Why Being Real Matters: The Case for Authentic Leadership
(or, How to Inspire Your Employees to Walk Through Walls for You)
“Make it your business to know yourself, which is the most difficult lesson in the world.” - Miguel De Cervantes
Years ago, at a morning gathering of entrepreneurs in the Shoreditch neighborhood in London, Jerry did a talk about the challenges of entrepreneurship and why resilience is a key element of leadership. One of the first questions he posed to the group was “Why did you start your company?” In other words, why do you do what you do? Why are you signing up for this emotional roller-coaster ride of entrepreneurship?
A brave soul opened up about why he was doing his current startup by saying: “I had a startup that I quit working on to do something safe: go back to school and get a salary. We had a good product then. Shortly after I quit, a competitor with a similar product that was not as good as ours was bought by Google. I know our product was better. I regret that I was so close and missed my chance. I want to do this again.”
“How do you feel sharing this with the group here today?” Jerry asked him.
With his hand on his chest and a slight tremble in his voice, the brave soul replied: “I feel very vulnerable.”
The room was quiet in the way rooms get when there’s attentive listening and empathy. Jerry looked at the man’s co-founder, who was sitting right next to him, and asked: “What do you think of this guy right now that he’s revealed that?” The man’s co-founder answered with solid conviction: “I’d walk through walls for him.”
Turning back to the whole group who showed up that morning, Jerry asked, “How many of you would work for this guy?” Everyone raised their hand with the sort of awe that comes when one recognizes a strong leader.
At Reboot, we witness this happening repeatedly in our work. The moment a leader faces the heart of the challenge or considers what their work means to them is a moment in which a leader can connect deeper with their purpose and the purpose of their company. While it’s often a vulnerable place, that connection is forged in heart and is something that employees, customers, or investors can get behind.
Later that day, I sat with a pair of co-founders in the 1–1 sessions. One of them asked, “Ok, what do you see most often? What do I need to watch out for?” I smiled. He wanted the checklist of things to do, read, know and have in place so they would be all set in the face of the uncertainty that is startup life.
That list doesn’t exist, of course, except in a very general sense. No one has an antidote to uncertainty. What I find that does kill startups in big and small ways is a leader’s lack of willingness to grow authentically in their role.
So often we see entrepreneurs trying to fit into the startup mold, versus creating something out of the box. Fitting into something prescribed by the latest top ten list, or modeling your company after the hottest startup in the headlines leaves something to be desired.
That something is what you would like, what you want to build, and how you want to build it.
What values are you infusing into your organization and why? What kind of company do you want to build? What kind of adult do you want to be?
These questions come from a place within you and, likely, haven’t been written up in a blog post for mass consumption yet. Being an authentic leader means bringing all of you in to your work, not leaving the best parts of you at the door.
As a coaching company, we are with our clients as they go through a lot: fundraising, short runways, crucial hires, critical fires, building a top-notch management team, managing board members, scaling challenges, co-founder conflict, etc. Each issue has its own nuances in each company context, and each challenge can be moved through with clarity and mindfulness. How someone is as a leader in the face of and through all that comes your way is key. These crucible moments are where true leadership emerges.
There are very real issues that leaders face in their startups. Being authentic through it all is a challenging and fulfilling practice. Challenging in that it will provoke some of your deepest fears and feelings. Fulfilling in that increasing your awareness of those feelings creates freedom for how you choose to respond to them.
How can you use the challenges inherent in startup and fast-scaling life to enhance your leadership and resiliency?
How does this, then, ripple throughout your organization — the organization you are building every day, with each interaction, conversation, and decision?
JOURNAL PROMPT
- Who are you, really?
- Why do you do what you do?
- How does the totality of you shape and define the best and most challenging aspects of your company?
EXERCISE
What kind of leader do you want to be? What kind of company do you want to build? How can you connect to purpose and lead from that place? We’ve created a 5-day self-guided email course to help you reboot your leadership and reboot your life. Each day has a short written piece, an audio clip, and some thought-provoking prompts that are bound to open up meaningful conversations amongst peers, partners, and significant others.
LISTEN
Know You’re Not Alone. A core tenet of everything we do at Reboot is the belief that sharing experiences with peers (a cohort of similarly-experienced people) is an essential element in creating personal resiliency. There’s magic in knowing you’re not alone.
One way to join the conversation on things that founders struggle with is to listen to our podcast. The Reboot Podcast showcases the heart and soul, the wins and losses, and the ups and downs of startup leadership. In each episode, entrepreneurs, CEOs, and startup leaders discuss with Jerry the emotional and psychological challenges they face daily as leaders.
The Reboot Podcast Listening Guide sorts all our current episodes by topic:
- Leadership, Development, & Community
- Major Transitions & Connecting to Purpose
- Fear & Failure
- Mindfulness & Meditation
- Communication, Conflict Management, & Scaling
- Anxiety, Mental Health, Depression, & Burnout
- Venture Capital, Boards, & Raising Funds
- Confidence, Believing in Yourself, & Imposter Syndrome
- Shadow & Superpower
- Partnerships & Co-founder Conflict
- Resiliency & Radical Self-Inquiry
