Leading with Culture: Joel Bennett's Approach to Team Success

Joel's move from in-house HR roles to fractional leadership was driven by his passion for tackling tough issues and building open, transparent communities within organizations. As he puts it, "I enjoy helping business owners and managers wrestle with the elephants in the room." His approach fosters trust and accountability, creating stronger, more resilient company cultures. 

Q: Can you tell us a bit about yourself and your career journey? 

A: I've been an operations professional for over 15 years with a background in non-profit management For a decade, I had my dream job and ran summer camps for kids up in Wisconsin and Pennsylvania. There's no better way to do a one-on-one supervision meeting than on a stand-up paddleboard! But dreams have a way of evolving once your family consideration change and spending half the year on the road was not what I had in mind as a new Dad. I left my full-time role and founded Deep Dive HR Consulting, focusing on Human Resources support for small, medium, and growing businesses. We launched two and a half months before the pandemic, and that was a big pivot for me.  

Originally, the focus was going to be in the camp world and the non-profit space. But my first client was a marketing and advertising agency, and my second was a not-for-profit working with adolescents and teens with developmental disabilities. Today, we serve clients ranging from cafés and coffee shops to behavior therapy clinics and outsourced IT. What distinguishes us in the market is that we have experience across different industries, and we provide support either on a short-term basis (e.g., when someone is on parental leave or a business owner needs an interim solution) or fully outsource their HR department to our team. We just hit our five year anniversary. 

Q: What initially drew you to non-profit work, and then to consulting? 

A: I’d say my family had a lot to do with it. My dad is a social worker, so dinner conversations often revolved around community involvement and helping others. My first job out of college was with a not-for-profit focused on student and faculty coalitions. I’ve always felt strongly about working towards a greater mission—it feels great to make an impact beyond just a bottom line. Consulting was a natural extension of that because it lets me apply those skills and experiences to a wide range of organizations. 

Q: Speaking of challenges, what’s one of the biggest problems you've faced as a consultant, and how did you approach it? 

A: Two major issues come up a lot. First, many growing businesses don’t invest in systems and processes. They’re focused on delivering their product or service, so when we come in, we often start with a "deep dive" to ensure their foundational aspects are covered. Second, management challenges are common—managers may think they know how to lead, but often lack the skills needed to engage their teams effectively. We do a lot of management coaching to help leaders set their teams up for success. 

An example: The summer of 2020 the COVID pandemic was a huge curveball for everyone. In particular, the unrest and frustration in communities around the country regarding the murder of George Floyd and others that summer. Many employees were isolated while working from home, and they were grappling with how to bring their full selves to work. There was a shift from “I put an emotional mask on to be at work”, and “I am my whole self at work”. And so, how am I seen? How am I viewed? How is my voice relevant, and can it be heard? Balance that with the fact that work isn't a support group. The goal of work is to do whatever the work is. And it’s often the job of HR to help negotiate that balancing act.  

My experience, working with nonprofits, working with companies that had been in person, working with companies that were always remote has given me a range of tools and perspectives. We helped clients establish support groups, create resource lists, and develop best practices around inclusion—things that became essential for employee well-being during such a chaotic time. 

Q: How did you provide support during this time when people and companies were being hit physically, emotionally, and mentally? 

A: It was important to give people a sense of community, even through a screen. Early on, we used phrases like “we’re all in the same storm but not in the same boat,” recognizing that everyone’s needs were different. We leveraged technology in new ways, like Zoom and Slack, to keep people connected. We held virtual happy hours and encouraged people to express their personalities. Onboarding became intentional, with two-week plans to include virtual coffee dates and lunches. As we transitioned out of the pandemic, the focus shifted from remote work logistics to defining how and why community is vital in the workplace. 

I think the other significant focus was authenticity. People want to work with companies that are true to who they are. In our work with clients, we help them define their culture and values in ways that go beyond perks or physical objects.  

Q: When you were doing this at the time, was helping companies define their culture a new concept for them? 

A: Pre-pandemic, culture questions were often answered with things like “we have a foosball table” or “we celebrate birthdays with specialty cupcakes.” But during the pandemic, we couldn’t rely on those kinds of physical perks. So we worked with business owners and managers to intentionally create moments of gathering and community in virtual ways. This included hosting virtual talent shows, garden tours, and even virtual whiskey tastings. 

But it's not about those activities themselves. The culture isn’t the activities; it’s about why those activities matter. We focus on articulating the importance of community and creating “sticky” work environments. That’s what drives engagement and retention. 

Q: What motivated you to transition from more of a traditional HR role to consulting? And what's been fulfilling about that change? 

A: I had been in traditional HR for about 10 years. As we’ve discussed about, the pull was wanting to be present for my family and have control over my own time. The pandemic meant I basically ended up not leaving my house for two years, so the universe really gave me the right push. 

What I love about consulting is helping business owners and managers navigate those difficult conversations—identifying the elephants in the room, calling them out, and tackling big problems that often feel insurmountable. The approach isn’t to move the whole mountain at once but to break it down into smaller, more manageable steps. I find it fulfilling to help businesses work through these issues by setting goals and making incremental positive progress.   

I enjoy asking questions, listening, and being able to provide that outside perspective. As an external consultant, I’m able to offer a more honest approach. When I’m in-house, there are politics and dynamics that prevent me from being completely direct. As a consultant, I can be much more candid, and I think that adds a lot of value to the work I do.