Five Things You Need To Be A Highly Effective Leader During Uncertain & Turbulent Times

Authority Magazine interview with Jack Craven

Interview with Yitzi Weiner and Jack Craven.

With a diverse background as a trial lawyer, seasoned CEO, long-time member of Young Presidents Organization (YPO) mindset author, distinguished executive coach, and C-Suite team facilitator, Jack Craven has spent the last nine years leading countless CEOs and their C-Suite teams into more fulfilling, authentic lives.

In his work over the past decade, Jack continually found what he personally experienced in his long-term CEO role–executives aren’t necessarily satisfied with their lives but feel guilty asking for more because they know they are privileged and blessed. Through his “Living All In” philosophy, he has helped leaders and their companies reach the pinnacle of their potential. He aids leaders in honing their effectiveness and fulfillment by pinpointing drivers, strengths, and blind spots and helps them discover deeper purpose, joy, and happiness in their lives. Jack seamlessly blends his experience with neuroscience-based practices and insights from the Enneagram personality system to facilitate transformative coaching results.

Since 2007, Jack has also been an active member and one of only 120 certified facilitators worldwide for the Young Presidents’ Organization (YPO), the world’s leading community for chief executives, giving him a profound understanding of contemporary leadership dynamics.

Prior to his work with executive leadership, Jack was the CEO of his family’s business, Craven Closeouts, for nearly two decades. He began his career as a trial lawyer with the Chicago State’s Attorney’s Office and then moved into private practice.

To help executives become fully immersed in their aliveness and live their best professional and personal lives, on April 2, 2024, Jack will launch his first book, Aliveness Mindset: Lead and Live with More Passion, Purpose, and Joy, with publisher Forefront Books.

Jack received his J.D. from the Chicago-Kent College of Law, Illinois Institute of Technology, and his B.A. in Political Science, Criminal Justice from Indiana University Bloomington.

Just as passionate about his personal pursuits, Jack loves keeping fit, reading, volunteering for his Chicago community, and spending quality time with his wife, three daughters, and dog, Riley.

Thank you so much for doing this with us! 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?

Ihave been a trial lawyer with the State’s Attorney’s Office, ran a family business for over 20 years, and then pivoted to becoming an executive coach nine years ago. I was at a leadership retreat in 2012, feeling burnt out, unfulfilled, and frustrated at the direction of my life. I learned about taking responsibility for all of the results in my life. After that retreat, I began to take steps to get clear on what I wanted. Over the next three years, I had many hard conversations and realized that I no longer wanted to run the business. I wanted a career that had more impact, so decided to become an executive coach, helping other leaders find more fulfillment and engagement.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

An early mistake being an executive coach was having a large PowerPoint with one of the first teams I led. The deck was a safety net for me in case I forgot a point or got scared. I could not get Wi-Fi in their conference room, and I had to wing it over the next two days. It ended up being liberating. I was more present, realized that I did not need the deck, and I was far more engaged.

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?

I am fortunate that I have several people. That retreat in 2012 that served as a catalyst for change was led by Jim Dethmer and Diana Chapman, co-founders of the Conscious Leadership Group. The tools that I learned from them and their support over the years were indispensable. My wife Judy supported me, as did my YPO (Young Presidents Organization) forum.

Extensive research suggests that “purpose-driven businesses” are more successful in many areas. When your organization started, what was its vision, what was its purpose?

My coaching practice’s purpose remains the same nine years later: to help leaders feel more authentic, fulfilled, and alive, and take responsibility for all areas of their lives.

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?

After I joined the family business, we had 10 consecutive years of growth culminating in a record year in the 50-year history of the company. The next year, our revenue dropped by almost 50%. I recognized that there were seismic changes in the landscape of our industry, both in sourcing new products and selling to a consolidated customer base. We had to change from a “one category” company to a diversified company selling over 50 categories of products. The only way to succeed was by taking risks and placing several calculated bets in products and categories that we didn’t have a lot of experience selling. We hired new buyers, used our instincts, researched as much as we could, and relied on our customers to help us identify categories to sell.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

I never considered giving up, but I had a lot of fear and stress during the time we diversified the company. We didn’t know if we would be successful. I was driven by continuing the legacy of a family business that was over 50 years old. What I learned during that time helped me better understand the challenges of my CEO clients.

I’m an author and I believe that books have the power to change lives. Do you have a book in your life that impacted you and inspired you to be an effective leader? Can you share a story?

The 15 Commitments of Conscious Leadership impacted me. The framework reminded me to take ownership of my life, to be curious, to feel my feelings, and to speak my truth, even when it’s hard. It helped me spend more of my time taking action and getting clear on what I wanted.

What would you say is the most critical role of a leader during challenging times?

Model whatever traits you want your team to exhibit. Being open, vulnerable, candid, and transparent as events change. Being clear on the vision and direction. Pivoting when needed. Allowing the team to express their concerns in a psychologically safe environment. Being a rock to ground others.

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?

Have them view the current situation as a challenge versus a threat. Identify opportunities in the current environment. Get the team excited about their role in the success of the company and the potential for the company. Ask for their input and get their buy-in.

What is the best way to communicate difficult news to one’s team and customers?

Let them know you care. That you have the best intentions for them. Be candid and direct. Avoid sugarcoating the news. Teams trust leaders who are authentic. Conversely, they don’t trust leaders who are overly optimistic or minimize real challenges. I worked with an executive team whose leader was overly optimistic about the significant challenges the company was facing. I saw firsthand that the executive team lost trust in the CEO. Within a year, several leaders quit, the CEO was forced out, and the company was sold.

How can a leader make plans when the future is so unpredictable?

As a team, decide on a few bets that can have a real impact. Each bet is a lever. Some levers may increase revenue, while other levers will reduce expenses. Not all of the levers have to hit for the company to succeed. A few successful levers can have an incremental impact. Give each lever an appropriate amount of time to play out. If a lever isn’t working, replace it.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

Have a unified mindset. The mindset could be: We have the ability to ride through the turbulence; determination, winning as a team. What we tell ourselves becomes our reality. A lot of my coaching practice is helping leaders create their own mindset to help them navigate challenges. Change your mindset, and you will think more clearly and confidently and take action.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times?

The CEO isolates themselves and doesn’t seek out input or advice from others. I call this bunker mentality. I learned this lesson the hard way.

Companies try to do too many things at once, and the teams are overwhelmed, stretched thin, and lacking focus.

Teams blame one another. This leads to a toxic culture and erodes trust when it is needed most.

What should one keep in mind to avoid that?

Bring in new perspectives from different departments. If possible, have an offsite. Research shows new voices to a challenge stimulates creativity. Quantity of ideas leads to quality of ideas.

As a team, identify a few areas that will have the most impact, and have all leaders stack hands.

Rather than blame a team or leader, have each team leader own their responsibility for the current situation and what they need to do moving forward. It is far more productive.

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.

It starts with the leader’s mindset. If their mindset is, “We have threats all around us,” they will be approaching the situation from fear. Their brain will be in fight/flight mode. That limits creativity and options. Your team will sense your fear, and they will likely respond from a place of fear. I worked with a leader who was facing new challenges and talked about how work was a grind. That became her experience. We shifted her mindset to, “I’ve overcome industry threats five times in my career, and I’ll overcome this challenge too.” Her body language changed. Her team rallied with her and came up with a solid plan that was successful.

Feel your emotions. It makes sense to have fear during uncertainty. We are looking to tame their emotions and make them productive. Fear, by nature, is our body’s way of saying we are in the unknown. Most leaders just go to action mode but don’t actually move through the emotion. I help leaders develop a practice to be more aware of their emotions in the moment and to incorporate a breathing practice. This allows the emotional energy to be acknowledged and moved rather than recirculated, draining the leader’s energy. I’ve had countless leaders tell me how much energy and lightness they feel once they complete this brief exercise.

Tighten the connection of the teams. Have an attitude that we are in this together. This is not the time for blame. It’s a time to rally the team and be one. Then, get hyper-focused on what is within your control (attitude, mindset, behavior, and actions) and what needs to be done. I was working with a team that had a serious sales miss for the quarter, and their Board was reactive and demanding stiff action. The Board was justified for being concerned, but it was more focused on who to blame. When we met as a team, there was a lot of tension, blame, and distrust. I opened the meeting, telling them we were not going to blame. I find blame to be unproductive and negative energy. I asked each department head what was their responsibility for the sales miss, and started with the CEO. Each leader owned what they could have done differently. The tension eased. Each leader shared what they would be committed to doing going forward in the next quarter. The team left energized and optimistic.

Be open. I read a quote that a change in perspective is worth 80 IQ points
(Computer Scientist Alan Kay). I also like Julia Galef’s work in her book Scout Mindset. When we are locked in our perspective, we close ourselves off and look for confirmation that we are right. I led an executive team session and created ground rules focused on being open. Rule 1: Everyone would get a chance to speak. Rule 2: Everyone would get to finish their sentences. Rule 3: When a person was done speaking, the next person would mirror back what they thought the person had just said. Typically, after someone speaks, the next person says if they agree or disagree. When we do that, we are actually not present and make assumptions. That behavior can shut down a conversation and others’ ideas. Having everyone feel heard is key to fostering psychological safety and contrary points of view. The best leaders encourage dissent.

Have a clear plan on who is going to do what and by when. Have each leader explicitly share what they (and their team) are going to do by a specific date. Be clear on what “done” looks like for everyone. Trust builds when leaders are clear on how they each contribute to the action plan. Have metrics for progress and celebrate successes. It’s critical that leaders know that they are making progress.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

What we tell ourselves becomes our reality. When I was an unhappy CEO a decade ago, I was telling myself that my life should be better; that I wasn’t fulfilled; that work was a grind. That became my reality. What I tell myself now: I want to show up every day: playful, connected, and curious, and be impactful. That creates a reality of feeling alive every day.

How can our readers further follow your work?

They can follow me on LinkedIn ( or check out my website (

Thank you so much for sharing these important insights. We wish you continued success and good health!