Last updated: 20.06.24

Difficult Conversations: Workplace Conversations That Employees and Employers are Struggling with the Most


In today’s workplace, emotional intelligence is an important skill. So much so that it was actually named the most important leadership skill in 2024 by experts at Forbes.

Otherwise known as EQ, emotional intelligence is defined as the ability to understand and manage our own emotions, as well as recognise and influence those of others. 

Yet, despite the importance of the skill that shapes the way we communicate, collaborate and resolve conflicts, it appears that employees and employers alike are struggling with one particular aspect of emotional intelligence: having difficult conversations.

According to reports, as many as half of managers cite difficult conversations as the biggest challenge they face in their role, and over a third (34%) admit to having put a difficult conversation off for at least a month and a quarter have put it off for over a year!

This avoidance can stem from a range of different factors: fear of conflict, concern about damaging relationships or uncertainty about how to express feelings effectively.

However, the impact of not communicating effectively can be significant, leading to unresolved issues, decreased productivity and even a toxic workplace environment.

At Virtual College, we have found out the type of workplace conversations that both employees and employers appear to be struggling with the most, looking at Google search results to see which challenging situations people are most frequently seeking advice for.

Key findings

  • Almost half (48%) of the total search volume relates to conversations around salary and recompensation, highlighting that there is a significant concern about discussing financial matters with employers.
  • Navigating workplace relationships is also a significant concern for many employees. Searches for ‘signs my boss wants me to quit’ are as high as 1,900 each month, which indicates that employees are struggling to read the emotions of their superiors.
  • Similarly, ‘signs your boss is testing you’ sees 1,600 searches each month, which shows a desire from employees to understand whether they are being scrutinised or evaluated by their superiors. This figure would indicate a lack of conversation around this.
  • With an average of around 3,600 worldwide searches for ‘how to ask for feedback’ each month, it is clear that employees and job seekers alike are highly motivated to receive an external evaluation of their efforts but knowing how to ask for it seems to be a clear concern.
  • The data highlights there is a need for guidance on how to request feedback via email, which suggests that employees might find face-to-face or verbal requests either intimidating or less effective.

If you struggle with difficult conversations, here is what to do about it

You can’t shy away from difficult conversations in today’s workplace environment, especially if you want to progress in your career.

In a study of 500 people managers, figures revealed that as many as 75% used emotional intelligence levels as criteria for considering a team member for a promotion or salary increase. 

Further research reveals that 90% of top performers have high emotional intelligence too, so it seems that it’s an important skill for anyone wanting to be a front-runner in their field.

At Virtual College, we have a range of courses for anyone looking to develop their emotional intelligence including emotional intelligence, dealing with difficult situations, and tackling difficult conversations specifically.

We’ve also put together some short but effective tips below for anyone wanting to know how best to approach difficult conversations.

#1 Don’t Come Out The Blue

One of the most important things to remember when approaching a difficult conversation is not to spring it on someone unannounced, but research shows that as many as 57% of workers aren’t likely to provide forewarning. 

Letting people know about the chat in advance will allow them to enter the discussion feeling more comfortable and confident, which shows you are considering their emotions. 

Also, letting people know what you’re going to specifically talk about in advance can be particularly useful in emotionally charged situations as it can remove the initial shock and make the conversation easier to navigate.

#2 Have Empathy

One of the best ways to handle difficult situations in a positive manner is to have empathy and ensure you recognise other people’s feelings and experiences. It enables you to understand someone else's perspective, better connect with others and develop a better general outlook.

Empathy - and showing it - is more important than ever, as research reveals a sharp decline in the empathy of managers since the start of the pandemic. In May 2020, nearly half of workers surveyed said they felt their boss cared about their wellbeing but that number has since more than halved.

Phrases like “I understand that this must feel…”, “I appreciate that this may be hard to hear…”, or “I imagine that you are feeling...” are effective ways to demonstrate empathy and indicate that you are considering others’ feelings.

#3 Get To The Point

When approaching a difficult conversation, it can be tempting to beat around the bush as some people might think that padding out the context around the subject will make the impact less severe. 

Almost a quarter (22%) of workers admit that they aren’t communicating directly when having difficult conversations in the workplace, according to a survey

However, being direct when dealing with these situations will eradicate the chance that the recipient might misunderstand what you’re trying to convey. Ways of being direct include beginning the conversation by highlighting why you are there, presenting the facts clearly and concisely, and allowing those in the room to clarify anything you have said.


We used Google Keyword Planner to analyse over 5,000 keywords relating to difficult conversations in the workplace, ranking them on the average monthly search volume.

Data is correct as of June 2024. A full dataset is available upon request.