Hiring for culture fit is one of the hardest and most important parts of starting a company. There's no way to avoid this challenge, but you can certainly get a lot better at handling it. In my last piece I offered the 4 interview questions that have helped me hire for culture fit. After giving 1,000 interviews, those questions have made all the difference for me at Triplemint.

In this piece, I want to go one level deeper and offer four exercises that have helped me truly test for culture fit in second-round interviews. This isn't about convincing you that hiring for culture fit is important, this is about how to actually do it. This is the detailed stuff, the second-round interview stuff. This is the stuff to do once you've decided the candidate could be a great fit and it's time to roll up your sleeves and dig in deep before committing to a key hire.

Hires are expensive. Making a hire takes time, which is expensive. Onboarding a new hire takes time and resources, which is expensive. Most importantly, realizing you made the wrong hire and need to start over takes a lot of time, which is really expensive. These four exercises will help you avoid these costly mistakes and hire the right people. Oh, and did I mention that having the right people on your team helps you get more sleep?

Brainstorm a current strategic challenge you're facing with the candidate

One of the biggest mistakes founders make when hiring is they think they need to "pitch" the hire on why their company is amazing. It's one thing to get a candidate excited about the potential of the company, but it's equally important that they genuinely understand the state of the business and the challenges they're signing on to face.

Going over a current challenge you're facing accomplishes two things. First, it allows you to see how the candidate thinks through a challenge and gives you a sense of their decision making process. Do they think there's only one solution and aren't open to exploring others? Do they avoid committing to any solutions at all during the conversation to hedge against being wrong?

Secondly, and as important, going over a current challenge creates greater transparency about the state of the company and gives you an indicator of their excitement or fear about facing those challenges with you. Every startup has challenges, it's unlikely you're going to find a strong culture fit with a candidate who cuts and runs when they find out you're facing real challenges.

Give a "roll up the sleeves" test

If you're a startup, there's a good chance you're looking for hires that can roll up their sleeves and get their hands dirty on execution. One of the best ways to test this is to actually give the candidate a test! If you're hiring for a customer service role, ask the candidate to respond to a series of customer emails. If you're hiring for an analyst, ask the candidate to build out a mini excel model.

Their response to a "roll up the sleeves" test will tell you a lot about their potential cultural fit. Do they balk at being asked to do something remedial? Do they shy away under pressure and struggle through a task that should be simple in their role? Or do they jump on it enthusiastically because they know that at startups whatever needs to get done needs to get done.

Make a first 30 days impact plan

As a follow up to the previous question, which is all about execution, I like to do an exercise that shows how the candidate connects their role to the growth of the entire company. I ask candidates how they would make an impact on the company's growth in the first 30 days through their role.

Are they able to connect the dots between their role and the growth of the entire organization? While their plan may not work in reality for reasons they couldn't possibly know about without more context, you shouldn't really look at the content of their answer anyway. You're really looking to see if they see their job as just performing their role, or if they see it as growing the overall company.

Ask them to play CEO for this hire

Finally, I find it very effective to run through an exercise in which the candidate thinks about the hire from your perspective. I ask candidates to tell me what they would look for in this role if they were the CEO and why.

Instead of asking a candidate the age old question "why do you think you'd be good in this role", which just leads them to list their own positive qualities, changing the context to ask them to think like a CEO gives you much more information. Can the candidate think critically about the role? Do they understand the attributes and characteristics that would make someone successful in the role?