By Tom O’Connor

I’m young enough to have spent all of my professional career with email, and old enough that a former assistant had to practically wrench my physical Rolodex from my hands to convert it to a digital contact file (to be clear, I had both for different purposes, but that’s enough of story hour). Now, years later, there is still a phrase that I hear in almost every executive search proposal process: “how strong is your rolodex for [x position]?”

It’s a fair question—connections do matter. But a search grounded only within the limits of one person’s (or even business’s) pre-existing network can be surprisingly narrow and is not bringing you the type of responsive and informed candidate pool you deserve. If you are selecting a search partner, here are some additional areas we suggest exploring.

Ask About Systems

The strength of an executive search partner doesn’t just live in who they know off the top of their heads. It also lives in the systems they’ve built to reach far beyond the people they know already and to extend the invitation to people who are just right for your job. If an executive search partner tells you they have everyone they need in their existing database, kindly excuse yourself and run away. Fast.

Robust candidate research is what ensures that you don’t just see the usual suspects, and that a diverse array of qualified candidates are given an equitable shot. It means combining deep industry knowledge with thoughtful analysis of transferable skills and sector nuances, structured sourcing strategies including robust technology tools, and targeted, personalized outreach. It’s the discipline of uncovering great candidates who might not be in anyone’s “Rolodex,” and who could bring exactly the vision and experience your organization needs.

Ask About Process Facilitation

The contacts are important, but most searches that we hear of that are not successful—or honestly, that we “inherit” to finish—have fallen down on process. It is important to understand how the process itself is designed and facilitated when speaking with a prospective search partner. A strong search partner helps you move through the work in a way that is organized, transparent, and tailored to your context, and has a clear point of view on what their role in the process is and is not.

In our case, that role includes co-creating clear selection criteria, ensuring stakeholder alignment, soliciting thoughtful and intentional feedback from stakeholders invited to meet the candidates (and making it clear who is and is not making the decision), and guiding the search committee or hiring manager through interviews and deliberation with a sense of purpose. Meeting agreements are about more than guardrails and rules of engagement. They can define group expectations, ensure all voices are heard, and make space for challenging conventional wisdom or groupthink. All of this is essential to an equitable outcome and one that all constituencies represented on your committee can feel good about.

Good facilitation isn’t just about keeping things on schedule—it’s about fostering clarity and confidence in the decisions you make together, and building buy-in at every step. As I often cite from my social work training, “process becomes content,” and the way we work together informs the decisions we make and strengthens our relationships.

Ask About Candidate Care

And finally, there is the matter of candidate care, which is a large part of what drives us in this work. The way candidates experience your search process will shape how they feel about your organization whether or not they become your next leader. It is an extension of the brand promise you carry. Respectful communication, timely updates, and thoughtful engagement at every step are not incidental details. They are central to building trust and demonstrating your values in action.

When candidate care is treated as a priority rather than an afterthought, the process becomes more humane and more effective. As my colleague Jordan often says, “in everything that we do, we should be building a community of good will” and I just can’t say that any better. In competitive job markets and at critical consideration points in an individual’s career path, our work demands a profound degree of humanity…and yes, one that AI cannot replace. Ask your prospective search partners what their practice standards are around candidate care. Even better, ask some of their candidates.

So yes, ask about the Rolodex. But also ask about the systems, the facilitation, and the care. Because a successful search isn’t only about who you know—it’s about how you do the work. And it matters.

Tom O’Connor is the President of Tom O’Connor Consulting Group. TOCG is a NYC-based consultancy for arts and cultural institutions and leaders, offering two complementary services: organizational strategy and executive search. Tom has spent nearly 20 years working in the cultural sector, has served on the faculty of graduate programs at Yale University and Brooklyn College, and received his MSW in Clinical Social Work from Fordham University. He also hosts the podcast “Changing Arts with Tom O’Connor.”