The HoneyBook team

Designing a Culture that Matters

Leadership Strategies to Fuel a Team of Entrepreneurs

33voices
WeFestival Confab
Published in
10 min readApr 4, 2016

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Founders often cite the critical turning point where they are required to shift from an operator to a motivator. While mentally and physically challenging, the evolution is the most telling of a company’s success.

Today, sixteen WeFestival entrepreneurs share personal stories and techniques on the following topics to help you overcome the internal and external leadership challenges that accompany scaling.

  • Clear frameworks to set and track company goals
  • Strategies that will empower your team members to feel and operate like owners
  • The direct link between transparency and your team’s output
  • The wide-spanning benefits of holistic cultural development and practices you can implement today
  • Advice to help you navigate your most challenging responsibilities as a founder

Setting Company Goals

How to Shape Your Startup’s Roadmap

Adrian Granzella Larssen, Editor-in-Chief at The Muse

Adrian Granzella Larssen

Editor-in-Chief at The Muse

The Muse utilizes OKRs — the performance tool used by Google and Intel — to set quarterly objectives and key results for each team member, department, and the company as a whole. Adrian (@adriangranzella) introduces their process as well as the bi-annual performance reviews they conduct to refine it.

Kelsey Meyer

Co-founder and President of Influence & Co.

When Kelsey (@Kelsey_M_Meyer) was asked which tool she’d never cut from the Influence & Co. budget she responded, 15Five: Employee engagement software that enables individuals to personally review their performance and receive feedback from their peers and managers. She explains how the team uses it to measure and reward exceptional contributions.

Self evaluation, peer evaluation, and a review from your direct report enables a 360 degree view of how an individual is performing, how they’re being received by their peers, and the areas where we can help them improve.

The Ownership Culture

How to Lead a Team of Entrepreneurs

Amanda Kahlow and the 6sense team

Nicole Glaros

Chief Product Officer at Techstars

The first step to empowering your team members to feel and operate like owners is uncovering their strengths and weaknesses. Nicole (@nicoleglaros) addresses leaders’ responsibility to identify what excites and discourages individuals and how to place them in the right environment to shine.

Leadership is about paying attention to the details.

“When you give people the space to excel, they do,” Nicole says. She explains how to empower your team members to own their roles while being a strong support system to provide feedback and remove obstacles.

I give my team full responsibility to do what they want. I say ‘Hey, This is your decision. I’m here to help you. But at the end of the day, you need to make the decision. It’s totally up to you.’

Individuals attitudes completely change when they realize that the success or failure of a project is solely in their hands.

Jordana Kier and Alex Friedman

Founders of LOLA

At LOLA, every team member drives a piece of daily strategy and operations to help the startup achieve its goals. Alex (@friedgal) and Jordana (@kieroyale) detail the structure they use streamline the process.

We expect everyone on the team to be running solo against a specific goal. Everyone outlines their goals for their area of the business, executes, and then presents their progress at weekly team meetings. It promotes a real sense of ownership because everyone is building what they own.

Adrian Granzella Larssen

Editor-in-Chief at The Muse

Two of The Muse’s core values are ownership and teamwork. Despite sounding contradictory, Adrian shares how the two co-exist to create an environment where individual’s are empowered to spearhead projects while feeling entirely supported by their peers and managers.

Team members can own their roles without feeling like they’re in a silo. No one should be afraid to ask for help.

Kelsey Meyer

Co-founder and President of Influence & Co.

For new and young team members especially, a critical part of empowering them to act like owners is developing their confidence. Kelsey shares the questions, role-playing techniques, and policies Influence & Co. institutes to communicate that team members are capable and trusted by the organization.

When a team member in a new role comes to me and asks ‘What should I do? Can you help me with this?’ The first thing I say is ‘What would you do if I wasn’t here?’ Most of the time, that’s the right decision.

Kimberly Dawson

Founder of K.Dawson Company

Creating an open and honest culture where team members feel empowered to contribute is equally rooted in founders exercising a democratized approach to leadership. Kim (@SassyStrategist) addresses how to lead your team with equal and mutual respect.

Don’t look at yourself as the boss because you own a company. You can’t think ‘I’m in charge. Everyone works for me.’ You’re all working together. Be reflective and ask yourself: ‘How would I want this company to be run if I wasn’t running it?’

Always Default to Transparency

How to Maintain Open Communication Through Scale

Heather Hartnett and Megan O’Connor, Human Ventures

Milena Berry

Co-founder and CEO of PowerToFly

Every three weeks PowerToFly has a video conference with all 58 team members from around the world where they assess their goals and discuss company updates. Milena (@MilenaBerry) describes how and why transparency is the foundation of all of their interactions.

Whether it’s our most recent board deck, insights from our investors, or business vitals, like how we’re doing on revenue, we share everything with our team.

I am super transparent and I find that people really appreciate it.

Grace Garey

Co-founder of Watsi

Watsi is adamant that the transparency they are known for as a non-profit thrives within the organization. Grace (@gracegarey) shares the tools and strategies they use to make it a reality and how the mentality influences their culture.

Our goal is not only to make information accessible and available but digestible. It’s really important that we aren’t setting goals and throwing up pie in the sky numbers, then opaquely giving a team member an objective without being clear about how his or her contribution is forwarding our mission. You can’t expect people to connect the dots all the way up.

Your team needs to be able to look at a very transparent representation of what you are doing, where you are going, how you performing against that goal, and then see exactly how their piece fits in. It’s very motivating and establishes a strong sense of trust that nobody has any more information than anyone else. We’re all in this together.

Alex Friedman and Jordana Kier

Founders of LOLA

From an always open door policy to visible calendars, Alex and Jordana make transparency a priority at LOLA. They address the information they actively share, and the tasks they handle themselves (but are always open to discuss), to keep their team focused.

Especially as a small team, it’s important to be very honest and share as much as we can about what we’re working on because we expect it go both ways.

Commit to Holistic Development

How to Shape a Values Driven Culture

Brittany Hodak and the ZinePak team

Brittany Hodak

Co-founder of ZinePak and Per Diems Against Poverty

Brittany (@BrittanyHodak) shares the three practices — goal sheets, creativity stipends, and superfan stipends — that ZinePak uses to stimulate their team’s creativity.

If people are creative outside of their jobs they’ll be more creative inside their jobs.

In 2013, ZinePak instituted a Culture Captain program where each month a different team member coordinates events — from birthday parties to movie screenings — to assemble the team for fun activities. In addition to fostering camaraderie, the program develops team members’ operational capacity to plan events and manage a budget.

In one way, activities have nothing to do with the job. In another way, they’re everything.

Amanda Kahlow

Founder and CEO of 6sense

From her very first pitch deck, Amanda (@AmandaKahlow) was adamant about making giving the foundation of 6sesne’s culture. She describes how the mentality thrives internally and externally at the organization.

Giving isn’t about doing community service once a month. It’s about giving ourselves fully to everything we do — To our customers, product, and back to the community. It’s about how we give to each other.

Giving is about showing up as your full, best, 100% self in every moment.

The result of ingraining giving into your culture is the natural evolution of your company’s values. Amanda shares how their commitment to give 100% shaped 6sense’s FAMILY mantra: Fun, Accountability, Mindfulness, Integrity, Love, and Yes.

Amanda discusses her personal calling to ground 6sense in a culture that strongly nurtures every team member’s health, spirituality, and wellness.

I came from very little. People took a chance on me and gave me opportunities. I feel like I have an obligation to give back wherever I possibly can.

We can’t just look at ourselves. We have to look at everything around us.

Kim Plyler

Founder and CEO of Sahl Communications Inc.

Between Yoga Wednesdays, Philosopher's Notes, and company retreats, Sahl Communications takes a holistic approach to developing their team. Kim (@KimPlyler) addresses why her team members happiness is a critical priority for her as a founder.

You have to be happy and have fun at work to be productive. We believe that a holistic approach to developing a human being, their health, and wellness, benefits the company as a whole.

Heather Hartnett

Co-founder and CEO of Human Ventures

Heather (@HeatherHartnett) highlights entrepreneurs’ unique opportunity to “see where someone wants to be in their life and help them raise and attain their goals.”

Even if you don’t have it all figured out, you can be a force to help someone be the best person they can be.

Kelsey Meyer

Co-founder and President of Influence & Co.

As your company scales, it’s important to recognize that each individual on your team — Whether they’re an intern or a co-founder — is working diligently to make the strongest contribution possible. Kelsey shares her personal habit of writing weekly thank you notes to her team members as well as the WWE belt tradition Influence & Co. uses to acknowledge and celebrate individuals’ work.

Fulfilling Your Responsibility as a Leader

How to Maintain Your Company’s Pulse

Katharine Zaleski and Milena Berry, Founders of PowerToFly

Nicole Glaros

Chief Product Officer at Techstars

As Box SVP Karen Appleton affirms: “You can’t go grow completely without the good and the bad.” Nicole discusses your responsibility to give your team members honest feedback and the most effective way to deliver it.

Establishing trust and giving effective feedback goes hand in hand. When you start by building trust, your team knows that you’ve got their back. You’re here to make them better and stronger not to tear them down.

Rebecca Kaden

Partner at Maveron

While each of these leadership habits and strategies will enable you to develop and guide your team, it’s wise for entrepreneurs to prepare for an imperfect path. Rebecca (@rebeccak46) explains why.

All companies would be perfect except they employ people. People are unpredictable and emotional.

All best plans go awry. You can have the perfect business plan, the perfect hiring plan, and the perfect execution plan but your employees have bad days. They act out. They have surprising events come up. If you aren’t in the headspace to deal with the unexpected, all of the best plans you’ve made don’t matter.

Kellee Khalil

Founder and CEO of Loverly

As a founder, you’re responsible for maintaining team chemistry which is the foundation of your company’s culture. Kellee (@kellee) shares how to respond when an individual isn’t the right fit and why she regrets not letting go of toxic team members sooner.

When you have a pain in the pit of your stomach that a team member isn’t working out don’t try to force it.

Amanda Kahlow

Founder and CEO of 6sense

Amanda discusses a founder’s moral obligation to his or her company, team, and the specific individual to make firing decisions as quickly and efficiently as possibly.

When you see that somebody has the capability to do something that is not morally or ethically aligned with who you are you have to cut the cord.

When someone shows you their true colors, believe them.

Camille Ricketts

Head of Content and Marketing at First Round Capital

While your outward role as a leader will always be guiding and motivating your team, the most telling part of your evolution is your ability to continually grow as a founder. Camille (@CamilleRicketts) cites leadership coach Katia Verresen’s framework on how to balance your emotional, mental, and physical energy to optimize your potential.

Only when you have those two building blocks, the emotional and the physical, can you harness your mental and intellectual energy to go the distance as a leader.

Elham AyoubZadeh

Founder, CEO, and Creative Director at Zvelle

It is undeniable that the stress of launching and scaling a business can only be grasped by fellow builders. However, Elle (@elleazadeh) urges founders to remember that being an entrepreneur is a choice.

You have to manage your psyche while managing your business; Sometimes every hour. Don’t get too excited about the highs or too down on the lows.

Every day, whatever it is that you’re making, it is your choice to be an entrepreneur. Knowing and embracing that choice puts you in a place of power.

Have a leadership technique that’s been essential to developing your team? We’d love to hear it. Share your strategy in the comments and join the WeFestival conversation on Slack.

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WeFestival Confab

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