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How To Have 5 Difficult Work Conversations That You've Been Avoiding

Difficult work conversations: we all dread them. Whether it’s giving a coworker constructive feedback, telling your boss you’re resigning, saying no to a project or dealing with a workplace bully, it’s important to know how to approach these difficult and often awkward conversations at work with grace and poise. Here are a few tips on how to handle tough conversations effectively.

“We need to talk.”

Those 4 little words can send shivers down your spine.

Nobody likes confrontation. Not at home, not at school, and especially not at work.

That’s why we become experts at avoiding these painful conversations. We tell ourselves it’s not that bad, that we’re blowing things out of proportion – and we end up putting them off.

We’d rather suffer in silence than awkwardly work through a conflict with a colleague or ask the boss for a well-deserved pay rise.

But we avoid these conversations at our own peril.

At some point in your career, you’ll need to have ‘that talk’. You’ll need to quit, tell someone their work isn’t up to scratch, or receive feedback that you’re less-than-thrilled about.

Sounds tough, right? Well that's because it is.

That’s why we’ve made life easier for you. Here are 5 common workplace conversations (with example scripts!) to navigate those awkward moments like a pro. 


1. How To Tell Your Boss You’re Quitting 

Much like breaking up with a partner, this is a conversation where you’ll need to tell your employer that you’re leaving them (and possibly also that you’ve found someone else.) Even if you can’t wait to leave, it’s important not to burn any bridges and leave on a high note.

Schedule a meeting with your manager or boss and when you sit down with them, remember to keep things neutral, professional, and wherever possible, positive. This is not the moment to complain about your current role (after all, your manager could be a future reference) or gloat about your new one (it’s not classy, and may cause unnecessary resentment.) Here’s an example:

I want to let you know that I’m resigning from my position. This was a difficult decision for me – I’ve really enjoyed working with the team and I’ve learned a lot during my time here. However I’ve received a job offer that will allow me to progress further in my career. As per my contract, I am providing X weeks of notice. Please let me know how I can help to ease the transition. 


2. How To Have The Conversation About Negotiating Your Salary

Going into a negotiation conversation is never fun. Whether it’s talking about your starting salary with a new employer or asking for a remuneration increase at your annual performance review, you need to be prepared to put a number on the table – often one that is considerably higher than what's on offer. Rather than balking at the thought (and avoiding the situation entirely, which could leave you $600,000 poorer by the end of your career), here's how to approach the conversation:

For a new job:

Thank you so much for the offer! I'm really excited about the role and I'm confident that I'll be able to contribute to the team's success. However, according to my research, the typical salary range for this position is around $X. Would you be able to match this figure?

For your current job:

As you know, I've been overperforming in my role over the past year, and my accomplishments have (made the company X amount of money/reduced turnover/reduced time spent on X tasks). I really love working here, and I would love to continue giving my best to the company. Can we explore whether I'm being compensated accordingly? According to my research, the typical base salary for someone in my position is $X.

If the prospect of asking for a raise still makes you queasy, use our science-backed tips to negotiate the salary you deserve


3. How to Give Constructive Feedback

Giving feedback is the best way to help someone recognise (and hopefully change) their behaviour. Whether you need to give feedback to a subordinate, a peer or even your manager, how you phrase it can make all the difference. Start off with asking them for permission, and then use the BIO model (Behaviour, Impact, Outcome) to keep things from getting personal. It’s important to focus on the behaviour that you observed, rather than your perception of the person's intention or the outcome of the situation. Here’s a sample script:

‘Sally, do you have a minute so I can share some quick feedback with you? In the meeting today, I noticed that you were checking Facebook (B). As a result, you appeared uninterested in the meeting, and it made me feel that you did not want to be there (I). I know the meeting went on for longer than expected, but it would be great if everyone agreed to leave our phones outside the meeting room, so we can all contribute to the discussion (O). What do you think?”

As in the example above, it’s a good idea to use phrases like ‘I noticed’, ‘It appeared’ and ‘It made me feel’ which are hard to argue with, compared to something like ‘You’re always looking at your phone during meetings – that’s just rude’. After delivering the feedback, pause and listen to what the other person has to say, so it’s not a one-sided conversation. 


4. How to Receive Negative Feedback

Getting critiqued on your work can sting. But no matter how much it hurts to hear it, receiving constructive criticism will help you improve and develop professionally.

When you receive feedback, start off by thanking the person for taking the time to share it with you, then try and understand the situation and your options moving forward. Here’s a sample script:

Hi Vinh, thank you for your feedback about my presentation. I just wanted to clarify: when you said that I seemed nervous, what did you mean by that? I really want to improve my presentation skills, and it would help me if you described what I did today that made me seem nervous, and what I could do differently.

While it’s never fun to hear less-than-glowing feedback, it will help you to mature and grow as a person. If people see you as someone who welcomes feedback, they will be more likely to share it. Better still, if you actively solicit feedback, you’re going to be seen as someone who cares about improving, and you can use the insights to your advantage for your personal and professional development


5. How to Say No To Your Boss

Saying no to your boss is right up there on the fun-o-meter with filing your taxes and getting root canal therapy at the dentist. But sometimes you just have to say no to a task that your boss is asking you to do.

There are lots of ways to say no (we found at least 49!) but when you have to refuse something your boss has asked you to do, you have to phrase it in a way that is tactful and still makes you seem like you're a team player.

Here's a sample script for what to say to your manager when you already have too much on your plate:

Thanks so much for thinking of me! At the moment, I've been working on the TPS reports as my top priority. I want to make sure that I give this my best, so could you please help me prioritise my current projects to figure out where this fits in?

By telling your boss exactly where you stand with other projects, and asking them for advice, you're demonstrating that you're responsible, on top of your workload and good with time management


Having difficult conversations is never fun, but following the 5 tips above will help you stop avoiding them. 

Dealing with a difficult coworker? Here’s how to handle many different types of toxic colleagues, including bullies, know-it-alls, gossips and backstabbers. 




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