Can We Talk? by Roberta Chinsky Matuson

Seven Principles for Managing Difficult Conversations at Work

Learn the seven fundamental principles for navigating difficult discussions well.








Quiet is only sometimes valuable.


Consider the statistics: as per the startup Bravely, a significant 70 per cent of employees confess to evading difficult discussions with their colleagues. It is worth noting that a 2016 study revealed the substantial impact of failed conversations on companies, resulting in a loss of $7,500 and 7 days of work. In addition, a report from 2008 uncovered that the typical employee dedicates 2.8 hours per week to handling challenging situations. These situations could have been prevented if we were more willing to engage in difficult conversations from the start.


Workplace issues cannot be resolved by simply ignoring them. Instead, they become harmful. Effective workplace communication is crucial for maintaining organisational trust, worker satisfaction, and productivity. It is essential to address challenging matters instead of avoiding them. Start a conversation to resolve them.


Mastering the art of effective communication in various workplace scenarios significantly enhances your chances of achieving desired outcomes. Whether it's negotiating a raise, providing constructive feedback, or handling delicate office situations, taking control of the conversation is critical.


Regarding the summary of "Can We Talk?"In this program, you will gain valuable knowledge and skills.


Understanding the dynamics of a balanced conversation and strategies to prevent it from becoming one-sided;


The one mistake that always disrupts negotiations; and


Discover the valuable lessons workplace communication can learn from your inner child.



1. Having confidence is crucial for effective communication.


Would you prefer to hear the bad news or the good news first?


Unfortunately, we need to begin with some not-so-great news. Navigating difficult workplace conversations can be challenging, especially when it comes to addressing issues like micromanagement or personal hygiene. With a clear handbook or step-by-step guide, it can be easier to know how to approach these situations professionally.


Understanding the seven principles of effective workplace communication can make these difficult conversations much more accessible.


Now, let's begin with the first principle: confidence.


Having confidence is crucial for effectively handling challenging workplace situations.


Marketing manager Rishi felt hesitant to approach his boss and discuss the possibility of a raise despite shouldering additional responsibilities following his team's downsizing. Instead, he found himself caught in a common pitfall. He mentally replayed the conversation. Repetitively. Every time, Rishi envisioned his boss providing an increasing number of justifications to deny his raise. Eventually, he convinced himself not to approach his boss. What seems to be the issue? It is impossible to predict how someone else will react. Had Rishi possessed more confidence, his boss might have been inclined to approve his request for a raise.


Confidence is crucial in order to trust your instincts and maintain positive working relationships. That’s precisely what occurred to Danielle, as her boss called her out on a subpar report. Danielle recognised that the report fell short of her usual standards, and she felt compelled to sincerely apologize to her boss. However, self-doubt crept in, and Danielle found herself reaching for excuses. She attributed the incorrect numbers to another department. She suggested that her boss had not provided her with sufficient time to complete the report. Danielle understood her boss's expectation for her to take ownership of her actions, but she struggled with a lack of confidence. Consequently, her rapport with her supervisor declined.


However, when you can inspire confidence in others, you immediately transform your challenging requests into reasonable demands. Louise had recently begun a new position when she found herself needing to request time off to address a personal issue. She promised her boss that she would complete the work at a later time. Her boss readily approved the leave. Why? Louise had already built a strong foundation of trust by going the extra mile to meet a deadline and stepping in for a sick coworker. If Louise hadn't demonstrated her strong work ethic, her dedication to catching up on missed work may have seemed insincere.


Confidence plays a crucial role in starting conversations, trusting your instincts to guide your dialogue, and influencing others to respond positively to your requests. Alright. ..Is it advisable for individuals with low self-confidence to simply abandon challenging conversations at this point?


Absolutely not. Confidence is not something we are born with but rather a skill that can be developed through practice. According to the teachings of the Buddha, our thoughts have the power to shape our reality. Therefore, it is essential to cultivate a mindset of confidence. Begin your day by embracing an affirmation, a powerful phrase that transforms your aspirations and goals into a positive declaration. Feel free to come up with your own, or give these a try: I can achieve anything I put my mind to. I am confident and competent. I am confident in my ability to overcome any obstacle. Once you have developed a strong sense of confidence, it can be beneficial to push yourself to engage in challenging conversations. However, it is advisable to begin with more minor, more manageable dialogues whenever possible. Start by addressing the more straightforward tasks on your to-do list, and gradually move on to more challenging issues.



2. Ensure that clarity is given top priority.


It can be frustrating when your boss expects you to enhance your performance without providing specific areas for improvement. You're being approached by a colleague who needs your assistance on a project, but you need clarification on the level of time and effort required. You attempt to express your dissatisfaction with your current role to your manager, and he acknowledges your concerns, but weeks later, there has been no improvement in your situation.


What's the issue with all of these discussions? There needs to be more clarity from one or both of you regarding your expectations and objectives for the discussion.


Now, let's move on to the second principle in our discussion: clarity. When it comes to challenging workplace discussions, ensuring clarity should be your top focus.


Prior to initiating a conversation, it is essential to determine your desired outcomes. Establish a specific objective, such as "I aim to collaborate more closely with the design department," instead of expressing a desire for a more creative role. Consider the desired outcome you want to achieve from the conversation – perhaps you seek a salary increase, a reassignment to a different team, or more comprehensive feedback during your following performance review. And determine in advance what you are willing to sacrifice in order to attain your desired outcome. It can be pretty challenging when you express your intention to leave your job, and your boss unexpectedly accepts it! On the other hand, if you are willing to assume additional responsibilities or relocate in order to accomplish your goal, it is essential to communicate this to your partner.


Regardless of how the conversation progresses, always stay focused on your goal. You need to have precise clarity, but the other person may not share the same focus. When faced with attempts to divert attention, it's essential to remain focused on your objective and rely on factual information. As an illustration, when faced with a negative performance review, someone who deflects responsibility might respond by saying, "Sharon's numbers are even worse than mine!"Respond with a statement focused on the individual and their potential to achieve a 5 per cent increase in sales by the next quarter. Alternatively, they may try to divert the conversation with a personal tale. Here, you can maintain a balance between kindness and firmness. Apologies for the difficult situation you're facing at home. But unfortunately, we still need to talk about your poor performance. Is now a good time, or should we reschedule for tomorrow morning?”


While you should be prepared for the conversation to go poorly, don’t be surprised if it goes well. If the other person offers to meet your objective, that’s your cue to close the conversation, establishing the following steps if necessary. If your boss says, “I’d hate to lose you, but I guess I could talk to HR about a transfer,” don’t ask, “Are you sure?” Get your boss’s commitment to set up an HR meeting, and then thank them for their time.



3. Compassion has a place in professional communication


It’s essential to be clear about what you want from a conversation and to stick to your guns about getting it. But there’s one communication principle that trumps clarity – and that’s compassion, our third principle. Let’s look at this exchange between Matt, a manager, and Damian, his report. Damian, a star player on Matt’s team, was recently promoted at Matt’s insistence. But Damian has been disappointed in this new role. Matt wants to know why. The conversation starts well. Demonstrating confidence and clarity, Matt lays out his concerns and asks Damian to account for his poor performance.


Damian tries to explain, but his answers aren’t satisfactory. Matt pushes. Damian breaks down. He’s going through a divorce, and his father is terminally ill. Note that Damian hasn’t defaulted to a sob story to explain away his performance – he’s genuinely struggling. But – at precisely the point where he should have stopped to empathize with Damian – Matt brings the conversation back to Damian’s job and how he can improve. In doing so, he misses an opportunity to do something more powerful than simply achieving his conversational objective – to demonstrate compassion.


So, why is compassion so important?


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 complex workplace interactions.


What’s more, demonstrating compassion can often turn an adversarial conversation into an opportunity. Let’s say a colleague mistakenly accuses you of leaving some essential info out of a report, and you don’t like his agitated manner. You’re tempted to say something snarky like, “If you read the report properly, you might see that the numbers are right there.” But, you choose not to escalate and practice compassion instead. You say, “I’m certain I did include those numbers – the index shows they’re on page 35. 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 he’s working hard in a stressful situation. You had to put your ego aside – after all, you weren’t at fault here – but you’ve effectively defused a complex discussion.


Some people are naturally skilled at practising compassion. Don’t worry if that’s not you! The deeper your connection is with someone, the easier it is to show mercy toward them. So, work on your connections with your colleagues. Try and find shared interests – they’re an excellent foundation for building professional relationships. Put in time to get to know them as individuals. But remember, you can’t build rapport instantly. All that chit-chat in the shared kitchen and small talk before Zoom meetings is an investment in your workplace connections. And watch your nonverbal communication as well. Expressing empathy while also leaning away or failing to make eye contact will only make you come off as insincere – in which case, you’d be better off keeping your mouth shut!



4. Curiosity is a virtue.


Getting in touch with your inner child can pay dividends when it comes to workplace communication. Before you get too excited, We’re not suggesting finger-painting sessions instead of weekly stand-ups or mandatory afternoon naps. But we are suggesting you tap into a childlike sense of inquisitiveness next time you face a difficult conversation.


Kids are full of questions – Why is the sky blue? Why can’t I eat chocolate for dinner? As adults, we’re less likely to ask questions than to form judgments. And more often than not, our decisions are likely to be wrong, or at least only partially correct. To get the whole picture, you need to get curious, which is our fourth principle.


Asking lots of questions not only helps you get a better handle on the issue you’re discussing but 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 your partner to collaborate on achieving a constructive outcome from your discussion.


Conversations that shut down before you achieve your objective can be frustrating. So, curiosity is your friend here! When you sense someone is trying to close down a conversational topic, try asking an open-ended question, the kind of question that can’t be answered with a simple yes or no. These questions can reignite dialogue and allow you to steer the conversation back to where you want it.


But beware of too many conversational tangents. When a dialogue wanders off-topic, that can be because you’re thinking creatively and considering new angles. But, there are times you need to stay on topic and focus on delivering a performance review rather than musing over your favourite ice cream flavours. There’s nothing wrong with a firm but polite statement along the lines of, “Well, back to the topic at hand – let’s take a look at those conversion metrics.”



5. You can win through compromise.


Conversation isn’t a competitive sport – in order to “win” what you want out of a dialogue, your partner doesn’t necessarily have to lose. When you meet each other halfway, everyone can walk away from a conversation feeling like they’ve won. This brings us to our fifth principle, compromise. 


Here’s how to have win-win discussions:


Keep things respectful. You might be making a straightforward request for time off, or you might be grappling with a big-picture issue on which you and your teammate can’t see eye to eye. No matter how simple or complex the conversation, you’ll derail it the moment you disrespect the other person. The perceived disrespect will take precedence over the topic at hand, whether they show it or not.


If you know, you’re about to initiate a tough conversation and you’re anticipating some pushback, put in some work prediscussion. Clarify why you’re talking and keep that at the top of your mind during the discussion. If your dialogue drifts away from the why, pull it back. And if you’re making a request, work ahead of time to make sure you articulate it as clearly as possible. Don’t just ask your boss for “more responsibility” – say exactly which tasks you’re interested in taking on and suggest a timeframe for doing so.


In the middle of negotiations, it can be easy to forget your objective and focus instead on trying to force the other person to agree with you on every point. Remember, you don’t need to agree with each other on everything in order to reach a satisfactory result. You might think a client is underpaying you, while your colleague might think they’re a terrible fit for your brand – competing rationales shouldn’t stop you both from deciding to drop them as a customer.


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, such as  “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 at a later date.



6. Build credibility to win better communication outcomes


As you work your way up the corporate ladder, there are a few things you can expect to automatically accrue along the way: more money, more status, and a more impressive job title. But there’s one quality that won’t automatically accrue no matter how close you get to the C-suite – and it also happens to be a prerequisite for professional success. I’m talking about our sixth principle: credibility. You can be an intern yet still inspire trust and confidence in others. You can be a CEO, yet you still struggle to bring others on board with your vision.


Luckily, credibility is a quality that you can cultivate. Here’s how:


This may sound obvious, but make sure you know what you’re talking about. Learn about the field you’re working in – and remember, developments in your area will continue to take place long after you’ve received your qualifications. Stay on top of current research and trends. The same principle applies to meetings and presentations. If you’re pitching a client, make sure you’ve researched their business model thoroughly. If you’re attending a budget meeting, have the latest figures on hand.


Next, aim for consistency. Acing a presentation or dazzling a client once won’t win you credibility points. But making a habit of performing your work to a high standard will. So, you will consistently prioritize your team’s success above your own, respond promptly to requests and queries and complete projects by a deadline. When people know they can count on you, that’s when they see you as credible.


Finally, own your mistakes. You can be knowledgeable, skilled, and a consistent high performer and still make mistakes. That’s okay! But 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. Say something like, “I rushed those proofs through without seeking input from the graphics department – I know now how important their input is at this stage, and I won’t do it again.”


So, how does credibility come into communication specifically? It’s simple. If you demonstrate credibility in what you do, your colleagues will trust what you say during conversations. Do you want to push an employee to take on a new role? Recommend a left-field new hire to the hiring manager? Implement a new high-risk, high-reward marketing strategy? If your partner thinks you can walk the walk as well as talk the talk – that is, if they trust you – then you’re much more likely to get a positive response.



7. Develop the courage to initiate tough conversations – it’s worth your while.


Here’s the honest truth: sometimes workplace conversations are downright unpleasant. You can clarify your objectives beforehand, ask the other person all the right questions, compromise adeptly, and reach a mutually satisfactory outcome – and still find every second of the discussion deeply uncomfortable. What’s more, some of the high-stakes situations where you most need to advocate for yourself – like if you’re experiencing workplace harassment, for example – are the most nerve-wracking to broach with your colleagues. So, how can you muscle through tricky conversations and stand up for yourself effectively? That’s where our seventh and final principle comes in: 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 choose 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. Moreover, if you consistently fail to assert yourself, your colleagues may take advantage of that fact. If you don’t push back when others pawn their work off on you, odds are they’ll continue to overload you with work.


Still on the fence about whether to start a tough 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?


Let’s say you’re ready to start a complex dialogue, but you’re still feeling nervous. That’s okay. Some people are born with courage. The rest of us can practice it. Unless the issue at hand is time-sensitive, it can be helpful to build your courage by doing a dry run. Choose a low-risk conversation. Perhaps a colleague takes too long to answer your emails, and you want to confront them about it. Write a short script, refine it, and then run through it a few times before you embark on the conversation itself.


Only some of these low-risk conversations will go smoothly. Some may be total failures. And that’s fine! Remember the words of entrepreneur Alan Weiss, “If you’re not failing, you’re not trying!” The idea here is to build the courage and confidence you need to stand up for yourself where it really counts.



Final summary


The only thing worse than having difficult workplace discussions is not having difficult workplace discussions! Draw on the critical principles of confidence, clarity, compassion, compromise, curiosity, credibility, and courage to communicate problems and resolve them successfully.



And here’s some actionable advice to get started: Don’t be blindsided by difficult conversations. 


There are a few surefire signs that your boss is about to sit you down for a difficult discussion. They no longer seek out your opinion. Previously, long conversations were terminated after a minute or two. They refrain from returning your calls or responding to your emails. If you’ve spotted one or more of these signs – act! Brush up on the seven principles of effective workplace communication, and get ready to make your case.

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