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Career Success

How To Have Difficult Conversations At Work: 3 Key Steps

Written by Dr. Erik Reis
Co-Founder, Director of Health and Wellness at Nobody Studios
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Having difficult conversations at work is one of the most challenging things we have to do as employers and employees. We all dread it, no one looks forward to it, and only a very few people can do it well.

But having difficult conversations can make all the difference and is a pivotal part of being a part of a team, regardless of the status or role you play within that team. And these hard conversations are often far worse than we make them out to be because our minds take things to the extreme to protect ourselves.

“We suffer more often in imagination than in reality.”—Seneca

Why Do We Avoid Difficult Conversations at Work?

Why do we do this to ourselves? Why do we like to avoid having difficult conversations? We would have already figured it out if the answer was that easy.

Our brains are wired to keep us safe, not to take risks.[1] We will always want to avoid conflict and resist change because that’s far easier than being challenged to grow and get uncomfortable. But leaning into this fear of change is what we need to do to develop the skills and resources to have difficult conversations with our peers, colleagues, and teams.

Businesses solve problems, and problems will always present difficulties that will need to be overcome through complex discussions, in-depth conversations, and challenging people’s capacities.

Yet, that’s the beauty of being a part of a team or organization. Overcoming a challenge can bring people together. But when that achievement is accomplished alongside the collateral damage of poor communication, blame, or pointing fingers throughout the process, then it becomes a failure in the long run.


3 Key Steps to Tackle Difficult Conversations at Work

Research shows that having better employee relationships equate to having better well-being and work performance. Moreover, positive work relationships also affect the behavior and manners of employees positively.[2]

Hence, it’s crucial for employees to be able to learn how to start difficult conversations at work in order to strengthen work relationships or rebuild old ones.

If you want to improve your ability to start difficult conversations at the office, then start with these three key steps.

1. Have the Discussion in Person

Before my fellow millennials start shaking in their seats behind their devices, we need to understand why this is such an essential piece of the puzzle.

The idea is that it all comes down to respect.

It’s easy to hide behind a screen, because you dissociate yourself from the person you’re speaking to. If you’re willing to sit down with someone and discuss an emotionally challenging topic or point of tension, mutual respect is needed to make that happen.

If you don’t respect someone’s opinion, what they say or do won’t matter because you have already decided that you won’t change your mind.[3] This distasteful mentality of ghosting or leaving someone hanging is a significant sign of disrespect and overall lack of maturity.


If you truly want to have a difficult, meaningful conversation to move forward with a personal or professional relationship, it must be done in person. According to Margaret Schweer, “relationships with colleagues start with a human face.”[4]

You need to be physically present to share your perspective, and you must also be willing to listen to the other person share their perspective. And in the moment, body language can often tell us far more about what someone is trying to say than merely listening to their words.

People will often tell you far more than what they are actually saying to you, so your ability to pick up on subtle nuances will vastly improve when you’re physically present and sitting across from them.

Being present is far more than being physically present because it also involves being cognitively and emotionally there.

2. Listen to Understand, Not to Respond

Difficult conversations don’t come about because of a minor slight or gesture. In many cases, they arise from repeated outcomes that never resolve on their own, which causes even more emotional angst and stress because of the length it has occurred over.

Your mentality going into any conversation, whether it be a good one or a bad one, should be to make sure that you master your communication skills.

And while communication in a traditional sense is something you can control with your words and use of gestures, it also heavily involves actively listening and understanding where the other person is coming from.


Emotional intelligence is a highly regarded trait that many leaders seek to master because it allows them to better understand the person they’re communicating with.[5] It also allows them to put their feet in another person’s shoes and find empathy for where they may be coming from.

We often forget that our ego is the enemy. We’re usually more worried about preserving our own image, which may cause us to dismiss how the other person is feeling during a conversation.

If we don’t actively seek opportunities to understand what they’re saying, then we will miss out on a chance to appreciate their perspective. And whenever we fail to effectively connect, it’s often because we’ve failed to communicate.

3. Ask For Feedback

If having difficult conversations is hard, then asking for feedback should be easy.

When you finally overcome your fear and initiate the discussion, you’ll often find that there has been a lack of communication and that both parties have made assumptions.

These assumptions and poor dialogue usually get us into trouble because they fester and completely change our perspective of the individual sitting across from us.

Research about preconceived bias in the context of technology shows that “while different types of experience have a significant effect on the decision to use a technology product, this effect is completely blocked by the preconceived bias of the individual about the technology.”[6] While this study was done in the context of technology, we can also observe it in the context of relationships.


Our impressions or assumptions about someone can prevent us from fully and genuinely knowing them because our preconceived notions block us from accepting information that does not fit our preconceived idea of that person.

However, when you become open to feedback, you consequently become open to hearing the other person’s input. Being open to feedback can open the doors for future discussions and allow you the opportunity to learn from your mistakes while also owning your errors from the past.

We all make mistakes, but those who repeat those mistakes develop bad habits and poor rapport with their colleagues as time goes on.

Being open to feedback will allow your colleagues to be more open to sharing their viewpoints, which inherently builds trust, communication, and bonding between individuals within the company.

Remember that having a solid relationship doesn’t always mean fewer disagreements. More often than not, it means having more efficient communication, which inherently allows for higher levels of trust and understanding.

Taking Action Cures All Pains

In most situations, difficult conversations arise because of repeated errors in judgment or mistakes that were never corrected from the start. So, if you want to create change and facilitate renewed trust in a relationship at work, then you must take action and ownership of your actions.

Actions will always speak louder than words, so time will tell how both parties respond to difficult discussions. Therefore, owning up to your actions is the only option in this equation.


And when you can take ownership of your intentions moving forward, you will be more willing to have difficult conversations. You will also find that you will need to have fewer of these hard conversations because you can continuously adapt to higher standards.

Difficult conversations will never go away, so the better you are at having them, the more efficient you will be at your job.

Take pride in owning your results, and you will have no problems with starting difficult conversations at work.

Featured photo credit: LinkedIn Sales Solutions via unsplash.com


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