Importance of difficult conversations and how to ace them

Tanya Dutta
Published on 
Apr 27, 2023
Combining her psychology education with her research experience, Tanya has the powers to derive deep insights from data.
The importance of difficult conversations lies in the potential benefits they can bring to a workplace. Here is how to handle tough conversations at work.

Must-read insights for managers looking to share feedback effectively

Research has time and again found that while beginners prefer positive feedback as it motivates them to do more, once people become experienced in an area of work, they actually prefer negative feedback so as to step up their game.

In one Harvard Business Review survey, nearly 6 in 10 survey respondents prefered corrective feedback over straight praise,. A Gallup study also showed that employees also prefer receiving negative feedback over no feedback at all.

When constructive feedback is so actively sought after by employees, why is it so hard for managers to hold difficult conversations and communicate constructive feedback in a timely manner? Our conversations and experience with leaders and managers bring up a clear pattern behind this hesitation - anticipating hurting someone’s feelings, having a defensive reaction, or being unliked afterward. While these are valid fears, managers often discover these fears are more to do with their own thought patterns than actual employee reactions.

Hence, we’ve tried to take insights from the best feedback conversations and jot down some tips for managers looking for ways to deliver constructive feedback effectively.

Understanding the Need to Have a Difficult Conversation

It is critical to understand the importance of difficult conversations at work as these discussions are one of the essential aspects of working efficiently and harmoniously with others. An organization must balance engagement, productivity, and challenging arguments to build a culture geared towards achieving success.

Engaging in difficult conversations at work instead of avoiding them is very important for a healthy environment at the workplace. Once you have the right reasons and the expected benefit for the organization clear in your head, it is easier to go ahead. Without clarity on the need for having a difficult conversation, the overall approach towards the discussion suffers.

As you aim for an understanding above consensus, you would focus on facts and not feelings. At the same time, you can set the talking points in advance once the whole idea behind having a difficult conversation is clear.

How to Prepare for the Conversation

Managers need to understand how to execute difficult conversations with employees. Once this is taken care of, they can handle the conflict at work productively. For top management, it is crucial to address the problem as soon as it is identified. Difficult conversations should be held across all levels so that the team is better equipped to handle them. Here are some of the ways you can prepare for the discussion:

i) Don’t Avoid it

That is the thing about difficult conversations. The longer you wait, the more difficult they become. It would help if you addressed the elephant in the room to avoid anxiety build-up and avoid making the situation bigger in your head than it is. Follow Apple co-founder Steve Jobs' advice - your job is not to be easy on people but to make them better. It will help you build a culture of feedback and addressing issues as soon as they are highlighted.

ii) Move with a Clear Purpose

You can start by putting down the three things you want to achieve from the conversation. It will help you reach a clear purpose and focus on your desired aspects. You would avoid distractions and steer a focused discussion with a proper sense. All employees are human, and you should consider it and avoid making a long list of issues for a single meeting.

iii) Be Direct in Communication

Your energy in the meeting will drive the situation. If you are uncomfortable, it will reflect in the conversation. Feeling confident is different than pretending to feel secure. Plan conversation with facts and direct communication, as it will help you stay and move confidently. By asking the right questions directly, there is a better chance to move out of the situation quickly rather than going around the issue repeatedly.

iv) Be Open to Differing Perspectives

A conversation is a two-way process, not a monologue. You should always keep it in mind and be open to differing perspectives. You should be aware that there can be a viewpoint that can compel you to change your mind. As a result, it is better to don't commit to your initial assessment and be prepared for change.

v) Be Empathetic

Empathy is one of the best qualities you can bring to a tough conversation. When you think about the situation from the other person’s perspective and how it may make them feel, the empathy in your approach increases. If the situation turns emotional, be focused on the larger goal, drive conversation positively, and explain the potential benefits.

Following up After the Conversation

An uncomfortable conversation would take a toll on you, even if you do not get the outcome you were hoping for. It is wrong to expect everything to work smoothly only because you have dared to initiate the conversation. Here is how you can follow up correctly:

i) Focus on the Road Ahead

It is critical to find the road ahead and build from the conversation that has just taken place. More importantly, both parties should be open to self-reflection and keep the lines of communication open even after a tough talk.

ii) Prioritize Self-Care

Self-care is one of the most vital priorities of the tough conversation. It is time to realize that it takes courage to learn and practice how to carry out a difficult conversation. As a result, it is the right time to pat yourself on the back for successfully carrying out a tough conversation.

iii) Time to Reflect

It is essential to reflect on the issue and use this as a benchmark for the upcoming experiences. It is the right time to look at what you did right and wrong during the conversation. As you are learning about the importance of difficult conversations, it is critical to understand how you can get better at offering feedback. Providing better input at an early stage is better than confronting tough talk later.

However, if you are learning about how to have a difficult conversation with your boss, you should consider how you can be more open with them. There is a possibility that you will be able to get more confident after this conversation.

Tips on having difficult conversations at workplace.

1. Focus on behavior

It’s way easier to change an action you do than to change who you are.

For example, if you have an assertive / outgoing / confident employee that is a star performer but doesn’t put too much effort into building up junior team members / considering alternate point of views, you could try framing your feedback like this:

“I could tell you’re very excited about the project. You also know a lot about this field which is a major plus. But sometimes, when you get excited and start sharing your ideas, you don’t leave room for others to voice their ideas. In particular, I noticed that our junior analyst Emily was trying to share her idea but it got shot down pretty quickly. Did you notice this too?”

2. Be specific

Zoom in on a certain problematic area instead of creating negativity around their general work. You want to come out of this having helped them find a way to improve, not leave them feeling disheartened and unproductive.

For example, if you find yourself chasing an employee for deliverable or constantly having to remind them for updates, try saying this:

“I can’t help but notice this is the third deadline that’s been difficult for you this month. I appreciate you let me know in advance that you’re running behind, but I’m wondering if I can be of any help in getting you up to speed. Let’s take a look at everything that’s on your plate right now and how you’re spending your time — maybe we can figure out a solution together.”

3. Be inclusive

People are more accepting of corrective feedback if they feel that it’s a two-way conversation rather than a reprimand by someone talking down to them. A good way to do this is to encourage employees to give themselves feedback on their own work. Ask them something like this:

“I’ve told you before it’s great that you think big-picture, but in the last two projects some important details were missed, like X and Y. Ultimately that set us back as we had to do A and B. Do you think there is anything you could do differently for next time?”

4. Be approachable

Show your team it’s okay to make mistakes as long as we’re willing to learn from them, and fast. If feedback comes with a sense of ‘holier than thou’, it can be difficult for team members to open up and feel comfortable in voicing their challenges before it’s too late. A good way to fix this is to make a personal connection. When giving feedback to an employee, try saying something like:

“I remember when I had to do that, I was so bad at my first attempt. (Include a relevant incident) But I learnt the hard way that you have to do X and it doubled my results…”

5. Be a good listener

The more your employees feel heard, the more they feel you care, and greater the amount of trust they place in you. If you have developed a transparent, trust-based relationship with your team, then they will know that you have their best interests at heart and that the feedback, be it good or bad, is for their own benefit. Even if you feel you have the answers, instead of telling your employees where they need to improve, start by asking them how they feel about a certain situation. For example:

“I wanted to discuss your last sales pitch. How do you feel it went?”

Employees generally know when their work isn’t strong and giving them the opportunity to own up to it and offer insights into their own mistakes is a way to make the negative feedback more productive. Let it come from them, then respectfully agree and guide them with solutions.

6. Be supportive

When ending the conversation, review the discussion’s essence and try to avoid the feedback’s negative aspects but focus on action points. Make sure to emphasize on what the employee could do differently and end by sharing that you’re confident of his/her ability to solve the issue.

Lastly, remember that negative feedback is only constructive if shared at the right moment, which is almost always ASAP. People aren’t perfect, and will be less likely to get offended / defensive if you share actionable insights in real time when they have the opportunity to better themselves rather than a mid-year or year end review when it’s too late.

When Can You Avoid Difficult Conversations?

It is equally important to create opportunities to avoid difficult conversations. As an employer or an HR manager, it makes sense to keep the lines of communication open. At the same time, you should encourage regular and confidential catch-ups to allow employees to talk about their experiences and air grievances, if any. It would help if you opted for a quiet word with any of the employees in case any sign of poor performance or unhappiness is noticed within the team.

It is vital to build open lines of communication. Being on good terms with your manager and being approachable is a good idea. A simmering problem on the back burner can be counter-productive for business and impact several areas of an employee's job. It is better to raise the complaints and concerns immediately and solve the issue at the right time.


The thing about difficult conversations is you can't avoid them. Therefore, it is better to focus on the goals and your approach to handling a difficult conversation rather than expecting that you wouldn't have to be in one. According to a study, 8 out of 10 employees fear a difficult conversation at work. So, it is essential to stop thinking about conflict with a negative mindset. Avoiding a difficult conversation will only make matters worse. Focusing on achieving a positive outcome from a difficult conversation is better. It will help you stay focused and grounded.

Delivering feedback effectively is a key management skill and extremely crucial to building a high performing team. So look at each exchange with your employees as a development opportunity for both them and yourself!

Do you have any other tips or advise for managers to be better at leading teams? We’d love to hear from you. Write to us at

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About the Author
Tanya Dutta
People Science Associate
With a BA and MA in psychology - she is an organizational behavior nerd through and through. She previously worked in consumer insights, where she refined the ability to derive insights from data. Combining her passion for psychology and data, she found a sweet intersection in the People Science team at Mesh, helping organizations optimize their talent strategies while keeping people at heart. Outside work, she enjoys ticking off items from her IMDB and Yelp wishlist.
About the Author
Tanya Dutta
People Science Associate
With a BA and MA in psychology - she is an organizational behavior nerd through and through. She previously worked in consumer insights, where she refined the ability to derive insights from data. Combining her passion for psychology and data, she found a sweet intersection in the People Science team at Mesh, helping organizations optimize their talent strategies while keeping people at heart. Outside work, she enjoys ticking off items from her IMDB and Yelp wishlist.

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