Courageous conversations: How to speak up with confidence
- Janelle Kee-Sue
- Oct 28
- 12 min read
Do you struggle to have tough conversations and speak up for yourself?
Perhaps you want to call out toxic behaviour at work or in your personal life, but don’t know how to go about it?
Don’t worry, you’re not alone… many of us don’t like conflict and aim to keep the peace, which can make it easy for toxic people to pull the wool over our eyes and get away with crappy behaviour.
But it’s never too late to put a stake in the ground and say no more!
And you don’t have to change who you are to do this, either.
So let’s talk about how to have courageous conversations (and deal with toxic people without causing conflict or spiraling).
Because we all experience challenging people and moments where we need to speak up and say the hard things sometimes.
What is a ‘courageous conversation’?
There are probably a bunch of definitions on the internet, but here’s what courageous conversations mean to me, as the introvert who naturally avoids conflict at all costs.
Firstly, the word courage is in there for good reason. It does take courage to speak up, especially when other people don’t agree and you’re going against the grain.
It goes against our natural survival instincts of being accepted by the group. So when you do it, your survival brain thinks: “Danger DANGER”. So we pause, and hold back.
Often we also hate to feel uncomfortable, or make others feel uncomfortable.
We don’t like offending people, or making others feel uncomfortable.
We also don’t like to make ourselves feel uncomfortable, so we decide in the moment it’s easier and more comfortable to not say the thing that really needs to be said, rather than say the thing.
It takes courage to ignore our survival instincts and to feel the fear and do it anyway.
So, a courageous conversation is having a conversation that takes courage. Simple.
What do courageous conversations look like?
So. Many. Different. Ways. But here are a few examples:
It could be telling someone you don’t like the way they spoke about another person.
It could be letting someone know how their actions made you feel or affected you.
It could be telling someone they have a booger in their nose or something stuck in their teeth.
It could be telling your boss you’re already snowed under and can’t take on any more work.
It could be telling someone you won’t tolerate their behaviour or language.
A courageous conversation is when you tackle the conversation head on and say what you think and feel, despite how uncomfortable it could make you, or them, feel.
Why do we need to have courageous conversations?
To answer this question, let me ask you a question first:
Do you want to be a cow or a buffalo?
This might sound like a strange question, but stick with me—because the way these two animals react to storms can teach us a powerful lesson about resilience and doing hard things.
When a storm rolls across the plains, cows run away from it. They try to outrun the dark clouds, but because they’re slower, the storm eventually catches up and follows them for longer.
By avoiding the storm, they actually make their suffering worse.
Buffaloes, on the other hand? They charge straight into the storm. They know the fastest way through is to face it head-on. The result? They move through the storm quicker and get to the other side with less suffering.
Short term pain, long term gain.
The same principle applies to having courageous conversations.
When we avoid difficult conversations, uncomfortable decisions, or personal struggles, we only prolong the pain.
But when we choose to confront them, we gain confidence, clarity, and freedom faster than we ever imagined.
Let’s break this down further.
Why avoiding tough conversations makes things worse
Avoidance might feel like relief in the moment, but in the long run, it creates more stress and anxiety. Here’s why:
1. The problem doesn’t go away, it usually festers and grows
Think about an overdue bill, a tough conversation you’ve been putting off, or a goal you’ve been procrastinating on. Avoiding it doesn’t make it disappear; it only increases the pressure, stress, and potential consequences.
Just like the cow running from the storm, avoidance keeps you stuck in discomfort longer than necessary.
2. Not speaking up condones the behaviour
If you don’t speak up about the stuff that’s troubling you, you’re actually condoning it.
What I mean by that, is people don’t know what they don’t know and they have their own goals and versions of reality. So if you let something slide once, chances are they’ll subconsciously think it’s ok and that they can get away with it, so they’ll keep doing the thing you don’t like.
Same happens if you’re not consistent with your response. Letting it slide sometimes, while saying something other times, doesn’t send a clear message. Be consistent.
When we bring people’s awareness to the consequences of their actions, it immediately opens up the opportunity for it to be addressed. That, teamed with consistency, shows we mean business.
4. Anxiety thrives in avoidance
When you dodge challenges, you subconsciously reinforce a belief that you can’t handle them.
Over time, this makes your fears seem bigger and your confidence shrink. Your brain starts to associate difficult things with unbearable stress, making future challenges even harder to face.
Plus, often we are catastrophising things and imagining they’ll go worse than they actually will. Ever made a tough convo out to go way worse in your mind than it actually went? Yeah, thanks brain.
We also start thinking we’re fortune tellers who can predict the future, by assuming we already know what their response will be. Sorry hon, but no one actually can do that!
4. You give away your power
Every time you avoid something difficult, you tell yourself (even subconsciously) that the challenge is bigger than you are. This keeps you feeling small, stuck, and helpless. Instead of leading your life, you become reactive—letting problems control you rather than taking control of them.
Tips for having courageous conversations (work + personal life)
Now that we’re clear on why it’s so important to be the buffalo and face our fears head on by having courageous conversations, it’s time for tips on how to have them!
Courageous conversations aren’t about confrontation for its own sake. They always have a purpose and are about clarity, respect and dignity.
Use this five-step structure to keep it tight:
1. Prep: decide your purpose and ideal outcome
There should be a purpose to the courageous conversation and you should have an understanding of what you’d like to get from the conversation.
What do you want? A change in behaviour? An apology? To be heard? It shouldn’t be purely to complain, instead it should be to make a request and find a resolution in some way, otherwise what’s the point?
Of course conversations will end badly if we make the other person feel like we’re attacking them without any other purpose for the conversation.
Ask yourself: What’s the goal here?
Be clear in your own mind before you speak.
For example: If my boss keeps giving me heaps of work that I can’t handle, instead of complaining that I have too much work, a good purpose and ideal outcome will be to let them know I’m at capacity and struggling to get through the workload, and ask for help with prioritisation of projects and tasks, if anything can be dropped or handed over, and agree on more realistic deadlines.
This way, you go into the conversation with your own ideas and thoughts on how a resolution can be found.
2. Start with a calm opener
Example: “Can we please talk? I want to share something that’s important to me.”
If right now isn’t a good time, ask when is, and put it in the calendar.
Make sure you talk instead of email! Things can get taken differently to intended in email. In person, video call, or phone calls are best.
3. Use the facts + the impact
Say what happened, then name the impact on you:
For example: “I’ve noticed you interrupt me in meetings (fact). When that happens, I can’t share my ideas and I feel overlooked (impact).”
4. State the boundary or request
Be direct: “I would appreciate it if you would let me finish my point before responding and not talk over me.”
5. Close with consequence and invite collaboration
“Are you willing to do this in the next meeting?” This invites buy-in while keeping you in the driver’s seat.
Thank them if they agree.
If not, let them know what the consequence will be.
For example: Let them know you’ll be speaking with their manager about it (always speak UP - and by UP, I mean to the person who can do something about it).
Ideas for ways to handle different situations
Work (manager who micromanages): “I appreciate your input. I’d like autonomy on X. If that’s not possible, can we schedule a weekly check-in so I can update you and we can avoid interruptions during my work time?”
Friend who belittles: “When you joke about my choices, it makes me feel like sh*t. Please stop comments like that.”
Family member who guilt-trips: “I hear your concern, but I’m making this decision for my wellbeing. I’m not open to debate on it right now.”
To summarise the 5 key steps to having courageous conversations:
1. Prep: decide your purpose and ideal outcome
What’s the goal here? (Don’t just complain, find the request under the complaint)
2. Start with a calm opener
Can I please talk with you about something?
3. Use the facts + the impact
What’s the problem, and the flow on effects (for you and others if relevant)
4. State the boundary or request
Make your request and draw the line in the sand
5. Close with consequence and invite collaboration
Invite them to collaborate, and let them know the consequences.
Dealing with toxic people
Ok, so sometimes the person is genuinely toxic and is well aware of their behaviour and its effects on others, and they keep doing it even after you’ve had a courageous conversation.
Watch for these recurring signs:
Constant criticism, belittling or invalidation — they say mean things, make you feel wrong, incompetent or “too sensitive.”
Manipulation and control — gaslighting, guilt-tripping, or using your vulnerabilities against you.
Boundary-pushing and disrespect — they ignore “no,” trivialise your limits, or keep asking after you’ve said no.
Emotional volatility that keeps you walking on eggshells — you never know which version of them you’ll get.
Consistent draining of your energy — you feel exhausted, anxious, or depleted after interacting with them.
If this is the case, after you’ve tried the steps above, here are a few things you can do.
Calling out toxic behaviour/comments
When say something nasty or do something stupid, one of the best things you can do is pretend you are a curious 5-year-old by asking them questions in the moment, like:
“I noticed you laughed when I said X. I’m curious, what was it about it that you found funny?”
“I noticed your eyes roll at that comment - why was that?”
“That’s an interesting thing to say, what made you say that?”
“That was an interesting thing to do, what made you decide to do that?”
“What do you mean by that / what exactly did you mean by that comment?”
“That sounded really offensive, was that your intention?”
“That’s one way to look at it. I see it this way: <insert thoughts/feelings>.”
Ever had to explain a joke? It’s just not funny after that is it? This is the strategy.
The goal here is to call out the behaviour in a really neutral way through questioning it.
Be as emotionally neutral as possible, inviting them to explain themselves and giving off the impression that you must have misinterpreted their words/behaviour.
Ideally, this is done in the moment, and can be done in a group situation as well as 1:1 if you feel safe enough to.
And then, if necessary, let them know exactly where the boundary is by saying something like:
“Just so you know, I don’t tolerate being spoken to like that/that behaviour, so I’d appreciate it if you didn’t do that again.”
Then mic drop and walk away with your head held high.
Important to note: This takes guts! But you can do it. If you question from a place of curiosity and a desire to understand, instead of a place of attacking, it will feel easier and come across as respectful.
Stonewalling
Ok, so stonewalling isn’t our preference in any situation (have courageous conversations FIRST!) because it’s a type of avoidance, and is often a manipulative tactic that narcissists use to avoid accountability, but I argue that when it’s used against them it can be very effective.
Don’t engage with them. Give short, one word answers. Avoid getting into conversation with them.
Because it’s your reaction they want, so when they don’t get it, they don’t win.
Remember that hurt people, hurt people
Toxic behaviour often stems from a deep feeling of not feeling good enough, so someone’s toxic behaviour is really a projection of their own insecurities and need for external validation created by putting others down, making them feel more significant.
It says a lot about them when they behave like this. Keep that in mind next time, and focus on your own strengths and what makes you unique and who you are.
More tips for having courageous convos
Here are some things you can do:
1. Prioritise your safety and energy first
Ask: What do you need in this moment/situation to feel safe/protect yourself? This will be different for every person and situation. It may be having a support person there, removing yourself from the conversation, having a breather, etc.
2. Name the behaviour, not the person
Focus your language on actions: “When you interrupt me in meetings, I can’t finish my points.” Naming behaviour reduces defensiveness and keeps the conversation grounded.
3. Use boundaries with consequences
Set a clear boundary and the consequence if it’s crossed: “I won’t take calls after 8pm. If you call then, I’ll respond the next morning.” And make sure you follow through! Consistency builds credibility.
4. Keep your emotional regulation tools ready
Tough conversations can trigger fight/flight/freeze/fawn responses. Use grounding (feet on floor, 4–4 breathing) or a short pause before answering to avoid saying something you’ll regret.
Breathwork and slow-paced breathing have measurable benefits for calming the nervous system and reducing stress, making it easier to stay present during tough interactions.
5. Use allies and documentation If it’s a colleague or manager, document incidents (dates, what happened) and, where possible, involve HR or a trusted manager. Witnesses and records matter.
And in personal relationships I recommend doing this too. Keep a journal that you can keep safe, or notes on your phone, documenting the interactions and behaviours. This is because often if we’re being gaslit, we question our own version of events, but having things written down that we can look back on later can help us to see and trust our own truth.
6. Decide on distance vs repair
Some relationships can be repaired if the other person acknowledges harm and commits to change. But often the healthiest option is limiting contact or exiting the relationship.
Reprogram your Subconscious Mind to speak up with confidence
The fear of public speaking, speaking up and being seen is one of the most common confidence blocks, and it often runs much deeper than you think.
Most people try to fix it by practising more, memorising lines, or forcing themselves to “just be confident.” But the truth is, this fear doesn’t live in your conscious mind — it’s rooted in your subconscious.
From childhood experiences, critical teachers, or moments of embarrassment, your subconscious may have learned that being seen equals being unsafe or judged. Over time, that protective pattern can become automatic—triggering anxiety before you even open your mouth.
That’s where hypnotherapy comes in.
Hypnotherapy helps you access the subconscious mind—the part responsible for habits, emotions, and beliefs—and gently reprogram it for confidence, calm, and self-assurance.
Through working with me (a qualified hypnotherapist) 1:1, or doing self-hypnosis, you can retrain your brain to associate speaking up with safety and empowerment, instead of fear.
Speak Up & Be Seen With Confidence Self-Hypnosis Program
Speak Up & Be Seen With Confidence is a powerful self-hypnosis program designed to help you overcome the fear of being seen, calm your inner critic, and feel grounded and confident when expressing yourself—whether in meetings, presentations, interviews, or everyday conversations.
Through guided morning and evening meditations, you’ll rewire your subconscious mind for success and confidence while you rest and reset.
Inside you’ll receive:
💖 3x 10-minute morning self-hypnosis meditations to start your day with confidence
💖 6x 25-minute night-time self-hypnosis meditations to release fear and reprogram your mind while you sleep
💖 Journaling prompts for reflection and integration
💖 Tips and insights to tame your inner critic and build lasting self-belief
This program will help you:
🌟 Alleviate the fear of public speaking
🌟 Build confidence to speak up and be seen
🌟 Harness the power of your subconscious mind to create deep, lasting change
Ready to claim your confidence?
Let’s unlock your quiet confidence that's within you!
If this blog resonated with you, be sure to check out the Finally Thriving Podcast on Spotify and Apple Podcasts for more conversations on healing, growth, and reclaiming your confidence.🎙️✨
Thanks for reading! If you want more, check out my other blogs, follow me on TikTok: @janelle.keesue and Instagram: @janellekeesue.coaching
About the Author
Janelle Kee-Sue is a Transformational Coach, Hypnotherapist, NLP and Somatic Practitioner, and the host of the Finally Thriving podcast. Based in Wellington, New Zealand, Janelle specialises in helping women of all ages rebuild their confidence and self-worth—especially after toxic relationships, workplaces, or experiences that left them questioning their value.
Combining the power of the subconscious mind with science-backed tools for fast and long-lasting transformation, she empowers her clients to overcome anxiety, people-pleasing, low self-esteem, negative body image, and limiting beliefs and habits in record time so they can feel confident, calm, and in control of their lives again.
When she’s not guiding her clients through powerful life-changing shifts, you’ll find her at reformer Pilates, writing her first novel, or enjoying quiet moments with her husband Ricky and their fluffy Samoyed sidekick, Zeus.
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