Dan Prince of illumisoft

    We Spoke to Dan Prince of illumisoft 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 Dan Prince, CEO illumisoft.

    Dan is a life-long technologist and technology entrepreneur starting his first tech company in 1993. Dan has always taken a pragmatic approach to technology, opting for simplicity over perfection, people over processes, and communication over documentation. He believes in continual improvement, both personally, and in business. He is often noted as saying that reduction in someone’s cognitive computational effort is the key to improving their experience. This is true whether you’re talking about user interface design, or interpersonal communication. He is a futurist that believes with technology that we can significantly increase our average lifespan.

    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 got my start very early in life. I was lucky to have entrepreneurial parents. They were early adopters of computers for their deposition service back in the mid-seventies and having access to those allowed me to learn about computer architecture and coding at an early age. Playing with computers back then was like a game to me. I played on the computer much like I played on my Atari. I didn’t imagine that it would turn into a life-long interest or a career. In my 20s I worked in construction and it wasn’t until I was a father of 4 with all the bills that accompany 4 children that I decided to get a college degree. I worked part time and my wife watched the kids while I went to school full time for 4 years to earn the piece of paper that would begin my journey into professional technology development.

    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?

    I don’t know how funny it is, but when I first started out I was a little skittish about talking about money. For instance I would make sure that I qualified all my bids with disclaimers saying there was no way I could guarantee the bid unless there was absolutely zero changes to what I thought the client wanted at the time of the bid. This approach prevented me from getting some bids, but the ones that I did get I made sure to fulfill on my promises. One time I had a client propose to prepay me $100,000 for a 2 1/2% discount on my rate. I accepted it and we did about $150,000 worth of work over the next 9 to 10 months. When the client received the final bill, they were astonished. They couldn’t believe that it was over $100,000 since that is what they had paid me. I discussed with them that the contract clearly says it’s time and materials and our rate is what it is per hour. After many hours of discussion, I was convinced that I was not going to get paid the additional $50,000 that we had worked and billed for.

    In retrospect, I knew that I could have resolved this problem from the very beginning by having many discussions about money with the client at the beginning of the projects as opposed to after a misunderstanding arose. But, because I was afraid of not getting the job I was afraid to have those conversations because of the risk that it would cause the prospect to accept somebody else’s bid. The loss of that 50K played directly into us having to lay everyone off in mid-2018 and that, as I said, was a very dark time.

    Again this isn’t the funniest of stories, although I can laugh about it now, I definitely could not at the time. That said, I learned a valuable lesson, and that is that my fear of having the crucial conversation about money was not a $50,000 fear. It had no value whatsoever and that I had to overcome it if I was going to continue to build large system projects for major regional hospitals and Fortune 500 clients.

    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’ve got a lot of people in my life that have supported me along the way and I’m very grateful for every one of them. But there are a couple people that have helped me through the early stages of business growth that I want to give special appreciation to. Tyler Prince, my son, one of four there’s also an entrepreneurial type a person. He started a business right before I started mine. Against all odds he struggled and pushed and grew his business into a sustainable window cleaning company. He has grown his revenue by over 50% every year that he’s been in business. But it hasn’t been easy for him and at times it was very very difficult. We decided to form somewhat of a mastermind group where we would meet every week and talk about our business challenges and successes and help each other strategize how to move forward. We did this for several years and if it wasn’t for those weekly accountability sessions I could have very easily given up.

    For recently I’d like to give a word of appreciation for Matt Heelan. I hired Matt back in the end of 2017 and because of his dedication his hard work his willingness to think like the owner and think like the client we were able to make it through one of the darkest periods in illumisoft’s history. But not only make it through, we are now thriving, and a large part of that as a result of his efforts.

    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?

    When I first started illumisoft, we were not a purpose driven company. My only goal at that time was simply to stay in business and to do so we aimed to provide our services to anyone and everyone that needed them. I didn’t even know what a purpose driven company was, but I knew I could help any business reduce costs and increase efficiency by modernizing their processes with technology and intelligence.

    A couple of years into it we completed a project that helped a local hospital doing diabetes research and we learned something very valuable. At the conclusion of the project, we learned that the results of the work that we had done was going to benefit hundreds of thousands of children with type one diabetes live longer, happier, healthier lives. The joy that I felt personally provided such a great level of satisfaction that simply reducing business costs paled in comparison. Knowing that the work we had done helped so many people was a real-life changing experience. Since that day we have revamped illumisoft and turned our focus on providing services only within healthcare and healthcare research companies. We realized that it’s not enough to build good solutions; it’s not enough to delight our clients; We want to provide a benefit to the world or it’s just not worth doing.

    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?

    When I first started out in business, I knew very little about anything that I needed to know about. For example, I didn’t know anything about contract management, resource management, taxes, or accounting. I did know a bit about building a highly capable team. I knew how to speak a potential clients’ language and how to understand what they wanted and needed. So, I was able to acquire several well-paying projects all around the same time. Accordingly, I then hired teams of people to complete those projects.

    As the projects proceeded, I spent a lot of time focused on the quality of the teams’ interactions and the quality of their results. But what I didn’t spend a lot of time on, was making sure that new projects were being won. So, when my existing projects ended, all about the same time, I had zero work for my teams to continue to work on. I look back and I think it’s funny now that I was so naive. But at the time it didn’t feel funny at all. I had to let go of about 17 people all at once, including two of my sons! It really was not fun at all. At the time I thought it was one of the worst days of my life. In retrospect I’m happy it happened because I learned a lot of valuable lessons through having the experience. I learned about process management and how not having processes in place prevented me from seeing the writing on the wall. I learned about estimating project completion dates and matching those with accounting numbers. I learned about team management and resource management.

    There were a lot of benefits to that experience as well. One benefit was that I was able to get rid of the bad hires that I had made. I had been slightly afraid to let go of those people because I had allowed them to become the people that had the most knowledge on their projects and losing them would have been very bad for their projects and I was also worried they would have some form of retribution to my company. But, with the projects ending, they were no longer critical. I learned that if I had let them go when I learned that they were problematic I would have been a lot better off than I was keeping them around until the end of the project.

    Another lesson I learned was that I needed to be focusing my time on getting new business to replace projects long before the projects were finished. That meant also that I would need key people in place to build teams, architect projects, and manage results.

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

    Yeah I think back in 2018 when I had just laid off all of those people it was rough, a very dark time. I considered throwing in the towel and even looked for a CIO position for a few weeks. But, it dawned on me that I still had clients that needed their projects finished and so we continued to work. We changed our model from onshore developers to off shore, from rapid turn around time to scheduling projects a bit further out, and we made it through.

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

    I would say:

    a) having the discipline to pull yourself out of the daily crisis management mode and lean on the tools, systems and frameworks that have helped us succeed in the past. What does this mean? In our experience we have relied on things like systems thinking, design thinking, agile methodologies and purely creative exercises to help us navigate challenging times.

    b) the ability to create a vision about how we will overcome the challenges which means also having the skills to communicate that clearly to your team. One our values as an organization is transparency both with our team members and our clients. During challenging times, the way that we create certainty that we will overcome is communicating our plans and thoughts while being empathetic to the fact that people cope with difficult times in different ways.

    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?


    I am only slightly kidding but having a sense of humor during these intense times does help and kind of acts as a bit of a reset to go back to the work of problems solving our way through those moments.

    When things are most uncertain, leaders especially in small business can take on “saving the company” as their job and not realize the value of getting their team involved in helping him/her figure it out as a team exercise. The team I have is highly capable, intelligent, experienced, and creative and when we face challenges in the future, I will have them at the table. They can provide insights and expertise in looking at challenges in their own unique way.

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

    I want to highlight that a company’s values in these situations are crucial to revisit. Whenever we face difficult times and the need to deliver difficult news, I revisit the list below. The last two are the ones I have had to reflect on when we delivered difficult news to a team member or client. These values guide our behavior as people within an organization and sets the expectation for our clients when they work with us. Our team members and clients have confidence that we will always be truthful and transparent regardless of the situation.

    • Continuous Personal Improvement — We cannot be the best in business if we cannot be our best selves.
    • Craftsmanship — We do it right. Right means it solves the solution in the simplest, lowest cost way.
    • Consistency — it is not enough to be the best only part of the time.
    • Confident — Confidence comes from having built the skills through personal development.
    • Courageous & Tactful — it can be difficult to voice opinions to a client but necessary. Well-earned confidence allows for tactfulness.
    • Honesty and Accountability through Transparency — We communicate to our team and our clients our achievements and the challenges we face and our plans to overcome.

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

    I had mentioned earlier our use of tools, systems and frameworks and in this case relying on systems thinking tools helps you as a leader understand how you can make your future more likely to be predictable and then what is likely to always be unpredictable.

    Within systems thinking and other tools they ask that you are always vigilant about scanning your environment especially around how social, political and economic policy may be shaping your factors that impact your industry. I see this sort of analysis in large part to be rather unpredictable in terms of our ability to influence these policies but what is predictable is our ability to plan and organize with this sort of information.

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

    I would point to two things:

    1) Goals and Strategy. As we experience the ups and downs, we always like to revisit our goals both in the short term and long term. We also discuss our strategy as a company and when it makes sense we adjust.

    2) Values. As I mentioned this earlier, the principles that guide us our the values that we have created and modified as we have grown.

    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?

    1) Leaders let their ego get in the way of making the best decision for the company. I often think business leaders think it makes them look weak if they change plans or strategies and I think of it differently. If our environment is always changing and evolving, then we are fools if we do not adapt to it.

    2) Stop listening to your team, advisors and experts. As I mentioned earlier, when things are difficult leaders need to be more inclusive and in my experience I have seen some leaders kind of retreat into a shell to try and figure it out on their own.

    3) Lack of transparency and honest communication with your team and clients.

    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?

    Every business leader (and especially in small business) we are always thinking of different ways to grow our business. In early 2020, right before the pandemic hit, I worked with Matt Heelan our COO to create a healthcare specific business strategy because we knew we could successfully leverage our existing healthcare clients’ relationships. We also created a separate entity to handle our non-healthcare clients.

    Additionally, I think we need to think creatively about where we go to find new opportunities. There was recently some news where Netflix announced they were creating an e-commerce store offering to sell apparel, jewelry and collectibles. This will be an entirely new set of revenues streams for the original streaming company.

    We are undertaking a similar shift by developing our very own product and service for the healthcare industry. We are in the early stages of development but going from a purely services based business into building an actual product has it’s own set of challenges but with our team I am confident we will be successful.

    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.

    We have covered a lot of these already but:

    1) Listen and then listen some more. Listen to the what the market is telling you, listen to your team and listen to your instincts, gut, and experience.

    2) Use the systems, tools, frameworks that can help you lead.

    3) Communicate and then communicate some more. During uncertain times people want more information so often these may be daily check-ins with your team and your clients.

    4) Revisit plans, goals, strategies, and values. Often when we are going through challenging times when we reflect on these areas it can help us reset or in some cases adjust our strategy.

    5) Keep a sense of humor. Yes overcoming difficult situations is stressful but sometimes a little levity helps us get through these moments.

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

    You haven’t failed until you quit trying.” If you attempt to do anything worthwhile you will stumble. You will make mistakes. You will not take a direct path to success unless you are simply lucky. If you believe in what you’re trying to accomplish and you’re willing to learn from your mistakes, the only other thing you must do is keep trying. This is not something you have to remember as much as it is simply a way of life. Accept that struggle and challenge are natural and embrace them as the path to success. Doing so allows you to take more chances and thereby increase your risk of finding the path to success. In my life it is true that making incorrect guesses are far more valuable than guessing correctly. This is because guessing incorrectly moves you in the right direction and give you additional knowledge. Making correct guesses only move you in the right direction, but often without the knowledge of knowing why they were correct.

    How can our readers further follow your work?