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How 'Nice' Leaders can Master Difficult Conversations

2 Weeks


Cohort-based Course

Learn to have powerful career-changing conversations, win more arguments, and effectively manage conflict.

Hosted by

Prateek Singhal

Stanford- and Harvard-Trained Leader & Coach. Past: Wayfair, Allstate, McKinsey

Course overview

Communicate effectively in challenging conversations

Great leaders are excellent at navigating difficult conversations. This course will provide the tools you need to master challenging conversations and get the outcomes you want. Think about:

👉 Influencing board members or senior leaders

👉 Inspiring a direct report to resolve performance issues

👉 Convincing your manager that you deserve that promotion

👉 Creating a win-win outcome in a difficult negotiation

The course packs-in knowledge from the foremost leaders and coaches on this topic, and combines that with hands-on practice and feedback in a risk-free environment for the most impact. You can expect proven, practical techniques and frameworks and lots of reflection and practice to ensure you come out feeling ready and equipped.

By the end of the course, you should have the tools and conviction you need to prepare for a variety of difficult conversations, frame and navigate them effectively, handle defensiveness and blockers, and create outcomes that work for you.

Who is this course for


People leaders and founders who want to better navigate disagreements and friction at work


High-performers who want to earn greater influence in their organizations


Leaders who want to make greater impact by winning more negotiations

After this course, you will...

Get out of your own way

You will have looked inward and identified your fears and challenges that are getting in the way of effective conversations. And learnt to move ahead despite them.

Frame contentious topics effectively

You will practice framing the problem objectively and clearly. You will learn to understand and articulate the situation from the point of view of all parties involved.

Develop a toolkit to navigate tough conversations

You will walk away with proven techniques to confidently set up, drive and conclude difficult conversations, and actions beyond the conversation.

Create a greater set of possibilities

You will start defining a “win” in different ways, and develop tactics to broaden the set of solutions acceptable to all parties.

Refine the necessary interpersonal skills

You will practice and hone your interpersonal skills to enhance empathy, language, listening, and emotional regulation that are important for successful outcomes.

Meet your instructor

Prateek Singhal

Prateek Singhal

Founder, F500 Executive, and Leadership Coach

I am an operations executive and leadership coach with 15 years in leadership roles at startups and large companies like McKinsey, eBay, Allstate and Wayfair. In my career, I have built 100+ person teams and $200M+ businesses. I coach founders, CEOs, and other leaders 1:1 on some of their most pressing leadership challenges.

But it wasn't a straight line to get here. I've made every mistake in the book and learnt the hard way. I have been promoted, and denied promotions. I have gone through successful acquisitions, and failed startups. I've also been fortunate to have observed and learned from some of the best in the industry. And I am eager to share those learnings with you.

I have a CS undergrad from Indian Institute of Technology, MBA from Stanford University, and MPA/ID from Harvard University. I live in the San Francisco Bay Area. You can find me on LinkedIn here.

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Course syllabus


Why Conversations Fail

We start with diving into reasons certain conversations fail. Why we might fear them, why they might stay superficial, and why we aren’t able to get the outcomes that seem so obvious and within reach. You will develop greater awareness of what needs to change for you to have more effective conversations.


​​Identifying Your Fears and Challenges

Powerful conversations start with looking inward, exploring your needs, choices and fears, and their impact on your conversations and their outcomes. As a result, you develop the ability to push for the right outcomes despite your internal blockers.


Focusing on Interests Rather than Positions

Meeting half-way is almost always not the best outcome. You will look past stated positions to identify underlying interests, and create possibilities that are compatible with shared interests of both parties.


Framing The Problem Effectively

Identifying a problem clearly and crisply is important to avoid creating a defensive or adversarial atmosphere. You will create alternative ways to frame the problem and your position that are direct, trust-building, and productive.


Effective Communication Tactics

Using the right language makes a big difference in high-stakes conversations. You will develop vocabulary that is clear, inspiring, and solution-oriented to tear down walls and make progress.


Going beyond the spoken word

Listening is a key part of communicating, and the ability to listen to what hasn't been uttered can be a superpower. You will practice being truly present and anticipating the other person’s needs, feelings and reactions.


Emotional Regulation

Important conversations involve emotions, whether we acknowledge it or not. To be most effective, it’s important to identify and steer your emotions rather than suppressing them, or worse, them steering you. In this module, you’ll practice exactly that.


After the conversation

The conversation isn’t over once you click “End Meeting” or walk out of the room. You will develop the tools you need to use after the conversation to ensure you get the results you expect.

Course schedule

4-6 hours over 2 weeks
  • Tuesday, May 2, 2023

    6pm - 7:30pm US Pacific Time

    9pm - 10:30pm US Eastern Time

    6:30am - 8am India Time (Wed, May 3)


    • Why Conversations Fail
    • ​​Identifying Your Fears and Challenges
    • Focusing on Interests Rather than Positions
  • Thursday, May 4, 2023

    6pm - 7:30pm US Pacific Time

    9pm - 10:30pm US Eastern Time

    6:30am - 8am India Time (Fri, May 5)

    During the conversation:

    • Framing The Problem Effectively
    • Effective Communication Tactics
    • Going beyond the spoken word
    • Emotional Regulation
  • Tuesday, May 9, 2023

    6pm - 7:30pm US Pacific Time

    9pm - 10:30pm US Eastern Time

    6:30am - 8am India Time (Wed, May 10)


    • After the conversation
    • Reflection and integration
    • Open Discussion

Learning is better with cohorts

Learning is better with cohorts

Active hands-on learning

This course builds on live workshops and hands-on projects

Interactive and project-based

You’ll be interacting with other learners through breakout rooms and project teams

Learn with a cohort of peers

Join a community of like-minded people who want to learn and grow alongside you

Frequently Asked Questions

What happens if I can’t make a live session?
I work full-time, what is the expected time commitment?
What’s the cancellation/refund policy?
What if I have more questions about the course?
How do I get this course reimbursed by my company?
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How 'Nice' Leaders can Master Difficult Conversations