Cover letters are a copy-n-paste waste of space. If we want to get better applicants and sift through a smaller stack of resumes, we gotta ask better questions.

Better questions ensure that the applicants most passionate about our mission will surface in the application pool.

When presented with good questions, folks in “mass application mode” will either abandon the application or put such little effort into their answers that they can easily be filtered out.

Questions about you for them

• What problem is [your startup name] trying to solve?

• Why is the time right for [your startup name] to solve its customers’ needs?

• Based on what you know about our [your startup name], what would discourage you from working here?

• What are the biggest risks facing a startup company in our industry?

• Which of [your startup name]’s competitors has the best homepage? Why?

• What are three skills you possess that you feel are most relevant to [your startup name]?

• How do you imagine spending your first month at [your startup name] if you were hired for this role?

Questions about them for you

• Tell me about your last project or campaign. What worked and what didn’t?

• What about your prior work has prepared you for this role?

• What books, podcasts, or articles have you found most beneficial to your career?

• What was a time when you needed to balance the needs of multiple stakeholders?

• What unofficial role do you usually assume on a team?

• Let’s say that you had an idea that would benefit the organization, but deviated from company guidelines or norms. How would you go about getting approval for the idea?

• Can you provide an example of a time that you had to work with someone that didn’t like you (or, maybe you didn’t like them)? What was the project and how did you handle the situation?