The Woodard Report

Better Questions. Better Hires. Stronger Firms.

Written by Jennifer Scott | Sep 3, 2025 5:26:54 PM

Editor’s Note: This article is part 2 of a 2-part series on better hiring. View all of the articles in this series here: Better Hires

Past behavior is often the best indicator of future performance. However, it does not always indicate future success. In the last article, we explored interview questions that help determine past behaviors, competencies, and skills to ensure a match with open roles. But having the right people on your team is just as much about culture and values as it is about skill; in fact, experience tells us the fit is even more crucial, as skills can be taught.

To help you determine if a candidate's core values are consistent with those of your business, consider the following questions related to culture fit / values alignment and why these are important to finding the right hire for your firm.  

6 Culture fit/values alignment questions (and why you want to know)  

Question 1: In thinking about this role, what attracts you to the position? Why are you interested in this job?  

Why? This is about the relevancy of work. A major factor in employee engagement and retention is impact. Employees want to see positive results and effective outcomes from their work. If alignment isn't obvious, retention will be a challenge.   

Question 2: Based on the research that you have done, what do you think you will like most about working with our company?  

Why? This is about the possible connection with the company, aside from the work. Another factor of employee engagement and retention is connection. Employees, like most people, require a sense of belonging and significance to feel good about their performance. And, since they are the people most likely speaking with your customers, you need them to feel good about their performance.   

Question 3: Tell me about the very first thing you did that you ever got paid for (the very first job you ever had - whether it was babysitting, a paper route, dog walking, anything. Think back – what did you learn from that experience? How does that track in your career now?  

Why? You want to learn about the values they adopted as a result of their "childhood" experience.   

Ex. "The first job I ever had was babysitting when I was 12. I worked one evening a week for a single mom of 2 who taught swimming exercises to a group of mastectomy patients. They needed her for so many reasons. And she needed me. I was never late. I never called out sick. I was reliable and dependable because that's what I had to be. 40-something years later, I am positive that any of my clients will say that I am reliable and dependable, and I always get the job done."  

You can ask this question about several early jobs.  

Question 4: I'm going to give you a list of five things. While they're all important, tell me the one thing that is most important to you in making your next career move. Is it money, recognition, stability, challenge, or environment?  

Why? While any answer may be acceptable in general, you need to know that the answer aligns with what your firm offers. If the candidate says "recognition" and your firm has a  culture of recognition, you're off to a great start. Suppose they say "money" is the most important, and you know money is tight at the moment. In that case, you know you have an issue to address.   

Another critical component to consider is how their answer fits in with what you already know about the candidate. If they have been laid off repeatedly throughout their career, perhaps due to company closures or lack of work, it makes perfect sense for "stability" to be the response. However, if the person says "challenge" but has held the same level of responsibility for the last 10 years, you need to explore that further.   

Question 5: In what type of environment do you feel you thrive?  

Why? Again, this question is about alignment. If you have an open office with no "privacy", and a candidate thrives in a traditional office environment, you need to explore that further.  

Question 6: What are the three things that are most important to you in a job?  

Why? You guessed it: alignment. If a candidate prefers to work independently, but this role is very collaborative, it will likely not work out.   

An example of a case study question  

Case questions help uncover a candidate's acumen for business, communication, logic, and reasoning by presenting them with real problems you face in your work. They will be specific to your business and the role. They can be based on problems you have already solved or current issues you are facing. Either way, you want to evaluate the candidate's thought process and critical thinking skills.  

Here is an example of a case question you can present if you are looking for a tech-savvy bookkeeper.  

Ex: We have a new client. They use Shopify for e-commerce sales, Square in a retail location, and PayPal for some online services. They also use QuickBooks Online, but the bank feed is missing a few weeks of transactions, and the client uploaded a CSV file to 'help you catch up.' They are behind on reconciliation and need financials ready for their tax preparer within three weeks. Walk me through how you would approach this situation.  

Here are some of the things we would listen for:  

  • They outline a clear step-by-step plan that makes sense, and they know what to tackle first. 
  • They prioritize clean-up and reconciliation, and they mention checking for duplicate entries from the manual upload. 
  • They mention apps/integrations (Synder, A2X), and they know how to map a CSV file. 
  • They explain how they would communicate progress or concerns to the client.  

Closing the interview  

To close out your interview, ask the candidate if there is anything else they believe is important for you to know that you have not already discussed. Then ask them again if they have any other questions.   

Creating a structured interview that blends these different types of questions will significantly decrease the subjectivity inherent in hiring decisions.   

And our best tip: Don't be afraid of silence as they compose their thoughts. We are often amazed by what people tell us when we let them.  

Read part 1 here: Interviewing on Purpose - Great Hires Through Better Questions