​Managing Difficult Conversations at Work


​Managing Difficult Conversations at Work

Posted on 20 July 2022

Managing Difficult Conversations at Work


Whether you’re asking your boss for a pay rise, delivering feedback to your team, or navigating a tricky office etiquette dilemma, learning to take charge of the conversation will get you one step closer to achieving the results you want.


Workplace issues don’t just go away when we ignore them. Instead, they can turn toxic.


Poor, or absent, workplace communication inevitably ends up eroding trust, employee satisfaction, and productivity.


Here are some key principles for navigating difficult discussions well:


1.     Confidence

When you can inspire confidence in others, you instantly reframe your tricky requests into reasonable asks.


Think yourself confident! Once you’re thinking confidently, challenge yourself to initiate difficult dialogues – but, where possible, try and start small. Tackle the least intimidating issues on your to-do list, then work up to bigger problems.


2.     Clarity

In difficult workplace discussions, clarity is your number one priority.


Before you begin a conversation, work out what you want from it. Set a concrete goal, like “I’d like to work more closely with the design department,” rather than, “I want a more creative role.” Ask yourself what you want the other person to do directly after your conversation – perhaps you’d like them to give you a raise, assign you to a new team, or give you more thorough feedback at your next performance review. Decide ahead of time what you’re prepared to risk to achieve your desired result. There’s nothing worse than threatening to quit your job, only to have your boss take you up on the offer! Then again, if you’re prepared to take on extra responsibilities or make a transfer to achieve your objective, then the other party needs to know that.


3.     Compassion


As a rule, people want to work with, and for, compassionate people. No one wants a boss who doesn’t care that their Grandma just died or a colleague who only grumbles about the extra workload when someone on their team breaks a leg. Demonstrating empathy and compassion for others helps establish goodwill and rapport – two things that go a long way toward smoothing out potentially difficult workplace interactions.


What’s more, demonstrating compassion can often turn an adversarial conversation into an opportunity. You could say “I know how easy it is to miss these things when you’re under pressure.” Now you’ve corrected your colleague’s mistake and signalled you know they are working hard in a stressful situation. Work on your connections with your colleagues. Try and find shared interests – they’re a great foundation for building professional relationships.


4.     Curiosity


Asking lots of questions not only helps you get a better handle on the issue you’re discussing, it signals to others that you welcome their input and value their opinions. Questions like “why do you think this happened?” and “What do you think our next steps should be?” invite the other party to collaborate on achieving a constructive outcome from your discussion.


5.     Compromise.


Keep things respectful. No matter how simple or complex the conversation, you’ll derail it the moment you disrespect the other person.

Difficult discussions and complex negotiations take a lot out of everyone involved. Even if the other person is saying things you don’t want to hear, make it clear you value their involvement. Thank them for their feedback and opinions. Don’t interrupt while they’re talking. Avoid accusatory language and prioritise I-centric statements – so, “I feel overwhelmed by my workload” rather than “You’ve offloaded way too much work onto me.” If you really feel like you’re hitting a wall, don’t be afraid to take a break. Set a time to pick up the conversation later.


6.     Credibility


You can be an apprentice, yet still inspire trust and confidence in others. You can also be a CEO, yet still struggle to bring others on board with your vision.


Learn about the field you’re working in – remember that developments in your area will continue to take place long after you’ve received your qualifications. Stay on top of current research and trends.


Own your mistakes. You can be knowledgeable, skilled, and a consistent high performer and still make mistakes. The moment you deflect blame for your failures onto someone or something else, all that credibility you’ve worked so long to build up evaporates. If you make a mistake – and you will – take full responsibility for it. What’s more, share your learnings.


7.     Courage


Fear of discomfort is often what holds us back from initiating difficult but necessary discussions. Someone takes credit for our work, but we decide not to call them out on it. Someone on our team isn’t pulling their weight, but we decide not to make waves by calling it to our boss’s attention. Here’s the thing: not talking about the problem won’t make it go away. As long as the problem persists, so do our feelings of discomfort and dissatisfaction. If you consistently fail to assert yourself, your colleagues may take advantage of that fact. If you don’t push back when others load their work off on you, odds are they’ll continue to overload you with work.


Still on the fence about whether to start a particularly difficult conversation?


Ask yourself these questions:

·       If I don’t do something about this now, will I regret it later?

·       What’s stopping me from initiating this discussion?

·       Is it a valid reason for not speaking out?

·       What’s the worst thing that could happen if I do say something?

·       What’s the worst thing that could happen if I don’t say something?


Draw on the key principles of confidence, clarity, compassion, compromise, curiosity, credibility, and courage to communicate problems and resolve them successfully.

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