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UdemyLeadership & ManagementPaid courseIntermediate levelCertificate

Dread-Free Difficult Conversations: Speak Up with Courage (Udemy.com)

Overcome your discomfort and assertively lead productive, empathetic conversations with win-win outcomes.

Created by: Andrea Wedell

Last updated November 2025

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What you will learn

  • Prepare for your difficult conversations
  • Overcome the common fears that keep you from having the conversation
  • Manage anxiety about the conversation before, during, and after
  • Keep your people-pleasing habits in check
  • Make sure your passion and direct style isn't being interpreted as aggressive
  • Integrate assertiveness skills to crisply articulate your message so it's heard
  • Get crystal clear on what you want to say and who you're saying it to
  • Discover frameworks to have hard conversations with a peer, your manager, a report or a friend
  • Handle manipulation and very difficult people

How it compares

Against the other 230 rated Udemy courses in Leadership & Management on CourseDuck:

  • Rating4.5 out of 5higher than 42% of them
  • Reviews3,683#65 of 231 by number of reviews
  • Length1.8 hoursshorter than 56% of them
  • Last updatedNovember 2025more recently than 55% of them

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Course Description

You know the feeling: you have something difficult you want to say to a colleague or friend. But you’re worried about how they’ll react, figure, “Why rock the boat?,” and talk yourself out of it. You attempt to ignore it, but of course, nothing changes, and you find yourself dwelling on what it is you want to tell them. You want to keep the peace and avoid a conflict, so again, you stay quiet. You try to let it go to avoid an uncomfortable conversation, but that discomfort just stays with you.

My aim in creating this course was to teach you to be able to speak up when it really matters no matter how uncomfortable that idea seems to you now. The benefits of being able to do this far outweigh the discomfort, I promise. You may have trouble speaking up when you disagree, struggle to give difficult feedback to a report, need to shape the way your manager manages you, or figure out how to say “no” to what a stakeholder wants you to do.

Most people shy away from these types of tough conversations, because they don’t have the skills to approach them in a way that makes them feel safe. They may downplay the impact not having the conversation is having on their self-esteem but also the sheer amount of time they spend thinking about the unresolved issue.

I’ve been teaching and coaching people on this subject for over two decades and have worked with my clients on it across industries, jobs levels and cultures. I’d like to give you all of my own hard-earned tools to help you tackle your difficult conversations and develop the muscle that will only grow stronger with practice.

In this course, you will:

  • Learn why having difficult conversations is so important

  • Tame your anxious thinking around speaking up

  • Speak assertively (not passively or aggressively) to get the best outcome from your conversation

  • Prepare your message by understanding the other person’s point of view and finding common ground

  • Tackle those tough conversations, whether with a peer, manager, direct report, or friend

  • Deal with manipulation when passive-aggression is at play

The course is full of practical tips, examples and exercises you can build on one step at a time along with invitations to put what you’re learning into practice, immediately.

There are no prerequisites to taking this course. If the title pulled you in, then this course is for you. Please join me in this course!



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Instructor Details

Andrea Wedell

I Help Established And Emerging Professionals Become Powerful Advocates For Themselves, Their Careers And The Organizations They Work For.

For more than twenty years, I’ve had the privilege of helping thousands of executive leaders and entrepreneurs get clarity on what’s most meaningful to them. I’ve coached them to take bold, purposeful action to fast-track their success. And, perhaps most importantly, I’ve helped them become powerful advocates for themselves inside and outside of the workplace.

My passion lies in coaching you towards your true potential, helping you uncover what is most rewarding to you, finding that thing that makes you feel truly on purpose. I help you develop a direct and clear roadmap to success as you define it, through heart-centered, laser-sharp coaching.

Whether you’re an executive leader, an aspiring entrepreneur, or a business owner, I know that you want your professional contribution to have meaning and that you want to use the best of yourself and your skills. I know you need financial security and also want to impact your world and our collective world. You were born to do that. I know it, you feel it. You probably strive for autonomy over your career and your life. I also know that you want to cultivate the relationships, skills, and mindset to level up.

I’m here to help you get there.

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Reviews

4.5

3,683 ratings on Udemy

Select a bar to show only those reviews.Select the bar again to show every rating.

By Jacob Bradford on 8/12/2026

Loved the part about multiple manipulation styles and gaslighting haha. I have had multiple encounters in which it turns into a temper tantrum and all you could do was just walk away. 9 times out of 10 the individual would only act out Infront of groups but in a 1-1 would express issues not even related to work causing them to act this way. I also enjoyed the relative examples and role play skits. Very good presentation.

By Kizito Mukhwana on 2/18/2026

This course can help handle difficult conversations. I have issues at workplace and even at home that these skills will come in handy in resolving the issues. From the learnings here, I will need to prepare ahead, choose the right time and place, listen actively and stay calm and empathetic. It is important for me to focus on the issue and not the person. I have been having difficult giving feedback from the community (service users) to services providers for fear of it being taken as incitement. But this course has empowered me with the necessary skills to do that effectively.

By Lisa Fox on 2/3/2026

This course addressed the real topics we encounter in our daily interactions. The role play component was an excellent tool that reinforced my understanding of the material. It would be even more beneficial to include a role play video demonstrating these techniques in real conversations, alongside the interactive practice we already have.

By Jessica B on 1/21/2026

The instructor was knowledgeable, easy to understand, and provided relevant examples. I liked that the course provided resources, though I wish I could have participated in the role-play scenarios (my agency blocked the AI content). Overall, the content was constructive and thought-provoking.

By Anonymized User on 12/17/2025

AI sucks and really has a hard time getting out of its own loop it created and responding to real conversations

By Brandy Huerta on 9/19/2023

Thank you for creating this enlightening and extremally useful class. I have struggled with this my whole life and had to leave my previous job because I was unprepared to navigate some of the situations you cover. Now I know how to respectfully advocate for myself.

By Christy Michael on 8/15/2023

I loved the way Andrea taught the strategies. By the end of the course I felt like she was my best friend helping me navigate. Well-thought out lesson framework. I realized i myself use some of these manipulation tactics and make conversations difficult. Helped me recognize my errors and others that i have noticed and didnt think of it as an error. Thank you so much ! God Bless !

By Anonymized User on 8/17/2022

Excellent presentation and explanations. Great detail. Speaker presents extremely well with clear articulation and a style of delivery that is very appropriate to the content. Extensive exercises are included to further enhance the learning experience.

By Anonymized User on 4/3/2022

I love the teaching given. Practical and I have seen these behaviours in myself and others. I hope that I have more scenarios to practice on the things given. The current topics give me a general idea on how to prepare myself so I should try and review the notes often and practice it.

By Sinah Molifi on 3/7/2022

we must control and overcome our self to control by identifying our triggers and try to focus on positive out come to achieve our goal , when you control over your thoughts will help to handle your self in hard conversations and you must thinking about pattens of memories of a similar of past situation. Anticipation of persons behavior in the situation and we must pay attention

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Overall Score : 90 / 100