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 Kris Kelso, who is a leadership advisor and keynote speaker based in Nashville, TN. He is also the author of Overcoming The Impostor: Silence Your Inner Critic and Lead with Confidence (Dexterity, January 19, 2021). Kris has worked with hundreds of entrepreneurs, business owners, and their leadership teams, and he is an advisor and instructor at the Nashville Entrepreneur Center and a contributing writer for The Nashville Business Journal.
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 was a software developer in the healthcare industry before I set out as an entrepreneur. I started my first company in 2007 (right before an economic crisis), with no business training or education — I don’t even have a college degree. Needless to say, I learned a lot of things through trial and error, but I built a successful IT consulting firm over several years, and then co-founded a cloud computing company.
After I left my second company, I did a little consulting with a private equity firm then decided to transition into leadership development and executive coaching, which is what I primarily do today (along with a lot of public speaking and writing). Most of my clients now are business owners themselves.
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?
Before I even formally started my first company, I had been doing some freelance website development as a side hustle. I got an opportunity to talk to a fast-growing healthcare technology company who needed to completely rebuild their web presence. I pitched them on a website redesign, with a price tag somewhere in the neighborhood of five thousand dollars.
Not only did I not get the job, but I found out they later signed a contract with a firm for more than a hundred thousand dollars. I didn’t lose the job because of price — I lost it because I had no clue about the scope and scale of what they were trying to achieve. I was so naive.
My eyes were opened in two ways. First, I realized that I just wasn’t ready to do the kind of work that a company like that needed. My ideas were too small, and my understanding of what they wanted to do was very limited. But the other way my eyes were opened was to realize what’s possible — to see that there were possibilities that I hadn’t even imagined, and I just needed to grow and learn my way to being qualified.
A couple of years later, I was doing six-figure deals on a regular basis.
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?
You are absolutely right that no one achieves success entirely on their own. When I started my consulting firm, a colleague named Larry Powell, who had founded his own consulting firm several years earlier, spent a lot of time with me and let me “pick his brain” on all sorts of topics. He was so generous with his time and his expertise.
In my first few years, I definitely struggled with Impostor Syndrome — the feeling that I wasn’t actually qualified to do what I was doing, and that at any minute, everyone was going to figure out that I was just making it up as I went. But having people like Larry to encourage me, and to share their own learnings and experiences, helped me maintain my confidence and push past my inner critic.
There have been several people like Larry who were generous and kind to me, and for many of them, there’s not much I can do to repay them. Instead, I try to “pay it forward” by making time for other entrepreneurs who are just starting out on the path I have been on for 14 years now.
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?
This is something I got completely wrong in the beginning. If I’m honest, the purpose of my business when I started was to allow me to do the kind of work that I wanted to do, and to give me independence and freedom. That’s a fair reason to want to own a business, but it’s not a vision or purpose that you’re going to be able to get many other people excited about.
Eventually, I realized that your business needs a purpose that is bigger than you and is about more than just making money. Now, as an executive coach, one of the things that I help my clients do is to discover, clarify, and communicate that vision.
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?
Several years ago, I was leading a startup that I co-founded. We were not yet profitable, so I was simultaneously raising money from investors and working to bring on new customers. Our team was small, so there was a lot of work being done by only a few people.
We had an investment group that was all set to lead our funding round, and some other investors had committed to invest, contingent on that group’s involvement. It seemed like a sure thing, but at the last minute, the investment group backed out, and our funding round collapsed.
On the same day, I got a call from our largest customer, who represented 20% of our revenue, who told me they were leaving us. Their board decided it was too risky to rely on an outside vendor for the particular service we were providing, and they wanted to bring it in-house.
It was a devastating day. I told the team that it would be OK, that we would get through it, and the only thing to do was to keep moving forward. But I’ll confess that I went home and crawled right into bed. I felt terrible.
Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?
The next morning, I woke up, and decided that this was day one of the next chapter. Every good story has one or more crisis moments, and we’d just experienced one of ours. But a good story doesn’t end with crisis — it ends with triumph over crisis.
We never did complete that funding round, and we weren’t able to retain that large customer, but we kept pushing forward, one customer and employee at a time. Today, it’s a profitable company with very few outside investors. We didn’t grow it the way we originally planned to (with a lot of venture capital money), but we found a way. That’s what entrepreneurship is really about — finding a way.
What would you say is the most critical role of a leader during challenging times?
Communication. People look to their leaders for clarity and reassurance during difficult times, but when a leader goes silent, the people are left to fill in the blanks on their own — and they always do. It’s human nature to fill the gaps in our understanding of a situation with theories and assumptions, but those are usually wrong, and often damaging.
Even when a leader doesn’t have all the answers, there needs to be regular, consistent communication about what is known and what is being done. If nothing else, a leader can communicate empathy and encouragement to make sure that people don’t feel forgotten or abandoned.
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?
It seems counterintuitive, but you can remind people that we’ve been through uncertainty before, and we’ll go through it again. The specific challenges we’re facing may be new, but facing challenges is not new. We can use what we’ve learned in the past to get through this difficult time, and we can be confident that we’re learning things now that will help us get through the next one.
What is the best way to communicate difficult news to one’s team and customers?
Be direct, honest, and clear. Don’t assume they will assume what you want them to assume — make the information as clear and complete as possible. Even then, expect that you’ll have to explain it more than once. People don’t always completely grasp all the information the first time they hear it, especially if emotion is involved.
How can a leader make plans when the future is so unpredictable?
The future has been becoming less and less predictable for a long time. I spoke to the CEO of a billion-dollar company several years ago, and he told me that they’d determined there was no point in planning beyond about 18 months. The world is just changing too fast for you to know what’s going to happen several years out.
What is important is to set long-term goals and targets, and then build your short-term plans in service of those long-term goals. Keep the plans short and iterate often, but know where you want to go in the long run.
Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?
In Jim Collins’ book Good to Great, he quoted Admiral James Stockdale as saying “You must never confuse faith that you will prevail in the end — which you can never afford to lose — with the discipline to confront the most brutal facts of your current reality, whatever they might be.” Collins called it the Stockdale Paradox, and it’s an important balance that keeps you from being overly optimistic or overly pessimistic. Leaders need to model that.
Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?
One is what I call “cocooning” — just hunkering down and trying to survive. The reason it’s a mistake is that there’s almost always opportunity to be found during difficult times, but you have to be paying attention to see it. Second is almost the opposite of that — changing too much too fast. If you pivot constantly, always looking for the next thing that’s going to work, you are essentially allowing the crisis to define your business model. Both of those are unhealthy extremes.
A third mistake is to expect your customers, vendors, and employees to have grace and empathy for you, but not giving it equally to them. When a crisis is widespread and far-reaching, everyone is being impacted by it in some way, and you have to recognize that.
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?
There are things you do to benefit your business in the long-run that don’t produce revenue in the short term, such as marketing / branding, networking, developing new product ideas, building partnerships, etc. In a crisis, these often get completely set aside in the frenzy for survival. The problem is, there’s not much point in surviving if you immediately go into a decline because of short-term thinking.
One of the things I do to combat that is dedicate specific days or at least large blocks of time to long-term thinking and working. Maybe that means spending four days a week focusing on the near-term crisis management, but spending one day or part of a day specifically ignoring the crisis and thinking about the bigger picture. It can actually be a great relief to give yourself permission to ignore the crisis for a little while and think about the future.
Focusing your attention in this way helps you feel confident that you’re giving enough attention in the short term to survival, without losing sight of the long-term work that will keep you going.
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.
Communicate — People are constantly creating stories in their heads about what is really going on. As a leader, you either contribute to those stories, or you let them go in whatever direction people take them, and people can be very creative. When a leader remains silent, there’s a zero percent chance of everyone being on the same page.
Look for Opportunities — Crisis creates opportunities, whether it’s opportunities in the marketplace or opportunities to make internal changes that probably should have been made long ago. To paraphrase Warren Buffet — you should make bold moves when others are pulling back in fear.
Adapt — Some adaptations are temporary, while others are permanent, but “sit tight and wait it out” is rarely the right response to a crisis. You have to be flexible, and sometimes flexibility makes the difference between those who survive and those who don’t.
“Be Exceedingly Human” — I stole this one from Patrick Lencioni, because it’s so valuable. Leaders must relate to their people as people, not just as employees. Remember that a crisis is often impacting their personal lives as well. Don’t act as if your business is the only thing being affected. If you care for your people, they will care for your business.
Communicate — yes, that’s right, I said it twice. It’s that important.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“It takes a long time to become an overnight success” (Author unknown)
Most of the things I’ve accomplished have not come easy or quick — they take time, trial and error, and perseverance. There have been plenty of mistakes along the way, but each one is a learning experience. I believe that failure leads to learning which leads to success. When someone does something so well that they “make it look easy”, you can almost guarantee that it wasn’t easy to get to that point.
How can our readers further follow your work?
The easiest way to find me is to visit kriskelso.com, or find me on most of the major social media platforms — LinkedIn, Facebook, Twitter, Instagram, YouTube, etc.
I’ve just published a book about Impostor Syndrome, written specifically for entrepreneurs. It includes a little more of my story, along with a collection of stories from dozens of other entrepreneurs. You can read more about that at overcomingtheimpostor.com
I’m also speaking frequently at entrepreneurship and leadership conferences — I hope to meet some of your readers there!
