Jennifer Edwards Of Winning Streak Ventures: Five Things You Need To Be A Highly Effective Leader During Turbulent Times
An Interview With Fotis Georgiadis
Be open to change. Times of turbulence and uncertainty will reveal your maturity as a leader and your ability to pivot, be curious, seek to see things differently that you never have before. What don’t you know you don’t know? Lean into curiosity and find new solutions from a new way of thinking!
As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, we had the pleasure of interviewing Jennifer Edwards.
Jennifer Edwards is a business and leadership advisor working with Fortune 500 companies and boards, equipping them to perform and collaborate optimally when pressure and stress hit. Her clients include top leaders at global companies, including Microsoft and WeWork. She is a partner at Winning Streak Ventures, an early-stage venture capital fund which invests in disruptive technology companies. More at https://howtobridgethegap.com/about-us/.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
I grew up in a small town with family members everywhere. We camped, fished, played games and were constantly active in our church and community. I grew up pretty scrappy — I was always competing or starting a business — piano school, tennis coach, or cooking for families. I have always had a deep thirst to learn. I became completely consumed with understanding how the mind, body and spirit handle pressure and performance. After earning my degrees, I spent a few years teaching high school French and Spanish and loved it — I have a passion for teenagers. After that, I began teaching junior college, then started a small consulting practice with grit and passion. Today, all my work has evolved into opening a learning and development company, How To Bridge the Gap, with my “work wife,” Katie McCleary. Our forthcoming book is Bridge the Gap: Breakthrough Communication Tools to Transform Work Relationships from Challenging to Collaborative (McGraw Hill, February 2022) and it’s what I train and speak upon all day long.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?
One funny — or might I say awkward, assumptive mistake I made — was becoming way too informal way too fast. A few weeks into working with a new client, I gave them a “nickname” and started using it playfully and often. It was all good and well (or so I unwisely assumed) until I used it in front of one of his prospects. The nickname caught like wildfire and over the next month, the new name stuck. The problem was that I never asked permission from my client. I acted too cavalier and made the shy client feel little and manipulated. Even in writing this, I can feel how what I did was harmful to them and our relationship. I “created” and “shoved” a label on someone without any caring thought. It was a pivotal point for me and I learned, after a breakdown with the client, how the lack of partnering, asking, being curious and seeking permission is a critical part of building trust and respect. This mistake shook me to my core and started me down a path of becoming hyper curious before making assumptions or projecting one of mine on another person.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?
My aunt Sal Edwards started and grew a national franchise called Fleet Feet, a shoe store that connected athletes to their local communities. She was a pioneer and a huge influence in how I saw who I could be as a businesswoman. She was — and IS — brave, bold, kind, encouraging and in-my-face about honing my skills and craft. Our book, Bridge the Gap: Breakthrough Communication Tools to Transform Work Relationships from Challenging to Collaborative (McGraw Hill, February 2022), comes partially as a result of her pushing and kicking me in the butt to get my knowledge and passion into written form and to play a bigger game. She not only models for me business practices that are fair, ethical, and focused on people first, but she challenges me to rethink long-held beliefs, be curious and compassionate, and to explore and strengthen new muscles in my life.
Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?
My purpose and vision was and has always been to help people “play” in business (by opening doors they may have thought were closed). I am a partner with my clients. They become a part of my DNA — I think, dream, wrestle and am ALL IN for supporting and equipping them to excel past their perceived limits and bridge the gap to a new level of success.
Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?
Challenges and uncertainty come with every contract. This is just a truth. I have never in fact met a strong team or company that hasn’t experienced challenges. One particular challenge was a huge layoff that was necessary due to some unusual circumstances. How we showed up as leaders during this time was to “go first.” In anticipation of a change in the economics of the business, our team got ahead of the challenge and took pay cuts and furlough days, and changed commission structures to demonstrate transparency in the way the business would behave. We actually lost a few of our executive team leads who were not willing to choose this path of “go first” leadership. They chose to opt out and find other jobs. Those who stayed earned the respect of the larger team, demonstrating sacrifice and commitment to the organization as a whole.
Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?
I grind. I don’t quit. I look to build teams where the “we” is really strong. I give all my effort because I love people and working with them is my passion. So when I get stuck or disillusioned, I go and talk with my personal Board of Directors and my Coach. I get real with them about where I am stuck, what I am feeling and seek support at all levels of my “human suit” to create a meaningful breakthrough. Support is the number one place where a leader can lean into when times are challenging. Knowing that you are not alone, being heard and understood, and having the caliber of support that pushes you past a fear or worry is game-changing.
What would you say is the most critical role of a leader during challenging times?
#howyoushowupmatters
A strong, calm, grounding PRESENCE makes all the difference when there is a storm or a challenge. When the squeeze feels so tight, all of us look to the energetic presence and confidence of our leaders.
This is THE core role of a leader in challenging times: to show up present and constantly articulate cleanly and with confidence this 3-point leader narrative:
1. Here is what I know
2. Here is what I don’t know
3. Here is what you can count on me for during this time.
When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?
The best leaders that I have watched inspire and motivate their teams. They engage them with a strong energetic presence and give an experience of “being with” their team. They lead from the back, not hesitating to dig in and have a “whatever it takes” energy. When any future is uncertain, we as humans look to our leaders to be transparent and honest with us about the state of the future but we also look for them to elevate beyond the current pressure or worry they may be under and to hold the vision and mission past the pain point. We look for them to lead clearly and that in and of itself calms and motivates the team to keep their heads down, eyes forward, and heart motivated to do meaningful work.
What is the best way to communicate difficult news to one’s team and customers?
Honestly and simply. I bring us back to the 3-point leader narrative which consistently offers a simple approach to deliver information to a team or customer group. It is transparent, consistent, and focused:
1. Here is what I know
2. Here is what I don’t know
3. Here is what you can count on me for during this time
This approach is a framework which allows for flexibility in how it is communicated but gives an architecture to the listener that helps them hear and understand what’s happening.
How can a leader make plans when the future is so unpredictable?
During unpredictable times, we need to make things simple. The more noise, worry, and pressure people experience, then the harder it is for the brain to listen. To engage our brain’s full executive function and really help others hear clearly in all the unpredictability, a leader can communicate with transparency. They should communicate often and be energetically stable and committed to their people and business. A great leader sticks to the 3-point leader narrative when times are confusing:
1. Here is what I know
2. Here is what I don’t know
3. Here is what you can count on me for during this time
Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?
The “number one principle” is Clarity Kills Drama. Be clear. Don’t feed the drama and the noise or turbulence. Noise creates confusion and more insecurity. Your job during turbulent times is to be present and clear.
Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?
During a difficult economy it is important to remember that this is a season of the business, a cycle that the business is experiencing and that there is opportunity in every season for growth. When there is a squeeze or tough time, our firm focuses on increasing the curiosity quotient of the organization and supporting them. We begin by asking questions that are new and open the door on a variety of different approaches. When things are hard, we ask a question that they may not know the answer to. . . and great learning always arises out of understanding “what you don’t know that you don’t know.” Curiosity is often the cure.
Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.
- As a leader, be in the healthiest spot you can be personally. When pressure and stress hit, it is YOUR job to lead and that means being in the best mental, physical, and spiritual health you can be in. As you go, so goes your team. It’s crucial to focus on eating well, sleep, water intake, fresh air and exercise, gratitude or a spiritual practice. Lead by leading yourself to optimize your brain and mind’s ability to perform exceptionally well under this stress. Be sure to have a support system outside your business where you can process your worry or concern without censoring it. Your health will be a determinant to how the organizations manage through this season of uncertainty.
- Be available and present with your team. When uncertainty hits, it is so easy to hide and put on your thinking cap and try to work your way through the turbulence. Thinking is critical — so please find plenty of time with your first strategy but not at the expense of being extra-available to your team. Your best motto is to “Be With” them. You may not know the answers, you may not have a path yet forward, but the simple act of being present and available will build confidence and trust in your team. You will become a leader worth following.
- Be the best listener you can be. And what does listening really mean… it means to put down your biases, agendas, perspectives, and judgments to fully be present and curious while exploring with another human or idea. In our book Bridge the Gap: Breakthrough Communication Tools to Transform Work Relationships from Challenging to Collaborative (McGraw Hill, February 2022), we spend time exploring the power of listening and the hurdles we all face in listening…especially when pressure hits. Be attentive, get curious and be present with your team. Remember LISTEN and SILENT have the same letters — let’s close our mouths and open our ears.
- Be open to change. Times of turbulence and uncertainty will reveal your maturity as a leader and your ability to pivot, be curious, seek to see things differently that you never have before. What don’t you know you don’t know? Lean into curiosity and find new solutions from a new way of thinking!
- Remember — everyone is having their own experience during uncertain times and your job is to support moving the team from their fear into new possibility. You are the coach and your job is to have a strong pulse on what each individual and team is experiencing and feeling. Have empathy for your team and leaders. They may feel scared or uncertain. Your role will be to help them bridge the gap between those fears into new possibility by leading well and having a strong curiosity about what their needs are and how you can be their partner.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“It’s impossible,” said pride.
“It’s risky,” said experience.
“It’s pointless,” said reason.
“Give it a try,” whispered the heart.
There is always a tug between my mind and thinking and my heart and intuition. I aim to acknowledge all the ways wisdom is brought into the world! And — the best things I have in my life all came from trusting the small voice in my heart which offers light, hope and love to me in the most unexpected of situations.
How can our readers further follow your work?
Join us and be a part of #howyoushowupmatters — www.howtobridgethegap.com and we look forward to a conversation with you!
Thank you so much for sharing these important insights. We wish you continued success and good health!
Jennifer Edwards Of Winning Streak Ventures: Five Things You Need To Be A Highly Effective Leader… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.
