.

At work, you might stay silent when someone asks for opinions on the strategy they want to implement. Deep down, you know that it can be improved but you don’t want to offend that person.

At home, your significant other has been behaving differently which has caused problems between you two. You want to address it but also want to avoid the argument so you stay quiet.

By voicing your opinions and concerns, you give yourself a chance to be understood by the person on the receiving end of a difficult conversation.

You’ll often find that something you feared happening doesn’t come to fruition when you speak up.

After, you’ll realize all the stress and running of scenarios through your head was for nothing.


Often, we hear that if we work hard, we will be rewarded at work and move up the corporate ladder.

While there is truth to this, there are times when you can take matters into your own hands to expedite the progress in your career.

Asking for a raise or a promotion is a tough conversation to have, but you’ll never know what will happen until you just ask.

This famous Ted Talk below is presented by a gentleman that went around asking strangers a list of absurd requests to study rejection. He surprisingly found that people actually said yes more often than he expected.

His point of the talk was to show the effects of simply asking for things.

You’ll never know what people will say yes to or what other viable solutions they will have to your requests unless you ask.

I can confirm this myself.

Any time that I have spoken up and asked for things that I thought were likely to lead to a “no,” I was surprised to not only receive a “yes,” but a willing “yes.”

Always shoot your shot and initiate difficult conversations.

It can open up opportunities for you that others that are unwilling to have those conversations won’t have.


The difficult conversations themselves may last a few minutes or less, but the time you spend contemplating what you should say or thinking about potential scenarios can consume your thoughts.

This wastes time and energy that can be put towards other things in your life.

You’ll induce your own anxiety and stress that can affect your mental health and well-being.

By taking action and confronting what’s on your mind, you’ll get the result of the conversation faster which will clear your mind.


If you have been in the workplace, you find that it is filled with passive-aggressive individuals that have opinions or concerns that they avoid bringing up. Your colleagues might bring things up to you at lunch about your bosses and their plans.

They choose to avoid conflict and stay silent. Because no one has voiced any concerns, the management team continues to run things the way they always have.

If you have a true desire for your company to succeed, you would bring up anything that could be improved.

Many companies actually encourage this type of behavior. By receiving feedback from their employees, the people who run the company are exposed to blind spots they may have for certain areas of the business.

While they may be intelligent and have years of experience, they can’t see it all.

Feedback is how companies improve and innovate.

Bringing up these conversations are difficult because you may feel that you have no voice or saying something will result in punishment.

You can constructively bring up suggestions you have and see what happens. More times than not, the leaders of the company will appreciate your input and may implement your suggestions.

By initiating difficult conversations, improvements and efficiencies can result from it.


The final top reason you should know how to have difficult conversations is a result of 4 steps above.

Tying all things together, you’ll gain respect.

In your social life, being able to have difficult conversations will show that you are willing to express your concerns and be constructive about it.

By avoiding passive-aggressiveness, the person you are talking to will know that you say what is on your mind and nothing is left to the imagination.

They themselves will feel more comfortable communicating and working with you because they respect how you handle things.

In college, you work in groups of teams frequently.

Everyone has a story of a group member than has slacked off with contribution to a team project. Most people won’t address that team member and will express their concerns to the rest of the group behind their backs.

By being the one who confronts the lacking individual, the others will take note of your leadership and their respect for you will grow. Because of your actions, the group benefits.

The biggest gain of respect is to be had for your career.

Large companies have a hierarchy and average employees tend to stay within the hierarchy they came in at.

Because of this, individuals don’t feel like they have enough power to have an opinion and have that opinion lead to change.

Speak up in meetings.

Suggest another way of doing things to your boss.

Ask for that raise and promotion.

Doing these things takes guts and management at your company knows this.

By stepping up and initiating difficult conversations, everyone’s respect for you will grow.

You can come off as a go-getter and contributor which are qualities of leaders.

If you are currently in an entry-level position but exhibit the qualities of a leader, it is only a matter of time before you are rewarded with a promotion that fits the level of quality you show through your actions.


Take small steps

Becoming comfortable with having tough conversations is a process that is best tackled through small steps and habits.

Try to have minor difficult conversations to build up your confidence and comfort with conflict.

These can be simple things such as asking your boss for time off to travel or asking for a favor from a friend.

By starting small, you’ll see how often conversations with conflict in them can end in a positive result. This will boost your confidence to address more difficult topics in other areas in the future.

Aim to get out of your comfort zone

In my post on the top ways to grow in your career, I discussed how getting out of your comfort zone was the best thing you can do.

The same applies to difficult conversations. When you get out of your comfort zone, your comfort zone will eventually grow.

Conversations that you are accustomed to shying away from will soon become normal.

Don’t procrastinate

Procrastination has no value for difficult conversations. All the thinking and stressing over the conversation and potential outcomes just waste your time and your effort.

Rip the bandage off quickly and get the conversation done with.

Initiate conversations in a constructive and non-abrasive manner.

The main reason individuals avoid difficult conversations is due to the tension that they think it will create.

When you approach a conversation in the right way, you minimize this risk and will have a better chance for the outcome you want.

Keep these things in mind:

  • Know your desired outcome
  • Know your assumptions
  • Come in friendly and with seriousness
  • Don’t sugarcoat things
  • Listen and understand the person you are talking to
  • Work together to come to an outcome that benefits both parties


These are the top 5 reasons you should know how to have difficult conversations.

It is a skill that can be acquired, developed, and practiced and can lead to many benefits for your everyday and professional life.

I recommend and personally live by the idea that one should always seek to get out of their comfort zone. That is where growth happens.

It has been said in the books I have read, the presentations I have watched and the mentors I have looked up to.

After implementing this into my own life, I applied it to engaging more in difficult conversations and have found results.

Try it out for yourself!

About Post Author

Brandon Hill

I'm Brandon Hill with Bizness Professionals. We serve content to help young professionals develop personally, professionally, and financially. Well-rounded improvement is a theme we live by. As such, this website will cover a variety of topics aimed to help you have a successful life and career.

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