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How to have tough conversations at work (courageous convos for women)

Do you struggle to say what you really think at work due to fear of starting conflict or your words being taken the wrong way? Unsure how to say things that really need to be said, so you avoid the conversation altogether?

You're not alone!

In this blog, we're going to deep dive into Having Tough Conversations in the workplace—why it's important, why we often fear or avoid it, and strategies for making these conversations easier to get the best possible outcomes (all while mitigating conflict).

If you want to be able to have courageous conversations and speak your mind when it most counts, keep reading!

What are examples of tough conversations in the workplace?

Tough conversations in the workplace can take many forms and can be challenging for both employees and managers. These challenging conversations usually typically involve addressing sensitive or difficult topics that may be related to performance, behaviour, conflicts, or other work-related problems.

Here are some common examples of tough conversations in the workplace:

  • Giving negative feedback

  • Disagreements with colleagues

  • Performance reviews

  • Salary and compensation

  • Conflict resolution

  • Disciplinary action

  • Employee termination

  • Layoffs or restructuring

  • Changes in role or job duties

  • Personal issues

And so much more… can you recall a tough conversation you’ve had at work in the past? Consider whether it was about any of these things, or something else entirely.

Why do we fear having tough conversations?

Why is it so hard for so many ambitious, career-focused women to speak up and have these conversations?

Speaking up and saying what we really think can be challenging for a variety of reasons, which will of course vary from person-to-person. But here are some of the most common – as you read through them, pay close attention to those that resonate with you.

Avoiding discomfort

As human beings, we don’t like to be uncomfortable. In fact, we spend the majority of our time actively avoiding pain and discomfort, and chasing pleasure, whether we’re aware of this or not.

In philosophical psychology psychological hedonism is the view that all human action is ultimately motivated by desires for pleasure and the avoidance of pain.

People will do much more to avoid short-term pain than they will to gain short-term pleasure, and if having a conversation is perceived to be more painful than not having it, we’ll do our very best to avoid it.

Fear of starting conflict

For the majority of us, conflict is uncomfortable and should be avoided at all costs. Well, that’s what our brains tell us, anyway!

Many people naturally want to avoid conflict or confrontation, so they worry that by speaking up and saying what they really think it could lead to arguments or other negative consequences, so they avoid it altogether, or downplay the actual severity of the issue.

People pleasing

We want to be liked and accepted, and we don’t want to be barred from the pack, so we have a natural tendency to want to please others. A “people pleaser” personality means a person feels a strong urge to please others, even at their own expense. They may feel that their wants and needs do not matter or alter their personality around others.

People-pleasers may prioritise keeping others happy over expressing their true thoughts and feelings. They avoid rocking the boat at all costs, which holds them back from being able to speak their mind and disagree.

Fear of rejection, being judged or being disliked

Being rejected, feeling like we’re being judged, or disliked, leads to feelings of shame and embarrassment – which are negative feelings that people tend to want to avoid wherever possible. If you say what you think and someone criticises or ridicules you for it, argues with you or tells you you’re wrong, you’re likely to not want to feel that way again.

Past negative experiences

If you’ve spoken up in the past or been part of a tough conversation that didn’t go very well, that’s going to have an impact on how you believe your future conversations are going to go.

Past experiences of being ignored, dismissed, or punished for speaking up can create a fear of repeating those negative outcomes.

Lack of confidence

If you don’t believe you’re ‘qualified’ enough or experienced enough to have an opinion, this is a sign that you’re lacking the confidence and self-belief to speak up and participate in ‘tough’ conversations.

Low self-esteem and self-doubt can make it difficult to share your thoughts and opinions because you may not feel confident in your ideas or believe that your input is valuable.

Cultural and societal norms

Cultural and societal norms can have a big influence on whether people feel comfortable expressing themselves. In some cultures, speaking up, initiating tough conversations and pointing out the elephant in the room may be discouraged or considered impolite.

For example, due to gender ‘norms’, women may be less inclined to speak up than men if they’re in a room full of them.

Hierarchy and power dynamics

In workplaces with hierarchical structures and a clear top-down culture, rather than ‘flatter’ organisational structures, employees may feel intimidated by higher authority figures and be hesitant to voice their opinions or concerns due to the hierarchy and power dynamics at play.

Perceived risk

Whether we’re aware of it or not, our mind is constantly on the lookout for perceived risks that could cause us harm (emotional or physical). Speaking up and initiating tough conversations can carry perceived risks, such as jeopardising one's job or relationships with colleagues.

People may worry that their honesty could have negative consequences, so it seems ‘safer’ not to speak up in the first place.

Communication skills

If you don’t think you’re a very good communicator, it can make it challenging to express your thoughts and opinions clearly and persuasively. This can cause anxiety in the lead-up to speaking-up, and prevent you from doing it due to the feelings it causes.


Overthinking or excessive self-criticism can lead to analysis paralysis, where people think so much about what they want to say that they become hesitant to speak up, and then they leave it for so long it’s no longer timely enough and they’ve missed the opportunity.

If they bring it up months later, it loses its effectiveness and seems more like they’ve been storing evidence to build a case, which the other person may take as an attack.

Imposter syndrome

Imposter syndrome can lead individuals to doubt their expertise and feel like they don't belong, or they aren’t qualified to have an opinion, making them hesitant to share their thoughts.

Social anxiety

Those with social anxiety may find it particularly challenging to speak up in group settings due to intense anxiety about social interactions.

Did any of that resonate with you?

Perhaps a couple of those key factors resonated with you, or perhaps most of them did. The most important thing is that you’re reading this which means you’re aware you have a problem with speaking up and you’re ready to do something about it. Great!

The first step to being able to have more courageous conversations starts with self-awareness and understanding why we’re so hesitant to have them – often it’s due to a combination of things.

Once you have clarity on what’s holding you back, you can make a plan for working on those areas, so you can have tough conversations with confidence!

Tips for speaking up and having tough conversations at work

Having tough conversations at work and speaking your mind without fear can be challenging and somewhat terrifying, but is an essential skill for personal and professional growth.

While the ways to handle these conversations will vary depending on the content, here are some strategies to help you navigate difficult conversations more effectively.

Plan and prepare

If you have forewarning that a challenging conversation is going to take place, such as a project meeting where expectations need to be reset, or a one-on-one performance conversation, take time to think through the conversation beforehand.

  • Start with the end in mind: What are your objectives and what you hope to achieve from the conversation?

    • Are you providing feedback to help achieve a result? (Eg, performance management)

    • Are you pitching/selling something? (Eg, asking for a pay rise, or presenting a new idea or process?)

  • List the key things that need to be discussed/addressed to reach the objective.

    • What needs to happen in order to get the desired result? (Remember: you don’t need to have all the answers, that’s why you’re having a CONVERSATION to work together to achieve a result).

  • Consider the other person's perspective and emotions. What are their objectives likely to be, and are they likely to align with yours? (Often we’re on the same team and want the same result, we’re just not on the same page for some reason!).

  • Think about the questions they may have so you can prepare (but don’t over prepare – you can always tell them you don’t know the answer to that but you’ll find out!).

You don’t need a 15-page document to prepare for a conversation. Just a few bullet points will do.

Initiate the conversation and choose an appropriate time and place

Whether you’re scheduling a meeting or pulling the person aside, it’s important to let them know what you’d like to talk to them about, give them a compelling reason why, and choose an appropriate time and place to have the conversation.

For example, you could request the conversation by saying something like: “I’ve noticed some confusion around responsibilities for this project, do you have time this week so we can sit down and figure this all out?”

Or, if you’d like to discuss your workload, you could say something like: “I’d like to catch up with you about my current projects and priorities to make sure I’m focusing on the right things, when would it suit you this week?”

  • Choose an appropriate time and place for the conversation (make sure it’s timely).

  • Find a private and neutral space.

  • Schedule the conversation at a time when both parties can focus without distractions.

  • Try not to have distracting objects, like phones or laptops, open or creating a barrier between you and the person.

Visualise the conversation going well

Mental rehearsal, or visualisation, is a powerful tool used by athletes as part of their training to help them achieve their desired results. It works for things like having tough conversations, too!

Visualise the conversation going well, being as detailed as possible, such as how it would feel, what you would see, and introduce the senses to make it feel real. This will help reduce any feelings of anxiety around the upcoming conversation taking place, and help to put you in a good mindset, which will make it more likely that the conversation will in fact go well.

Our minds can’t tell the difference between what’s real and imagined, so by visualising the conversation going well, it’s more likely that this will be your experience.

Change your inner narrative

Cortisol is a stress hormone that can be caused by anticipation of things you don't want to do.

To change the pattern, disrupt it by switching up your narrative around it.

For example, change the inner narrative from; “This is going to be a horrible conversation and I’m absolutely sh**ting bricks”, to something like; “I’m looking forward to us having the opportunity to get on the same page and find a way forward that works for the both of us.”

See if you can change the pattern and the reactivity to the thought of the upcoming conversation, and it may just shift something that will help you have a more courageous and productive one (plus it can help alleviate some of the anxiety).

Start the conversation on a positive note

Depending on the type of challenging conversation you’re about to have, starting off with something positive, such as something they’re doing well, can be a good way to warm up and ease into the conversation, positioning it as a feedback conversation where you care about their growth and want them to succeed.

However, don’t force it as it will come across as insincere! You don’t want to be seen as creating a bullsh*t sandwich to butter them up.

If you’re going to provide positive feedback, it needs to be just as detailed and valuable as the negative feedback you’re delivering. Otherwise they’ll smell a rat.

For example: “Congratulations on the product launch last week! I wanted to take this opportunity to provide you with some feedback on what I think you excelled at, and also areas I think could be improved for next time.”

For serious misconduct and other similar conversations, it’s important to get straight into the point and not beat around the bush.

Be specific and concrete

Clearly articulate the issue or concern you want to address, provide specific examples or evidence to support your points, and explain the impact of the behaviour to help bring their awareness to it.

People only know what they know, so helping open up their perspective to the effects of their words or behaviours can help to have more effective conversations.

For example, you could say something like:

“I’d like to discuss how we can ensure you’re able to meet your deadlines, and what barriers you’re facing. When deadlines aren’t met, such as earlier this week, it meant we weren’t able to launch on time and reach our deadline as a business, and our customers didn’t have access to the product when we intended. It also meant different departments needed to adjust their calendars and workflows to accommodate the new launch date, which takes time and creates more work.

Use "I" statements and be curious

Express your thoughts and feelings using "I" statements, which can make your message less accusatory and more about your perspective. Coming from a place of curiosity and seeking to understand will prevent your statements from being taken negatively and enable the conversation to be more productive and solutions-focused.

For example, you could say, "I feel concerned about… " or “I noticed that…” instead of "You always..."

Instead of saying: “You’re not meeting your deadlines – why is that?”, which sounds accusatory and can cause people to feel attacked and get defensive, you could say: “I noticed that the deadlines aren’t always being met – what are the roadblocks and challenges you’re experiencing that’s preventing you from being able to meet the deadlines?

Don’t presume ill intent

Give the person the benefit of the doubt and assume there is no ill-intent from their behaviour or what they say or have said. This will help prevent the conversation from turning into an argument, and gives them the opportunity to explain themselves properly.

If they have said something you’ve taken negatively, you can simply ask them for clarification of what they meant by that. Often, how things come across to others is not how we intended! If you’ve misinterpreted what they’ve said, give them the opportunity to explain what they actually meant, or, the opportunity to bring awareness to how they came across so they can correct themselves if necessary.

For example: “You said you didn’t like where the project was going. Can you please explain what you mean by that?”

Be a great listener

Practise active listening by giving the other person your full attention, and don’t listen to respond, instead listen to try to fully understand.

Allow them to express their thoughts and feelings without interruption, and make sure you repeat back what the person has said and ask them if you have understood – try to use their words so that you’re not changing the message too much.

Then, they can either explain what they meant further if how you interpreted their message wasn’t quite right, or they’ll say you’ve got it.

For example: “Correct me if I misunderstood, but from what you’ve told me, the leading factor that’s preventing you from meeting your deadlines is because you’re struggling to get sign-off from the other departments in time. Is that right?

Empathise and validate

Show empathy and validate the other person's feelings, even if you disagree. Acknowledging their perspective can help build rapport and help them to feel heard. “I hear you and I understand your frustration.

Come from a place of empathy and love (an open heart) you will be able to communicate more effectively, especially during tough conversations. When you're in a reactive state it's much harder to have effective conversations. When you have an open heart you can't be in that place of reactivity.

How do you have an open heart? Think of moments where you have a heart warming/melting moment. For example, when I look at my adorable floofy samoyed Zeus I just feel love. He does things that irritate me, like eating the bathroom lino, but I still love him. You might get that feeling of unconditional love when you look at your pet, partner, child. Cultivate that feeling when you're talking to someone.

You could visualise your cute dog every time you're about to have a tough conversation, or take deep breaths and remember the sensation so you can bring it back into your awareness. This helps to develop your empathy and compassion for others.

Be mindful of nonverbal communication

It’s not always the words you use that have the biggest impact, it's how you say them. Be mindful of your body language and tone of voice, as these can convey important messages.

Maintain open and approachable body language. Don’t cross your arms, or example, as that can come across as confrontational. Showing your wrists indicates you’re being open and have nothing to hide.

Be wary of the tone of your voice and your facial expressions. People are very attuned to picking up on subtle cues of body language and often misinterpret them.

Find common ground (and be aware of what’s triggering you)

We tend to focus on the negative and what we don’t like about the person, so looking for common ground or what we like about them is a tool for disrupting his behaviour.

What do you admire about this person? For example, you might like that they have confidence and assert themselves.

It can be hard sometimes, but there’s always something you can admire about someone if you try! This will prevent you from focusing on all the negative things, and help you to have a more productive conversation.

When people are triggering us, it’s usually for one of two reasons:

  1. They either mirror something we do and don’t like about ourselves, or,

  2. they can do something we can’t do, and wish we could.

Every time you point the finger at someone else, think about how many people are pointing it back at you.

Ask yourself:

  • Can you recall any times where you’ve done a similar thing to the person in question?

  • Where can you see this as a lesson for yourself?

  • What are you not doing in these conversations? For example, are you not saying what you think, or rolling over every time they speak up?

Stay calm and emotionally grounded

Manage your emotions and stay composed during the conversation. Take deep breaths if you start feeling anxious, frustrated or upset. Try not to shut down or be avoidant, and step into your confident and assertive energy.

If the other person is getting visibly upset, you can simply pause the conversation and arrange to revisit it later after the person has time to cool down. When emotions are high, and fight, flight or freeze mode is activated, it’s very difficult to have a conversation with the rational brain. It’s often best to wait and schedule another time to finish the conversation.

For example: “I’m noticing that this conversation is affecting you, so I feel it’s best if we take a break and continue this conversation later this week. That will ensure we come back fresh so we can reach a solution. How does that sound?”

Stay solution-focused

Instead of dwelling solely on the problem, work together to find solutions, and make sure they’re clear on the benefits of finding a solution – what’s in it for them and others?

Remember: you’re not responsible for having all the answers. Ask them how you can figure this out together. Brainstorm ideas and alternatives collaboratively, and try taking a coaching approach where instead of you telling them all the answers, you ask them how they think the problem could be solved, and what they would like to try. This puts the power (and responsibility) back in their hands.

Encourage them to share their thoughts and suggestions, be receptive to feedback from the other person, and be willing to adjust your perspective if necessary.

You want them to succeed, you don’t want them to fail, and they probably want to succeed, too! So come up with a solution together.

Make a plan and set expectations

Once you have possible solutions to try, run through the pros and cons of each, and determine the next steps together.

Clearly define the expectations moving forward to prevent similar issues in the future, decide on a timeframe for implementing the changes, and how you’re going to determine whether the actions/changes were successful. Make sure you end with the positive benefits of fixing the issue so they’re clear on their ‘why’.

Make sure you get their buy-in, or nothing’s going to change!

Follow up

After the conversation, follow up with any agreed-upon actions or next steps. Continue to communicate as needed to ensure the steps are taken within the agreed timeframe, and whether the desired result was achieved or if further changes need to be made until a resolution is reached.

Seek mediation if needed

If the conversation becomes too difficult to manage one-on-one, consider involving a neutral third party, such as a manager or HR professional, to mediate the discussion. Always think about the possible risks to the business (or yourself) before entering into these types of conversations, and get HR help if you think there’s possible risk.

Exposure and practice

Practice with a trusted friend, mentor or coach to help prepare. The more you engage in tough conversations, the better you'll become at handling them. So don’t shy away, instead see them as an opportunity to learn and grow!

Evaluate and get feedback

After having a challenging conversation, taking time to do a quick self-evaluation will help you to gain clarity on what worked, what didn’t, and what you can do differently next time.

Write down:

  • What went well?

  • What didn’t work well?

  • What can I do differently next time?

By answering these three simple questions, you’ll have a simple plan you can follow the next time you need to speak up or have a challenging conversation.

If it’s appropriate, ask for feedback from your manager or trusted colleague who witnessed the interaction or was part of the conversation. This will help you to get a new perspective that can assist you with your growth and development.

Practice self-care

After a difficult conversation, take time for self-care to recharge emotionally and mentally.

Are you ready to tackle tough conversations like a boss?

Remember that tough conversations are a part of professional life (and life in general), and mastering this skill can lead to improved relationships, better problem-solving, and a more positive work environment. Over time, you will become more confident in your ability to express yourself without fear!

If you’re looking for support with increasing your confidence at work, I’m a life and career coach who specialises in working with ambitious career-focused women who want to have amazing careers AND amazing personal lives.

You can book a free 1-hour Career-Life Clarity Session with me to help get clarity on what’s not working in your career and life, where you’d like to get to, and how you can get there. Limited spaces available, so make sure you get in quick to secure your spot. Learn more here.

Thanks for reading! If you want more, check out my other blogs, follow me on Facebook: @Janellekeesue and IG: @janellekeesue. You can also book a free session with me here!

About the author, Janelle Kee-Sue

Janelle Kee-Sue is a certified life and career coach, accredited cognitive behavioural therapy (CBT) practitioner, business owner, writer, speaker, and marketing specialist based in Wellington, New Zealand. She’s been to almost 50 countries, is a former professional bikini bodybuilding champion with a world title under her belt, and is passionate about helping women who are feeling stuck and unfulfilled in their careers and lives to get clarity on their next steps and start living the life they're meant for. In her spare time, you’ll find her at the gym, working on her novel, or hanging with her floofy Samoyed Zeus and her husband Ricky. Learn more.


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