A stressed man sitting at his desk in front of his computer after a difficult conversation

The Embarrassing Truth About Difficult Conversations!

I remember when I first embarked on this new journey several years ago, I would often avoid ‘high risk’ situations because I felt like an imposter. It felt easier to circumnavigate the issue rather than squirm in my discomfort of sharing that I didn’t know the answer.

I was afraid of ‘doing things wrong’, asking stupid questions, looking incompetent or foolish in front of those more experienced.

And for quite a while that was debilitating. I stayed stuck, yet also frustrated. Avoidance felt comfortable and low risk.

But here’s the thing.

We don’t know what we don’t know! And that’s ok.

In leadership there will be a plethora of difficult circumstances or conversations you might sidestep because you are unsure how to navigate them.

There’s no shame not knowing what to say or do but sometimes there’s a great deal of embarrassment or fear of judgement if you get it wrong.

‘What will my teams think if I don’t have an answer?’
‘I should know how to deal with this because I’m a manager’.
‘What will my boss think if I can’t manage my team?’
‘I’m great at running my business but I’m lousy at managing people and having uncomfortable conversations’.

All these fears and anxieties might be whispering in your ear, telling you that you’re going to mess up or no-one will take you seriously or that this big promotion was a mistake.

There’s not a book that I can think of that states you should be knowledgeable and self-assured in managing those conversations. So give yourself a break!

Navigating difficult conversations is an art but like anything new in life, it’s a skill that can be easily learnt. So here are 5 suggestions that will help you become more confident and competent as you embark on these uncomfortable dialogues.

The Approach:

The way you launch into the conversation will invariably dictate the outcome. Approach it too bullishly and it would come as no surprise if you were faced with pushback or a defensive response. Or if your approach is too insipid, you might observe a lack of respect or disdain from your teams. Find a balance in your tone and your manner that will engage and open up the dialogue rather than deflect and shut it down.


Your mindset plays an intrinsic role in the success or failure of the conversation and impacts how you show up. Check in with yourself beforehand and notice your state. Are you nervous, angry, impatient, concerned? There are a number of tools you can embrace that will support to calm you if are infuriated or empower you if you feel anxious or exasperated. Go for a walk to clear your head, talk it out with a trusted colleague or friend, meditate, listen to an inspiring podcast. Find something that works for you and never begin the conversation until you are mentally prepared for it.


Be clear about the purpose of the conversation which will be helpful if you become derailed or caught off guard. What would an ideal outcome look like to you and consider whether this is in fact realistic.


Two of the biggest concerns in any challenging conversation are the fear of becoming derailed or being ill prepared for pushback. Prepare bullet points to keep you focused and on track. Take some time to consider possible responses so that if you are met with a confrontational reaction, you won’t be blindsided and will feel able to respond confidently.

Seek Support:

There may well be times when you aren’t equipped to manage some conversations and the skill is recognizing that. In these situations, seek support from a mentor, your boss or an experienced colleague to direct and support you to navigate it more effectively than you might have done without their guidance or worse still, avoid it altogether.

Good communication skills are essential in leadership. They simply take time and practice to master but they will support you to build rapport, connection, trust and great relationships with your teams and colleagues.