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This article is written by Ramanuj Mukherjee, CEO, LawSikho.

Do you succeed in life by following what everyone else wants you to do, by being the most agreeable person in the room, by not speaking your mind?

I have met people who have managed to survive through life in that way, and even have climbed some organizational hierarchies. 

However, outlier success does not come from that. If you want to succeed big, you succeed one tough conversation at a time.

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A tough conversation does not mean a rude conversation or a mean conversation, it does not mean a conversation where you win and the other person loses.

A tough conversation is a conversation that requires emotional commitment, clear intention and hard work. It is a conversation where you have to step out of your comfort zone. And perhaps, you have to push the other side in the conversation out of their comfort zone too.

Imagine that you are infatuated with someone and you have to ask her or him out. It is a tough conversation.

Imagine that you need a raise at your job, and you need to ask for it. It is statistically proven that those who ask for a raise, when they deserve it, are many times more likely to get it than those who do not ask.

It’s a tough conversation, it is sort of confrontational, but it is key to progress.

Maybe an employee or a vendor is not performing. You need to have that tough conversation about letting them go. 

I have learned from experience how hard those conversations can be, to the detriment of the interests of my organization, and how prone I am to postponing such conversations. 

A tough conversation is at times pointing out hypocrisy or calling people out on their bigotry.

Sales is also hated by so many people as a job option because it involves a lot of emotionally draining, tough conversations. Cold calling is tough conversations of another level, but watch Wolf of Wall Street if you want to know the kind of results it can lead to. It has power.

I would never study law if I did not have certain tough conversations with my parents and held my ground.

Deal negotiations are tough conversations. Arguing before the judge is a tough conversation. Talking to a client about charging the fee that you deserve requires a tough conversation. Following up when you are not getting paid is also a tough conversation.

When you are just a law student or an intern, it is a tough conversation to ask for work, to ask for opportunity, to ask what you have to do in order to get a PPO.

Most people will never ask their boss what it would take for them to get a raise or get a promotion, simply because they find it impossible to have such a tough conversation.

People suffer in silence than have a tough conversation that could change everything.

Talking to my coach about what I am doing wrong and what I am not doing enough and facing the shortcomings of my character and approach and analyzing the reasons for my failure – those are tough conversations.

To write about my misdeeds and sharing my failures and misadventures openly with everyone also count as tough conversations for me, and that’s how I train myself to be habituated to having tough conversations. 

So many people would never share their best wisdom and the most exciting stories of their life because they are scared of the conversations that may follow their revelations!

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We need to reframe our approach to tough conversations. When we stand up and speak of our interests and our views, when we confront those whose interests are against those of ours, when we stand up for our values and principles, when we confront our own failures, none of that is easy or palatable, and we will certainly face pushback, but our progress entirely depends on how successfully we handle those tough conversations. 

Tough conversations are not only about rebellion, or speaking your mind or speaking truth to power, it is also very often about speaking with compassion, about restoring integrity, about being kind where we have failed to do so in the past.

It is often about setting aside our self interest and talking about collective good.

It is often about finding a solution to a problem that is considered too hairy, too scary to be touched. It is about opening up old wounds so they can finally heal.

For me, it is about moving the conversation towards fairness, towards my vision of a better world, towards a world where we can take justice for granted.

A tough conversation at a time led to our constitution being drawn up, a document that has survived the test of time.

Tough conversations make history. Tough conversations build careers. 

Tough conversations set apart those destined for greatness, from the hoi polloi who will leave no mark in this world. 

Do you have those tough conversations? With yourself, with parents, with colleagues, with clients?

With the people you hate and the people you love?

Would you like to get on a call with me and have a tough conversation about your career, about what’s happening, about what’s next, about how you can jump to the next orbit? Respond to this mail and let us know. My team will schedule a call between us.

We deliver our courses to you, one tough conversation at a time. Come and experience how that works: 


Diploma in Intellectual Property, Media and Entertainment Laws

Diploma in Advanced Contract Drafting, Negotiation and Dispute Resolution

Diploma in Cyber Law, Fintech Regulations and Technology Contracts


Certificate Course in Labour, Employment and Industrial Laws for HR Managers

Certificate Course in Capital Markets, Securities Laws, Insider Trading and SEBI Litigation

Certificate Course in Media and Entertainment Law: Contracts, Licensing and Regulations

Certificate Course in Prevention of Sexual Harassment at the Workplace

Students of Lawsikho courses regularly produce writing assignments and work on practical exercises as a part of their coursework and develop themselves in real-life practical skill.

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