33 Questions Great Executive Directors Use to Coach Their Teams

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​Strong Executive Directors are often distinguished not simply by the answers they have, but by the questions they ask.

In senior living, an Executive Director can easily become the person everyone turns to for a solution.

A department head has a staffing problem. Sales is behind pace. A family is unhappy. A process has broken down. Something needs to be fixed—and the Executive Director is expected to know what to do.

When a problem lands on an Executive Director’s desk, it can be tempting to solve it immediately. Sometimes that is exactly what the situation requires.

But when the goal is to develop stronger department leaders, the better approach may be to ask the question that helps them think through the problem, exercise their own judgment and take ownership of the solution.

Great Executive Directors also know when to coach rather than direct. They ask questions that help department leaders think more clearly, recognize problems earlier, take greater ownership and become stronger leaders themselves.

The right question can change an entire conversation.

Here are 33 questions Executive Directors can use to coach stronger teams and build better communities.

People & Culture

Culture is shaped by what leaders encourage, recognize, confront—and tolerate.

An Executive Director cannot personally manage every interaction in a community. Strong department heads must be able to lead their own teams, address difficult issues and develop the people around them.

These questions can help uncover what is happening beneath the surface.

1. What does your team need from you right now to do its best work?

2. Which expectations need to be more clearly defined?

3. What conversation are you avoiding that needs to happen?

4. Who on your team is ready for more responsibility?

5. Who needs coaching right now, and what outcome are you trying to create?

6. What behavior are we tolerating that is hurting our culture?

7. What is creating unnecessary frustration for your team?

8. If you worked for you, what would you want changed?

9. Who deserves specific recognition this week?

10. What would make this a place where great people want to stay?

11. Who are you developing to take on more leadership?

Some of these questions may lead to uncomfortable conversations. That is often where the value is.

A strong culture does not result from avoiding difficult issues. It comes from addressing them thoughtfully and consistently.

Performance & Accountability

Senior living leadership requires balancing people, operations, occupancy, financial performance, compliance and the daily realities of running a community.

When something goes wrong, it is easy to jump immediately into problem-solving mode. But before prescribing a solution, an Executive Director may first need to determine whether the team has correctly identified the problem.

These questions can help move the conversation from activity to accountability.

12. What are the three most important outcomes we need to achieve right now?

13. Which metric or trend is telling us something we should not ignore?

14. Where are we confusing activity with results?

15. What is the root cause of this problem—not just the symptom?

16. What decision are we postponing that needs to be made?

17. Who owns the next step, and by when?

18. If occupancy is below goal, what is really driving it?

19. Where are departmental handoffs breaking down?

20. Where are we most vulnerable operationally, financially, or from a compliance standpoint?

21. If we rebuilt this process from scratch today, what would we do differently?

22. How will we know this problem is truly solved?

That final question is particularly important.

Many problems in a community are not actually solved. They are temporarily quiet.

Good leadership creates clarity about the desired outcome, who owns it, what will change and how everyone will know when the issue has truly been resolved.

Resident & Family Experience

Ultimately, virtually everything happening inside a senior living community affects the people who live there.

Staffing affects residents.

Communication affects families.

Dining, maintenance, programming, sales, care, housekeeping and leadership all intersect in the resident experience.

The Executive Director is uniquely positioned to help department leaders see beyond their individual functions and understand the community through the eyes of residents and families.

These questions can help.

23. What are residents and families telling us—both directly and indirectly?

24. What inconvenience have we allowed to become “normal”?

25. If you were a resident here today, what would delight you—and what would disappoint you?

26. Are we consistently delivering what we promise during the sales process?

27. What matters most during a new resident’s first 30 days?

28. Is there a resident or family whose trust we may be losing? Why?

29. Where could we personalize the experience instead of simply following a process?

30. Where could two departments work together better for residents?

31. What improvement would residents or families notice immediately?

32. What feedback might we be missing because people have stopped telling us?

33. What is one thing we can do this week that would meaningfully improve a resident’s life?

That last question brings the conversation back to something fundamental.

Senior living organizations have budgets, metrics, regulations, staffing models, occupancy goals and operational priorities.

But ultimately, leadership is about people.

You Don’t Need to Ask All 33

This is not intended to become another checklist for Executive Directors.

The goal is not to sit down with a department head and work through all 33 questions.

The value is having the right question available at the right moment.

Sometimes the right question is:

What is really driving this?

Sometimes it is:

What conversation are you avoiding?

And sometimes it may simply be:

What can we do this week that would meaningfully improve a resident’s life?

Great coaching does not mean withholding answers when clear direction is needed.

It means recognizing that some situations call for a decision, while others create an opportunity to develop another leader.

In those moments, one thoughtful question can help a department head think more deeply, take greater ownership and become better prepared for the next challenge.

Keep These Questions Handy

We created a printable version of 33 Questions Great Executive Directors Use to Coach Their Teams that can be saved, printed and shared with your leadership team.

You may never use all 33.

But having a few of the right questions available when a difficult conversation begins can make a meaningful difference.

LM Hurley & Associates has specialized in executive search for the senior living profession for more than 25 years.

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