Kerry Siggins Podcast

Guest: Jessica Billingsley has learned many leadership lessons from extreme rock climbing. Currently, as Chairman of the Board and CEO of Akerna (Nasdaq: KERN), a Software as a Service ag-tech company serving the cannabis, hemp, and CBD industry, Jessica has successfully taken the company public, completed multiple accretive acquisitions, and maintained market leadership for over a decade. Before Akerna, she founded and led Zoco, a technology services firm with a diverse nationwide client base.
She has been recognized with numerous awards, including the Titan 100 CEO, Outstanding Women in Business, Inc. Top 100 Female Founder, and Fortune's Most Promising Woman Entrepreneur. Her thought leadership has been featured in prominent media outlets, including Business Insider, Bloomberg, CNN, Cheddar, Fortune, and Forbes, in addition to her contributions to Entrepreneur and Rolling Stone publications.
Episode in a Tweet: At the end of the day, climbing, like business, is a mental game. It's all about creating mental resilience and being able to think about climbing, not falling. In other words, playing to win, not to lose.
Background: Jessica Billingsley is one of the most inspiring CEOs I’ve met. Not only did she take the company she founded public, but she also pioneered the cannabis software industry. I met Jessica through Young President’s Organization (YPO) and have grown to admire, respect and love her as a dear friend.
During the episode, Jessica and I discuss how to get and keep more women in tech and what was like to start a bleeding-edge company and then take it public. Jessica, an avid climber, shares the most difficult climb she’s adventured upon and what she learned about leadership and growing a business from climbing. I love her description of the “sharp end of the rope.” In rock climbing, the rope attached to the lead climber is called the “sharp end.” It is the risky end of the rope, where falls are possible. This is a fun and insightful interview and I know you’ll enjoy it!
How to find Jessica:
LinkedIn: https://www.linkedin.com/in/jessicabillingsley/
Instagram: jessicabillingsley
Twitter: jessbillingsley
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

You know that feeling when you’ve hit the wall, and the thought of going to work drains you of every ounce of energy? Burnout is a real struggle that can sneak up on even the most dedicated employees. In this episode of Reflect Forward: Advice From a CEO, we’ll explore the causes of burnout, practical steps you can take to address it, and how leaders can lend a helping hand.
Here are a few common causes:
Excessive workload: When you feel like you’re carrying the weight of the world on your shoulders, it’s no surprise burnout might be lurking around the corner. Unrealistic deadlines, constant overtime, and a never-ending to-do list can all contribute to burnout.
Lack of control: Feeling you have no say in decision-making can be incredibly demoralizing. Burnout can creep in when you cannot influence your work environment or have a sense of autonomy.
Lack of recognition and reward: When employees consistently go above and beyond without receiving acknowledgment or appropriate rewards, it can lead to burnout. Feeling undervalued and underappreciated can chip away at motivation and ultimately result in exhaustion.
Poor work-life balance: Burnout can take hold when work takes precedence over personal life, and there are neglecting self-care can leave individuals feeling drained and overwhelmed.
Poor internal communication: When communication within an organization is ineffective or lacking, it can lead to misunderstandings, confusion, and unnecessary stress. Unclear expectations, misaligned priorities, and a lack of information flow can contribute to burnout among employees.
Lack of job satisfaction: Burnout can loom large when employees feel disconnected from their work or lack a sense of purpose. Performing monotonous tasks, feeling unchallenged, or experiencing a mismatch between skills and job responsibilities can drain motivation and lead to burnout.
Leaders play a pivotal role in cultivating a positive work environment and preventing burnout among their team members. Some ways they can lend a helping hand are by encouraging open communication, promoting work-life balance, providing growth opportunities, and talking openly about burnout.
Burnout may seem unavoidable in our fast-paced work culture, but it doesn’t have to be. By understanding the causes of burnout, taking proactive steps as individuals, and creating supportive environments as leaders, we can tackle this issue head-on.
Question of the Week
This question comes from one of my employees, and she asked, “How can I productively disagree with my colleagues?”
Disagreements don’t have to result in conflict. Instead, use them to build a stronger relationship. My suggestions:
• Assume good intentions. Trust that the person has the best interest of the team and company in mind, even when you don’t agree with their ideas or comments. Give them the benefit of the doubt and hear them out.
• Use this as a way to learn. Are you missing a critical piece of information? Are you sure you’ve considered all the possibilities? What can you learn from their perspective? What if your way isn’t the best?
• Look for solutions. Instead of looking at the situation as black or white, look for ways to compromise to find a solution. Incorporate their ideas and suggestions into the outcome.
• Pick your battles. You don’t always have to win or be right. Look for opportunities to let people try their way and support their efforts rather than silently sabotaging them because you didn’t get your way.
• Never let it get personal. Ask questions, debate ideas, and disagree on policy, but never make it personal. Doing so shuts people down and damages relationships.
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Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

Velveth Schmitz knows better than anyone that leadership is a journey. Recently named CEO of Hire Better, an award-winning strategic talent partner for entrepreneurial, growth-minded, middle-market companies, Velveth is on a mission to grow herself and others. Velveth builds partnerships with leaders of high-growth, entrepreneurial organizations by delivering end-to-end solutions that put the right people and strategies in place to build strong corporate cultures and ensure positive financial results. This includes helping founders and CEOs find the right team members to grow their businesses.
Velveth also served as Mayor for Rolling Hills Estates in 2020 and continues to serve as Councilmember. She is involved in various 501(c)3 and county boards where she serves as chair or vice-chair. Velveth is a proud alum of the University of California, Berkeley, where she remains involved in various roles.
Episode in a Tweet: Lead with love. At the end of the day, we are all doing the best we can with what we have. When leaders show compassion and grace, they help their employees become the best versions of themselves.
Background: Velveth Schmitz is a connector by nature and has successfully managed individuals and teams, developed and grown businesses, developed strategic initiatives and effectively managed change. She is a collaborator working to bring out the best in people. During this week’s episode of Reflect Forward, Velveth and I discuss why a leader’s number one job is to bring the best out in their people. She shares how she transitioned from executive team member to CEO and why feedback is so important. She also tells a bit about her experience as Mayor of her community during COVID and what she learned about giving the people she worked with agency to make decisions in the face of the unknown. And finally, she brings me to tears are she shares her experience with mental health, suicide and finding love in the face of tragedy. You’ll love this episode and I can’t wait to hear your thoughts!
How to find Velveth:
www.linkedin.com/in/velvethschmitz
https://hirebetter.com/
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

In this week's episode of Reflect Forward, we discuss the most common employee complaints and what managers can address to improve employee morale and productivity. By improving communication, treating employees fairly, addressing workload concerns, providing recognition, offering adequate resources, improving management practices, and creating a positive workplace culture, managers can help ensure their employees feel valued and supported.
One of the most common employee complaints is poor communication. Employees often feel left in the dark about important decisions, changes, or updates within the company. To address this, managers can implement regular check-ins with their employees to keep them updated and informed. One-on-one meetings, team meetings, or even email updates can all be effective ways to improve communication and keep employees in the loop.
Another common complaint is unfair treatment. Employees want to feel like they are being treated equally and fairly compared to their peers. To address this, managers can be transparent and consistent in their decision-making processes. This means ensuring that everyone is treated fairly regarding pay, promotions, and work assignments.
Excessive workload is another common complaint that can lead to burnout and dissatisfaction among employees. To address this, managers can work with their team members to prioritize tasks and set realistic deadlines. They can also consider hiring additional staff or outsourcing certain tasks to help alleviate the workload.
Lack of recognition is also a common complaint that can impact employee morale and productivity. Managers can recognize and celebrate their employees' achievements and contributions to address this. This can be done through verbal recognition, rewards and incentives, or even promotions.
Inadequate resources can also be a source of frustration for employees. To address this, managers can work with their team members to identify the resources they need to do their job effectively and then work to provide those resources.
Poor management is a complaint that can significantly impact employee morale and productivity. To address this, managers can work on developing their leadership skills, such as communication, delegation, and conflict resolution. They can also seek feedback from their employees and work on improving their management practices based on that feedback.
Workplace culture and job insecurity can also impact employee morale and engagement. To address these issues, managers can work to create a positive and supportive workplace culture by promoting open communication, collaboration, and teamwork. They can also provide clear expectations and feedback to their employees to help alleviate concerns about job insecurity.
Question of the Week
My boss is incredibly insecure and is so worried about looking bad that she doesn't trust her team. What can I do to earn her trust?
Dealing with an insecure boss can be challenging. Still, there are some steps you can take to earn their trust, such as communicating effectively, being dependable, building a relationship, and offering solutions to problems.
Remember, it's not your responsibility to fix your boss's insecurities. However, being a reliable and trustworthy team member can help create a more positive work environment for everyone.
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

Dr. Benjamin Ritter, founder of Live for Yourself Consulting, is passionate about helping people achieve their goals. Ben is a leadership and career coach, Talent Development Executive, values geek, international speaker, and podcaster passionate about guiding leaders to be the leader of their own career and create a career they love.
With over ten years of experience working with clients from companies such as Amazon, Coursera, Doordash, Google, Fiserv, Northwestern, Pinterest, and Yelp, Ben understands how to navigate any career path you decide you want to travel.
Since launching his coaching practice, he has guided hundreds of professionals toward creating the career they love and has impacted thousands through his events and media content.
Ben received his Doctorate in Organizational Leadership, focusing on value congruence and job satisfaction, and earned an MBA in entrepreneurial management and an MPH in health policy administration.
Episode in a Tweet: People don’t start disengaged; they become disengaged. As a leader, you must recognize your employees and help them grow in their careers and lives.
Background: From empowering young professionals to get unstuck to guiding senior leadership on how to stand out from the competition, develop executive presence, and feel confident in being a leader, Ben Ritter is an expert in his field and will guide you toward truly living for yourself at work and in life.
During this week’s episode of Reflect Forward, Ben and I discuss why employees become disengaged and what leaders can do about it. We discuss the importance of leaning into tough conversations and having weekly tag-ups that help your employees achieve their career development goals. I love what Ben says, “Let your employees know you are rooting for them!” Who doesn’t want that?
Ben’s expertise is incredibly helpful and he gives actional advice and tips on how to help your employees perform better, achieve their goals, and get the promotions they are hoping for and working for.
How to find Ben:
https://www.liveforyourselfconsulting.com/
www.linkedin.com/in/ritterbenj
instagram.com/in/ritterbenj
https://benjamin-ritter.com/
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!

Throughout my teens and twenties, I let other people’s opinions dictate much of my life. I was constantly worried that people wouldn’t like me, and I compared my success to others. Caring deeply about what others thought of me led me to a dark, destructive place. As I matured, I realized that I spent far too much energy caring about opinions that really didn’t matter. Over time, with practice and much self-reflection, I learned to relinquish the need for so much external validation. Doing so opened my eyes to what’s possible. I finally started going after my dreams and creating the life I wanted. I became a more confident leader who wasn’t afraid to admit mistakes, pivot away from poor decisions, and ultimately make bold moves that transformed our company and industry.
And that’s what this week’s episode of Reflect Forward: Advice From a CEO is about. How to let go of the need for external validation. How to stop letting other people’s opinions dictate your life. This doesn’t mean you shouldn’t ask for feedback or understand your impact on others. Self-awareness is a critical leadership trait; you should value the opinions of the people you work for and with. But far too often, we don’t go after our dreams and live our best lives because we worry, we will be disliked, judged or shunned for our life decisions. And this is a path to an unfulfilling life.
It’s essential to understand that people’s opinions of you do not reflect your worth. Just because someone doesn’t like you or disagrees with your choices doesn’t mean you are less valuable or deserving of love and respect. It’s important to remember that everyone is entitled to their opinions and beliefs, but that doesn’t mean they are valid.
If you’re constantly worrying about what others think of you, it can be a significant source of stress and anxiety and can make it challenging to be yourself so you can pursue your passions and goals. You may find yourself changing your behavior or beliefs to please others, which can ultimately lead to unhappiness and dissatisfaction.
Caring too much about what others think of you can hold you back from taking risks and trying new things. If you’re constantly worried about how others will perceive you, you may be hesitant to step outside of your comfort zone and pursue important things. This can ultimately limit your personal growth and prevent you from reaching your full potential.
The most important thing is to focus on your happiness and well-being. Don’t let the opinions of others dictate your life and your choices. You are the only one who knows what is truly best for you, and you should never compromise your values and beliefs to please others.
Of course, this is easier said than done. It can be difficult to let go of the need for external validation, especially if you’ve been conditioned to seek it out for most of your life. But with practice and self-reflection, you can learn to prioritize your feelings and needs above the opinions of others.
Question of the Week
This week’s question came from one of my employees who came to talk t me about feeling like she had lost some of her motivation at work. As we talked through how she was feeling, she asked, “Do you ever lose motivation at work, and if so, what do you do?”
My answer: Absolutely. We all go through motivation ebbs and flows, and a leader who tells you they never lose motivation is lying to you. But it’s our responsibility to figure out why we have lost motivation and recommit to making an impact. Listen in to learn how I recommit and some hacks I use to find inspiration when it’s waned.
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Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

Joel Trammell is the founder and CEO of American CEO and Khorus Systems, a business management system that empowers CEOs to lead high performance organizations, and the owner of Texas CEO Magazine, which reaches more than 10,000 CEOs across the state. A successful entrepreneur and CEO with 30 years of experience, Joel is a pioneer in CEO education.
After decades as a CEO – a field in which the average shelf life is only five years – Joel identified a pervasive problem: many of his fellow business leaders seriously lacked the fundamental tools and education to make their companies genuinely great. He launched The American CEO to provide the support and guidance his peers lacked. He also wrote a book titled The CEO Tightrope, a comprehensive guide featuring proven techniques and approaches for overcoming the unique challenges of being a CEO.
Episode in a Tweet: Being a CEO is demanding and there’s no one way to do it well, but the best CEOs embody the three Cs: credibility, competence, and caring. If you have the three Cs, you’re far more likely to succeed in the CEO role.
Background: Joel Trammell is on a mission to teach new and current CEOs what almost no one else is teaching: how to successfully perform the CEO job. Most people enter the CEO job with lots of knowledge and experience in certain aspects of business but no specific training for the CEO role. I understand this well. As a new and young CEO, I made many mistakes, like deciding by trial and error, changing direction too often, and letting underperformers stay too long. I had to learn how to be a CEO by being a CEO.
American CEO’s mission is to prevent the issues I experienced all those years ago through a professional, systematic approach to the CEO role. And that’s what Joel and I talk about during this week’s episode of Reflect Forward. Joel shares how the CEO role is different from other leadership roles. He says (and I agree) that people think of the CEO as just one step up from other executive jobs. However, the CEO job is a difference of kind, not of degree. It comes with a very different set of responsibilities and challenges.
If you want to be a CEO or simply understand the CEO role better, you’ll gain so much insight from this interview with Joel. Have a listen and let me know what you think!
How to find Joel:
Website: www.AmericanCEO.com
Twitter account: @TheAmericanCEO
Book: https://americanceo.com/ceotightrope/
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

In this week’s episode of Reflect Forward, I share why people are change resistant and what you can do to help your employees embrace change.
Change is a natural part of life, and it’s no different in the workplace. But let’s face it; not everyone is excited about the idea of change, and many people are hesitant or even resistant to change in the workplace. To help their employees embrace change, leaders must understand why their team members resist change and know how to address it.
Why are people afraid of change?
• Fear of the unknown: When people don’t know what’s going to happen or how a change will affect their job, it can be scary. They may worry that they won’t be able to perform their duties or that their job will become obsolete.
• Comfort with status quo: People may have gotten used to the current system and may not see the need for change. Why change if the present method is working well enough?
• Loss of control: People get frustrated and resentful when they feel that they have little control over the changes and that their input doesn’t matter.
• Fear of failure: People may worry that the change will not work out as planned and that they will be held responsible for any adverse consequences.
• Lack of communication: No one likes being in the dark or the last to know; if leaders aren’t communicating frequently, their employees will be more resistant to change.
Despite these challenges, change can be positive and necessary for growth and progress. In fact, if a company isn’t changing and evolving, it will be left behind in this rapidly changing world. So if you want to be an impactful leader, you need to help your employees embrace change.
Here are a few tips:
Communicate openly and effectively: Be transparent about the reasons for the change and how it will affect the company and its employees. Listen to employees’ concerns and address them proactively.
Provide training and resources: Employees may need new skills or tools to adapt to the change. Provide training and resources to help employees develop the necessary skills and adapt to the new way of working.
Involve employees in the process: When employees feel like they have a say in the change process, they are more likely to be invested in the outcome. Involve employees in decision-making, gather feedback and ideas, and encourage participation in the change process.
Lead by example: Model the behavior you want to see in your employees. Your employees are more likely to follow suit if you are positive and enthusiastic about the change.
Celebrate progress and success: Celebrate the milestones and successes achieved along the way. Frequent acknowledgment of wins helps to reinforce the benefits of the change and creates a sense of momentum and excitement.
Change can be difficult, but it’s a necessary part of growth and progress in the workplace. By taking the right approach, leaders can help employees embrace change and create a positive work environment.
Question of the week
This week’s question comes from a student I am mentoring considering multiple job opportunities upon graduation this spring. He asked me, “Kerry, how should I evaluate these opportunities? How do I know which is best, and what are the most critical criteria for choosing?
My answer is to choose the one with the best manager who cares about your growth, well-being and career development, especially for your first job. Listen in to hear more!
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

As a leader, navigating complexity and uncertainty can feel like trying to sail a ship through a stormy sea without a map or compass. In this week’s episode of Reflect Forward: Advice From a CEO, we discuss navigating complexity and uncertainty. In today’s fast-paced and ever-changing world, complexity and uncertainty are becoming the norm rather than the exception. Leaders must be able to navigate these challenges if they want to succeed and thrive.
So, how do you navigate complexity and uncertainty as a leader?
Embrace the chaos: Instead of fighting or controlling the complexity and uncertainty around you, try embracing it. Recognize that it’s a natural part of the business world and that you can learn and grow from it.
Develop a growth mindset: Approach complexity and uncertainty as opportunities to learn and grow rather than obstacles to overcome. Be open to new ideas, feedback, and perspectives and be willing to adapt and change as needed.
Build a strong network: Surround yourself with people who can help you navigate complexity and uncertainty, including mentors, colleagues, and experts in your field. This network can provide you with valuable advice, support, and insights.
Stay focused on your goals: Amid complexity and uncertainty, it can be easy to lose sight of your goals. Stay focused on what you’re trying to achieve, and be willing to adjust your approach as needed.
Communicate clearly and frequently: Communication is more important than ever in times of complexity and uncertainty. Ensure you’re communicating clearly and frequently with your team, stakeholders, and customers and that you’re listening to their concerns and feedback.
During the episode, I share real-life examples demonstrating how to navigate the chaos and make good decisions. I also discuss why some leaders fail at leading well through complexity and uncertainty.
And finally, I share the most leadership trait you must possess to lead well through uncertainty: adaptability. Ultimately, adaptable leaders can lead their teams through uncertainty with confidence and clarity, keeping everyone focused on the end goal while navigating the twists and turns of the journey. Listen in to learn more.
Question of the Week
This week’s question comes from a Reflect Forward listener who asked, “After listening to your podcast on staying calm under pressure, I was left wondering about your relationship with stress and how that impacts your ability to remain calm under pressure. Can you share your thoughts on this?”
I love this question, and during that podcast, I failed to address the fact that each of us has a unique relationship with stress which determines how we handle it. And each of us has different triggers, so what stresses one person out may not phase the next. There is no one (or right) way to deal with stress, so developing self-awareness is critical. Listen in to find out why.
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!

Rajeev Kapur believes that now is the time to lead forward and chase greatness.
Rajeev is a seasoned high-tech and media executive with broad global experience leading and driving innovation. Rajeev is the CEO of 1105 Media, a leading provider of business-to-business marketing, events, and media services. In 2021 and 2022, he was a finalist for Entrepreneur and Innovator of The Year from the Orange County Business Journal and was named one of the Top 500 Leaders in Orange County.
Rajeev has been a YPO (Young President’s Organization) member for over 15 years and has been a guest contributor to CNBC. In November 2021, he became a bestselling author when he launched his new leadership book – Chase Greatness: Enlightened Leadership for The Next Generation of Disruption. The book was the most downloaded leadership book on Amazon. He is an accomplished keynote speaker and executive coach for companies like ATT, Google, Amazon and Hugo Boss about the future of leadership. He is also an accomplished screenplay writer, represented by The Rêve Agency.
Episode in a Tweet: Enlightened leadership goes beyond servant leadership. Enlightened leaders help their teams live their best lives and make their dreams come true.
Background: I met Rajeev at a YPO event in Rio di Janeiro, and we hit it off immediately. I loved his leadership philosophy and his “Kapur Rules” on Instagram, where he serves up bite-sized leadership tips you can act on immediately.
During this episode, Rajeev and I discuss the future of leadership, which he describes in his book Chase Greatness: Enlightened Leadership for The Next Generation of Disruption. He shares his vision of the future of work and how leaders must prepare for the next phase of disruption. Rajeev also tells us about TWGNs, which stands for This Week’s Good News, a practice he put in place to get his team to focus on the current week’s positives rather than what didn’t get done. He shares how he came up with the title of his book and why he believes enlightened leadership is the new servant leadership. Have a listen and let me know what you think!
How to find Rajeev:
LinkedIn: https://www.linkedin.com/in/rajeevkapur1
Instagram: @therajeevkapur
Website: www.rajeevkapur.com
Here is a link to his book, Chase Greatness
Follow me on Instagram or LinkedIn.
Subscribe to my podcast Reflect Forward on iTunes
Or check out my new YouTube Channel, where you can watch full-length episodes of Advice From a CEO!
And if you are looking for a keynote speaker or a podcast guest, click here to book a meeting with me to discuss what you are looking for!