Chris Berry of PDI Software

    We Spoke to Chris Berry of PDI Software

    As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Chris Berry.

    Chris Berry joined PDI in 2017 as CTO. She’s had a significant impact on the business, including spearheading many initiatives, modernizing PDI’s internal infrastructure and processes, accelerating PDI’s cloud-based solutions, and unifying the global development team. In addition to her role as CTO, she oversees the PDI Security Solutions line of business, extending the company’s capabilities in cloud security.

    Chris has over 30 years of experience and is passionate about exploring the art-of-the-possible and fostering a culture of innovation. Prior to joining PDI, Chris was CTO for PeopleAdmin and SVP of Engineering at Accruent. Chris started her technology career in the United States Air Force in 1991 as a software developer.

    Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

    At my core, I thrive on opportunities to be a free thinker who gets to engage in creative problem solving on a daily basis. Ever since I was a young child back in pre-school, I’ve always loved putting puzzles together, and that seems to be a common thread across my career.

    I started out working in technology in the United States Air Force, where I was a software engineer for eight years. After moving into the private sector, I spent several years in engineering roles before I ultimately raised my hand to take on a new management opportunity.

    I had always enjoyed using technology to solve problems, and I soon realized how much I loved expanding my leadership skills and building high-performing teams to solve even more complex puzzles. When one of the companies I was working for–SirsiDynix–was acquired by Vista Equity Partners, that kicked off what has now become 15 years as a technology leader in private equity-backed companies.

    Can you share the most interesting story that happened to you since you started your career?

    My most recent job has allowed me to travel quite a bit — including an around-the-globe trip to PDI locations in just 12 days. While visiting our team in Chennai, India, a group of employees told me they had a surprise for me. They actually brought in a seamstress, took my measurements late in the day, and left me wondering what was going on.

    The first surprise was walking into the office the next morning and discovering a custom-made sari waiting for me. The second surprise was realizing there was absolutely no way I would be able to put the sari on by myself and I had to ask for help. I felt so fortunate to be welcomed into such a wonderful cultural event, and we had a fantastic “Women at PDI” meeting all dressed in our saris.

    Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

    I love Zig Ziglar’s quote “Success occurs when opportunity meets preparation.” That really sums up a lot of my leadership career. You have to put in the work, you have to be ready, and you have to recognize the right opportunities at the right time.

    In retrospect, a lot of things that might have seemed like great opportunities earlier in my career probably wouldn’t have played out like I thought they would. Being self-aware and understanding your surrounding environment allows you to merge your preparation with an opportunity. You have to be a sponge and soak up all the knowledge and experiences you can. If you don’t know something, go out and learn about it.

    For instance, I recognized a great opportunity to broaden out from my functional CTO role to become the general manager of a new line of business. My entire career had prepared me to take on that additional responsibility, but I also had to know that my team was prepared to step up and backfill some of my existing responsibilities. If I hadn’t properly prepared my team with highly qualified successors, the opportunity wouldn’t have been nearly as enticing. And my chances of success wouldn’t have been nearly as high.

    Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?

    I really like the book “Drive” by Daniel Pink, primarily for the way it has helped me understand what individual employees value and respond to. If you know someone’s personal values list, or PVL, you can get amazing insight into their motivation. The more you understand what motivates someone, the easier it is to support them, recognize them, and reward them accordingly.

    From my perspective, anything you can do as a leader to raise your emotional intelligence and relate to your team members will only enhance your overall success. Especially today, we don’t live in a one-size-fits-all world, and you absolutely must be able to adjust your management style to different individuals on your team. When they realize how much you appreciate their unique needs and abilities, they’ll go the extra mile for you. It’s a great way to build trust and shared purpose.

    What do you think makes your company stand out? Can you share a story?

    One differentiator about PDI is that the entire executive team has worked their way up the management ladder based on hard work and hands-on experience. We all had to earn it, and most of us had some pretty humbling jobs earlier in our careers.

    When I was younger, I used to envision executives as being so far removed from the daily experiences of “regular” employees. Now that I’m an executive, I realize how opposite that perception was compared to reality. Your core personality doesn’t change because of a promotion or job title. PDI executives have a real blue-collar, roll-up-your-sleeves mentality of doing whatever it takes to get the job done.

    It’s very refreshing that we don’t have to manage a bunch of competing egos. Yes, we disagree at times, but we have such a deep well of respect that we always put the company first. If we ever had a me-first personality in the executive suite, it would stick out immediately, because it just wouldn’t be a cultural fit at PDI.

    We have genuine respect and concern for each other — and that allows us to get through the tough times. I was so proud that the executive team was unified in choosing to take pay cuts when the pandemic hit so we could help preserve employee jobs or avoid them being financially impacted. Those are the types of people I want to be associated with.

    That mindset really mirrors the personality of the entire company. PDI is sort of a grass-roots company that keeps growing thanks to smart, dedicated employees who want to deliver an outstanding solution to our customers. It’s both a top-down and bottom-up mentality that’s deeply engrained in the corporate culture. When you combine that mentality with deep domain expertise, you get the true essence of PDI as a market leader.

    The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?

    My first piece of advice would be to avoid trying to emulate anyone else too closely. Yes, you need mentors and role models you respect and admire. But it’s best to focus on becoming an executive in your own unique way.

    There’s no right or wrong career path. Some people like to map it out from the start like it’s a paved road, while others end up taking the lazy river approach. Some just happen to stumble upon it by accident. Either way, it’s great to have bold aspirations, but what you uniquely contribute to a company is yourself. That’s your value and differentiation.

    I recommend finding heroes from all types of areas, but you have to put your own spin on it. Even if you think you might not be the ideal candidate for a particular position, take a look around and ask yourself if there’s anyone more suited than you. A lot of times you’ll realize you have a unique expertise, capability, or personality characteristic that makes you exactly the right person for the role.

    Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

    This is an easy one. I can’t count how many times I’ve been advised to act swiftly and decisively — yet that advice has often backfired. Yes, there are many situations where a quick decision works best. But most of my “do-overs” would stem from not taking enough time to listen, learn, and better understand a certain situation before I acted.

    The perfect example of this is a merger or acquisition. I’ve been through a lot of acquisitions in my career, and the sheer nature of the confidentiality means that you don’t always have time for as much due diligence as you’d like. For instance, even if the financials pencil out and the products or solutions are well aligned, you can’t make hasty judgements about people. There will always be pleasant surprises.

    If you don’t take the time to know the people and what they do, you could be missing out on some fantastic employees that you really should retain. If you rely solely on job titles, you might not realize how valuable an employee is — especially in smaller companies.

    I’ve learned that it’s good to take more time and listen carefully before you decide which employees to retain following an acquisition. I’ve seen some great employees walk away after their transition period ended, because we didn’t see their true value until we’d had an opportunity to see them in action. And by then it was too late for them.

    You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

    Perseverance, agility, and self-awareness all go a long way toward setting the foundation for a successful career. In terms of perseverance, I simply don’t know how to quit. I’m stubborn, and I’ve experienced a lot of skinned knees and elbows. When your team members see how invested you are, they know they can count on you regardless of the circumstances.

    In terms of agility, you simply can’t be rigid as a leader. The days of “my way or the highway” might as well be the Middle Ages. If you’re not versatile, you won’t last long in today’s dynamic business world. In fact, you really need to be hyper-adaptive to thrive in a world where everything seems to be mission-critical and time-sensitive. The speed of business is only going to accelerate, so make peace with change and uncertainty or you’ll end up being miserable.

    I definitely didn’t take a straight path to become a CTO. I had several job shifts, I ended up taking pay cuts for what I thought would be a better experience, and I learned what I needed to round out my leadership skills. The key is to adapt before someone else asks you to adapt…because then it’s too late.

    Self-awareness is all about recognizing your strengths and weaknesses. Guess what? We all have flaws and limitations. The faster you recognize yours, the faster your career will progress. It’s essential to surround yourself with colleagues who make up for your weaknesses. I’m not in my current role because of my knowledge. I’m here because I have a great team that allows me to focus on what I do best. You can’t pretend to have all the answers, and that’s where a strong team is vital to your success.

    Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?

    It’s all about broadening your leadership for the entire company rather than a product or a project. The horizon is so much wider and you have so many more people counting on you. You have to see the entire circle — your company, peers, partners, and any others who are part of your ecosystem — along with your shareholders.

    Think about dropping a pebble into a pond. When you make a decision or take an action, that’s the pebble hitting the water. It makes a small splash. But then you start seeing all the ripples emanating from the center as they spread out further and further. Those ripples are how your action impacts everyone else in your ecosystem. If you can’t recognize the ultimate impact and consequences your actions and choices have, it’s really difficult to be an effective leader.

    What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

    One of the biggest myths — and I certainly hope this is changing — is that C-suite executives have no concern or feelings for their employees. The stereotype of the self-serving boss just isn’t reality, at least in my experience. If you lack emotional intelligence, you better surround yourself with a team that can make up for it. If you’re not looking out for your employees’ best interests, they’ll see right through you.

    On the other hand, if they know you’re invested in their individual success, it will ultimately benefit you along with your company’s bottom line. With the way business tends to operate these days, rank-and-file employees typically have more insight into their executives’ personalities than ever before. Smart leaders are finding the tools to connect with employees and show them how tightly integrated everyone’s success is.

    What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?

    It drives me crazy when I see executives acting on preconceived assumptions or only what they’ve been told by others. When you’re building a team, start with a clean slate and give everyone the benefit of the doubt. That’s the very least you can do.

    Take the time to listen and learn before making any bold decisions. This is where you need to think like the best sports coaches. If you’re a coach who insists on running your own particular system regardless of the skills of your current players, you won’t win many games. The best coaches are flexible enough to adapt their style and approach to make sure their teams are positioned to succeed and have a better chance of winning.

    Recognize what your team does well, where you might need to supplement it with some expertise, and how you can get them the tools and resources they need to grow.

    In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

    Time commitment is number one. If you run a global company that is mission-critical to your customers, you are always on twenty-four by seven. When you start a new position, the job often works you until you manage to build your team, figure out the right processes, and generally get aligned with the rest of the business.

    Being a technology executive means that I’m involved in every aspect of the business — PDI’s IT environment as well as every product or service that our customers rely on. Expectations around technology have changed so much over the years. There’s no downtime. Everyone demands always-on availability and everything is mission-critical. Payments can’t stop. Logistics can never shut down. The support center has to be available around the clock.

    When you factor in a truly global business environment and all the different time zones, that means you always have to be ready. If there’s a big enough issue in Hong Kong or Sydney, it won’t wait for me to get my eight hours of sleep back in Austin, Texas.

    If you’re not prepared to go above and beyond what any other member of your team would do, you have to question whether you’re ready to lead. And, yes, that means making sacrifices and tradeoffs in your personal life.

    Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading From the C-Suite”? Please share a story or an example for each.

    The five things I wish someone had told me are:

    1. Do the work.
    2. You will make mistakes.
    3. You can’t do it all by yourself.
    4. Raise your hand.
    5. Enjoy the ride.

    Doing the work means you have to understand the different functions and teams across the business. Don’t be afraid to work your way up to a C-suite position. There’s simply no substitute for getting involved and learning through trial and error. You can’t rely on others in your network to help you leapfrog your way up to certain roles. You have to put in the work or you won’t be prepared when you actually do achieve the role you aspire to.

    Making mistakes is practically a prerequisite for a C-suite role. If you’ve only experienced success, you won’t know how to function when challenges arise. I personally don’t feel comfortable with a leader unless they’ve bruised their shins a few times on their way up the ladder. As long as you’re accountable and course-correct quickly, you can learn a lot more from your mistakes. Incorporate that learning into future decision-making to become a smarter and more empathetic leader versus dwelling on your mistakes in a negative way.

    Understanding that you can’t do it all by yourself is critical. You have to be self-aware and realistic about when to say no or defer to someone else. If you build a strong team, find a great mentor, and are willing to rely on others (both personally and professionally), you’ll have the support system for success. You must be able to delegate and trust your team to make the right decisions.

    Raising your hand seems like a no-brainer, but it’s remarkable how many people are afraid to volunteer. Usually that comes from a place of fear, intimidation, or lack of confidence. Good leaders let their teams know they can volunteer with the expectation that they’ll inevitably make mistakes. The willingness to take chances is often commensurate with the potential gains you can achieve. It’s good to take calculated risks, embrace change, and aim higher.

    You have to enjoy the ride because, if you’re not having fun, it’s not worth it. Your career is a journey, and some jobs will be harder than others. You’ll experience good days and bad days. It’s extremely important to remain human, develop positive relationships, learn new things, and prioritize self-care. But once you’ve built the right team and can look at things strategically, that’s when the fun really starts. There’s nothing more rewarding and enjoyable than watching your team members grow and succeed.

    In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?

    Always remember that you are just one member of the team, so you can’t work in a vacuum. You have to empower your employees and make it safe for them to share their opinions, perspectives, and feedback. Open expression of ideas only happens with trust and that is so critical to business success. Listen and be willing to adapt based on what your team needs at any particular time.

    Another key aspect of creating a great work culture is being vulnerable. Let everyone know you’re human. When I went through a difficult time with the health of my father half way across the country, I carried that burden by myself for a long time. When I finally shared it with my team, their support was overwhelming. When they see you as vulnerable, they’ll respect you even more and be open about their own challenges.

    The bottom line is that a leader’s role is to elevate every member of the team for their own career growth and for the success of the company. Business success is often a byproduct of cultivating a culture of shared purpose and respect where everyone feels good about their role and contributions.

    You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

    I was talking with my mother about this one, and we almost immediately thought of Mr. Rogers. That’s why I would start the Mr. Rogers Movement. He always taught children that they are valuable just the way they are. Fundamentally, your uniqueness has value and your aspiration should be to “Be Your Best You.”

    This hits very close to home for me, because my daughter is dyslexic. Reading is difficult for her and she sometimes gets frustrated — especially when she compares her reading ability to her brother or other students in her class. When that happens, I try to remind her that we all have strengths and weaknesses. She has so many other gifts and talents that stand out to everyone she meets.

    When you bring something unique to the world, that’s extremely valuable on both a personal and professional level. I encourage leaders to think about how much more effective they could be by welcoming unique ideas and diversity into the work environment. You have to open yourself to fresh perspectives, new ideas, and outside-the-box thinking. Those are the tangible drivers of innovation and success.

    I’d just like to close with a fantastic quote from Mr. Rogers. “We all have different gifts, so we all have different ways of saying to the world who we are.” That’s how we leaders need to view the world and our teams. We need to celebrate what makes each of us unique and valuable — and the success will follow.

    How can our readers further follow you online?

    One of my goals is to continue building my communications skills, so I’m hoping to do a bit more blogging in the future on PDI’s website. But the best way for people to connect with me is through LinkedIn.