How to Spot and Succeed in a Pain Point Leadership Role
- Martin Hill
- 3 hours ago
- 4 min read
In 2025, nearly 74% of global employers report difficulty filling roles, according to Man power Group a figure that has more than doubled since 2014. (ManpowerGroup Talent Shortage Report 2025)
But here’s what’s quietly changed: senior roles aren’t being created to seize opportunity. They’re being created to solve urgent, internal problems, often ones that have been ignored for too long.
Executives aren’t stepping into growth mode anymore, they’re stepping into messes. Whether it’s broken systems, toxic teams, or revenue decline, senior hires are now “pain point hires.”
The problem? You rarely see the full scope until after you sign. This article is your guide to spotting the warning signs early and making smarter choices when you’re in the room.
Why Pain Point Hiring Is on the Rise
Companies used to hire senior leaders for the future: expansion, innovation, scale. Now, leaders are being brought in to fix the past.
Why the shift?
Delayed decision making: Budgets and headcounts are tight. Leadership often waits until dysfunction is undeniable before approving a hire.
The illusion of stability: Roles are posted under optimistic banners, “growth,” “transformation,” “scale” but what they really need is a fixer.
Executive turnover and burnout: When executives exit, new leaders are expected to clean up legacy issues without full context or support.
As a result, many senior leaders are finding themselves blindsided. They walk into roles that looked strategic but are actually fire drills. And often, the hiring team doesn’t disclose how bad it is or doesn’t fully know themselves.
Red Flags to Watch for During the Interview
The interview process is often your only window into what’s really going on. Here’s what to look (and listen) for:
Vague Language
Phrases like “we need fresh thinking” or “we’re at an inflection point” can sound exciting, but if they’re not backed by specifics, they often signal uncertainty or crisis.
Ask:
What specific challenge am I being hired to solve?
What would success look like in my first 90 days?
Defensiveness or Evasion
If you ask about prior leadership turnover or what hasn’t worked and the response is cagey take note. Avoiding hard truths often means deeper problems lie beneath.
Ask:
What’s the history of this role?
What has already been tried that didn’t work?
Why now? Why not six months ago?
Lack of Role Clarity
When senior roles are reactionary, scopes tend to be murky. If your job description includes “build strategy” and “solve operations” but also “lead culture” chances are, the org hasn’t decided what it actually needs.
Ask:
What are the top 3 priorities for this role?
How will I be measured?
What’s the first decision I’ll need to make in this role?
Thin Support Structure
You’re being asked to fix a fire, but are they giving you the hose? If budget, team, or authority are vague or “TBD,” you’ll likely lack the tools to succeed.
Ask:
What budget and team are allocated to this role today?
What decision rights will I have from Day One?
What to Clarify Before Accepting the Offer
If you’ve made it through the process and an offer is on the table, if the market is tough you might still be considering the offer.
Here’s a are 5 Questions to Ask Before Accepting so you know what your really getting into:
What are the top 3 things I need to fix in my first 90 days?
Who owns this problem today, and why can’t they solve it internally?
What’s the performance history of this role or team?
What are the constraints, political, budgetary, cultural that I need to know now?
What happens if this fix takes longer than expected am I supported or replaced?
If the answers are unclear, inconsistent, or sugar coated, take pause. The bigger the gap between the sales pitch and reality, the harder your landing.
Reclaiming Your Leadership Narrative
Once you’re in, your job is two fold: survive the immediate fix + reframe the role for growth.
Here’s how you reclaim your leadership narrative:
Frame your first 90 days not just as damage control, but as groundwork for sustainable growth.
Publish a roadmap: Stabilisation → Capability Build → Expansion. Share that with key stakeholders.
Build wins early: even small wins build credibility, clean up an operational bottleneck, improve team morale, fix a key metric.
Align with future strategy: Show how the fix you’ve delivered enables the next phase of growth. Then position yourself for that.
Communicate your value: Use the stabilised foundation as a platform for your own brand: “I came in to fix X, we’ve resolved X, now here’s how we move to Y.”
By doing this, you turn what could feel like a high stress firefighting role into a strategic leadership story and one that bolsters your career rather than drains it.
Conclusion: Know the Fire Before You Walk Into It
Pain point hiring is the new normal. Senior roles are no longer bets on the future they’re fixing the past. But that doesn’t mean you have to walk in blind.
By asking the right questions during interviews, spotting misalignment early, and negotiating terms that reflect the real scope, you can take on these roles with clarity and strength.
For more strategic tools to navigate your next leadership move, check out: Ageism in the Workplace: The Hidden Bias Costing You Top Talent, How to give feedback in the workplace: Tailor your approach to 7 types of learners, 6 Ways to Lead Without Been the Boss