“We need someone who will challenge us.”
When taking a brief for a senior financial-services role, there’s plenty to cover: technical expertise, leadership experience, regulatory responsibilities, salary, team fit and why the right person would want the job.
But when a hiring manager says they want someone who will challenge decisions, it’s worth spending a little longer on that point.
Challenge whom? On what? And what happens when they disagree?
It’s easy to welcome challenge in an interview. The real test comes when your new hire questions a decision you’ve already made, pushes back on group headquarters or tells a longstanding colleague that their approach needs to change.
That’s where the recruitment brief needs to go beyond “confident communicator” and “strong stakeholder management”.
I want to understand how decisions are made internally. Where will this person have authority? Will their manager back them when their judgement is sound but their message is unpopular?
And can the people receiving that challenge take it professionally, without treating disagreement as a personal attack?
If a reasonable challenge leads to defensiveness, strained relationships or an extra layer of approval every time that person wants to act, you’ve created a bottleneck. You’ve also taught them that speaking up comes at a cost.
Equally, we need to assess how the candidate challenges. Can they explain their concerns, offer a workable alternative and hold their ground respectfully? Can they accept challenge themselves?
In a small Irish financial-services team, those relationships matter enormously. You may need someone who can challenge a board decision in the morning and work constructively with the same people that afternoon.
Getting the hire right means understanding both the person’s ability to speak up and the organisation’s willingness to listen.
A senior title is only useful if the person can actually challenge decisions.
When you ask for someone who will challenge you, what will happen the first time they do?