Stop Guessing: How to Actually Interview for Fit

You finally hire someone who looks perfect on paper (great resume, references, confident in the interview) and three months later, you realize something’s off. They’re doing the job, but it’s not clicking. The team feels it. Members feel it. You feel it.

That’s not a skills problem. It’s a cultural problem.

When a search goes sideways, it’s rarely because you chose the wrong résumé. It’s usually because you hired the wrong fit. Not the wrong person. That happens when the hiring team never aligns on what “fit” actually means.

You’re looking for alignment, how someone leads, works, and communicates, and what your club truly needs right now.

Before the next round of interviews, slow down and take this process step by step:

Step 1: Start With Self-Reflection

Most hiring teams skip this part, but you can’t recognize the right fit if you haven’t defined what you’re looking for. Before writing a single interview question (or posting the job description!), ask your team to reflect on these. This step doesn’t need to be formal. Grab coffee, sit around a table, and get honest about what working here really looks like. The goal isn’t to paint a perfect picture; it’s to be real about the environment someone’s walking into.

• How would we describe our culture? How do we actually behave? We rotate closings and Sundays, but everyone’s here on holidays and most weekends. It’s part of the deal. We show up because we care about the operation’s success and supporting each other.
• What kind of leadership thrives here? What type doesn’t? Be honest! This team runs on a mix of blind optimism (it gets us through the busy season) and genuine care for what we do. A few natural questioners help keep us grounded and moving forward. Leaders who thrive here bring energy and curiosity.
• What are the non-negotiables for this team? What are the unspoken expectations from the team? When you’re here, be here. We don’t blur lines with staff by hanging out after hours, and that’s intentional. We keep professional boundaries because that’s how we stay respected and consistent.
• Where do we expect this role to make an impact in 30, 60, 90 days, and at one year? We need this person to start by observing and learning, especially by understanding the members, the team, and the operation's rhythm. If they’re behind a desk more than 25% of the time in the first 90 days, they’re missing the point. Visibility and connection come first.
• What challenges will they absolutely face in the first year? We have a new dining room opening, and the leadership team’s already stretched. This person will need to jump in quickly, get up to speed, and take ownership of that space (with our support, but also with confidence).

A reflection like this grounds your hiring team in reality. It makes the interview process more intentional, the questions sharper, and the conversations more relevant. Everyone walks into interviews with the same understanding of what success actually looks like.

Step 2: Prepare the Interview Team

Don’t underestimate how much confusion a poorly prepped interview can cause. Who’s leading? Who’s observing? Who’s taking notes? Who’s just here to listen and smile? Get clear on:

• Who’s involved and why. Each person should know their lane.
• What’s most important to listen for? Share the role’s goals, cultural priorities, and red flags.
• How to capture impressions. Assign a note-taker and debrief the same day. Never wait until tomorrow; you’ll lose clarity and energy.

Do a quick gut-check the day before the interview, ask: “Are we aligned on what good looks like?” If the answer’s anything other than yes, pause and fix that first. 

Note: If you don’t have time for the first two steps, then you won’t have time to onboard them properly either.

Once you’ve done the work to get aligned and prepare your team, you’re ready to see how candidates think in action. That starts before the interview even begins.

Step 3: Prepare the Candidate

Cultural fit isn’t a test. Don’t make candidates guess what matters most. Be upfront about the process: who they’ll meet, how long interviews run, and what you’re hoping to learn. If a certain trait or skill is especially important, tell them. You’ll have better conversations and a clearer picture of who’s genuinely a fit. Transparency builds trust. It also gives you a more confident, thoughtful candidate.

Step 4: Add a Written Reflection Before the Interview

This is where the process gets intentional. Before you bring a finalist onsite or into a virtual panel, ask them to complete a short written reflection. This step slows everyone down in a productive way. It gives the candidate time to think and helps you see how they approach real situations. You can frame it like this:

“We’d like for you to complete the following questions in written form before the interview. These questions identify the most important aspects of this role, and we want to ensure that you have the time to answer them thoroughly.”

Keep it to three or four questions at most. Focus on the responsibilities that matter most to the role's success. If you need someone to lead a new dining outlet, make that clear and ask for specific examples of how they’ve done that in the past. The goal is to understand their thinking and how they’ve applied their experience.

Read their responses before the interview and use them to shape your follow-up questions. This helps the conversation go deeper and keeps it focused on what’s relevant. You learn how someone leads, solves problems, and thinks about improvement.

If a candidate realizes while writing that they’re not interested in parts of the job, that’s still a positive outcome. The process worked. You’ve saved everyone time and found clarity before the interview even starts.

Example: Director of Food & Beverage Written Questions

1. Describe your approach to leading a high-performing service team in à la carte. Our team mentioned that, given the high tenure in à la carte, we need someone who knows how to work with and through the team, not someone who barks orders. We already know that style doesn’t last here. 
2. How do you build trust and accountability among supervisors and hourly staff? This one came from how much we value trust on our current team. We’ve built it over time, and we don’t want to lose it. We wanted to see if the candidate naturally invests in relationships (checking in, listening, following through) because that’s what keeps things running when it’s busy.
3. Tell us about a time you elevated a dining experience without increasing costs. Budgets are tight, but expectations aren’t. We were curious about how they find creative wins, small tweaks that improve the member experience without adding expense or stress.
4. What’s one challenge in food and beverage operations you’ve successfully turned around, and what did you learn? We wanted to hear how they navigate that without losing their cool or pointing fingers.

You’ll be surprised by how much clarity this brings to the interview. You start to see patterns in who’s thoughtful, who’s curious, and who’s just saying what sounds right.

When your questions are built from honest team reflection, you end up with better interviews and clearer insight into who will thrive in the role.

Step 5: Ask the Right Questions in the Interview

At this point, you’ve done the reflection, prepped your team, and heard from the candidate in writing. Now it’s time to sit down and see how they think on their feet. Your interview questions should be specific to the role and your culture. Not generic, not recycled. Here are categories to build from:

Values & Behavior

• Tell us about a time you disagreed with a member or colleague. How did you handle it?
• What’s one behavior you believe defines a healthy service culture?
• How do you handle feedback when you disagree with it?

Adaptability & Growth

• What part of your job has changed the most in recent years?
• What motivates you when things get repetitive or frustrating?
• How do you keep learning and improving in your work?

Collaboration & Leadership

• How do you build trust with a new team?
• Describe a time you turned a skeptical employee into a supporter.
• How do you balance visibility with empowerment?

Member-Centered Thinking

• What makes a great member interaction?
• Tell us about a time you improved a process because of member feedback.

Impact & Alignment

• What kind of results are you most proud of? How did you measure success?
• What will you prioritize in your first 30, 60, and 90 days?

Use the answers from their written reflection to go deeper. Ask why they made those choices. What they learned. What they’d do differently now.

You find real cultural alignment in how someone thinks, not just what they’ve done.

Step 6: Debrief with Intention

When the interviews wrap, don’t just swap quick impressions or “gut feels.”
Meet the same day. Review notes. Compare how each candidate’s actions and communication align with your culture and the realities of the role.

Stick to evidence, not charisma. Ask: “Did they show the traits we said we value most?”

Hiring isn’t about finding someone you’d have lunch with. It’s about finding someone who will help your club grow, strengthen your culture, and raise the standard for everyone around them.

Every hire either strengthens or strains your culture. The difference comes down to how much time you spend understanding what “fit” really means for your team. The more intentional you are upfront, the fewer surprises you’ll have later and the stronger your team will be for it.