I had the pleasure to interview Brett Derricott. Brett is a serial entrepreneur, software expert, and angel investor. He is the founder and CEO of Objective, a software development company and Built for Teams, an HR intelligence platform.
Thank you so much for joining us! Can you tell us the story about what brought you to this specific career path?
As a kid, I was always interested in anything creative or technical. If I saw something, I wanted to understand how it worked and how it could be improved. Thankfully, I had supportive parents who didn’t get upset when I took apart the telephone and wired it into the home stereo system.
I discovered software development in college — I loved the speed and freedom it afforded. I could imagine something and then set to work creating it. This was back in 1994, so the internet had only just started to gain traction with the general public. I was hooked. It was like the phone in my parents’ house — I just wanted to take it apart, understand it, and make it my own.
Granted, I had my doubts about whether I could actually make a career out of working on software. That all changed my senior year of college. At a networking dinner, a professor was going around asking people what they wanted to do after they graduated. I mentioned I wanted to work on something related to web development and coding. Within a few weeks, he had hired me to do some freelance work for his own business and put his products online.
That relationship helped me realize that a career in software development could be both profitable and fulfilling. The demand was there, I just had to offer a product. So, after I graduated, I spent a few years working for a startup as a developer to get experience. When the startup failed a few years later, I started my own company. I’ve been in the tech industry for nearly 20 years and I’ve never looked back.
Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?
I love getting in the trenches and solving problems. It’s why I started a tech company — I thought I would get to do that every day until I retired. I had no idea I would have to give that up when I started a company. No one tells you when you’re starting a business how much your day-to-day life will revolve around management.
Six months into my first company, I hired my first full-time employee. I wanted someone who could do projects the exact same way I would, no questions or guidance needed. The guy I ended up hiring had just graduated from college. It was his first full-time job, and he needed me to lead, to set the goals, the vision, the direction, and to oversee his work. Every minute I spent teaching him was a moment taken away from creating and solving problems — the passions that drove me to start a company in the first place.
Being a CEO often means trading the satisfaction that comes from the creative process for a chance to build something bigger than yourself. But wrapping my head around that was a real struggle. I fought against the realities of the CEO role for years. It took gradual, incremental growth to get me to where I am today. I had to give up control of the creative process to provide strategic vision and grow my company.
What are some of the factors that you believe led to your eventual success?
Success is a difficult word for me. At every stage of my career, I’ve focused on what was coming next, not what I have accomplished. However, a few key things got me to where I am today:
- Grit: Being successful in any field, at any level, means doing difficult things for far longer than others are willing to. As a CEO, especially if you’re leading a young, small company, that means sacrificing everything if it means your company keeps operating for another year.
- Empathy: Succeeding as a CEO often requires you to put yourself in someone else’s shoes, whether that’s a client or an employee, and understand what they want. When customers explain what they need to accomplish using my product, empathy helps me get beyond the words they use to truly understand them. For my employees, that means remembering what it’s like to be on the other side of the desk and being able to understand their needs. It helps retention — many of my employees have told me the reason they stay is that they feel valued and understood.
- A Great Team: A CEO, no matter how talented, emotionally intelligent, and hardworking, is not an island. You need mentors to guide you through challenging situations, friends you can confide in, and employees you can depend on. My team is filled with talented, smart people, who think in ways I don’t and who can be there when I can’t. When I gave up on being the sole source of ideas and creativity and relied on others, I succeeded.
What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.
- Being a CEO Requires More Than You Expect: You have to pace yourself. Running a business is overwhelming; at any given moment, there are 20 other things that have to be done that you don’t know how to do. There was a period, back when I was first starting out, where I was trying to run it all on my own. I had to be my company’s accountant, lead salesperson, HR department, developer, and project manager, on top of being a CEO. It wasn’t sustainable, and I burned out. This advice mostly applies for the CEOs of small companies and startups, but even for a larger, more established company, you are going to have to wear a number of different hats every day. It can be draining. So, know what you are getting yourself into and prepare.
- Ask for Help: The old phrase “it’s lonely at the top” doesn’t have to apply to you. It’s important to build relationships with other CEOs who can truly relate and may even have advice for the challenges you face and the doubts you have. Ultimately, there is no rulebook for being a CEO, especially for the wild west of running a startup. You can learn some hard lessons if you’re just shooting from the hip without any guidance. Early in my career, a lot of my advice came from the CEO of the startup I worked for right out of college. Even now, two decades into my career, whenever I have a problem and I don’t know the answer, I look to my network. More often than not, I get helpful advice. Granted, no one’s situation is exactly the same as mine, but my friends, colleagues, and peers often provide perspective and context for whatever problem I’m having.
- Have a Plan: Successfully running a company requires a clear vision for what your business will look like six months, five years, or even a decade from now. I wish I had been told to plan for how my company would grow and change as time went on. I never lost sight of what I wanted the product or culture to look like, which are both important. But for logistical concerns like staffing, some foresight would have been helpful. There were multiple points in my career where I managed too many direct reports and projects. Once I hired people to help, everything improved, but I should have done it sooner.
- Learn What Opportunities Not to Pursue: Early on, I was told this but I didn’t believe it. Many opportunities arise when you’re running a company, but you have to choose which to pursue and which to ignore or save for later. Saying yes to too many things can lead to failure. That’s why my rule of thumb is if it’s not “hell yeah,” it’s no. Take my company, Built for Teams. Our product touches so many parts of how a business operates, from PTO tracking to organizational charts. We could take the product in so many different directions, and clients regularly ask us to do so. We’ve had to say no to developing new features or incorporating new ideas that, while potentially lucrative, would have been time-consuming and distract us from our primary objectives. If you, as a CEO, say yes to every request and idea, there is no real direction and you will find yourself leading a company without a clear path or vision.
- Embrace Problems: Get used to dealing with more problems in a week than most people will deal with in a month. Problems can’t always be anticipated, and they’ll happen no matter how hard you try. When I was starting out in my career, I equated problems with failure; I was convinced that if I worked hard, did my best, and made no mistakes, nothing would go wrong. When something did go wrong, I blamed myself and felt it should have been prevented. I once hired an employee who brought in and managed a sizable new project. For several months the project went well and the client seemed happy. But the client fell behind on payments so I had to confront them about it. To my surprise, they said they weren’t happy with the work and didn’t want to pay. When I brought this up with the employee who was managing the project, he further surprised me by informing me he had accepted a job to go work for this very client. I spent a lot of time blaming myself for not preventing this difficult situation but eventually learned to let this be the result of others’ choices.
What advice would you give to your colleagues to help them to thrive and not “burn out”?
I’ve had to learn some lessons the hard way on this topic. When I was first starting out, I naively believed that I was immune to burnout. I heard plenty of warnings about burnout, whether from articles I’d read or from people telling me I needed to work less. I had no symptoms and felt invincible, so I ignored all of it. That worked for over a decade until the 18-hour days caught up to me.
Since then, I’ve worked to set better boundaries. I used to believe my job was whatever the business demanded of me. I prioritized the business over pretty much everything else. For the last few years, I’ve drawn a line in the sand to protect my health and wellbeing.
It isn’t easy to change after nearly two decades of thinking differently. I have to be conscious of how I feel, how much I’ve been sleeping, whether I’ve worked out, and whether I remembered to eat. I still work hard, but I’m getting better at being able to tell when I need to stop.
The biggest piece of advice I can give to a fellow CEO is to empower the people around you to tell you when you need to slow down. And, when they do tell you to take care of yourself, listen to them. Don’t wait until you’ve already collapsed under the stress and the work schedule; get ahead of the issue.
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?
Todd Hougaard was the CEO of the startup I worked at after graduation. Despite my lack of experience, Todd was willing to give me responsibility. His faith and trust gave me confidence and set the stage for my own ventures. When that company went under, I was lost. I knew I eventually wanted to try my hand at entrepreneurship, but I thought I needed to be older and more experienced.
Todd was the one person consistently telling me that I was ready to try it now, at age 26. He took the time to take me out to lunch and make his case for why I needed to start my own company. I shared my doubts, concerns, and fears. In response, he pointed out my skills and how I, at 26, had very little to lose and everything to gain. Without Todd’s encouragement, I doubt I would have started my first company, and I’m incredibly grateful to him.
What are some of the goals you still have and are working to accomplish, both personally and professionally?
Professionally, I want to improve my ability to identify talent in people early in their careers. I’ve loved discovering and mentoring young professionals who have exceptional abilities, but it’s not always easy to spot in an interview.
Personally, I want to improve how I manage stress. My fight or flight instincts are pretty strong, so I’ve always admired people who are calm under pressure and keep the right perspective.
What do you hope to leave as your lasting legacy?
I want every employee to remember their time working for me in a positive light. They spend 40 hours a week with me — I want them to know I have their best interests at heart and genuinely want to help them grow and succeed. I want them to feel like people, not just resources or cogs in a machine. That’s why I try to tailor the company and its processes around my amazing employees.
You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!
That’s easy — I want every company that can manage it to give its employees every other Friday off. In today’s workplaces, most employees aren’t working the standard nine to five, it’s more commonly 9- or 10-hour workdays. That’s not sustainable and, for many companies, it’s not necessary. For the sake of our hardworking employees, the business community should explore shorter workweeks or more creative, consistent PTO offerings.
How can our readers follow you on social media?
It’s hard enough to keep up with meaningful personal relationships when I work this much, so I’m not on social media. Thankfully, I have a few employees who post about the work we’re up to. You can connect with Built for Teams on LinkedIn or follow us at @builtforteams on Twitter.