Welcome to the Stop Sabotaging Your Success podcast, episode one hundred and thirty-three. I’m your host, Cindy Esliger. This is the podcast focusing on what we can do today to take control of our careers and overcome the inevitable barriers to success that we encounter along the way. 

Navigating difficult conversations can feel a bit like trying to diffuse a bomb – you know it’s risky, you know it’s uncomfortable, and yet, deep down, you understand that it’s absolutely necessary if you want to avoid a bigger explosion down the line. Whether it’s a long-ignored problem that’s been festering or a potential conflict you’ve been dreading, these conversations are an unavoidable part of our working lives. And while we might wish we could sidestep them altogether, the truth is that mastering the skill of tackling tough discussions head-on is key to both personal success and building stronger, more resilient relationships. 

In this episode, we explore those dreaded, difficult conversations. For some of us, just hearing the phrase is enough to make us want to dive headfirst into our inbox or any other convenient distraction. But here’s the thing: whether we like it or not, difficult conversations are inevitable. They’re a necessary evil we have to face if we want to get anywhere, especially in complex work environments. Unfortunately, dodging them isn’t really an option, at least not if you want to maintain your sanity and avoid becoming the office doormat. 

We all have those moments where we’d rather sweep our concerns under the rug and keep the peace for just one more day. But the reality is, avoiding these courageous conversations often makes things worse. Addressing problems directly might feel like opening a can of worms, but it’s also the first step toward clearing the air, resolving conflicts, and ultimately creating an environment where everyone can thrive. 

Getting more comfortable with the discomfort is not just about fixing the problem at hand; it’s about learning how to approach difficult discussions with confidence and clarity, knowing that the rewards of facing them far outweigh the temporary awkwardness.

The discomfort we experience with difficult conversations is pretty much universal. I don’t think anyone wakes up in the morning excited about the prospect of telling a colleague their work is subpar, or confronting a boss about their micromanaging tendencies. It’s awkward, it’s uncomfortable, and sometimes it can feel downright terrifying. But, some form of these conversations are going to happen whether we like it or not. So, wouldn’t it be better to learn how to navigate them like a pro, rather than just hoping they’ll go away magically on their own?

Here’s where reframing the issue could be of benefit. What if we were to consider these types of discussions not just inevitable, but essential. When everyone’s juggling a million tasks and deadlines, misunderstandings, conflicts, and unmet expectations are bound to crop up. Ignoring them might keep the peace for the time being, but it’s unlikely they will just disappear. 

So, what are the benefits of leaning into these uncomfortable discussions, you ask? Well, for starters, it clears the air. Nothing festers like unresolved conflict. And, by addressing issues head-on, you can prevent minor annoyances from snowballing into full-blown office drama. It’s also an opportunity to resolve conflicts before they become entrenched and to build stronger, more authentic relationships with your colleagues. Trust me, there’s something almost magical about the relief you feel after a tough conversation ends, especially when it leads to a positive outcome.

There is a somewhat transformative power in learning to handle these difficult conversations. Sure, it’s easier to avoid them. We’ve all done it – pushed those nagging concerns aside, telling ourselves we’ll figure them out later. But, when later finally arrives, those issues have usually grown bigger, messier, and more complex. By that point, addressing them feels not just uncomfortable, but downright daunting. And yet, if we don’t face these problems head-on, they’ll continue to nag at us, undermining our relationships, our work, and our peace of mind.

One of the biggest reasons we’re reluctant to initiate difficult conversations is that we fear they’ll make things worse. What if the other person gets defensive? What if they don’t even realize there’s a problem and think you’re blowing things out of proportion? Or worse, what if they dismiss your concerns entirely, leaving you feeling like a fool for even bringing it up? These are all legitimate fears. But, avoiding these types of conversations doesn’t solve the problem either. It just kicks the can down the road, where it’ll be waiting for you – bigger, uglier, and harder to deal with when it finally becomes unavoidable. 

So, how do we get past this reluctance to take that first scary step toward addressing our concerns? First, we need to create an environment of trust and transparency. Now, that’s easier said than done. But, without trust, any attempt at a difficult conversation is likely to end in disaster. When people trust each other, they’re more likely to interpret our intentions as constructive rather than confrontational. They’re also more willing to engage in a dialogue rather than shutting down or getting defensive. 

But, here’s the thing: we’re often so afraid of stirring the pot that we find ourselves tackling problems in the most roundabout ways possible. We might drop hints, make vague suggestions, or try to nudge things in a different direction without ever coming out and saying, “Hey, we have a problem here”. It’s a strategy that can work in the short term – sometimes you can resolve an issue without ever directly confronting it – but it’s not always sustainable. Some issues just need to be tackled head-on. 

I can’t stress this enough, that if you avoid difficult conversations, you’re signing yourself up for a difficult relationship. I’m speaking from experience here. Whether it’s with a colleague, a boss, or a direct report, that unspoken tension will linger. And, while it might feel like you’re keeping the peace by not bringing up the problem, you’re really just delaying the issue, which might actually make things worse in the process.

So, let’s take a few minutes to reflect on why you’ve avoided these tough discussions in the past – or why you’re avoiding them right now. Maybe the problem crept up on you so slowly that you never felt there was a moment when it needed to be addressed. Or maybe you’ve convinced yourself the problem can’t be solved, and that discussing it will just lead to a massive blowout you’d rather avoid. Sometimes, it’s easier to keep the peace than to stir up issues, especially if the problem is vague and hard to pinpoint.

However, disagreements often aren’t about the problem itself. They’re usually a symptom of a much bigger issue that has yet to be addressed. So, it pays to spend a little time reflecting on the situation. Ask yourself whether the issue you’re concerned about is the real problem or just a symptom of an underlying issue. Think about how the other person might define the problem from their perspective. You don’t necessarily need to confront them about it right now, just try to make sense of it to yourself first.

And remember, not every problem needs to be addressed head-on. Sometimes, addressing every single issue can actually make things worse, especially if the problem is more difficult or impossible to resolve. Focus on the problems that can be solved and let go of the ones that can’t. Pick your battles. Addressing problems quickly and in a healthy way doesn’t mean you’ll always agree on a solution, but it might mean you’ll be able to differentiate between the problems that can be solved and the ones that can’t.

Mastering the art of difficult conversations is all about balance. It’s about knowing when to speak up, and when to let things go, when to confront an issue directly, and when to approach it more subtly. It’s not easy, and it’s not always comfortable, but it’s a crucial skill that will serve you well in the workplace. And, the more you practice it, the better you’ll get at navigating those tricky, uncomfortable conversations with grace and confidence.

But, it’s important to remember that by ignoring the problem, you’re not making it go away, you’re just letting it simmer, and at some point it’s going to boil over. That’s why it’s so important to take the time to define what the problem actually is before you dive into trying to fix it. Is the real issue that you and your colleague have differing views about how something should be done? Or is it that you disagree about who should be doing it? Until you identify the core issue, you’re not likely to arrive at a solution, or at least not one you can both agree on. 

As I said, navigating these conversations is an art form. So, how do we approach these situations without making things worse? Here are five tips to do just that: 

Tip #1 – Define the Problem: 

This sounds basic, but you’d be surprised how often we focus on the wrong thing. We work hard to minimize our stress rather than fix the problem that’s actually creating our stress. But, even worse, we try to tackle a problem that isn’t within our ability to solve. Think about it – if you and your colleague have fundamentally different values, you aren’t going to convince one another to change. And honestly, you shouldn’t even try. Attempting to talk someone into valuing something they don’t value is futile, and it’ll also just leave you both frustrated and annoyed. That’s not to say people can’t change, but if they do, it’s unlikely that a lecture from you is what’s going to inspire that transformation. 

So, instead of wasting your energy on unsolvable problems, focus on what you can control, which is how you respond to those things. So, before you jump into action, take a moment to consider who thinks there is a problem and who is motivated to create change. If you’re the only one who sees an issue, it might be a sign that the problem is more about your perception than reality. On the flip side, if the other person also recognizes there’s a problem and seems open to finding a solution, you have a better chance of working together to develop a plan you’ll both be comfortable with. 

Tip #2 – Identify What it is You Want: 

Before you start any difficult conversation, identify what you want from the discussion. What’s your ideal outcome? And, more importantly, what are you willing to compromise on?

When you’re clear on what you want, you can start getting the ball rolling to make it happen. If you know what it is, try telling them what you want. Maybe you need something you’re not getting – like an apology, an acknowledgement, or a change in behavior. It sounds simple, but it can be surprisingly hard to figure out exactly what you’re looking for. This might mean initiating a conversation, or it might mean making changes on your end. Either way, clarity is key. If you’re struggling to let something go, it may be a sign that you could benefit from talking to someone who has a little distance from the issue. Sometimes, you need an outside perspective to help you untangle the knot of emotions and frustrations. 

Tip #3 – Decide How to Address It: 

Once you’ve defined the problem and decided what you want from the conversation, this is the next step. Talk to them about how you feel, rather than how things need to change. This subtle shift in approach can make all the difference. It’s easy to fall into the trap of thinking they need to do things differently, but this kind of mindset often puts people on the defensive. Instead, frame the conversation around your feelings and experiences – “I feel frustrated when deadlines are missed because it impacts my ability to do my job.” This approach makes the conversation less about blame and more about finding a solution together. 

Some problems can be addressed with a single conversation, while others might require a series of discussions. If you’re dealing with a complex issue, don’t expect to solve it all in one go. Instead, approach it as a process – a series of steps you’ll take together to get to the root of the problem and find a solution.

Asking, “How can we work together to develop a plan we’re both comfortable with?” is a great way to start solving problems as a team. This question shifts the focus from ‘you versus me’ to ‘us versus the problem’, which can make even the most difficult conversations feel less adversarial.

There is no one-size-fits-all solution to any workplace problems. Remember, you know this person and your situation better than anyone. You’re the expert on your own experience, and it’s up to you to decide if you need a sit-down conversation to address the problem or whether you want to work on a solution without necessarily announcing how you see the problem.

Contrary to popular belief, you don’t always have to talk about a problem to address it. Not every issue requires a formal meeting in a conference room. Sometimes, the best way to address a problem is by changing your own behavior or approach, without ever saying a word to anyone about it. For example, if you are frustrated by a colleague’s constant interruptions, you might start by setting clear boundaries during meetings or managing your time in a way that limits those interruptions – without ever explicitly bringing up the problem. This isn’t about avoiding the conversation; it’s about recognizing when a direct discussion is necessary, and when it’s not. Sometimes, a little self-reflection and a change in approach are all it takes to solve a problem.

Tip #4 – Stick to the Facts and Your Feelings: 

If you’ve tried to address a problem in the past and the other person hasn’t responded well, it might be time to change your approach. Using “I” statements and keeping things as positive as possible can make a huge difference. You’ll get a lot further when you don’t place blame on the other person, and you’ll get even further when you accept some responsibility for your role in the problem. Not too much, just the appropriate amount. Stick to the facts and how this makes you feel. They really can’t argue about your feelings, although I’ve had a few people try to tell me how I “should” feel. 

And, in situations where they were the ones to come to you with the problem, thank them for bringing it to your attention – regardless of how you feel about it. This can be tough, especially if your first response is to become defensive or argue about it. But, if you respond negatively, you might discourage them from bringing up concerns in the future, which might lead to bigger problems down the line. 

Tip #5 – Use the Power of Validation: 

Validate their feelings, even if you disagree. Don’t say they’re being overly sensitive or dramatic. Those kinds of statements can shutdown a conversation pretty fast. We’ve probably all experienced something like that in the past. Instead, acknowledge their feelings and the fact that they took the time to share them with you. This not only opens the door to a more respectful conversation, but it also shows that you’re willing to listen and engage, even when the discussion is uncomfortable for you. 

There’s definitely an art to managing difficult conversations. Let’s face it, sometimes the problem isn’t the problem. The real challenge is figuring out how to manage how we feel about it. Not every problem has a solution, and that’s okay. Some issues are just unsolvable, and that’s not your fault or theirs. Sometimes, the best you can do is acknowledge that fact and move on. 

This is where the all-important question comes into play: “Do I need to solve this problem, or do I need to solve how I feel about this problem?”. It’s a subtle difference, but it’s critical. The problem might be out of your control, but how you react to it is entirely up to you. And sometimes, compromise isn’t possible. Meeting in the middle might mean neither of you is happy with the result, and that’s okay too. 

Relationships are complex, and not every issue can be solved with a simple 50/50 split. This is where you need to focus on the second part of that all-important question, pertaining to addressing how you feel about the problem. If the problem itself can’t be fixed, maybe the real issue is your response to it. Addressing your feelings might be more productive than trying to force a compromise that leaves everyone dissatisfied. 

Think about it – there may be times when both of you know there’s a problem, but you’ve chosen to look the other way. Maybe it’s something minor that’s been simmering under the surface, or perhaps it’s an issue that’s been hanging around like a bad smell for years. You both may be aware of it, even if it’s never been discussed. But, whether it’s small or large, it takes courage to address any issue, especially when you know that the problem might not have a neat, tidy solution. 

Talking longer about a problem that can’t be resolved won’t help you find a solution or resolve your differences. Rehashing the problem won’t necessarily fix it. We all have a tendency to express the same frustrations over and over again, like somehow, by saying it just one more time, the problem will magically fix itself. But it won’t. At some point, you have to stop circling the issue and ask yourself, “Am I dwelling on the problem or am I working on a solution?”. Dwelling keeps you stuck in the same place, frustrated and exhausted. Working on a solution, whether that means changing your approach or adjusting your expectations, is what moves you forward. 

Let’s be honest, you may be able to continue to have an okay relationship if you simply ignore the problem. It’s the path of least resistance, and sometimes it feels easier to just let things slide. But sometimes, it takes more energy to ignore a problem than it does to just address it. All that tiptoeing around the issue, all those silent frustrations – they add up. And here’s the good news: if you do decide to address it, there’s a good chance you might improve the relationship. So, it’s up to you to decide for yourself. Because, as I said, you know this person and your situation better than anyone. You’re the expert on your own experience. 

If you do decide to tackle the problem head-on, you might feel a surge of relief. And, even more importantly, you’ll feel more confident that you can address problems sooner in the future. This doesn’t just make your professional relationships better, it makes you stronger as an individual. There’s a sense of empowerment that comes from knowing you can handle these tough conversations and that you don’t have to spend years walking on eggshells or pretending you don’t care about something that deeply troubles you. More often than not, the solution is simpler than you’d imagined. 

One more thing, let’s talk about timing. Yes, timing matters. You don’t want to bring up a sensitive issue in the middle of a high-stress project deadline or right after your colleague has just had a terrible day. But don’t convince yourself that you need to wait for the perfect time, because it doesn’t exist. When you tell yourself the timing needs to be just right, your anxiety builds and then, at some point, often during the worst time possible, your anxiety can spill over. You end up blurting out the problem during a disagreement about something else, or at a time when neither of you is prepared to have a rational discussion. Timing is important, but so is not waiting forever. 

So, how do you actually work towards a solution once you’ve decided to address the problem? Listening is one of the best places to start. Don’t wait for them to bring it up first, invite them to share how they’re feeling. Sometimes, just opening the door to conversation is enough to get things moving in the right direction. 

Finally, remember that just because a problem isn’t your fault, doesn’t mean it isn’t your responsibility. Sometimes, the best solutions involve both people working together, even if it’s technically ‘their’ problem. Take a moment to consider who thinks there’s a problem and who’s motivated to create change, and then decide how best to approach your situation. And, if all else fails, you can always exit the conversation by saying, “Let’s agree to disagree on this one”. 

We’re conditioned to think that every problem needs a solution, but in reality, some issues are unsolvable or outside of our control. Instead of fixating on finding a resolution that may not exist, focusing on managing your emotions and reactions to the problem can be more empowering and productive. This shift in perspective can transform how you approach tough conversations, helping you to find peace and clarity even when the issue itself remains unresolved.

So remember, the art of difficult conversations isn’t about finding the perfect solution. It’s about managing the inevitable challenges and frustrations that come with any relationship, professional or otherwise. And sometimes, the most courageous thing you can do is simply start the conversation. Because difficult conversations are just that – difficult. But they’re also an opportunity to solve problems and build stronger relationships, should you choose to do so. 

And that’s it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Finding the Courage to Address Any Issue at cindyesliger.com/podcast, episode one hundred and thirty-three.

Thank you to our producer, Alex Hochhausen and everyone at Astronomic Audio. Get in touch, I’m on Instagram @cindyesliger and my email address is info@cindyesliger.com.

If you enjoy listening to this podcast, you have to come check out The Confidence Collective. It’s my monthly coaching program where we dig a little deeper into what’s holding you back in your career, and we find the workarounds. We help you overcome the barriers and create the career you want. Join me over at cindyesliger.com/join. I’d love to have you join me in The Confidence Collective. 

Until next week, I’m Cindy Esliger. Thanks for listening.