Business Leaders’ Breakthrough Moments

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Andrew Ross Sorkin, host of last week’s DealBook conference in New York, with photos of experts taking part in the event.CreditCreditMike Cohen for The New York Times
Nov. 6, 2018

At the annual DealBook conference last week, business leaders joined a lunchtime conversation to talk about the state of innovation today. Before the event, The New York Times asked them to answer one of three questions about their careers. Their responses have been edited and condensed.

Peggy Johnson

Executive vice president of business
development, Microsoft

I’m naturally more introverted, but early in my career I was told that to be a leader I’d have to speak up and be more assertive in meetings. My breakthrough moment came when I decided that, for better or worse, I was going to be myself at work. That’s when my career started to take off. I learned that who I am matters more than how I’m supposed to be, and that to succeed on my terms, I had to define my own brand of leadership.

Jake Schwartz

Co-founder and chief executive,
General Assembly

Think impossibly big. You should feel embarrassed by the size of your vision. That kind of thinking can have its own gravitational pull and, as weird as it sounds, makes you more likely to succeed. Big thinking then has to be followed up by an obsessive attention to the tiny little details that will make or break your success.

Tony Schwartz

Founder and chief executive, the Energy Project

At the age of 47, eager to move from chronicling the work of others as a journalist to making a more direct difference in the world myself, I joined with a partner to launch a business that helps organizations to systematically build the capacity of their people physically, emotionally, mentally and spiritually. I realized that contributing creatively to address a huge problem was the purest joy I had ever experienced. I still feel that way 20 years later.

Steve Stoute

Founder and chief executive,
UnitedMasters and Translation

When I discovered the power of cultural currency, the trajectory of my career completely changed.

In 2002, I was with Paul Fireman, the founder of Reebok, who told me that Reebok was once bigger than Nike but had lost its way because young adults didn’t think it was cool anymore. I said, there is an insight you can tap into. All rappers want to be basketball players and vice versa. We’ve signed athletes, so we should partner with musicians who use Reeboks as a lifestyle shoe.

Despite everyone telling Paul this would fail (sneakers were about “performance”), he listened to me and I created a platform for Reebok called the Sound and Rhythm of Sport with Jay-Z as our first artist. Within one hour, all 10,000 pairs of the S. Carter Collection sold out. By realizing that hip-hop culture and basketball had a shared audience, we changed the landscape of footwear forever.

Afsaneh M. Beschloss

Founder and chief executive, RockCreek

Find work you like, and passionate people who take an interest in you! They will be the mentors and positive forces in your life.

John Hope Bryant

Founder, chairman and chief executive,
Operation HOPE

It is not about you. Being a leader even means being prepared to take yourself out. If you can get out of your own way, repeatedly, and are the personality type that can reimagine everything, and never give up — then you will win. On the worst days, this kind of leader remembers that rainbows follow storms.

Stephanie Cohen

Chief strategy officer, Goldman Sachs

If your goal is to innovate, then you have to be comfortable with failure. As a manager, that means setting the direction but allowing your people to explore, to try new things, to be creative and ask tough questions. Maybe things get done a bit differently than if you’d been making every single decision, but that’s part of the job description — teach people to think like entrepreneurs, and to own the results. It’s a more engaging way for people to work, it’s inspiring, and I think, ultimately, it leads to better outcomes.

Thasunda Duckett

Chief executive of consumer banking,
JPMorgan Chase

Be your unapologetic, authentic self. Build a brand that makes others want to trust you, partner with you and advocate on your behalf. Make meaningful connections with those around you. That doesn’t just mean looking up the hierarchy. Look to your left and right at your peers and to those who are up-and-coming.

Joelle Emerson

Founder and chief executive, Paradigm

My biggest piece of advice would be, do it! Companies have a significant impact on our world and play a powerful role in shaping our future. They influence what happens in our homes, our neighborhoods, our cities. They affect legal and policy outcomes. And they inform access to opportunity. Now more than ever before, companies have incredible potential to drive positive social change. But it matters who is at the table. When companies are more diverse and inclusive internally, they will drive more positive social change externally. By building more equitable companies, we can create a more equitable world.

Audrey Gelman

Co-founder and chief executive, the Wing

Remember, ‘no’ is a complete sentence. I have found that this is especially challenging for women who are starting their own businesses, given the structural and systemic barriers that we face in our journeys toward success. But saying no is often an act of self-care, and setting limits and boundaries is crucial. If you can’t say no, as a leader, your yes has very little meaning.

Brad Katsuyama

Co-founder and chief executive, IEX

My best advice to “groundbreakers” would be to experience firsthand the problems that they are trying to solve. That experience becomes critical whenever things get more difficult, or you are faced with a very tough decision, or doubt starts to creep in. Having conviction that your company is needed and can solve a problem, big or small, is necessary to succeed and to convince others to join your mission.

Steph Korey

Co-founder and chief executive, Away

If you’re looking to start a business, know that you don’t know everything, and be comfortable with taking calculated risks and embracing mistakes you’ll make along the way. Don’t be afraid of setbacks, because if you’re not failing, you’re probably not meaningfully winning either. You’ll make mistakes, sure, but you should view them as your competitive advantage — these moments will be the biggest opportunities for you and your team to iterate and improve and, ultimately, succeed.

Tom Patterson

Founder and chief executive, Tommy John

The best advice I can give fellow entrepreneurs trying to build a business is to always listen to your gut, the data will only take you so far. As entrepreneurs, we’re confronted with countless decisions every single day that have the power to redefine the business. If you let it, your gut will become your most valuable asset.

Rich Pierson

Co-founder and chief executive, Headspace

Starting a new concept like Headspace has been a huge undertaking and has required considerable commitment, time and resilience, so my biggest piece of advice is to make sure that when you build something new, you are deeply passionate about it and make sure it solves a real problem. Our vision to improve the health and happiness of the world has enabled me to keep going through the tougher moments.

Dov Seidman

Founder and chief executive, LRN

From my experience, it’s how you do things — even more than the opportunities you choose to pursue — that will determine whether you succeed long-term. So, rather than focus only on scaling the business, think about how to scale your values so you build an organization that is focused on the mission, passionate about the work and resilient. You will be much more effective if you earn the moral authority to lead, rather than rely on the formal authority that goes with your title.

Tien Tzuo

Founder and chief executive, Zuora

You need to edit your relationships. Choose your people carefully. With every new employee that you onboard, every V.C. you decide to partner with, every new board member you bring on and especially every new customer you acquire, you are building your identity. All these decisions add up. Surround yourself with good people — not just people that you want to be with, but people that you want to be.

Edward W. Stack

Chairman and chief executive,
Dick’s Sporting Goods

You can’t do it yourself. You need to bring people along with you to grow the business.

David Gorodyansky

Co-founder and chief executive,
AnchorFree Inc.

Stay loyal to your goals and dreams, and be ready to fight hard and never give up or change your values and mission — but be flexible on the plans to get there. The path to your goals and dreams will likely be different from how you plan, but as long as you stay loyal to your goals and dreams you’ll be able to reach them through ways that you might not have imagined.

Sara Menker

Founder and chief executive,
Gro Intelligence

Don’t let the fear of failure stop you from pursuing what could potentially be the most meaningful and fulfilling work you do.

Rosie Rios

Chief executive, Red River Associates;
former United States treasurer

Never let power overtake you to the point of feeling compromised in what you value. Money and power wield a very surreal influence over some people, for better and for worse and regardless of background and political affiliation. I think Tolkien had it right. You have to be a really good Hobbit to resist the ring of power. Be that Hobbit.

Andy Dunn

Senior vice president of digital consumer brands, Walmart U.S. eCommerce

I would postpone the multibrand dream until after we did the deal with Walmart. By trying to do it when we were a stand-alone company, I risked the entire business. It’s important to stay foolish, but it’s also important to know when to stay focused.

A version of this article appears in print on , on Page F14 of the New York edition with the headline: Breaking Through. Order Reprints | Today’s Paper | Subscribe

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