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The Employee Experience Platform | Culture Amp
Sophia Lee, author

Sophia Lee

Writer, Culture Amp

The burden of having difficult conversations with employees at work often falls on managers. It's up to managers to address everything from underwhelming performance to low motivation. But when we ask managers to have difficult conversations, we're not simply asking them to talk. We’re asking them to approach their direct reports with empathy, provide ongoing support, and coach employees towards a solution – among other things. This is a lot to ask, especially when their direct reports are maybe working remotely.

In this article, we’ll explore how to have difficult conversations with employees. We’ll also explain what HR can do to better support managers with these hard conversations and drive a more positive company culture and business outcomes.

Having difficult conversations at work through the lens of empathy

Before we dive into the specifics, let’s establish a framework for thinking about what these conversations should look like. Josh Bersin recently published an article about The Big Reset, which discusses the new ways we need to think about work, life, business, and leadership as a result of the pandemic. One of the points he makes is about the need for leadership to shift toward empathy, compassion, and understanding.

“High-performing leaders of today are different. They’re empathetic, they think about people and society, and they really listen. There will always be financially-driven executives, but they’re getting pummeled and won't be effective today. 

Why? This crisis is teaching us an important human lesson. It’s a health and safety crisis first, and an economic and business problem second. It’s as if we’re running a company that just had a massive explosion that blew up half of our facilities. We can’t just talk about fixing buildings, we have to talk about making people safe first.”

While empathetic leadership isn’t a new concept, it needs to be at the forefront of conversations instead of being an afterthought. To have a high-performing organization, HR and managers need to keep this lens of empathy in mind when having difficult conversations.

How to help managers have difficult conversations at work 

There are three common areas managers are likely to encounter hard conversations with their employees:

  1. Performance
  2. Engagement
  3. Wellbeing

Below, we explain what these conversations might look like and what your HR team can do to help managers approach them in an empathetic way. 


Performance is always a tricky topic to approach. The most common conversation usually revolves around employees who are underperforming. But the uncertainty of today's world of work introduces new complications, such as layoffs and promotion freezes.

How HR can enable managers:

  • Provide performance transparency. In order to have productive conversations about performance, managers and employees need to have access to the same information. One of the ways that HR teams can support this is to introduce a performance review platform that can provide data around an employee’s performance. Starting the conversation from a foundation that’s built on objective facts – rather than subjective feedback – can make conversations easier to digest for low-performing employees. This data can also help managers identify a clear area for the employee to focus on to improve their performance and show them that they’re not expected to manage this journey alone. 
  • Reset expectations at an organizational level. COVID-19 and today's economic uncertainty has completely changed the employee experience – including what success looks like at every company. It’s no longer relevant, for example, for an event planning company to have the same goals in 2023 they did the did the previous year. Given this, it’s HR’s responsibility to set the tone around performance during these tumultuous times. This includes encouraging managers to adjust goals with their teams, reprioritize what’s important to the organization, and review shorter-term goals more often. This will make conversations easier because it demonstrates to employees that their managers are empathetic to the current changing circumstances instead of pretending like things are “business as usual.” 
  • Adjust manager training. This may be a good time to revisit any existing resources around performance reviews. Given all the rapid changes that we’ve gone through, it may be necessary to make adjustments to these materials to ensure they still align with the current situation. For instance, you may want to make tweaks to your manager training on how to give performance feedback. Or you may have to update your performance guidebook to reflect any changes you made to the process during this period of uncertainty.


Employee engagement is likely top of mind for your team right now. You might have employees who are disengaged from work or are demotivated because your company recently went through a series of layoffs. Understanding exactly what’s causing the low engagement levels can help managers approach these conversations with more compassion and come up with the best solutions for their teams.

How HR can enable managers:

  • Provide managers with engagement data. HR can be most helpful to managers by enhancing their understanding of the engagement levels of their teams and direct reports. One of the most effective ways to do this is to give managers access to the data from engagement or pulse surveys so they can see the big picture. This will help them identify areas where they’re doing well and areas where there’s an opportunity to improve. 
  • Support next steps. After providing access to the data, HR teams need to go one step further. They should also involve managers in taking action on these survey results.  This means having conversations to ensure managers are on the same page about how the results were interpreted, identifying which areas to address first, and clarifying what their roles are in terms of making decisions. 


Whether you have people who are on the verge of (or actively experiencing) burnout or are struggling to have their personal and professional lives co-exist, wellbeing has never been a more prevalent issue than it is now. Of course, this is a topic that needs to be approached with sensitivity and compassion. There are a few ways that HR can make this easier for managers to do.

How HR can enable managers:

  • Create venues for conversations to happen. HR teams should take the initiative to create safe spaces for managers to have conversations about the unique challenges employees are facing in 2023 – beyond just 1-on-1 meetings. This can be done by hosting virtual events that focus on wellness topics, launching “empathy circles” for people to discuss their mental health struggles, or starting an employee resource group (ERG) that allows people to talk about topics that are sitting heavily with them. 
  • Have realistic expectations. It’s also critical for HR to clearly define boundaries when it comes to the manager’s role in employee wellbeing. Yes, managers should be trained to identify burnout and understand how to approach these conversations from a place of empathy. But it’s unfair to expect them to play the role of a therapist for employees. So make sure to clearly communicate these expectations to everyone at the organization.  
  • Consider the wellbeing of managers. If managers aren’t taking care of their own wellbeing, they won’t be in a place to effectively handle tough conversations about their employees’ wellbeing. HR should be mindful of this and make sure managers are up to the demands of their role. If not, you may consider moving managers into individual contributor roles if they’re unable or unwilling to handle management responsibilities – not as a demotion, but rather as a way to give managers the time and space they need for self-care. 

Navigating difficult conversations will always be part of a manager’s role – especially during these challenging times. But by providing the right type of support – whether it’s in the form of tools or training – HR teams can make these conversations much more approachable for both managers and employees.

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