Having Difficult Conversations is Inevitable – Here’s How to Manage Better

In life and business, challenging discussions are unavoidable. Whether it’s with a colleague, a client, the HR manager, or your boss, there will always be conversations that will test you – and sometimes, you just never know when they’re coming.

Given the fluctuating global economy, your anxiety about them is undestandable, too. For all we know, a casual meeting with your supervisor can instantly and dramatically shift your career trajectory, especially with the recent uptick in global layoffs – not just in tech but across many industries.

But like talks of job cuts and retrenchment, most difficult conversations – like salary negotiations and the resolution of office conflicts  – are just typical occurrences in the working life. That said, the sooner you accept this, the easier it’ll be to navigate your way through them.

Why We Avoid Difficult Conversations

If you’re the type to shy away from confrontations and other tricky scenarios, you’re not alone. In a U.S. poll, it was found that more than 80 per cent of workers cower from at least one dreaded conversation at work. The study also found that the respondents went as far as putting off the scary conversation for six months up to two years. They cited lack of confidence to speak up as the primary reason for keeping quiet, followed by fear of the consequences as well as repercussions from managers and team members.

This is not at all surprising. Usually revolving around conflict, differences, problems, and bad news, difficult conversations require intense mental effort and can tax the mind. This perceived cognitive cost, coupled with thoughts of the possible effects, motivate you to avoid them – because who wants a headache, really?

Plus, it often seems easier not to have “the talk” – or so you think. Imagine a toothache. It starts as a mild, throbbing pain that you shrug off, believing it will go away on its own. Days and weeks pass, and the pain worsens, yet you still do nothing. Until one day, you run to the dentist who tells you already need a root canal. You realise that you could’ve avoided such trouble if only you addressed the problem earlier.

The point? Avoiding a difficult conversation may be easier, but it can only aggravate things in the long run. To thrive and grow professionally, you must learn how to face the inevitable – and it starts with proper preparation.

Preparing for Tough Conversations

Leading social scientist for business performance Joseph Grenny, who wrote the New York Times bestselling book Crucial Conversations, says, “Crucial conversations are 60 per cent getting your head, heart, and gut right, and 40 per cent saying it right.” According to him, the primary predictor of success in a difficult conversation has less to do with how you use your mouth and much more with what you do before opening it.

Think about the last time you regretted something you said. Most likely, you said it because you were caught off guard or swept away by your emotions. You didn't prepare and likely responded without much thought. When this happens, things can go awry. Naturally, it isn’t something you’d want during a conversation at work.

The good news is you don’t necessarily have to be a smooth talker to survive a tough verbal ordeal. Here are some things you can do to be better prepared for your next difficult conversation:

Calm yourself down.

A perceived threat — like the anticipation of bad news — sets you on a defensive mode. Perhaps you become angry, tearful, or scared. The last thing you want to do during a work meeting is to allow your emotions to take control, as doing so can hinder a productive conversation.

Take a deep breath, go for a walk, and do what works to soothe your nerves. While doing so, try to shift your mindset and view the meeting as another typical work discussion. That said, if you’re in the dark about the agenda, you can always ask instead of worrying to no end. As for that mysterious email, you can send a reply like, “This is noted. May I ask what the agenda is so I can properly prepare?” and go from there. By approaching the situation positively, you’re likely to get better results.

Identify your motives and get them right.

It’s understandable to prioritise your needs and interests, especially during stressful times. But try to determine if your motives are beneficial for everyone.

Let’s say you want to talk to your boss about a problematic colleague who’s not doing his job. Before doing so, you can ask yourself these questions: What do I want to achieve? For myself? For the other person? For the team and the company? By pondering these, you can see the bigger picture and reset your motives in a productive way for everyone. This also helps you craft you sentences in a way that communicates your stance more accurately – and respectfully – even before the conversation starts.

Arm yourself with facts.

Whether you’re the one initiating the conversation or at the receiving end, do your homework and gather the facts relevant to the topic. For example, you requested a meeting with your manager to ask for a raise. You can’t just demand one without any explanation and expect to get a yes.

Lay out a well-thought-out list of reasons, ideally supported with numbers and data. Prep helps you go into the conversation more confidently and boosts your chances of achieving your desired goal.

Moreover, being ready with proof is crucial when discussing conflicts and settling issues. For example, a client claims you dropped the ball on a project when you delivered. You know the hold-up wasn’t from your end. Don’t go into that meeting without a detailed report or screenshots of your work so you have proof to back up your claims.

Have an open mindset.

People have differing views, right? A key ingredient to a productive conversation is listening to other people’s standpoints and empathising with them even if you disagree. Keep a neutral perspective and try not to let your beliefs and biases preempt your decisions – especially before the actual meeting.

Sample situation: Your newbie teammate is always contradicting your ideas and insisting on doing things his way. Instead of quickly labeling him as a villain who’s trying to undermine you, try to give him the benefit of the doubt. Maybe his preferred style worked wonders for him at his old workplace. Maybe he’s unfamiliar with your method and is simply scared to try it out. Sometimes, how we feel about others has less to do with them, and more about what we tell ourselves about them.

Tips for Actual Conversations

So you’ve already prepared and it’s time for the actual talk. Now what? Read below for quick tips on how to tackle common yet challenging work scenarios:

The Scenario: You’re being laid off.

How to deal: Even if there have been whispers of layoffs for quite a while, a job loss can still knock the wind out of you. It’s okay to ask for some time to process the news. You can say, “Thank you for informing me, but I will need a few minutes to take it all in.” If you feel you’re too emotional to talk, however, you can ask to reschedule another meeting at a later time.

Should you decide to proceed with the discussion, stay professional. Use the opportunity to ask important questions, such as if you can re-apply again after some time and how much severance you’re entitled to. (In case you didn’t know, there is no law requiring severance pay in Singapore, but the prevailing norm is to pay two weeks to one month's salary per year of employment.) Get the details about your final paycheck, health insurance, etc. And remember: You don’t have to sign or agree to anything on the same day. Tell your manager you’ll review all the information provided and will revert if you have any clarifications.

The Scenario: You want to tell your boss you're super stressed without sounding whiney.

How to deal: You can start by expressing how grateful you are for the opportunity, then explain your current feelings about your workload in a fact-based manner. Clarify what you’re experiencing and be proactive about how you want to move forward.

For example, “I’m feeling overwhelmed by the volume of projects assigned to me right now, and thought it would be best to discuss this with you so we can address this together.” After all, you both want to avoid signs of burnout.

The Scenario: You received a poor performance evaluation even though you know (or think) you’ve been doing well.

How to deal: Schedule a one-on-one meeting with your immediate superior and politely ask for the reasons for your appraisal. You can say, “Thank you for agreeing to discuss my latest evaluation with me. I’ve always strived to be a top performer, and I know you want that for me as well. I have to be honest, though: I’m a bit disappointed with my latest appraisal since I thought I’d been doing well all this time. (You can cite achievements here). I just want to understand where I’ve fallen short and what I can do better to get a higher rating.”

If you want tips on acing that year-end review, read this article.

The Scenario: A colleague is not pulling his weight and you’re tired of picking up the slack.

How to deal: While it may be tempting to report this to your supervisor stat, you may want to talk it out with your teammate first. Just make sure you don’t go into attack mode. You can start the discussion by saying you want to improve your working relationship. “Hi, I feel there are things we can do to improve the way we work on our projects. Do you have time to discuss this with me?” Then, during the actual meeting, agree on a process and work division that both of you are happy with. If your colleague still fails to do his part after this, you may raise the issue with your manager so they can intervene.

Tough talks can be dreadful and awkward, but they’re part of life – both in and out of the office. By preparing well, you’ve already won half the battle. The key is to approach difficult conversations with a positive mindset, honesty, mutual respect, and empathy.

Want more resources on how to navigate your career and professional relationships? Check out JobStreet’s Career Advice section for more expert insights. If you’re looking to#SEEKBetter, find new job opportunities here. Download the app, available on the App Store and Google Play, for easier access.