Millennial CEOs Share Their Top Leadership Hacks



Steal these battle-tested tips for evolving from a manager to a leader, compliments of two under-30 entrepreneurs who are building their empires through effective management.


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Kicking off the Millennial Manager Boot Camp at Social Media Week NY, Butterfly co-founder David Mendlewicz asked the mostly-millennial audience how many of them were managers. Most attendees raised their hands. Next, he asked how many of these managers had ever received formal leadership coaching. Crickets.

If Millennials comprise the lion’s share of today’s workforce, and hold a growing share of managerial posts, then why are we waiting so long to train them? The Harvard Business Review has reported that most organizations wait ten years to offer executive leadership coaching to managers.

The workshop was designed to provide young managers with a primer on leadership best practices, as shared by two successful entrepreneurs who rose through the ranks early in their careers: Tiffany Pham, Founder & CEO of Mogul, and Brian Wong, Founder & CEO of Kiip.

Here are some of their top leadership hacks for first-time managers.

Practice servitude management

Wong advocated moving to a modern management style called “servitude management.” Within this model, managing people is less about sitting around and telling people what to do and more about actively listening to your team members and presenting yourself as an available resource to help in their professional development.

“Tell your team members, ‘I’m here for you,’” says Wong, who entered the workforce at age 18 as an early employee at Digg. “Move obstacles, open doors. You don’t have to tell employees exactly what to do.”

Never eat alone

Pham said one of the simplest ways for managers to demonstrate that they’re listening is to invite team members to join them for breakfast or lunch. Pham says she “never eats alone,” instead using these windows to listen to her employees, ask how she can be helpful to them, and get to know them on a more personal level.

Collaborate on goal-setting

Both Wong and Pham advised millennial managers to work in partnership with their employees on goal-setting. “Too often than not, we set job descriptions and then shove people into them,” said Wong. “In the future, I believe people will create their own job descriptions that they then offer to companies.”

Follow the ‘two pizza’ rule

When it comes to building teams, Wong says he’s a believer in the “two pizza” rule, that is, if you can’t feed your team with two pizzas, then you have too many direct reports. The ideal number of direct reports? Five to eight, according to Wong.

Use a PPF framework to guide 1-on-1s

One-on-one meetings are important for managers to keep a constant pulse on their direct reports, but these types of check-ins can easily become redundant and non-actionable. Wong suggests focusing the conversation on PPFs–plans, progress and fires–to focus the conversation on what’s most important.

Get your boss out of the office

Managing up can be as critical to career success as managing those who report to you. In response to an audience question, Wong suggested practicing empathy with your manager and understanding what’s on his or her plate at all times. Pham echoed this sentiment, underscoring the importance of transparently communicating with your manager, so that you can then relay key information down through your team.

Manage expectations as a player-coach

Managers who take on new leadership responsibilities on top of their “day jobs” are challenged two juggle two worlds in the workplace. Pham said the most important thing to keep in mind as a player-coach is to be aware of the specific goals and metrics you’re being judged on. Then, she says, ensure your employees’ goals ladder up to the broader team goals.

Celebrate successes

Speaking to Mogul’s culture of “extreme support,” Pham said that celebrating successes is a regular occurrence at her company. Weekly Wins allow employees to share their triumphs across the organization, and each and every birthday (and new hire on-boarding) warrants its own celebration.

Looking for more insight on building culture? Pham recommends that managers read Built to Last: Successful Habits of Visionary Companies, which explains how organizations can build core values around micro-cultures.

Use communications tools to practice empathy

One of the most beneficial aspects of Slack, says Pham, is that you can have an instant purview into the dynamics and workflows of other teams. Department channels allow people to peek into the lives of their colleagues, recognizing when they might be putting out a fire (or celebrating a win!). At Mogul, monitoring what other teams are up to supports the company’s culture of “extreme support.”

Tell people what you’re like early on

Citing his new book, The Cheat Code, Wong suggested “telling people what you’re like before you do anything.” Bad with names? Guilty of sending late night emails? Let people know up front so they know what’s coming.

Know your superpower

Another hack from Wong’s book? Know your superpower, that is your top skill that comes easiest to you. Build your team with people whose own superpowers compliment yours. Are you visionary and motivational but notoriously bad at math? Find a detail-oriented Excel fiend to round out your finance team.

Walk the walk when managing your peers

An interesting scenario that many new managers find themselves in is all of a sudden being in charge of the very same people they had formerly hung out with at happy hour. Stepping into the role of manager can be awkward when your new team is comprised of mostly peers.

In these types of situations, Pham stresses the importance of walking the walk and behaving like a manager. Meet with each person on the team and establish yourself as a leader early on, she says.

“I would tell them you got demoted to manager,” adds Wong. “Reinforce that nothing changes, except you are now on the front lines, working for them and protecting them.” A little transparency and candor can go a long way.

Personalize career development plans

Wong says motivating millennials is a different beast than keeping older generations engaged. “Millennials don’t want to feel boxed in,” he says. “They want to expand and grow horizontally.” To support this, Kiip reimburses its employees for up to $2K of the professional development classes they take.

At Mogul, Pham actively listens to employees’ personal passions, so that she can seek opportunities to weave them into their daily roles. The ideal is to help develop them as a human and as a professional, she said.

Build diversity & inclusion into your culture

As one of the web’s largest platforms for millennial women (the site reaches 18M women weekly in 196 countries), Mogul partners with companies like Samsung, Nike, IBM, Facebook and many more to raise awareness for diversity and inclusion issues among prospective and current employees. They also offer ongoing trainings around unconscious bias, gender equity and inclusive leadership.

Wong says that a big part of being a manager is promoting diversity from the ground up. (Kiip’s executive team is 60 percent female.) “Biases come from where you source candidates from,” he says. “If your candidate pool isn’t diverse, rethink where and how you are surfacing talent. Audit where you source resumes and which schools you choose to partner with.”

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