Letter No 37 - 5 ways to connect with successful people

Dear friend,

Earlier this week, one of the student 'partner's at Enterprise India Fellowship asked me this question - 'How can I build a rapport with successful people?'

For the sake of this story, I will call her Sharmila. Sharmila's family owns a manufacturing business. She is just beginning to get involved in the business and has recently been going to the factory. Last week, an expert consultant who they have commissioned to help them grow, was visiting the factory. After a morning of discussions with the top management, in which Sharmila had the opportunity to sit through but obviously could not participate much, the entire group sat together for lunch.

This is where the struggle began. Sharmila wanted to connect with the consultant and get to know her better. She want to build a one to one rapport with him. She took the opportunity and sat right opposite to where he was sitting at the lunch table. Being a part of the Enterprise India Fellowship, asking deep questions is second nature to Sharmila. So, she made an attempt asked a few interesting questions. The consultant was fascinated for a few moments and patiently answered her questions. And that was that. The consultant said good bye, got into his cab and returned to his home. The business leadership team went back to their tasks, and Sharmila kept wondering - how could I have struck up a conversation with this person?

How can I become more confident in connecting with people?


We are all surrounded by opportunities to connect with interesting people. Meeting such people is an education by itself. More importantly, it increases our confidence, expands our perspective, opens doorways of opportunity, and feels really good! Secretly, every one of us holds this desire in their heart - 'I wish I could talk to anybody'.

Now, there are three different levels at which connections with people happen:

1 - Casual

General chit chat, small talk, speaking about the weather, politics, sports, etc. Usually these conversations are forgotten immediately after they are had. They are fun, and are an essential part of relationships. But, by themselves, they are just that - casual.

2 - Transactional

Work related, getting a task done, sometimes where money is exchanged, but always where parties feel obliged to completing a task committed to the other. E.g. A visit to the doctor, a house painting consultant who comes home to give an estimate, a meeting with a career counsellor, etc. Don't get me wrong, these connections are essentially transactional, but are very important. They form a significant part of our life and the economy. But there is the potential to take some of these connections to the next level.

3 - Meaningful

Reflective, where some emotions are involved, where new ideas emerge, new perspectives are shared, learning and discovery takes place, a memory is created, etc. Any interaction has the potential to be transformed into meaningful. Even a rickshaw ride may end up with a meaningful connection with your rickshaw driver. These connections sometimes take place by chance. But mostly, people who create these regularly have two qualities - they love connecting with people, and have cultivated some best practices that help them.

Meaningful connections are deeply satisfying, and often end up in long lasting friendships or associations. They can be of varying degrees of intensity - e.g. I have a rickshaw driver at the stand opposite my house who know where I usually go, knows my name, and always gives me a broad smile and tells me a little about what is happening in his life. It's not high intensity relationship, but still we have a meaningful connection.

Most of the time we are toggling between casual and transactional connections. The fun lies in flirting with meaningful connections. Some will happen and some won't. But is always worth the effort.


Here are a few suggestions that you could experiment with to create some more meaningful connections in your life. Especially when you are looking at connecting with people who are more experienced and more successful (in some aspect of life) than you.

1 - Appreciation and LinkedIn post

Find a unique way to appreciate something that they did or said that connected with you. Write to them in detail what it was that they did or said, and why exactly it was impactful for you. Share with them a story from your life in which you could have used what you learn't from them. Thank them. And then, write a LinkedIn post about what you learn't from them, about your own story or example and how you will use this newly acquired wisdom. Ask them for permission to tag them. This is a nice beginning of a deeper connect.

2 - Invite them for a 'charcha'

If you are a student, and their life story or their experiences are interesting to you, invite them for a 'Zoom' charcha with your group of 5 - 10 friends / classmates / colleagues. Everyone loves an opportunity to make an impact by sharing their knowledge. Host the interaction with them with style, plan questions to ask, and ensure to get a nice group of people enrolled. After the event, send them a handwritten thank you with summary of all the learnings you had. They will cherish your momento for a long time.

3 - Offer your services

If you have some specific skills - e.g. graphic design, spreadsheets, presentation making, content writing, user research, etc - tell them about it and offer to do a paid or voluntary project for them. Let them know how much time your can dedicate and for how long. Even nothing works out, people will remember you for the gumption and courage to have reached out to them with your offer.

4 - Send them a video or an article

Take some time to find an article or a video that changed your perspective on the topic that they spoke about or are an expert in. Take the time to scan enough things until you find something that really blows your mind away. Share it with them along with a note about what you liked in it. Also let them know what about they said or did connected with you and find a connection to it in the article or video you share. It takes some effort to do this, but smart people are always looking for fresh perspectives on their own area of expertise. They will certainly appreciate your effort and respond back with their take on it.

5 - Share a story or your vulnerability with them

This takes a little courage, but it always works. Write down something that you are struggling with currently (this is important, don't just write about issues you struggled with in the past and have now overcome). It could be a fear, a confusion, or a situation that you are really at odds with. Describe it in some detail, but don't make it too long either. Be very open and vulnerable. Say what you probably haven't even told your best friend. Of course, use your own sense of judgement in terms of how much to open. Let them know that you are sharing this with them because they inspire you. Tell them how they inspire you. Thank them for taking the time to read, and let them know that you don't expect a solution from them, but are happy to be able to share. You will be amazed how beautifully this opens up meaningful connections.


Meaningful connections happen naturally. Try some of these suggestions if and when you feel like. Don't be anxious. Do it with an open heart and allow things to emerge a little. Be playful. This is not about setting goals or being focussed. This is about reaching out and making some connections. Don't expect too much in terms of what will come out of it. Do it for the pure joy of it. And then trust that if something has to come out of it, it will. And if not, that's okay too!

Here is a song for you. Inspires me about relationships beyond the ordinary - 'atrangi' ones!

Sending lots of love and positive vibes your way!


The Enterprise India Fellowship