[Flash] Stand Near Closed Doors and Knock (Mentoring from Hootsuite CEO)

When Author David Novak interviewed Irina Novoselsky, CEO of Hootsuite and former CEO of CareerBuilder, for his podcast, How Leaders Lead, she shared some invaluable advice.  

Irina began her career in investment banking at Morgan Stanley, and then deliberately left finance to pursue a role on the operational side of business.    

Upon leaving, Irina embarked on a 9-month journey interviewing 100 CEOs. Irina viewed it not as a job search, but as a leader search. She interviewed CEOs to learn from them!  

She shared her strategy: Every day at 7am, I would set up meetings and say, “Here are the questions I have. What are your responses? How would you answer this?”  

Why did she orchestrate her journey in this way?  

“I was looking for a person who I could learn from, who had similar values to me, who had a similar approach, and who I wanted to emulate. I took my time to find somebody that I wanted to learn from, who was aligned with what I was looking for.”  

She reflected, “Of course, [these CEOs] thought they were interviewing me. They probably didn’t realize that they were mentoring me.”  

Irina revealed, “Where I’ve had success with mentoring is just bringing interesting people into my world of problems.”     

An immigrant from the Soviet Union, Irina set her target on investment banking during college because she learned that banking pays graduates the most money.  

The problem? They don’t hire freshmen.   

Undeterred, she grabbed a back-office job at Morgan Stanley that summer to thrust herself into the investment banking world.  

Once there, Irina spent evenings brazenly emailing Morgan Stanley Managing Directors (MD) – the equivalent of a Senior Vice President – and asked each of them to meet her for coffee. Why? She had questions and she wanted their advice!  

But only one responded. And that MD told her to graduate from college first before she could explore opportunities at the firm.  

Six months later, when a sophomore internship program opened up, the MD reached out to recommend that Irina apply. She got in, and her career launched!  

Irina shared this advice: “You’re either asking the wrong question or you’re asking the wrong person. Someone will open something if you knock. It’ll give you some opportunity. But if you do nothing, you’ll get nothing.”

And then she summarized her approach in six indelible words: “Stand near closed doors and knock.” 

© 2025. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved.

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