Life Lessons: Alexandra Greenhill

Let go of being the expert

Just over a year ago, Alexandra Greenhill made a dramatic career shift: the physician left her medical career to launch a tech startup, MyBestHelper, a website that connects families to caregivers. 

The company operates in cities across Canada and employs seven people. Greenhill plans to expand into the United States.

Now, instead of being the expert who knows all the answers, she’s usually the one who needs to learn from others. But letting go of her ego and embracing that state of constant learning is what is helping her business grow and thrive, she said.

“If you adopt the mindset of ‘we are lifelong learners and I actually want this to succeed,’ then it doesn’t become strife, it becomes the opposite,” Greenhill said.

“It’s people who are often coming in and giving you harsh lessons that you value, because you don’t need feedback saying, ‘You’re so accomplished, you’re so wonderful.’ … These are the things you really need to focus on to make your business succeed. If you don’t get these things right, your business is going to fail.”

For instance, the first few times Greenhill made pitches to investors, she was told that her presentation was too theoretical. She had spent a decade of honing a speaking style that was well suited to medical and university audiences, but she realized she had to “throw all that out” and start over.

“The first couple of times [I presented a pitch] some of my mentors and advisers said, ‘Whoa – this is not even New York Times level. … You’re starting with the scientific method and using too many big words.’ In business it’s a completely different structure.”

On what inspires her | “I saw the stress of the modern family as something that needed to be dealt with, because when it’s not dealt with it becomes [a contributor to ill health]. I wanted to start a company that was meaningful.”

Has a work or career challenge taught you a key career lesson? Contact Jen St. Denis at