These are the top 10 most difficult conversations to have at work

Nadia Vatalidis, Vice President of People at Remote

From giving negative feedback to asking for a raise, difficult conversations at work are unavoidable for both employees and managers. Many workers can be intimidated by addressing these topics because of apprehension towards their manager or a fear of conflict.

To investigate and find out more about the most difficult workplace conversations, the global HR Solutions company Remote has analysed Google search data around the world that reveals which conversations employees and workers are seeking the most guidance for online.

What were the most difficult questions to ask at work?



Monthly Google search volume


how to ask for a pay rise



how to tell your boss you’re sick



how to give negative feedback



what to say on your first day at work



how to report unfair treatment at work



what to say to someone leaving a job



how to report bullying at work



how to talk to your boss about burnout



what to say to an employee who is leaving



what to say when you’ve made a mistake at work


Asking for a raise was revealed as the most searched for workplace question, with an average of 8,100 people Googling ‘how to ask for a pay rise’ each month. Asking for a pay rise can be a nerve-wracking experience as employees may fear rejection or feel unequipped to negotiate a new salary. It’s important to be confident about your achievements and experience, and research comparable salaries to present a strong case for requesting more compensation.

With an average of 2,900 Google searches a month, ‘how to tell your boss you’re sick’ comes in second place. Even though everybody gets sick sometimes, many workers and employees worry that being off work could lead to them getting in trouble with their boss, or they may stress about their pending workload going incomplete. A clear and transparent sick leave policy will give employees peace of mind once they have followed the correct protocol.

Actively encourage your team members to care for their own physical and mental health. This will avoid burnout, increase productivity, and boost staff retention rates over the long term.

Workers wondering how to give negative feedback come next, with 720 Google searches a month. This can be a hard topic to address as discussing poor performance or inadequate work could upset some members of staff. When giving feedback to employees, it’s important to ensure it’s constructive so the person receiving it doesn’t feel demotivated or criticized.

Consider implementing a workable training module for team leaders to learn about practical tactics and strategies that can help with communicating feedback to workers and employees.

Another conversation employees struggle with is reporting mistreatment at work, with  ‘how to report unfair treatment at work’ and ‘how to report bullying at work’ getting 590 and 320 monthly searches respectively. These discussions can be difficult as the employee will have to talk about situations that have hurt them and  they may also feel anxious that without a resolution these matters could definitely get worse and hectic leading to more mistreatment.

What were the executive remarks?

Alongside this, Remote’s Vice President of People, Nadia Vatalidis has shared her advice on how to successfully navigate challenging conversations at work. This is what she had to say;

“Difficult conversations at work are bound to come up from time to time. All team members should be encouraged to proactively address problems, rather than avoid conversations and prolong an issue. Leaders should create a work environment that fosters open communication and honesty so when they are needed, these types of conversations don’t feel so hard.”

“Establishing regular one on one meetings with direct reports is a critical step to enabling this culture of direct and honest communication. Ensure that all team members have a designated a safe space to have these difficult conversations. To help both employers and employees with these conversations, we’ve put together 5 tips to assist during these challenging discussions.”

What tips can employees utilise for work conversations?

  1. Don’t wait. You may feel tempted to wait for the perfect time to have a hard discussion, but it’s unlikely the perfect time will come up. Organise a meeting as soon as an issue arises so they can be dealt with quickly.

  2. Preparation. Once you’ve organised a meeting, make sure you prepare for it. If you’re asking for a pay rise, make sure you know how much you want and why you deserve one. If you’re reporting unfair treatment, ensure you have any evidence you may need.

  3. Talking points. Set talking points in advance so both parties know what is going to be discussed. This is also the best way to ensure the issues are dealt with and you don’t get sidetracked.

  4. Remain professional. Throughout the discussion, ensure you keep your emotions in check and discuss the facts of the matter. Be wary of your tone of voice, shouting has rarely solved anything.

  5. Solution. Before the meeting ends, come up with a solution together. Having clear outcomes will help both parties remain positive about the meeting.


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