In this episode of Reboot IT, host Dave Coriale, President of DelCor, sits down with David Stephenson, SVP of Technology at Entrepreneurs’ Organization, to unpack what true collaboration really means in associations and nonprofits. Together, they explore the difference between transactional vendor relationships and deep strategic partnerships, how to build psychological safety within project teams, and why honest dialogue is essential for successful outcomes. David also shares practical tactics for selecting partners, navigating conflict, and reducing organizational risk through collaborative practices. Themes and Topics: What Collaboration Really Is (and Isn’t) Collaboration isn’t about being nice or making sure “everyone’s at the table.” It’s about having the right mix of people with different perspectives.When everyone thinks the same and has the same motivations, you end up with polite agreement, not real progress.There’s a big difference between just enlarging a meeting and actually collaborating with intention.Getting the Right Mix: Staff, Members, Vendors, and Partners Associations juggle vendors, partners, staff, and members, each with different levels of involvement and motivation.David distinguishes between people who are in the weeds with you (like design and development partners) and those who play a key but more behind‑the‑scenes role (like hosting providers).Upfront, he works to get everyone on the same page: What problem are we solving? What role do you play? What’s your motive (and recognizing that everyone has one, and that’s okay)?Vendors vs. Partners: Building the Right Kind of Relationship In his head, David does see a spectrum: some are more transactional services (SaaS products, integration tools), while others are strategic partners who need to understand mission, business objectives, and strategy.He tries not to use the word vendor in conversation and instead works to make everyone feel like a partner, even if their role is more narrow.When negotiating, he looks for a fair outcome on both sides — if a partner walks away with “really thin margins,” you end up with constant “change order” moments and a strained dynamic from day one.Honest Dialogue, Healthy Friction, and Psychological Safety David values partners who can say things like “That’s just not possible,” or “That doesn’t align with the strategy you described,” instead of always saying yes.He expects and welcomes friction and hard conversations around timelines, costs, and expectations. If there’s zero friction, something’s probably off.Psychological safety is key: people need to feel they can disagree, say “I don’t think this is working,” or ask tough questions without fearing for their job, contract, or relationship.Doing the Work: Projects, Postmortems, and “Disagree but Commit” David admits he hasn’t “cracked the code” on postmortems, but he knows they only work if people feel safe enough to speak up during the project, not just after.When collaboration is done well, it may feel slow at the beginning, but it ultimately makes the work go faster and smoother than siloed, go-it-alone approaches.He likes setting expectations from the start: speak up when it’s “cheap to disagree,” and embrace the idea of “disagree, but commit” so the team can move forward with one voice.Collaboration as Risk Reduction for the Future David sees collaboration as a way to de‑risk his future; the stronger his network and partnerships, the better prepared he is for what’s coming.Staying insular and only looking inside your own team or organization raises your risk, especially in fast-changing areas like technology and AI.By collaborating widely and intentionally, associati
