Tech & Finance Recruiting

By Ringside Talent Partners

January 25, 2023

If you want to make better hiring decisions, you might need to change how you interview.

We’ve all made hiring mistakes. We meet a stellar candidate with all the right experience and technical skills. They look great on paper and interview well. We’re excited to make them an offer and bring them on board. Then just months later, we’re wondering where we went wrong or what we missed. They’re underperforming, aren’t a cultural fit or don’t have the mindset we thought they did.

Most of us have been classically trained to focus on a candidate’s work history. We’re told that past behavior is the greatest predictor of future behavior, so we ask a lot of “tell me about a time when” questions. Those aren’t nearly as helpful as learning about someone’s values and belief systems. But because we’ve been trained to primarily ask “what would you do if” questions, we don’t recognize our interviewing skills as a possible source of the problem. We deem the situation a fluke and start our hiring process again, likely to make the same mistakes.

There’s a simple solution to this. Stop interviewing for what people have done. Start interviewing for who they are. If you’re wondering how to do this, here are several themes and questions you can start with.

1. Ask about mistakes and failure

Outstanding employees openly embrace mistakes and failures because they know it’s part of our learning process. Curious employees who want constant development and growth aren’t afraid of being uncomfortable or experiencing struggle. They embrace these things because they know it leads to their own evolution. These employees will be highly coachable. You’ll be able to talk straight and deliver tough messages because these employees are hungry for critical feedback.

Ask questions like: “Tell me about some of your biggest mistakes, failures or regrets” or “Tell me about a time you really screwed something up. How did you fix it and what did you learn from it?” When people struggle to answer these questions, it’s likely because they either haven’t spent much time thinking about their mistakes or it’s because they lack the self-awareness or humility to even know they’ve made mistakes. These are major red flags — it’s hard to learn from your mistakes if you haven’t spent any time thinking about them.

2. Look for signs of humility

Arrogant people have a hard time admitting that they’ve ever been wrong or are still under construction. Narcissists don’t like hearing they have weaknesses or opportunities for growth. It’s far easier to blame others for things that don’t go well and take too much credit for things that did.

Ask questions that will expose the egocentric. If your candidate is a leader, ask, “Tell me about some things that you learned from people reporting to you.” Poor leaders don’t recognize they can and should be learning from people underneath them, so this will be a tough question for them to answer. For individual contributors, asking them to talk about things they’ve learned from peers will expose how much they respect colleagues at their same level or if they only respect authority figures. Saying, “Tell me about a time you let someone down or failed a teammate” is a great way to know if your candidate takes accountability. Asking, “What do you expect to struggle with most in this role?” or “What are some weaknesses you’re continually working on?” can help you find out how realistic your candidate is.

Nearly everyone who starts a new job with a new organization has obstacles they’re up against, but arrogant candidates will have a tough time admitting these things because they’ll view these admissions as signs of weakness. People who struggle with humility rarely make good teammates and it’s hard to teach them much since they think they already know it all.

3. Ask about values and beliefs

Proactive people that are goal-driven and also conscious about their own learning and development are likely to have personal values and beliefs. The best candidates for hire will have their own core values and beliefs that align with your company’s values and beliefs, so find out what those are. Asking “What are some of your personal values that guide you through life?” is a good way to start. This will help you determine if someone has a vision for the future and is charting their own course or is more reactive and simply floating along. The latter aren’t likely to empower themselves, innovate and find their own solutions. They’d rather wait to be told what to do.

4. Find out how curious your candidate is

We all want candidates who are serious about learning. Employees who will do this best are the ones who are already focused on it at home and have made their own personal curriculum for learning. You’ll learn a lot about your candidate by asking what books they’re currently reading or where they gain new information. You can also ask, “Who do you look up to? Who are your role models? Who are your coaches or mentors?”

Successful people usually readily identify people who have influenced them and are actively reading or learning new things regularly. Candidates who can’t answer any of these questions probably aren’t terribly curious about themselves or the world, so you can count on them to not be terribly curious about your company’s mission, either.

5. Pay attention to what questions they ask

It blows my mind when a candidate doesn’t have any questions at the end of an interview. If hired, they’re about to devote as much time (if not more) to the organization as their family. Serious and curious candidates who are looking to become top performers will have quality questions. Watch out for questions that sound textbook: designed to impress you or show they’ve memorized facts from your website. Genuine and heartfelt questions about company culture and direction, the roles and responsibilities of the job or the team environment show an authentic curiosity and interest for what’s ahead.

These are just a few of the many places you can start if you’re wanting to get better candidates through your interview process.

Source:  Amy Chambers via