Let’s be honest - how many times have you played a difficult work conversation over in your head, again and again… and again?
You lie awake at night crafting the perfect sentence. You second-guess your tone, your timing, your word choice. You worry you’ll upset someone, or worse, they’ll think you’re being difficult.
And when the conversation finally happens? It’s over in five minutes.
If this sounds familiar, you’re not alone.
In fact, it’s one of the most common challenges I hear from managers - especially those who’ve been promoted because they’re great at the technical side of their role, but never really had training on how to manage people.
This fear of having tough conversations is incredibly human. We want to be kind. We don’t want to rock the boat. We tell ourselves, Maybe it’ll sort itself out, or I don’t want to make it worse.
But the truth is - avoiding the conversation does make it worse.
It chips away at trust, increases stress, and creates confusion. And deep down, most people would rather have a clear, kind conversation than feel like something’s going unsaid.
Lack of confidence is the real issue - and it’s more common than you think
Every time we run a training needs survey with WISH members, one theme comes up again and again: confidence.
Not confidence in what you do - you’re brilliant at that.
But confidence in managing people.
Feeling like you’re constantly second-guessing yourself.
Worrying you’ll say the wrong thing and lose trust.
Avoiding feedback or conflict for fear of being seen as harsh, bossy, or just not good at your job.
It’s not a lack of capability - it’s a lack of confidence.
And it’s making brilliant women feel like they’re failing at management when really, they just need a bit of support, structure, and a few tools they were never given.
So, how do you make these conversations easier?
Here are three simple, powerful tips that can make a real difference:
Tip 1: Start with clarity - not criticism
Most people avoid difficult conversations because they don’t want to hurt anyone’s feelings.
But being clear doesn’t mean being harsh. In fact, one of the most game-changing ideas I’ve learned is from Brené Brown: “Clarity is kindness.”
Start with a clear, calm explanation of what you’ve noticed—no fluff, no vague hints.
Something like:
“I’ve noticed you’ve been missing a few deadlines recently, and I wanted to check in to see how things are going.”
Tip 2: Prepare - but don’t over-prepare
Overthinking is a trap.
Yes, go in with a few key points and examples, but don’t write a novel or plan for every possible reaction.
That just increases anxiety.
Instead, ask yourself three quick questions:
• What do I need to say?
• What do I hope will happen as a result?
• How do I want the other person to feel when they leave the conversation?
Tip 3: Ask more questions than you give answers
It’s tempting to go in “armed with solutions,” but difficult conversations aren’t just about telling someone what’s wrong - they’re about understanding what’s going on.
Try saying:
“How do you feel things have been going lately?”
“What support would help you meet those expectations?”
These questions shift the tone from confrontation to collaboration.
That’s why I created “21 Tools for Having Difficult Conversations at Work”
It’s a free, practical guide packed with tools, tips, and real-world phrases to help you handle tricky situations with more confidence.
Whether you’re giving feedback, addressing performance, or trying to build trust in your team, it gives you the language and structure to feel less like you’re winging it.
You'll learn:
• What to say (and how to say it without sounding harsh or fake)
• How to manage your emotions (so you don’t go into panic mode)
• What to do when conversations feel like they’re going off track
• How to shift from avoiding to addressing—without losing yourself
If you're tired of:
❌ Overthinking every conversation
❌ Putting things off and hoping they’ll fix themselves
❌ Worrying you’re doing it “wrong”
…then this guide is for you.
Because managing people doesn’t have to feel like a constant confidence knock.
You just need the right tools.
👉 Click here to get your free copy of 21 Tools for Having Difficult Conversations at Work.
You’ll feel more confident, grounded, and ready to face those tricky conversations with clarity and compassion.
Hayley Gillard is the Managing Director of Compassionate Leaders Ltd. With over 15 years of experience supporting housing organisations to build inclusive, high-performing teams, she specialises in helping managers develop the confidence and skills to lead effectively.
Hayley has designed ILM-accredited leadership programmes, advised boards on leadership strategy, and delivered training to hundreds of managers across the sector. She is also the creator of Manager School Online, a 12-week accredited self-study programme designed to upskill managers with the tools they need to manage people with confidence.
