Lessons from Two Decades of Community Strategy: What's Changed, What Hasn't, and Where We're Headed

Highlights from my recent podcast interview

Yesterday, I had the pleasure of being Tom Diederich’s inaugural guest on his new podcast, Tribal Knowledge. We dove deep into community building, from my early days organizing Fast Company meetups in Louisville to helping shape strategies for companies like Autodesk and IBM. Here are the key insights from our conversation.

The Fundamentals That Haven’t Changed

I’ve been developing community strategies and experiences since the late 90s, and I still feel and try to act very much like a practitioner, learning every day when I allow myself. While anyone who claims to have it all figured out is likely missing the bigger picture, some truths about community development have remained constant.

One of my earliest lessons came from organizing Fast Company Magazine’s Company of Friends meetups in Louisville. I was terrified, trying to overplan every second of those two hours. But I learned that if you provide a quality space and some compelling topics, nine out of ten times, that alone will attract the right people to have a really solid conversation.

It just blew me away that you could convene a group through email invitations (at the dawn of the web) and have people who’d never met create something meaningful together. That taught me the persistent and sustained value of local, in-person events. Coming out of the digital isolation of the COVID-19 pandemic, there’s still a strong desire for people to gather face-to-face.

The Essential Community Strategy Framework

Through years of leading community at Autodesk and Dell, and working with clients at Structure3C, I’ve developed what I consider the essential components of community strategy. These aren’t nice-to-haves; they’re the foundational elements that separate thriving communities from those that struggle or fail.

• Strategic Alignment: The community is aligned with core business goals. It’s not a side project, but a layer of strategic infrastructure. As I mentioned on the podcast, community strategies and investments have to be strategically aligned with business objectives and resources internally. This provides the environment for success.

• Networked Ecosystem: The community is not confined to a platform. It lives across digital and physical spaces as an ecosystem. We’re beyond the age of community as a singular platform. In fact, I don’t know that we were ever really in that age, although platform vendors wanted us to believe it. We’re really building these networked ecosystems of in-person and online events.

• Community Co-Design: Programs are built around real member needs and motivations, not just organizational agendas. This is what I mean when I talk about empathy: doing things with and not for. It’s getting people on board way before you finish selecting vendors, co-developing your reputation system with MVPs before it sees the light of day.

• Long-term Commitments: Leadership understands that community value grows over time and invests accordingly. Communities come into play in moments of exception, celebration, and transition. There’s a dimension of that happening over an entire career that we’re just beginning to explore.

• Operational Clarity: Through programs and resources, there is structure, accountability, and measurement without losing soul. This translates operationally into a playbook that articulates programs, resources, and maintains a red thread throughout of why we’re doing this. That story of balanced corporate objectives and what the community actually wants.

Balance: Authenticity vs. Business Goals

I have a potentially prickly point of view on this. I’ve seen businesses exploit vibrant communities they’ve developed, but I’ve also seen well-intentioned community leaders try to protect the community from the organization. Both are damaging.

Why does the organization have a community in the first place? Why would there be such an adversarial relationship? One person isn’t going to solve that problem.

For me, trained as a designer, everything looks like a design problem. The key is research upfront, both with the business and with the existing or representative community members. You need to understand that balance of needs, predispositions to participate, and what the business wants to achieve.

One thread resonating with executives these days is centering on community as a way that customer relationships come together and are reinforced. You’d be hard-pressed to find an executive who doesn’t value customer relationships (at least not one who’ll remain an executive very long).

Measuring Success

When executives ask, “How do we measure community?” we start with a baseline scorecard with three components:

1. Reach: Based upon the potential size of your community and key components of your ecosystem (hosted presences, partner presences, platforms like Discord, social), how are you performing? It’s performance versus potential.

2. Engagement: What percentage of customers are actually participating? Participation could range from feeling a sense of community to going deep as an advocate or MVP.

3. Business Impact: Building a story around qualitative and quantitative data. Performance towards goals like renewals, retention, the role community plays in path to purchase. Balance this with qualitative data, pulling stories forward.

Reach, Engagement & Impact examples

The scorecards don’t have to be bland, lifeless dashboards. For example, at Autodesk, we had a cool (I think) gratitude index for our social help channel, tracking how many times someone said thank you or expressed positive sentiment. We measured against 20 other brands supposedly leading in social. It wasn’t just about our conversations, but our performance against other leaders in the space.

The Undervalued Skills of 2025

Tom asked about community leader skillsets, and in particular, which skills are undervalued or underdeveloped. I responded that when I hire or help place community professionals, I look for:

• Situational Leadership: Knowing how to lead within the community, lead their team, and manage up with senior stakeholders. They reconfigure themselves in any given context.

• Communication: Can they articulate value to the community in a way that reinforces participation? Can they present program performance to their team? Can they distill information for two minutes in a quarterly business review? It’s all configuration of the same data set.

• Creativity and Imagination: Creativity is the ability and willingness to solve problems. Imagination extends that ability to think forward. “What if we did X? How might we approach Y?”

• Self-Awareness and Self-Care: If your batteries aren’t full, you’re not going to transmit energy and enthusiasm to others. You’re Atlas with the whole community on your shoulders. The organization with thousands of people, the community potentially with millions, and you’re one of the tiny interfaces between those two gigantic dynamic systems. I wound up in the hospital after a community launch at Autodesk. It was terrifying.

Beyond Platforms and Peak Social

Looking ahead, I believe we’re emerging from what I call “peak social.” For years, social media hijacked the idea of community, sucking the attention and budget out of the room. Now, people understand the difference between an algorithmically driven experience on Facebook and an authentic, member-focused community that is designed to help people get to know each other over time. Authentic community leadership is taking back its rightful place.

This shift is fueling a renaissance in the community platform space. After years of commodification, I’m seeing platforms think more strategically about tying community into the overall customer experience. The vocabulary of interaction is finally expanding beyond just text to include richer exchanges based on more complex digital artifacts and more immersive digital environments.

Of course, AI is the accelerant in all of this, with both good and bad aspects. It brings challenges we haven’t solved, like who owns the training data in our 20-year-old knowledge bases and how contributors should be compensated. But it also opens up incredible possibilities. We need to start thinking about designing not just for transactional customer journeys, but for lifelong, career-long journeys where community supports members through moments of transition, celebration, and need.

Despite the layoffs and pressures our industry faces, there has never been a more interesting time to be in this field. There are so many frontiers to explore. We have an amazing playground to play on and experiment with right now.

Full Interview

You can watch the video of the full interview here:

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What resonates with you from these lessons? What challenges are you facing in your community work? What opportunities do you see?

I’d love to hear your thoughts in the comments.