As an entrepreneur and, later, facilitator working with Entrepreneurs’ Organization and Strategy Day in San Francisco, David Hassell saw a common pattern among companies of all sizes. Employees want to be heard, and managers want to stay connected, but precious one-on-one time is often hard to come by.

In 2011, Hassell founded 15Five, a platform designed to open the lines of communication with a handful of questions, covering everything from new ideas to big frustrations, asked and answered each week. The concept is inspired by Patagonia founder Yvon Chouinard, who reportedly used “5-15” reports to stay in touch with employees even if he spent weeks outside the office. Employees spend 15 minutes a week giving feedback in reports, and managers five minutes to read each of them.

Today, 15Five has roughly 700 clients of all sizes and in all industries, from Warby Parker eyeglasses to the University of Michigan Medical School. Hassell, meanwhile, uses his own program to stay in touch with his team of 10 people. “When it was just three of us it seemed silly,” he admits. “But we learned things about each other we didn’t know, even though we were sitting right next to each other.”

Entrepreneur spoke with David Hassell about how technology can help and hinder human interaction.

Entrepreneur: Entrepreneurs often complain there isn’t enough time in the day to juggle all the demands of growing a company and good leadership. What do think?
Hassell:
A good manager, in my mind, is someone who’s really more like a coach. We’ve moved out of paradigm where management is about getting another human being to do something as efficiently as possible. Now it’s about creativity, contribution and having people fully engaged because what we’re doing is increasingly knowledge work, not putting widgets together. As a good manager you need to understand what your employees care about. You could try to do that with one-on-one meetings, but if you have ten direct reports and they each have three, you’re talking about 30 people.

Entrepreneur: The cult classic “Office Space” pokes fun the weekly report, in their case the TPS Report. Don’t some employees resent having one more thing on their to-do list?
Hassell:
The problem with something like the TPS Report is it’s focused on giving all the value to the manager and none to the employee. Even though it’s the CEO paying the bill, the real customer, the end user, is really the frontline employee. Do we get pushback when it first rolls out? Definitely. But within two or three weeks there’s usually an aha moment when the employee realizes that not only is their manager listening, but maybe so are their manager’s managers.

Entrepreneur: What sorts of questions do you recommend go in a report?
Hassell:
Questions that cover successes, challenges, ideas and morale. How are you feeling and what’s the morale you see? The morale question is huge. If you’re only checking in once a year you might have missed something eight months ago. One of the questions someone put in on my team is something like “What was the most exciting thing you did outside of work this week?” Another question we ask at 15Five is “What is one of the ways you lived our core values this week?”

Entrepreneur: I gather that the types of questions asked in the report and the intent of those questions are important.
Hassell: Absolutely. There’s the actually content of what you’re asking but there’s the actual context of why you’re asking. Managers want to be helpful when employees share. That is ultimately the core foundation of building connections and caring. If you don’t have a company that cares about employees why will employees care about the company?

Entrepreneur: Entrepreneurs often say they don’t have time to be good managers or, frankly, don’t know how to be good managers. How can a system help?
Hassell: Different people have different management skills, some are good with people and some are more analytical. This guarantees that at least managers are asking the right questions. 

Entrepreneur: How do you balance technology and human interaction at your own company?
Hassell:
We look at technology as a tool for human beings to improve their interaction with each other, not get in the way of it.  I’m a big believer in face time. We have a hub in San Francisco and a hub in New York. We don’t have set office time or vacation time, but we have the structure that each team has a team meeting and each person has a one-on-one meeting with their manager every week.

Entrepreneur: Why not just ask the right questions via email? Why are quick updates so important?
Hassell:
It can be done between a manager and a direct report. When you get into an organization with multiple layers, you have to coordinate hundreds of people, copying and pasting and forwarding.

Entrepreneur:  Don’t project management systems allow for this kind of feedback?
Hassell: They’re great for what they do, but there’s a lot of stuff that ends up in project management system that is down in the weeds, too project focused. As the CEO I may not need to know all these details, but I do need to know that a project is on track. This gets you out of the weeds and gets people thinking big picture.

Interview has been edited and condensed.