
By: Retirement Home Insider retirementhomeinsider.com
If you’re in the business of senior living, you understand that a good (great) Executive Director, will make or break your property’s performance.
No other factor will determine how successful you are. Full stop.
Not the age of the building, not the location, not whether the home is for profit or not-for-profit.
Not the company sign on the big rock out front, not the proximity to hospitals.
Great Executive Director’s set the tone and tenor for the building, hire other outstanding leaders and show genuine hallmarks of hospitality to families, residents and their team members.
To be one of the best retirement communities out there, this is where you need to start.
I’ve been leading hospitality & senior living teams for almost 30 years, and I’ve gathered 7 (and 1/2) great questions to make the selection process of an amazing Executive Director – a little more accurate – shall we say.
In order to hire the best, you need to ask the right questions.
The questions below allow for strong follow up, broad discovery of “real” lived experiences by the candidate, and will give you a solid gauge on the quality of the individual that will represent your business.
I use variations of these interview guides for all of my leadership positions.
I also do everything possible to make candidates feel comfortable and relaxed during the beginning of the interview. Tight environments lead to tight answers.
It’s not to disarm them – I want them introspective and genuine so they will speak freer.
You’ll get more honest answers with this approach helping you get a true measure of their character – not some canned responses.
My opening jokes during the beginning banter of an interview, are killer.
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1 – Tell Me About Your Toughest Day On The Job?
When A Crisis Hits, Will They Be Able To Respond Well?
I once had a candidate for an Executive Chef role tell me his toughest day on the job, was his very first day in action as a United States Marine when he stepped off a helicopter in Kandahar Afghanistan.
After we talked about it, I was pretty confident he would respond well to pressure and rigor of being an Executive Chef, when his Sous Chef called in sick, the day’s food order was sitting in the back hallway, and the Health Inspector had just arrived.
I’m measuring what a candidate can handle emotionally when you have competing priorities and tremendous pressure to lessen the impact of whatever crisis they are facing.
The true measure of a leader is not when things are going well, it’s when things go badly.
Pay careful attention to how they marshalled the resources of their team. When it’s an extremely tense situation, how did they ask others for help? How did they assign duties and tasks to fix the problem? Did they step aside and defer to others in authority, or were they decisive?
Those who haven’t been exposed to very tough situations may still have a good answer. You can ask them to pivot and talk about difficult circumstances in their personal lives if they’re willing to.
One candidate I had, who was highly recommended for a large, complex retirement community told me her toughest day on the job was around a $300 rebate to a family.
Clearly she didn’t want to talk about difficult scenarios. Why would I want to hire someone who shies away from conflict?

2 – Who’s The Best Boss You’ve Ever Had? Why?
Follow Up By Asking Who Their Worst Boss Was….
We’ve all had our share of great bosses and mentors. People you’ve looked up to, respected their advice, or tried to follow throughout your career.
Presumably, you’ve had your share of asshats too. Leaders who’s ego made it impossible for them to see anything but their own reflection in the mirror.
I ask this question to gauge cultural fit. What specifically did they like about their best bosses’ leadership? Was it the autonomy they gave them, the involvement in special projects, the lack of micro management?
Ask them for specifics. How do their answers align with your own leadership tendencies? How do their answers align with your team’s tendencies?
It’s also interesting to see what they say about their experience with their worst boss. Do they balance their dislike of the worst boss they’ve ever had with things that they still learned from them?
How did they try to navigate/mitigate the relationship to make it better for themselves or their team?
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3 – From Your Last Role, If I Gathered All The Team Members Who Worked For You In A Room, Buttered Them Up With Coffee & Sweets, What Would They Tell Me – About You?
Have They Ever Asked Their Team For Feedback?
This is the classic strengths & weakness question with a twist.
It immediately paints the picture of the scenario in the candidates mind and raises the possibility that you might actually ask the question of some of their former colleagues.
Therefore, it’s usually answered relatively close to what their reality was.
The candidate will invariably speak to (or should speak to), all the good things their team members would say about them. It gives you the opportunity to drive for specifics.
Candidates that struggle with this question however, either have never asked their team for feedback in a meaningful way, or know the answer and aren’t sure how to respond.
The follow up question is something like “If there’s one thing your team wished you would do differently, what would they tell me?”
Again – this will help you hone in on specifics – what are the regular behaviors they exhibit, and how do those behaviors mesh with your team?

4 – How Would You Go About Selling a Full Community? Imagine We’re 100% Occupied.
Does The Candidate Strive For Continuous Improvement?
I know what you’re thinking – if you’re at 100% – isn’t that the objective? Shouldn’t you just be happy with 100%?
This question is a little unfair if you’re interviewing someone with a strong hospitality background who’s never been an ED. Those candidates might need to be helped a bit with their answer.
Still, I love this question because it strikes at the heart of what makes a great Executive Director – someone who’s not satisfied with the status quo – who’s always looking to make “things” better. This is what you’re looking for with this query.
How would they stay hungry if they’re crushing budget? Do they speak to leveraging higher occupancy into added benefits for the residents and team members?
I’ve worked with GM’s who were quite happy making budget every year at 98%. Why strive for more if you don’t have to?
Those GM’s were very good – but the great ones were the ones that said “I want to set occupancy records.”
Maybe it’s a competitive streak, maybe it’s recognition, or maybe they’re just wired that way – never quite satisfied with the way things are.
This line of questioning can help you uncover their strategic mindset, and maybe find out what drives them just by playing a game of “Let’s Pretend”.
This question is even better if they’ve gotten to 100% occupancy before…..
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5 – What Things Do You Do To Promote Collaboration Amongst Your Leaders?
How Do They Make Sure Their Leaders Work Well With Each Other?
Ego is the largest destroyer of collaboration in business.
We all have some measure of ego in our own DNA – we wouldn’t be leaders if we didn’t think we could make a difference.
For some, ego is what drives their performance, whether they care to admit it or not.
You want to understand how your ED will manage the egos on your team. There has to be a sense of harmony in the group.
Have the candidate give examples of good teams they’ve been on and bad teams they’ve been on – and what they did to make the good team even better, and how they went about fixing the bad team.
Again – look for actions that are specific and meaningful. There will always be some measure of conflict – but conflict that can be resolved in healthy ways, without taking sides.
Regular interaction and communication amongst the leaders will result in finding common ground – even if they’re on different sides of the bocce court.
I used to have a “No Email Shit Posting” rule – if you have a problem – you have to talk it out in person – period.
No complaining emails. Ain’t nobody got time for that.
Find out if the candidate has certain non negotiable behaviors, that they expect from their team.

6 – If Your Friends Had 3 Words To Describe You – What Would They Be?
Potential Clues To Their Personality
This question is almost always a curveball for the candidate – asking them why their friends like them – was not on their interview cheat sheet.
I use this question to understand their personality a bit more. It’s tough to use only 3 words – and it gives you an opportunity to ask why their friends would say they’re “outgoing”, or the “organizer” of the group. Why would your friends say that?
Of course there’s no proper answer here. Some people hate talking about themselves, and some can wax poetic for hours.
This (getting back to some of the other questions), is about fit with you and fit with your team.

7 – What’s The Best Piece Of Constructive Criticism You’ve Ever Had From One Of Your Leaders?
Can They Take What You Have To Say, Even If They May Not Like It?
A long time ago I was the General Manager of a restaurant. I had a regional leader that I didn’t like – but we mostly got along.
One day he said we should take a walk. We went around the building, and he pointed out the grass growing between the cracks in the sidewalk, the burnt out light bulbs on the patio, the sign that wasn’t hanging straight.
He asked me what I saw when he was pointing the deficiencies out. It was pretty obvious, that I saw a lack of focus and detail on my part.
His critique melded with a another piece of advice I got from a Chef I worked with years before. He always told me that “you eat with your eyes”.
That’s how the penny dropped.
Any leader I’ve had in the last 15 years will tell you, we always go for a walk when I visit.
Can the candidate relate a story where they’re taken direction and learned from it? Put into practice a new method, even though it wasn’t something they may not have agreed with?
I’ll admit – it’s hard to take the criticism sometimes – it’s the ego at play.

(And 1/2) Question: Why Do You Want To Be “The” Leader?
Why Do You Want All That Responsibility?
This can be tricky to answer.
What’s their motivation? Lots of candidates respond that they enjoy helping seniors – but any role in senior living can help the elderly.
Why are they interested in a role where if something goes wrong, they’re most likely the one responsible?
The best answers here are about building something. Of being able to point to something they’re proud of that they can accomplish in their role.
Of having confidence in their abilities to do good things – but not arrogance. Of having the satisfaction of a job well done.
Being able to take feedback, usually means you can give it – and you want that in order to ensure your operation is continuously improving.
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