If there's one thing that keeps every founder up at night, it's hiring. Hiring the best talent is a massive and never-ending challenge. It's hard to hire your first employee, it's hard to hire your 50th employee, and it's still hard to hire your 500th employee. If you're just starting your company, you may as well get over the fact that you'll likely lose sleep over hiring.

If you've read anything about hiring best practices, you've probably read about hiring for culture fit. This isn't an article about convincing you to hire on the basis of culture fit. This is an article on how to actually do that. While every company has a different culture, there are four questions that will help you identify if a candidate is a good culture fit, no matter where your company falls on the culture spectrum.

In my role as CEO of Triplemint, I've hired more than 100 people, therefore my co-founder and I have interviewed close to 1,000 (admittedly, with all the lost sleep over the challenges of hiring, I didn't keep track of the exact number of interviews I've conducted). I've made great hires who were a near-perfect culture fit, and I've made less-than-stellar hires who ultimately didn't work out. There is no such thing as batting a thousand with hiring. You're going to make mistakes no matter how good you are at it. That said, in my personal experience I've found these four questions to be hugely helpful in determining culture fit.

1. How did the culture at your last company empower or disempower you?

This is a really interesting question, because it will get candidates talking about their previous company through the lens of how they were affected by the company's culture. Getting candidates to talk about their past employer can be very telling. Do they openly throw the company under the bus? Do they recognize the positives even though it ultimately didn't work out?

Asking specifically about the culture of their last company also tells you a lot about how they view the importance of culture. Their response will tell you if they've thought a lot about company culture or if they don't really know what it is. The question will also reveal how they think they are empowered or disempowered, which will give you a look into their motivations.

2. What were the characteristics of the best boss you've ever had?

I like this question as a follow-up to the culture question, because it's somewhat similar but from a different angle. If you didn't get a sense for a candidate's view on culture and what motivates him or her, you likely will from this question.

Did the candidate thrive under a boss who was extremely direct and valued performance above all else? Did he or she thrive under a boss that put as much emphasis on communication and interpersonal skills as results within the role?

3. Describe how you handled a conflict with one of your co-workers.

It's always helpful to ask candidates about how they dealt with a conflict. As people, we tend to be more open and honest when recalling a specific event versus describing characteristics about ourselves. Understanding what the candidate perceives as a "conflict with a co-worker" will likely reveal information about the person's level of self-awareness.

Understanding how someone dealt with a conflict will also give you insights into what he or she perceives as a reasonable and positive response to a conflict. No matter how wonderful your culture is, conflicts will arise. How your team deals with conflicts is the true test of your culture.

4. What kind of feedback do you expect to receive in this role and how often do you expect to receive it?

Understanding a candidate's desire or hesitation to receive feedback tells you a lot about the person's expectations. The frequency and type of feedback that is shared within a company tends to be highly correlated to culture.

Does the candidate expect feedback to be tied to core values? Does the person think feedback is only about performance in the role? Does he or she see feedback as a once-a-year HR formality or as part of a constant process of growth and improvement?