Hiring rarely fails because you chose the wrong candidate.
It fails because someone didn’t ask the right question at the right moment, and everyone pretended everything was great.

Most recruitment failures start with everyone nodding along.
A job brief no one questions.
A salary everyone knows won’t attract the right people.
And unrealistic timelines.

Here’s the uncomfortable truth:
If your recruiter isn’t brave enough to say it out loud, the difficult issues left unchallenged will rear their ugly head - further down the line, are you willing to take that risk?

And I don’t say that from theory. Long before Skillfinder existed, and for many years after I co-founded it, I was still a hands-on recruiter delivering FS roles across Europe.
I’ve stepped out of day-to-day delivery as the business has grown, but I stay close enough to the work to understand exactly what our consultants deal with every day.

So, when I say hiring works best when the difficult conversations happen early, it’s because I’ve seen it play out time and time again across real hiring processes.

Professional courtesy matters.
But when it replaces honest challenges to the requirements gathering process - especially in a fast-moving environment, it becomes a vulnerability.

Great recruiters don’t avoid the awkward questions, they keep asking until there’s a full understanding of what’s needed and what’s at stake.

Why Hard Questions Make Your Hiring Better
If you’re hiring in financial services, fintech, or technology in general, you already know the stakes: one wrong hire can slow delivery, strain compliance, stall transformation, or overload an already stretched team. (not to mention the HR headache of fixing a bad hire).

You don’t need recruitment that tiptoes around the issues.
You need recruitment that brings clarity before the market exposes the gaps.

When those tougher questions happen early, three things shift:
1. Your brief becomes specific and manageable.
Roles often start with responsibilities added over time or requirements that don’t realistically belong in one position.
Early questioning helps you identify the essential responsibilities and the outcomes the role must deliver in the first 6–12 months. The rest of the skills and responsibilities, become the ‘growth’ potential for the role.
This prevents you from searching for a profile that doesn’t actually exist. (and if you do, by some miracle find someone with all the skills and experience you are looking for – why would they take the role – what’s left to learn?

2. You’re aligned with the market reality before you begin.
In FS, fintech, and tech, the market moves quickly:
•salary bands & rates shift
•remote working flexibility expectations change
•high-demand skills become even more difficult in certain locations
Getting the approach right before going to market ensure your expectations match what candidates will actually respond to today, not what worked a year ago.

3. You avoid the delays caused by misalignment.
Most hiring slowdowns come from unclear roles or mismatched expectations, not a lack of talent.
When these issues are resolved upfront, you get avoid:
•Better expectation management - between all parties
•Clearer Job descriptions
•Less candidate drop-outs at the last minute

The process moves faster because everyone is aligned.

A recruiter who avoids these questions is keeping things comfortable. A recruiter who asks them is keeping things safe.
And yes, we talk a lot about asking the hard questions, but the truth is, they’re simply the right questions. They’re the questions that stop a process drifting, protects project timelines, and make sure the hire actually succeeds.

What Those Questions Look Like in Practice
Here are the kinds of questions our consultants ask, direct, practical, and based on real hiring patterns:
• “This role expects senior-level delivery on a mid-level salary. Either we need a higher salary, or allow the person to grow into a Senior role?”
• “You’re asking for fully on-site, but every competitor hiring this skillset offers hybrid. Are you prepared for a smaller talent pool?”
• “Market-standard processes are two stages. If you keep three, are you okay with slower hiring?”

These aren’t confrontational questions, they’re designed to make you understand what your options are if the ideal candidate isn’t out there.

They prevent wasted search time, protect delivery deadlines, and ensure the process is built on reality, not assumptions.

Financial Services, Fintech, and Tech Have No use for ‘Polite Recruitment’
In these sectors, mis-hiring doesn’t just cause inconvenience.
It can:
• delay transformation programmes
• slow engineering or product delivery
• increase compliance pressure
• trigger re-hiring cycles
• inflate salary expectations due to delays
• strain already overloaded teams

None of these issues appear suddenly. They start when early conversations stay too soft or too vague.

Challenge isn’t confrontation.
It’s testing, probing and building a realistic plan.

Hard questions don’t slow you down.
They enable clarity, manage expectations and create realism – ultimately improving time to hire.

And finally, if your recruiter never challenges your assumptions, your timelines, or your brief, they’re not protecting you - they’re failing you.

The consultants who excel at Skillfinder aren’t difficult people. They’re deliberately challenging. They ask the questions that matter so you can make confident decisions in environments where results are expected.

If you want recruitment that protects your delivery, not just fills your vacancy, let’s talk.

Our specialists will show you what a genuinely challenging, genuinely useful partnership feels like.

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