Dave Colford Of Worksuite On How To Navigate The Generational Differences That Are Disrupting Workplaces

An Interview With Cynthia Corsetti

Constantly reinvent yourself — The generation you come from can be a point of pride but it shouldn’t be a reason for stagnation. Be open to learning across and learning from different generations the best you can. Committing to lifelong learning can lead to positive change and powerful leadership.

Today’s workplaces are a melting pot of Baby Boomers, Gen Xers, Millennials, and Gen Zers. Each generation brings its unique perspective, work ethics, communication styles, and values. While this diversity can foster innovation and creativity, it can also lead to misunderstandings, conflicts, and productivity challenges. How can businesses effectively bridge these generational gaps to create harmonious and thriving work environments? As part of this series, we had the pleasure of interviewing Dave Colford, Worksuite’s Chief Customer Officer.

Dave Colford is the Chief Customer Officer of Worksuite, the premier SaaS and professional services company focused on the global freelancer, contingent, and influencer workforces. As an industry leader Colford has been at the vanguard of enterprise-level digital transformations, management turnarounds, and ongoing value creation for over 25 years. In his private life, Colford is the proud father of five children, an active volunteer with the Boy Scouts of America, The Red Cross, and is a mentor with the Capital Partners for Education.

Thank you so much for joining us in this interview series. Before we dive into our discussion about succession, 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?

I have had the opportunity to lead two distinct careers, my first beginning in a way familiar to many Long Islanders — by working for one of the large local companies, CMP Publishing. In the late 80s and early 90s, CMP was known for being a progressive thought leader, particularly in cultivating and investing in local talent. I was fortunate enough to join this company, literally starting my career in the mailroom while I was still in college.

From there, I worked my way up to become a sales assistant, steadily climbing the ranks and making numerous connections in the B2B technology and publishing sectors. As CMP began its digital transformation initiatives, I was fortunate to be able to grow in the larger tech media space and eventually hold executive positions. This phase of my career, focusing on digital growth and turnarounds, led me to Hanley Wood, which prompted a move to Washington, DC. There, I became deeply involved in the media business and was introduced to what was then known as MetroStudy, which was my introduction to the SaaS (Software as a Service) world.

MetroStudy, a data business serving the residential housing community, paved the way for my role at DCN, which serves the commercial construction industry. Both of these data-driven businesses utilized the SaaS delivery model, marking my foray into the software business. This experience ultimately positioned me to land at Worksuite.

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

What makes Worksuite stand out is our vertical focus on the freelance economy. That focus is reflected in the way we work. Worksuite uses freelance talent in the same way our customers do. 50% of our company includes freelance talent from across the globe. So working with freelancers and seeing the freelance economy grow is not theoretical to us, but part of the fabric of who Worksuite is going back to the two co-founders of the company, who came out of the agency world.

Worksuite was launched in response to the rising demand for editorial, content, and creative management for freelance workers. Agencies bringing in freelance talent for projects need tools to help them manage this workforce. So Worksuite built its business with this in mind and decided to create its own contingent workforce as part of its staffing strategy.

We work with freelancers, we are freelance. It’s not just something that’s “nice to have” for us but something that’s part of our DNA.

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?

If I had to choose three key qualities, the first would be resilience. Whether resilience is a result of nature or nurture, or perhaps a combination of both, is difficult to say. Regardless, resilience is crucial because each day brings its own set of challenges. Even on the best days, there are areas that challenge you intellectually and emotionally. The ability to bounce back on hard days and leverage resilience on good days to perform even better is paramount. This quality has been especially important for me, given my roles in turnaround and transformation companies.

The second quality is truth and transparency, which I’ve adopted from the best leaders I’ve worked with. Delivering the truth isn’t always easy and can often be hard to accept. I’ve been fortunate to work in environments where my leaders and companies have consistently been honest about what is happening, why it is happening, and what we plan to do about it, whether in good times or bad. I strive to carry this forward. It’s decidedly human for us to feel frustrated with information we may not like, but in the end, most people ultimately appreciate being told the truth.

The third quality is servant leadership, which I practice in all aspects of my life, not just professionally. Servant leadership has various descriptions, including religious and professional ones. I define it simply: servant leaders always seek to give rather than get. True servant leaders understand that investing in their people, company, and training will yield returns, often exponentially. By investing in the right areas, the benefits will come back, doubling and tripling over time.

These qualities — resilience, truth and transparency, and servant leadership — have been fundamental to my success and approach in my career.

In your experience, what are the most distinct characteristics, values, and work preferences of each generation currently present in the workplace?

I love this question because the dynamics of different generations in the workplace are very close to my heart. Having moved into executive roles at a relatively young age, I’ve often found myself surrounded by peers who were chronologically much older than me. This experience has been immensely beneficial, and now, as one of the elder statesmen myself, I see the generational landscape of the workplace as particularly fascinating.

Today, we have up to four generations working side by side: Baby Boomers, Generation X, Millennials, and now Generation Z. While those from the Greatest Generation may still be involved, it’s primarily these four shaping the modern workplace.

Each generation’s motivations are heavily influenced by their formative years, roughly the first ten years of their lives. Research shows that the experiences during this period tend to shape lifelong values and motivations. Although these influences can evolve, they rarely disappear entirely.

Baby Boomers, the richest generation in history, are known for their strong work ethic and pursuit of success, often at the expense of work-life balance. This generation, raised to believe in a true meritocracy, values top-down leadership and has significantly shaped the modern workplace’s structure.

Generation X, often called the “Forgotten Generation,” is marked by cultural diversity and technical literacy. Many Gen Xers were latchkey kids, developing self-reliance and a healthy skepticism from a young age. While they appreciate clear leadership, they don’t necessarily favor a top-down approach but value direction and structure.

Millennials have brought profound changes to the workplace. As the largest generation, they are also the poorest due to substantial student debt. Millennials are known for their egalitarian and creative mindset, focusing on achieving success that drives positive societal change. Unlike their Baby Boomer parents, who valued traditional meritocracy, Millennials prioritize collective success and civic-minded initiatives. They introduced the concept of integrating feelings and satisfaction into workplace discussions, a significant shift from previous generations.

Generation Z, primarily the children of Generation X, share some similarities with Millennials but have distinct differences. They appreciate structure and a top-down leadership style, yet they prioritize work-life integration. Gen Z seeks a meritocratic workplace where their efforts are appropriately rewarded. They prefer flexibility in where and how they work, valuing an honest and equal relationship with employers. Similar to their Millennial predecessors, they are comfortable working in team based environments and knowing how to separate and prioritize their work and personal lives.

Understanding these generational nuances is crucial for creating a harmonious and productive workplace. Each generation brings unique strengths and perspectives, and by recognizing and respecting these differences, we can foster an environment where everyone thrives.

Can you describe a specific instance where generational differences caused a significant challenge in the workplace? How was it addressed, and what lessons were learned?

I have a presentation about generations in the workplace and anytime I give it at a company, it unlocks some difficult truths about generational dynamics. One of the key points I mention is how Millennials brought emotion and the perspective of the “total person, not just the employee” into the workplace for the first time. That might sound funny but older generations often valued a work environment where feelings were less important, so this period represented a big shift.

Millennials, the first digital natives, focus on work-life balance, now evolving into work-life integration, and Generation Z is focused on workplace satisfaction. Both encompass emotional and psychological safety, fairness, and overall job satisfaction, all of which are deeply personal. While this shift has been challenging for legacy workplaces and leaders to acknowledge and incorporate, it has been incredibly powerful. It forces us to challenge long-standing norms, especially those incredibly dangerous words, “We’ve always done it that way.”

Millennials bring their whole selves to work — their open, honest selves. They’ve shown that you don’t just get the professional when they come to the office; you get the entire human being. This transformative approach challenges the traditional mindset that employees should leave their personal lives at the door. It recognizes that personal issues can and do affect professional performance.

This shift has prompted companies to support the whole person, not just the employee. Millennials have taught us that the equation is incomplete if we ignore the human side of work. The companies that embrace this holistic approach to their employees are the ones best suited to succeed in the long term. It is not an overstatement to say that the Millennial generation has created more positive change in the workplace in the last 50 years than any other.

Technology adoption varies greatly between generations. How do you recommend companies bridge the tech-savviness gap without alienating any generational group?

First, it’s essential to acknowledge that a technology gap exists. The rapid pace of tech advancement and adoption can be daunting, even for the most tech-savvy generations.

Next, provide training opportunities while also setting clear expectations. If your organization embraces technology, every generation within the company must adhere to this policy. It’s a two-way street: the company sets the expectation, and it provides the necessary support to help everyone meet it. No generation should be allowed to opt out of using essential tools like email, Slack, CRM systems, Asana, etc.

It’s a combination of setting clear expectations, providing robust support, and all workers understanding that this is how the company operates. With these elements in place, everyone can succeed, regardless of their generational background.

How can organizations create cross-generational mentorship programs that allow older and younger employees to learn from each other?

I’ve personally benefited from cross-generational mentorship, and while it should ideally happen organically, the reality of our modern work environment necessitates intentionality. In our remote-first company, Slack serves as our office, and we must deliberately create opportunities for cross-generational mentorship and interaction.

Different generations bring varied perspectives and value sets to the table. It’s crucial to seek an understanding of these diverse viewpoints. For example, Generation Z’s experiences with COVID-19 have deeply impacted their outlooks, just as older generations have been shaped by events like wars and global terrorism. Each generation’s experiences inform their perspectives, making it essential to acknowledge and appreciate these differences.

To foster cross-generational learning, organizations should implement intentional mentorship programs based on need, desire and subject matter expertise. These programs should facilitate interactions not just across different disciplines, but across different generations. This is especially important as the traditional office environment moves to an increasingly remote model.

This approach ensures that everyone has the chance to learn from each other, leveraging the unique insights, experience and value that each generation brings to the workplace.

From face-to-face conversations to instant messaging, each generation has its communication preference. How can businesses foster effective communication that caters to these diverse preferences?

I believe it’s crucial to be intentional not only about mentorship programs but also about communication expectations. In today’s world, we use various tech platforms for communication, such as Slack, Salesforce for CRM, texting, email, and Zoom. Companies must establish clear guidelines about which types of communication belong on which platform.

For instance, it’s easy to miss a text if you’ve been on back-to-back Zoom calls all day. Questions arise: Why didn’t you send it via Slack where it would be more visible? Why wasn’t it included in a Zoom chat? With so many communication methods available, it’s vital for companies to decide what belongs where and to hold people accountable to these standards. Some communications, like customer interactions, are more appropriate for email, while quick, ad hoc messages might be best for Slack.

Without clear rules, important messages can be missed, leading to miscommunications and wasted time trying to track down information. Companies need to centralize communications on designated platforms to ensure efficiency and clarity.

We’re just beginning to tackle the evolving landscape of communication methods and platforms. No one has fully mastered it yet, and it’s reminiscent of how, 10 or 15 years ago, the law struggled to catch up with the internet. Think about Napster and how the technology was far ahead of the legal framework. Similarly, today’s communication platforms have outpaced many companies’ abilities to manage them effectively.

How should training and development programs be tailored to cater to the unique learning styles and expectations of different generations?

This is a big question, and it’s probably the hardest one to answer right now because it touches on employee development, mentorship, and a company’s ability to succeed within legacy timeframes. Take onboarding a new employee, for example. Many companies say it takes six to nine months for someone to be fully up to speed, especially for knowledge workers. This timeline holds regardless of how efficient the onboarding process is.

Now, consider that we have four generations working together, each with different worldviews and varying acceptance of technologies. Add to that the different work arrangements — remote, hybrid, or in-office — and we face a unique set of challenges. Companies will likely need to mandate a unified approach to onboarding and training, regardless of generational differences. This approach needs to be repeatable, scalable, and effective in driving the best results for the organization.

To achieve this, we need input from all generations in the workplace. Training and development should be a bottom-up process, where employees across generations share their preferred learning methods — whether video-based, live sessions, questionnaires, or other formats. By gathering feedback on what works best for them, companies can create a blended training and development experience that meets the needs of everyone. This inclusive approach ensures that everyone can connect with the training and development process, ultimately leading to better outcomes for the company.

In what ways can leaders ensure they’re being inclusive and not harboring unconscious biases towards one generation over another?

I have strong feelings about this topic because I’ve been trained to view feedback, both professional and personal, as a gift.

The first step is acknowledging that everyone has unconscious biases. We must recognize these biases and invite perspectives from others. This is a significant departure from the approach of some generational leaders, who often felt it was their job to explain things to others rather than seek feedback.

Encouraging and nurturing a culture of 360-degree reviews is crucial. While it can be hard to hear about gaps in our personality and skill set, receiving feedback as a gift helps us grow. It takes effort and openness, but the benefits are substantial.

As we look towards the future and the eventual integration of newer generations into the workforce, what strategies should businesses implement now to be prepared for even more diverse generational dynamics?

Here are my thoughts on the future of work, both from my perspective and Worksuite’s, driven by three main factors:

How We Work: It’s not just about the location anymore; it’s about embracing a different way of thinking. Flexibility in how we approach work is becoming increasingly important.

When We Work: The traditional 9–5 schedule is becoming obsolete. Not every full-time position requires employees to be available during those hours, especially across different time zones. The concept of a 40-hour workweek and constant availability is no longer what the future holds.

Embracing Technology: As we adapt to new work methods, leveraging technology becomes crucial. We need to utilize AI to access and manage knowledge, enhance communication, and explore other technological advancements to work more efficiently.

Additionally, we need to rethink employment structures. The rise of the freelance economy, especially post-COVID, is notable. Many professionals prefer working on special projects and for themselves rather than being tied to a single employer. This trend is not a luxury but a necessity as we move forward.

What are your “Five Things Leaders Need to Know About How to Navigate the Generational Differences that are Disrupting Workplaces”?

1 . Complete transparency — Truth and transparency are paramount — everybody we work with are intelligent and can sniff out the truth — even when it’s difficult — glean the benefits — have your reputation built completely on trust and truth.

2 . Servant leadership — Leaders today live in service of the people on an org chart that sits below them — org charts are an antiquated way of thinking of business — it’s about service and support — helping your co-workers, teams and company.

3 . Unconscious bias — Being open to our unconscious bias and feedback on our leadership style is extremely important. Accepting feedback on how we can lead and serve better is what leaders at all modern companies should embrace for success.

4 . Move with haste — I don’t know a leader from any generation who looks back on a decision they had to make and wishes they’d waited longer to make it.

5 . Constantly reinvent yourself — The generation you come from can be a point of pride but it shouldn’t be a reason for stagnation. Be open to learning across and learning from different generations the best you can. Committing to lifelong learning can lead to positive change and powerful leadership.

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

Lord Robert Baden-Powell, the founder of Scouting, once said, “The most worthwhile thing is to try to put happiness into the lives of others.”

This idea transcends work and touches our personal lives, and relationships with children, colleagues, spouses, and significant others. Happiness is a deeply personal thing, varying from person to person. If we can contribute to someone else’s happiness, why wouldn’t we do it? If we achieve nothing else in a day but bringing happiness to others we can consider that day a success.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

Two things tend to keep me up at night.

The first is personal growth. Am I adapting quickly enough to the changes taking place in the world to maintain my relevance and value? The second is stewardship of companies. Am I creating an environment where colleagues, customers, and prospective employees look at our company and say, “That’s where I want to be”? I know that I don’t get it right in either category everyday and thats why I reflect, and course-correct, on a regular basis.

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. 🙂

The movement I would start already exists — it’s the Scouting movement. Worldwide, every scouting program shares a common goal: to help youth make moral and ethical decisions over the course of their lifetime. I don’t know if there’s a higher calling. If we can achieve this, think of the remarkable adults we will create.

How can our readers further follow you online?

The best way to connect with me is on LinkedIn.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.