15 Questions Every New Hospital Leader Should Ask

Written By: Justin Wasserman

The best leaders don’t come in with answers. Often, they come in asking the right questions.

Stepping into hospital leadership (or any leadership role) – whether you’re a new CEO, COO, CNO, or system-level executive – is less about declaring bold plans and more about understanding what you're walking into.

What’s working, what’s hiding, what’s under-leveraged, and most importantly on what’s possible?

The highest-performing leaders I’ve worked with start by asking questions that pierce through surface-level reporting and reveal the real levers of change. These aren’t questions for an orientation packet. Instead, they’re diagnostic tools for transformation.

Here are 15 questions every hospital or health system leader should be asking in their first 90 days:

1. Do you know what your hospital is capable of achieving?

   Before we ask how to fix or grow, we have to ask: what’s possible? Most systems underestimate their own potential.

2. What are our current patient satisfaction scores, and what trends have emerged over the past two years?

   A point-in-time score doesn’t tell the full story. But the trend line and what’s driving it reveals more than you think.

3. Where do our quality metrics stand compared to industry benchmarks? Which areas show the greatest opportunity for improvement?

   You don’t need to fix everything. Just the right things.

4. How efficient are our operational workflows especially in high-volume areas like the ED and surgical services?

   Throughput tells you what your culture, systems, and collaboration habits look like under pressure.

5. What’s our staff turnover rate by department? What’s worked (and not worked) in retaining talent?

   You can’t fix what you can’t segment. And you can’t keep people without understanding why they stay.

6. Does our strategy reflect past performance or an aspirational future?

   Strategies rooted in past limitations often cap future potential before it even starts.

7. How aligned is the leadership team around current priorities and definitions of success?

   A misaligned leadership team is one of the most expensive liabilities in a hospital. And one of the most fixable.

8. How well do departments communicate with each other and with leadership?

   If the front line is surprised by leadership decisions, or vice versa, you're not leading. You're guessing.

9. What’s our current financial health, including revenue cycle performance, payer mix, and cost structure?

   The truth isn’t in the budget. It’s in the underlying behaviors that shape every dollar earned or lost.

10. What’s our technology infrastructure and what transformation efforts are already underway?

    Digital initiatives die not because they’re the wrong idea, but because they lack operational lift.

11. What are our most significant compliance or risk management concerns?

    Compliance is not just about passing audits. It’s an early warning system for systemic breakdowns.

12. What succession planning exists for key leadership roles? How are we developing our internal talent?

    If your best people leave or retire, do you have a next line ready or do you start from scratch?

13. How are we addressing health equity and local community needs?

    Equity isn’t a parallel track. It’s embedded in how care is accessed, delivered, and measured.

14. How well do we understand the interdependencies that affect strategy execution?

    Most execution fails not because the strategy was wrong, but because the system didn’t understand how everything connects.

15. Are the people closest to the work empowered to surface and solve problems?

    Execution accelerates when psychological safety and frontline trust are part of the operating model.

Bonus Insight: Real Change Often Comes from Counterintuitive Places

Some of the biggest performance breakthroughs I’ve seen didn’t come from million-dollar tech upgrades or sweeping reorganizations. They came from unexpected sources:

• A turnaround driven by a team choosing the counterintuitive option in a “Would You Rather” scenario.

• A physician’s frustration over coding that opened the door to tens of millions in margin improvement.

• An unusual department surfacing a LOS problem no one else could see – until they looked.

• A team that finally fixed on-time discharges not with new checklists, but by building real trust across roles.

Those stories start not with clever fixes, but with the courage to ask better questions.

New role. New system. New opportunity.

The questions you ask today will determine the results you unlock tomorrow. And in a field where the stakes are high and the margin for error is thin, there's no greater competitive advantage than clarity.

At Empactful Advisors, we're passionate about helping hospital and health system leaders uncover clarity, align their teams, and drive meaningful performance improvement. If your organization is ready to explore what's truly possible, book a free discovery call with us.