The Questions Your Search Partner Should Be Asking You

Before the pitch, before the candidate list, the quality of the questions predicts the quality of the hire.

This article draws on a Cornerstone International Group roundtable on earning the right to advise, featuring Antonio Cassano (Cornerstone International Italia), Samuel Dergel (Cornerstone Montreal), Dan Heiman (Global President, Cornerstone International Group), and Göran Jansson (Cornerstone Nordics), moderated by Larry Shoemaker (Vice Chairman, Cornerstone International Group). Client examples are shared with details withheld to protect confidentiality.

Dan Heiman, Global President of Cornerstone International Group, made an unusually candid admission during a recent Cornerstone roundtable. Reflecting on how his team had approached first meetings with prospective clients over the past two years, he realized they had drifted into pitching, leading with how good the firm was. And he concluded it was a mistake.

“It’s going in and asking thoughtful questions to understand what they’re looking for before you ever think about pitching,” he said. If a search firm spends your first meeting talking about itself, that tells you something about how it will run your search.

“Great advisors ask better questions before they provide answers.”  – Larry Shoemaker

The question that changes the search brief

Most organizations can describe the requirements of a role in detail. Far fewer have articulated what the person in that role must actually achieve. Göran Jansson, Managing Partner of Cornerstone Nordics, says one question consistently changes the direction of a search conversation: what are the objectives for this role? What must this person accomplish in the first six months, in two years, in three?

It sounds ordinary. 

In practice, clients often discover the answer has not been fully worked out, and once it is, the search profile changes. 

The background that fit the job description does not always fit the objectives.

Position or leadership challenge?

Samuel Dergel, Managing Partner of Cornerstone Montreal, opens with a sharper version of the same idea: are we trying to fill a position, or are we trying to solve a leadership challenge? 

He learned to ask it the hard way, by helping clients hire the person they said they needed and watching it fail to help the business. What a client asks for and what the business needs are not always the same thing, and a good partner is obligated to close that gap before the search begins, not after the hire struggles.

“We’re not here to fill a chair. We’re here to solve a challenge.”  – Samuel Dergel

Three expert-level questions to expect in a first meeting

Heiman offered three questions his team now asks early in every engagement, and each one protects the client’s outcome.

1. How healthy is the team this person will lead? 

The answer determines whether you need a turnaround leader, a stabilizer, or a technical expert. The same title can require three very different people.

2. What are the three to five things that must be true of this person? 

Not the full wish list. The short list that separates a real requirement from a preference, so the search targets what matters.

3. What does success look like one year and three years from now? 

If the hiring team cannot answer this together, the search is not ready to start, and running it anyway is how mishires happen.

From process to outcome

Antonio Cassano, Managing Partner of Cornerstone International Italia, frames the stakes plainly. Clients are not really buying a placement. They are buying performance, stability, and leadership impact. That is why his firm treats post-hire support as part of the work rather than an extra service, and why the early questions matter so much. 

A search designed around a placement ends at the offer letter. A search designed around an outcome ends when the leader is succeeding.

For buyers of search, the practical advice is this: pay attention to what a prospective partner asks in the first meeting. The rigor of those questions is a preview of the rigor they will apply to your candidates.

Cornerstone International Group is a global alliance of retained executive search and leadership consulting firms with 60+ offices in 40+ countries. To talk with a Cornerstone consultant about your next leadership decision, visit cornerstone-group.com.