Lessons from Strategic Leaders (Who Also Happen to Be Women)

Before heading to Innovation Enterprise’s Women in Strategy Summit, I was struck by the thought that, although we have a long way to go in the vision for equality, the focus in recent (and not so recent) media on old boys’ clubs, toxic work environments, pay equity, glass ceilings and sexual harassment has created groundbreaking conversations in corporate boardrooms and startups alike.

At this gathering of women from across diverse backgrounds and industries, it’s clear that this focus has started to shift long-standing dogmas. From startup founders to corporate executives, the following are lessons from thoughtful and forward-thinking strategic leaders (who also happened to be women):

Don’t let the stories in your head dictate the story that plays out. Your own self-doubt is your worst enemy, not the (customer, investor, partner) sitting across from you.
 Dawoon Kang, COO, Coffee Meets Bagel

Find the fastest route to the thing that needs to get done. If you wait 90 days to solve a problem, the rest of the world has moved onto another problem.
– Karina Kogan, Senior Vice President, Digital Media and Products, TBS & TNT

When choosing a path or focus, don’t follow market trends. By the time it’s a trend, it’s over. – Caroline Klatt, Founder and CEO, Headliner Labs

When you are about to give up, consider how close you could be to success. After spending 14 months experimenting with models without success, I was on the verge of pivoting to a new product. A mentor advised: You’ve just spent 14 months becoming an expert in fragrance, now you want to throw it away and start over again? The pivot didn’t happen.
– Mariya Nurislamova, Co-Founder and CEO, Scentbird

Ensure commitment before building. When launching a new product or service, pre-sell it to ensure what the community says they want is what they actually pay for.
­– Naomi Mdudu, Founder, CEO, and Editor, The Lifestyle Edit

When making organizational and cultural decisions, rip off the band aid. As a leader, by the time an issue gets to you, it’s gone through many other layers of people. You need to move decisively and quickly to do the right thing, even if it’s unpopular.
– Anjali Sud, CEO, Vimeo

When choosing between climbing the corporate ladder or choosing a path of entrepreneurship, consider this loosely-translated advice: A leaf in still water will eventually rot. To thrive, find the moving water.
– Dawoon Kang, COO, Coffee Meets Bagel

Women have a tendency to give and give. Don’t just give, make sure you’re paid for your time. – Sheila Ronning, CEO and Founder, Women in the Boardroom

You want to be confident as a leader. A’s hire A’s. B’s hire C’s. You can’t be afraid of people shining or outshining you. You look good when your people look good.
– Sarah Aubrey, Executive Vice President of Original Programming, TNT

Remain laser-focused on where you want to go, but don’t be dogmatic or overly philosophical about how you get there. While the mission doesn’t change, the tactics can and should. – Anjali Sud, CEO, Vimeo

Why are we talking about breaking the glass ceiling in a building built by others? Go and build your own building. – Sarah Aubrey, Executive Vice President of Original Programming, TNT

When you measure something, it is an act of power. Measuring signals its importance.
– Laura Freebairn-Smith, Lecturer, Yale University. Partner, Organizational Performance Group

Refuse to be tortured by your job. Your confidence will unlock when you can walk away from an unpleasant workplace. – Karina Kogan, Senior Vice President, Digital Media and Products, TBS & TNT

Listen to your community to shape the future of your organization. A deliberate growth path built on deeper engagement can yield a rich source of ideas to evolve the business. – Naomi Mdudu, Founder, CEO, and Editor, The Lifestyle Edit

Measuring is not doing the work. Information for information sake is meaningless, it’s what you do with it that matters. – Laura Freebairn-Smith, Lecturer, Yale University. Partner, Organizational Performance Group

In addition to all of these words of wisdom, an overarching message from all these leaders was as follows: Whether you want to start a new business, take the next step in your career, or pivot completely, don’t be afraid to carve your own path.

the author

Cheesan Chew

Cheesan Chew is a strategy, CX, and innovation advisor and the former CXO of Idea Couture.