Why Most People Struggle With Difficult Conversations

Difficult conversations are a bit like mushrooms in the dark. We all know they’re growing somewhere below the surface, but we try to avoid shining a light on them until they burst through, and we have no choice but to acknowledge them. That might be as far as that metaphor goes!

In a business context, avoiding or suppressing the difficult conversations is often a one-way ticket to a toxic environment. You miss feedback, resentment starts to fester among employees, your engagement rates take a turn for the worse, and you may even lose team members altogether.

As an HR consultant, it’s something I’ve seen again and again. Managers who freeze at the thought of giving ‘tough’ feedback, employees who don’t feel they can voice concerns to their managers, and conflicts that are left unspoken until one day they blow up, causing a fair amount of collateral damage along the way. That’s why I want to explore why those difficult conversations feel so hard (for both sides), and what you can do to turn them into genuine growth opportunities.

The Problem for Managers

Let’s face it, managers are often the ones who are faced with having difficult conversations. It’s part of their job description. Whether they need to help resolve a conflict between team members, address poor performance, or let someone know that redundancy is coming, none of it is easy. And there are a lot of things that can make those conversations feel even more difficult.

For a start, there’s a fine line between emotional distance and compassion, and they need to walk it carefully. If you’re too cold you sound uncaring and callous. Too soft, and the message is lost. Finding that sweet spot in the middle, where you can have the conversations with compassion without muddying the message, takes a lot of practice.

They can also feel a conflict with their role. Many managers see themselves as cheerleaders, collaborators or coaches. Which is absolutely true! But giving negative feedback often then feels counterintuitive to that identity, like taking the batteries out of a toy. There’s often a fear of ‘pulling the rug out’ with difficult conversations, damaging relationships or losing your rapport with employees. So it becomes easier to not have the conversations at all. Add to that that managers are often swamped with work, which means tough chats are deprioritised in favour of more urgent tasks, and issues left to simmer until they boil over.

Finally, there’s a lack of training. You’d be surprised just how many managers don’t receive much training when they’re promoted, instead being left to figure it out by themselves. They haven’t been taught how to plan and conduct these conversations, which means they worry about losing control, or going off script and saying the wrong thing. So, they end up either winging it (and floundering) or avoiding it altogether.

All of which means that most managers struggle to have difficult conversations effectively.

What About Employees?

Of course, these struggles don’t just go one way. Employees can also need to have difficult conversations, either with their managers or other team members, but shy away from them as long as they can. They might be worried about being labelled as negative or difficult for bringing issues up. No one wants to be seen as the trouble maker, and fear can make people self-censor just to be safe. If they do feel strongly enough to bring it up, there can still be uncertainty about the right words or moments to do it. ‘What if I use the wrong words?’, ‘how do I start?’, ‘What if I’m wrong?’. Uncertainty breeds paralysis.

Let’s not forget that the dynamics are different here too. Everyone knows that managers sometimes need to have difficult conversations with their employees, but many forget that it happens the other way around as well. Employees need to be able to bring up problems to their managers too. But there’s a worry that they don’t have all the information, or the right to do it, so their concerns will be dismissed.

Finally, there’s another fear. Fear of being dismissed or blamed. When you raise an issue, it often carries emotional weight with it. Feelings like shame, embarrassment, defensiveness or anxiety. It’s rarely just the bare facts – there’s a hidden emotional undercurrent that a lot of people want to avoid at all costs.

So the difficult conversations don’t happen.

How Can HR Help?

Give you structure: HR can give you some structure, so the conversations don’t feel off-the-cuff or out of control. Templates, conversation guide, roleplays, whatever your managers need so that they aren’t flying blind, and know that everything will be covered.

Coach & shadow conversations: Your HR consultant can sit in on the conversations, to observe, mediate or give guidance, intervene if things derail and help keep things fair.

Normalise it: It can help to embed regular check-ins and feedback into your culture, so that difficult conversations can be had when they’re smaller issues. That way people can see them as part of a healthy dialogue, not emergency situations.

Offer a safe space for employees: Sometimes an employee can’t or won’t raise a point directly with their manager. HR can act as a safe space to air their grievances, with the knowledge that they will be dealt with fairly.

Ensure accountability: HR can track the commitments made during conversations, check that follow-ups happen and hold everyone accountable to their actions.

Be a neutral party: By participating (or being on standby), HR can level the playing field, make sure the tone is reasonable, and help remove any perceptions of bias or retaliation.

Provide data and culture insights: HR can monitor patterns. Who’s avoiding conversations, where breakdowns cluster, which managers struggle, and intervene early at organisational levels.

Most people struggle with difficult conversations. Not because they can’t have them, but because those conversations live at the crossroads of emotion, power and uncertainty. That’s a risky, high-stakes place to be, and not many people are naturally able to navigate it. Not without help anyway.

With an experienced HR professional on your side, you can feel more confident in navigating those conversations. Taking those tense, silent gaps and turning them into opportunities for clarity, trust, alignment and psychological safety for everyone involved. If your leadership wants people to speak up, issues to be addressed, and culture to grow stronger, start by investing in the people who know how to make difficult conversations both safe and useful. If you’d like some support, or just to know more, just get in touch with me today and book your free consultation.