When a C-suite role opens up, most executives instinctively ask the same questions: Have you done this before? How many C-level executives have you placed in our sector? Do you know the competitive landscape? Who are your relationships? What candidates do you know?
All reasonable questions. But there’s a better one to ask.
To understand why, it helps to look at how executive search firms typically position themselves, and to be clear, these are real differentiators that reflect genuine value. Most firms lead with one of three things: their track record of placements, proprietary assessment tools that bring rigor to candidate evaluation, or deep sector relationships built over years. Each of these matters. But taken alone, none of them answers the question that should be driving the conversation.
Track record tells you where a firm has been, not whether they understand where you’re going. Assessment frameworks tell you how a candidate performed in a controlled conversation, not how they’ll perform in your business. And sector relationships, for most roles, can quietly narrow the field in ways you might not expect. A firm deeply embedded in your industry may have off-limits conflicts with the very candidates you’d want to consider. And even when those candidates are available, hiring directly from a competitor rarely delivers the advantage it appears to, they come with the same assumptions, the same playbook, and often the same blind spots.
Meanwhile, the strongest candidate for your role may never have considered your world as an option, either because they have preconceived ideas about your company, or simply because no one has ever put it in front of them. That said, this isn’t a universal rule: in some highly specialized fields, regulated financial services, for instance, deep sector focus is exactly what’s needed, and rightly so.
Here’s what actually matters across most searches: does the person you’re working with understand your business well enough to know what success looks like in this role, and then go find it, wherever it lives?
That’s a harder conversation to have. It requires asking uncomfortable questions early:
- Is this a status quo hire, or do you need someone to challenge and disrupt how things are done?
- What’s the real problem this hire needs to solve?
- What does the leadership team around this person look like, and what gaps does that create?
- What’s failed before, and why?
- Where is the business trying to get to in five years?
- What kind of leader does that version of the company need, not the current one?
The answer to that last question changes everything about where you should be looking.
Most search processes never get to this level of conversation. They lead with credentials and close with case studies. The business understanding, and the need to change, that part gets assumed, or skimmed over in the first meeting.
The briefing process deserves to be treated as seriously as the search itself.The brief is the search. Get it wrong, anchor too heavily on industry background, over-index on a particular pedigree, and you’ve already narrowed the field before you’ve even started.
Some of the most effective executive hires come from adjacent industries or roles that don’t look like an obvious match on paper. The pattern isn’t random, it’s the result of someone asking not “who’s done this job before?” but “who has the capabilities, the drive, and the leadership character to do it here, now, in this context?”
That’s the question worth being obsessed with.
So next time you’re evaluating who to work with on a search, ask them to explain your business back to you. Ask them what they’d need to understand before they start. Ask them where they’d look, and pay attention to whether that answer surprises you.
Sachin Sama
Partner
ssama@mbexec.com
(416) 238-1084
Sachin Sama serves as a Partner at McDermott + Bull Canada and is part of the firm’s Energy + Industrials Practice, based in Toronto. He also brings deep expertise in the Consumer sector, where he partners with clients to identify and place transformational leaders who drive growth and change.