Sukhinder Singh Cassidy, Founder & Chairman, Joyus | Founder, #chosepossibility and the Boardlist

What do you get when you combine leading technology entrepreneur Sukhinder Singh Cassidy with 60+ women from all backgrounds in a room?  The launch of Changemaker Chats in San Francisco!

Earlier this week we had the honor of hosting Sukhinder at LinkedIn’s San Francisco offices for an evening of honest conversation on the trials and exciting tribulations of growing your career, managing relationships, understanding oneself and having a great time along the way. It was a packed event and ran well over than the planned time, but Sukhinder graciously took question after question from the 60+ women in the room.

What we loved most about Sukhinder was her energy, candor and encouragement to work hard, while remaining unapologetically authentic. Sukhinder showed us that with the right amount of humility, humor, and smarts, you are bound to rise to your full potential.

Here are some gems from Tuesday night’s Chat with Sukhinder Singh Cassidy:


1. Position yourself for opportunity: Sukhinder knew she wanted to work in an entrepreneurial environment, so after some other moves to NYC and London, she drove from LA up to the Bay Area (in a beat-up, but good looking car!), to be close to the action. She didn’t know exactly where it would take her, but she found a way to position herself in the environment she wanted to work in, remained open to opportunity while also creating a few of her own!

2. Know yourself: The biggest investment you can make in being/becoming a leader is self-awareness and learning to forgive. We often have a hard time being truly honest about what our strengths and weakness are. Sukhinder’s solution: go ask someone you’ve worked with what they think you’re great at, and what you suck at. Once you know these qualities, you can capitalize on your strengths, and constructively address areas for improvement.

3. Be Authentic: People say this a lot, but what it means to Sukhinder is deeply personal. Her father not only passed along a strong entrepreneurial spirit, but also taught her to be authentic through living a life that did not entail being one person at work, and another at home. There was no distinction for her father, and she credits much of her success to learning this lesson early, and being authentic in everything she does.

4. Influencing Others: Sukhinder shared that she thought the path to a promotion was to put your head down, do your job and you will get the next move you want…think again. She learned the hard way that so much more can go into these decisions, and it is important to build skills in influencing others and take the time to ensure people have an accurate perception of who you are.

5. Letting Go: This is a big piece of leadership. How do you move from working in the trenches day-to-day, to working effectively in a more strategic role? The key is learning to let go. Sometimes it is forced upon you (e.g. an organization in hyper-growth), and sometimes you need to engineer it (e.g. leaving the room for a team brainstorm and empowering your colleagues to drive the project). Situations aside, it all ties back to balance. There will always be ebbs and flows to the demands in your schedule. Sukhinder manages time for her multiple businesses, board roles, and quality time with her three children (yep, you read that right!) and husband by being “ruthlessly efficient” with her time. There will be periods when your workload is on hyperdrive, and times when you can step back, log out of email, and focus on family. And that’s OK.

6. Assume Competence: Many women have a tendency to sell themselves short in interviews – why is that? Maybe we don’t want to commit to anything we are not 100% sure we can deliver. Her advice to nailing an interview…prepare well to build your confidence, and then assume you have the competence to figure out how to do any part of the job.

Thank you, Sukhinder, for helping us launch Changemaker Chats in San Francisco, and helping pave the way for women leaders across the Bay Area.

And Thank you to LinkedIn, Black Kite Cellars, and GoVino for helping us host the Chat, and to Erin Sullivan for capturing some of our favorite moments. Finally, don’t forget to access your Changemaker exclusive offer from JoyusClick here to learn more and access the promo code.