“I have no idea what I’m doing wrong!?” said a recent client as she shared with me the challenges she was having at work. “I’ve been told that my employees don’t like working with me and I don’t know what’s changed. I thought everything was going just fine! How did I get here?” Those difficult conversations – whether you’re on the receiving end or are the initiator, they’re not fun for anyone.
Honestly. This is now a trend. I’ve been getting more and more female leaders at the manager and director level reaching out to me because they’re having difficulty communicating at work. And it’s not an easy fix. They don’t know what’s wrong. Some of them get laid off. Some of them are sidelined at work. Still others are just left feeling miserable. The truth is: They don’t even know what the issue is.
Which means they aren’t self-aware.
Difficult Conversations at Work
I see so many female leaders who are strong; they are assertive; they get things done…. And they come to me because they are having relationship issues or communication challenges at work – often with their female colleagues. Many have successfully navigated a male-dominated workplace and when they use those skills in a female-dominated one, they don’t achieve the same results.
Still others find themselves in that male-dominated workplace and as they rise in the ranks notice that there are fewer and fewer women – until they’re the only one left standing in the room. And then they get nervous. Why were all the other women let go or reassigned? Somehow – and they’re not sure why – they have managed to be the only woman on the team left standing – and now they’re afraid because they don’t want to do what the others did to have their roles…. for no particular reason… made redundant.
Help?
What are Difficult Conversations?
The thing is, if we’re not self-aware, we don’t even know we’re walking into the difficult conversation to begin with. We’re blissfully doing what we’ve always done – executing on all the things, managing “up” successfully (which is a skill in itself) and doing what we do best. Getting stuff done!
So what’s this relationship stuff?
Years ago, when I first returned from maternity leave after my first child, our team was led through a team-building exercise called Insights Discovery. A psychometric tool based on the psychology of Carl Jung, Insights Discovery is built to help people understand themselves, understand others, and make the most of the relationships that affect them in the workplace. It helps determine how and why people behave the way they do.
I loved the whole process. Psychoanalying who I was and how I showed up with my colleagues… uncovering which colleagues I naturally connected with (knew that already – but now I knew why) and also why certain team leaders didn’t jive with me.
It was the first time a proverbial mirror had been held up in front of me to help me see how I was showing up. In fact, I showed up so differently, in this psychometric tool post-maternity leave, that my colleagues thought I would have showed up differently if I’d done the test before I went on Maternity leave. I was that different.
Interesting. Either way, it was my first introduction to psychometric and leadership styles that have now become a valid and informative way to understand how you show up at work, in the world and why you are the way you are.
They can also inform how you navigate those difficult conversations – those conversations that you don’t want to lead or receive, where you have to influence a colleague to act a different way or share some difficult news. It becomes even more difficult when you suspect the colleague is blissfully unaware that they’re doing anything “wrong.”
The good news is you can learn how to navigate those difficult conversations with ease. You can also learn new ways of being and of showing up. But if you keep on just showing up the way you show up, and have no idea it’s offensive to anyone until…. you get fired, or you find yourself in an HR meeting that’s telling you otherwise or you’re getting shut out of not only work meetings – but personal friendships that you’re no longer welcome in…. yikes. Then we have to take a look.

Why We Avoid Difficult Conversations
The thing is – we don’t even know we’re showing up like that. We’re just doing what we always did to be successful until it doesn’t work anymore. It’s also super easy to just avoid these difficult conversations. To not stand in the wilderness – as Brene Brown says – and remain blissfully unaware of what the problem is. The trouble is, that could result in you being more and more alone and unsuccessful in work and in life as time goes on. Because if you’re unaware of how you come across, then you don’t know what you’re doing to impact the relationship, for better or for worse.
Something we don’t always learn at school is that life, and business, is about relationships. It’s not all about just getting things done and ticking off a box. As you rise higher in your career and in the workplace, more and more of what you do is about HOW you get things done – not WHAT you’re doing. It’s no longer about how late you stay at work – it’s more about how you show up when you’re there. It’s about those side conversations you have with your team that shows you care about them as humans – not just about how much they can produce.
And it’s even more important with the generations coming behind us who care less and less about titles and more and more about lifestyle and relationships. They’ve learnt by watching us. Sometimes we’ve had to sacrifice too much to achieve the success we have enjoyed. And they don’t want that for themselves.
Ouch.
Examples of Difficult Conversations
And so we carry on.. Until we get stuck. Ok – you’re thinking – I need to get this thing to the client by X time and my team member is not doing it. I don’t even know if she’s doing it. She hasn’t told me even though I’ve asked her (via email) X number of times to do the thing.
How do I get her to do the thing?!?!? She asks herself.
Or, employee X is being really brash at work and people don’t like interacting with them. It’s become an issue not only with her work colleagues, but also your customers – and you need to have a conversation with them about it. Where do you even start?
Oftentimes, to solve the issue, organizations start with an HR representative in the room, their team lead, and the individual in question. This already feels like an ambush. What if we work towards a solution before it gets to this point of having to bring it to Human Resources to get resolved? What if we walked into the proverbial wilderness and explored what’s going on with the individual by talking to them, by building a workplace relationship with them, and by helping them build some self-awareness tools so they start to see it for themselves.
Difficult Conversations Can be Handled Successfully By…
The thing is – difficult conversations are difficult because of the emotions involved behind the conversation and the approach each person goes into it with. We cannot know how the receiver of the information is going to respond or react to the conversation, but we can control ourselves – and anticipate how they will receive the information and prepare for it.
Here are 5 things you can do to prepare for that difficult conversation:
1) Set an intention for the conversation.
What is the end result you’re looking for? Is it more important for you to be right, or for the relationship to remain intact? Frame the conversation positively, viewing it as a constructive discussion rather than a confrontation.
2) Set the tone.
Approach the conversation in partnership and in service. Provide background information to set the stage for the discussion. Make it safe: Embrace mutual purpose and offer mutual respect to create a comfortable environment. Use “I” statements: Share your perspective using phrases like “I feel” or “I think” to avoid sounding accusatory and to keep the issue to the one at hand.
3) Speak in specifics.
Use concrete examples and avoid vague generalizations – share real examples of acknowledgement and the challenges the situation has created. If you don’t speak in specifics, your colleague will likely go into panic mode and may catastrophise the situation still not knowing what they’re doing wrong because you haven’t been specific enough.
4) Remember that your team member is going to remember the negative more than the positive.
Remember the old saying – they’ll remember how you made them feel vs what you said? It’s true! What’s more, it’s been proven that we need to hear five positive things to counteract the one negative one.
5) Acknowledge and close on a positive note.
If you have a shared intention of working towards an aligned future, this will be easy. Acknowledge the other person’s perspective: Show that you care about their point of view. Ask open-ended questions: Encourage dialogue with questions like “Tell me more…” or “Help me understand… Validate their feelings: Thank them for their insights. Express appreciation for their willingness to engage in the difficult conversation. It hasn’t been easy for either of you.

The First Step to Navigating that Difficult Conversation
Difficult conversations are….. well… difficult. Why? Because there is a clash of values and perspective going into it that neither of you may be fully aware of. However, if you depersonalize the situation, go into it with a shared purpose, and focus on the relationship, not the task at hand, you will be one step closer to resolving the issue and repairing the relationship.
The first step to navigating difficult conversations with more ease is knowing yourself.
What are your unconscious biases? How does your communication style land? What are you expecting from your team? How do you expect them to show up? Have you told them? Your personal values show up in your leadership style and the conflict of personal values are at the root of plenty of challenging workplace relationships. Want to navigate those challenging workplace relationships and difficult conversations with more ease? The answer starts with you.
To your success,

Susan Elford is a Leadership Coach and Business Mentor who especially loves to work with women who want it all: a fulfilling career or business while living a full and satisfying life. Through powerful career coaching and business mentorship to get their career or business to the next level, Susan helps her clients get real about their strengths and celebrate and promote them so they get more of what they want: success at work; success in business & success in life.
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