Entrepreneurial Advice: Four Questions to Ask Employees

1. Do you know what you’re doing?

I was blown away by how many people didn’t understand what they were supposed to be doing and what our product is. It’s easy to get caught up in the details of a task without realizing how the job actually contributes to the product. The answers are more informational for me. I like to hear what people are working on.

2. Do you know why you’re doing it? 

This is a much deeper question. Typically, engineers know why the technical details are needed. However, there are often gaps in understanding why we’re developing the product and what problem we are looking to solve. With sales, marketing and business development folks, the discussion is more customer-focused. Being innovative enables you to sell both what your customer tells you they want, and what they don’t know they want yet. Engineers do a great job of being strategic, while salespeople are more opportunistic. Working “on” your company strategy is only as effective as your team’s ability to execute. Knowing why we’re executing daily is the most important and hardest question.

3. Do you have all the tools to do your job? 

My first internship required me to build my own computer out of random components. I’ll never forget how disgusting that used keyboard looked. Large businesses have IT departments and insane corporate rules for purchasing. As small businesses, we have the opportunity to provide the best tools and the perfect environment for individuals. We ask new employees what specific keyboard and mouse they prefer, along with their choice of laptop bag and headphones. We also get a new Mac for every employee, including interns. This speaks to how I want new people to feel on their first day on the job.

4. What do you want to be when you grow up? 

This is the most fun question I ask people, regardless of age. Some of the best answers come from the most seasoned veterans. The answers led to the creation of a culture budget at Tome, which has helped get people to do the things they enjoy and make their lives better. I have heard answers from career growth to becoming a CTO, to starting a small business or being a better parent. The important thing is my commitment to helping people be what they want to be. When business gets tough, I sleep at night knowing that I treat people the way I want to be treated. As someone who used to “work for the man,” part of that means I can change the mold and remind everyone that life is too short to not do what you love. My only caution is that asking this question requires a commitment on your part to help people get there.

The Bottom Line

Ask questions and keep it open. It usually takes two or three sessions with a new employee before he or she really opens up, but be patient. It’s absolutely worth it and it’s one of the most enjoyable parts of my job!