Jason Randall of Questco

    We Spoke to Jason Randall of Questco on Being an Effective Leader During Turbulent Times

    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 Jason Randall.

    Jason Randall ( is CEO of Questco, an HR outsourcing company, and ForbesBooks author of Beyond The Superhero: Executive Leadership For The Rest Of Us. Formerly he was director of brand marketing for Maritz and vice president/managing director of Insperity. Randall earned his MBA at Northwestern University’s Kellogg School Management.

    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?

    For my current role as the CEO of outsourced HR company Questco, I was recruited by our Private Equity Firm in early 2018 to lead our thirty year-old organization into a new era of national expansion and industry leadership. In the twenty-five years of my career prior to that, I’ve had a wide variety of roles, ranging from a CPA with a “Big 4” firm to the proprietor of a neighborhood pizza place. My prior experience as a CEO was gained in a fast-growing e-commerce company in the event ticketing space, in which I worked alongside my brother to harness the power of the great rocketship that he created. Collectively, these roles gave me both a deep understanding of the needs of small business leaders and a passionate drive to support them.

    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?

    Perhaps it’s more cringe-y than funny, but I made a pretty big mistake during my first few months at Questco. I was so excited to roll out a new compensation plan to the team, which included incentive pay that offered our teammates the chance to earn substantially more money…or so I thought. I didn’t know — because I acted too quickly and hadn’t asked — that many people had undocumented side deals, unwritten “understandings” and favoritism-based spot bonuses in their previous pay arrangements. So I, as the new guy, just came in and proudly announced an effective pay cut. Of course, I didn’t get the standing ovation I expected from that moment. And the bigger story is that it’s essential to really go deep with people when assuming a new executive role. Many things — important things — aren’t documented…and your success may well depend on knowing them anyway. And this is only possible through a sustained commitment to candid, individualized communication.

    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?

    To the extent that I’ve achieved success in my life, it’s because *many* people have believed in me, invested in me, and taken a chance on me. I named several dozen people in the acknowledgements section of my book, and I’m still haunted by many that I probably should have mentioned.

    One of my more recent examples is one that stays close to my heart. Soon after I assumed my current role as CEO of Questco, I realized that we needed to attract more help; our ambitions were just too big for the team we had. I had not lived in our home market of Houston all that long, and so I needed to talk to someone with a bigger Rolodex than my own to find great talent. As such, I reached out to an old friend and colleague, Brandon Hartsaw, who I trusted completely and who had an extensive local network. When I explained what we were building and the talent we needed, Brandon expressed interest personally in joining our team. I was floored — I hadn’t even considered that he would be at all interested in leaving his long-time employer. Brandon took an enormous leap of faith and joined Questco as our COO, and has been an essential driver of our growth and success. And I’l forever be honored in the trust he showed in me.

    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?

    At Questco, we are exceptionally clear about why we exist and who we serve: small businesses and the people that enable their success. We devote a lot of energy to living into this mission, and how each teammate has a role to play in its achievement. This commitment to mission has led directly to a very specific company culture: we are caregivers. To be this for our clients — so they are not alone in the challenges they face — we must also support each other. I’m most proud of the alignment we’ve achieved between our company’s purpose and the team that is responsible for fulfilling that purpose.

    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?

    One of our most painful dances with uncertainty happened earlier this year. A third party technology provider to our company suffered a ransomware attack. Although our own systems weren’t breached, the effect of this attack was the extremely sudden loss of the technology that not only powers our business, but also gives us the visibility into our operations. In an instant, we were unable to operate as usual, which is a herculean challenge when you are responsible for the payroll of tens of thousands of people. There was, and is, no grace period.

    This was the biggest professional challenge I’ve had in years, and impossible to transcend without a great team. I can’t process a payroll, administer benefits, or build computer systems. But what I can do is allocate resources to where they are most needed, prioritize tasks, and — most crucially — effectively communicate to all of our stakeholders.

    With our mission statement as a guide, I stayed focused on coordinating, prioritizing, and communicating. I was available to our clients and our people. I made sure everyone involved knew that — regardless of the financial implications to us — not a single client or employee would incur a loss because of this cyber event. I aged several years that week, but we ultimately were able to honor our commitments and maintain our hard-earned goodwill. Ultimately, others deserve the credit for the successful outcome here. I’m grateful that I was able to play a role in support.

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

    I think it’s only human to have some (or many) moments of doubt during times of struggle and challenge. Certainly, in my case, I have days where I feel like I suck at my job. What I find most helpful at shaking that feeling is a clear reminder that (1) talented people selected my for this role for specific reasons, and (2) I believe profoundly in the mission we have and the value that creates. By focusing on things larger than myself, I’m able to work through the bad emotional moments and sustain my commitment. In addition, one smaller-scale thing that I do when feeling low is to immediately reach out to several people in my organization to recognize them for something wonderful that they’ve done. Examples are (thankfully) abundant, and nothing reaffirms my purpose faster than celebrating the contributions of others.

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

    Maintaining the focus of your team on a productive way forward. You accomplish this in two key ways. First, nurture your healthy organizational culture, focusing on the people that make it so. Demonstrate this nurturing through very frequent, direct, authentic communication that displays your fundamental confidence in the team. Second, the content of the communication must clearly emphasize the decisions that have been made, what may have changed, and the reasoning that supports these decisions.

    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?

    When you really, authentically know the human beings on your team….and genuinely care about them….it’s far easier to draw on a reservoir of earned trust at times of stress.

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

    Quickly. Directly. Face-to-face if possible. As close to 1:1 as possible. There is a natural impulse to hide when things are rough or uncertain, and this usually leads to a spectrum of terrible outcomes. For issues of significance, the most senior leader should deliver the news with a “What — so what — now what” emphasis. First, deliver the news in a clear and unflinchingly honest way. Then make sure it’s placed in context (the “so what?” part). And, most critically, walk through what happens next and how we recover (and eventually thrive) going forward. I’m a huge fan of

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

    Has there ever been a time in the past, say, five hundred years when the future was predictable? Human beings are wonderful at overcoming unpredictability through adaptation. So an essential element of a great plan is to build in flexibility, so that there are multiple pathways to success. By doing so, you can have a more certain outcome in spite of fast-changing circumstances.

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

    Recruit and nurture a smart, hardworking, and confident team that is inherently curious, so that each teammate is always looking outside the company’s walls for both opportunity and threat. And empower the team to make quick, fact-based decisions. By doing so, you’re effectively building adaptation mechanisms into your organizational culture. And these mechanisms will support you when you encounter turbulent skies.

    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?

    Regrettably, I see organizations that fail to listen to their people. They make decisions that favor the extreme short-term profit interests of the company, in the process eroding employee affinity. Perhaps most damagingly, I see organizations that pay lip service to their teams (“our people are our most valuable asset”) while rendering such statements hollow with their daily actions.

    Avoiding these mistakes is challenging, but straightforward: know your authentic mission, behave in accordance with it, honor your commitments, and communicate candidly and frequently.

    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.

    1. Rely on your values, both organizational and personal. Like many businesses, safety concerns surrounding COVID-19 have pushed us to think (and re-think) our approach to return to the physical offices. This is not an easy call; we have close-knit teams that work better when physically together and we also have teammates that really need the remote environment. By rallying around a well-communicated set of values (we will keep you safe, our business productive, and our culture intact), we are thriving. We’ve grown dramatically, with very little employee turnover and record profitability.
    2. Invest time to *think*, so that you can react more successfully. A couple of years ago, we received an unexpected cancellation notice from one of our largest clients. There was an immediate impulse to throw the “Hail Mary” to desperately save the short-term business. Despite that temptation, we carefully considered options, and ultimately decided to roll out the “reverse red carpet” to provide exceptional resources to help them transition well, even if that meant saying goodbye. Of course, that’s not what ultimately happened. In less than a year, our client contacted us to return…and they even referred others to us.
    3. Make rock-solid commitments to authentic, regular communications….and live up to them. In the early days of the pandemic, our senior leaders produced all-team videos every single day, where we would share our candid perspectives of the day with a sprinkling of warmth and humor. I personally doubled my schedule of 1:1 conversations, and encouraged others to do so as well. We still produce regular videos weekly (they are now a part of our culture), and our Employee Net Promoter Score is currently a best-ever 76.
    4. Be an information sponge; listen well and often to a wide variety of resources. I spend no less than two hours/day listening to outside perspectives from a diverse set of sources that range from academic publications to pop culture podcasts. This helps me to not only be quick with a vintage movie quote, but also exposes me to a panorama of perspectives that’s ultimately helpful in building my own empathy. As a transplant to our home market, as well as a stranger to the geographies of businesses we acquire, I find it so helpful to regularly put myself in the shoes (or boots) of another.
    5. Conduct yourself with humility, because you will be wrong…a lot. This will enable you to embrace the inevitable course-correcting that every leader must do to be successful. I’m blessed to lead a business that is both multifaceted and highly relevant to its clients; we touch most everything that involves the employee experience. Among these high-dollar and high-emotion items is employee medical insurance. Our business model involves a honest-to-goodness better way for a small business to offer medical insurance to its employees: they can join our large group plan and take advantage of our skill and scale to offer their people better plan options, often at significant savings. The annual renewal of this medical plan is a massive undertaking, as we negotiate on behalf of hundred of clients and thousands of participants, and then must in turn communicate the outcome of this process to each client. Last year, we (I) thought it would be a good idea to ask our highly skilled outside consultant to present renewal cost information to our largest clients. The reason was well-intentioned: these professionals had unmatched expertise of a very complicated subject matter. The problem, though, was that they didn’t have the years of trust that our internal team had accumulated. As a result, I set up all sides for disappointment. But, because I was willing to listen early and often to some very painful feedback, we scrapped the well-intentioned plan. I was wrong, and I owned it. And ownership has its privileges, as we were able to recover and serve our clients well.

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

    In the context of this discussion, a quote that I love is from boxer Mike Tyson, who famously said “Everyone has a plan until they get punched in the mouth.” Beyond the striking imagery, this sure resonates with anyone that has led an organization during times of stress. As essential as a plan is, what’s even more vital is the ability to respond well — and quickly — when things don’t go as planned.

    How can our readers further follow your work?

    I can be reached directly at The site contains links to my book “Beyond the Superhero: Executive Leadership for the Rest of Us.” This recently reached bestseller status on Amazon, which makes my mom really proud. On the site, you will also see links to my podcast “Up In Your Business”, which features personal conversations with accomplished business leaders, focusing on the human side of success. And, finally, my organization, Questco, provides comprehensive HR support to over 20,000 people nationwide, and can be found at