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Coffee dates—the secret to good leadership?

When we started Ministry of Supply, my co-founders and I were doing all the tactical work, everything from manufacturing to customer service to logistics. But then we reached a point where we had to change from doers into leaders. By November 2015, Ministry of Supply had grown to about 25 employees, and so we were still doing a lot of tactical work, but also managing and learning that management takes time. It also takes thought, empathy, focus on being a good manager, leading your team, and on listening—making sure people’s thoughts and ideas are heard, and that you’re creating an environment where people are open to sharing.

This isn’t easy. As we began to grow, we thought, “Oh, we’re all people persons. This will come naturally.” We were kind of expecting that when we reached around 10 employees, the flip would switch, but really the transition into leadership really happens when you hire your first employee. No matter how flat the organization is, or how experienced that first employee, they’re still going to need some guidance. It’s really an amazing transition, and it’s something we have to work at every day.

The transition into leadership really happens when you hire your first employee. No matter how flat the organization is, or how experienced that first employee, they're still going to need some guidance.

Wake up with the team

Personally, It’s easy to get in the habit of sitting down first thing in the morning to check email and to dive into work, but dedicating the first hour of my day to thinking through where I can clear roadblocks has helped tremendously. It moves my team’s needs into the forefront and helps make sure I’m not addressing them as an afterthought.

It’s also been really helpful to talk to other entrepreneurs who have been through this transition and are farther along than we are now, and to have really open conversations about hiring and handling bad culture fits or other difficult situations.

Set professional and personal goals

At Ministry of Supply, we feel it’s really important to understand people’s personal and professional goals and to have open conversations with everyone on the team about them. At a startup, it might be really hard for employees to see where they’re going to be in two or three years because things are constantly fluctuating and you might be growing into a world that doesn’t even exist today.

We ask the team where they see themselves in two years, and to discuss how the company can help them reach their goals, and whether their goals make sense for the company. The co-founders are also available as counselors to everyone in the company.

Hit the pause button

In addition to setting quarterly goals, we do 360-reviews on a quarterly basis. Some people think this isn’t necessary for a smaller company, but we’ve found that having a structure and making it a conscious thing to sit down and think about where we’re going helps keep everyone motivated and feeling like the company is watching out for them in the long-term. Hopefully, we’re each actually growing as a person and professionally in our careers.

I will admit that we never hit the pause button during the first two years. We just kept going. Our focus was: get stuff done, get stuff done, get stuff done. Then one day we stopped and realized, “Wow, we got a lot of stuff done.” So unless you hit the pause button, you don’t have concrete moments where you can reflect on the past and plan for the future. We’ve found that stopping for the reviews and to have coffee every other week hasn’t actually taken much time at all, and it’s so beneficial to have those discrete moments in time.

Unless you hit the pause button, you don’t have concrete moments where you can reflect on the past and plan for the future. We’ve found that stopping for the reviews and to have coffee every other week hasn't actually taken much time at all, and it’s so beneficial to have those discrete moments in time.

Allow for balance

We’re really focused on bringing in the right people and focusing on culture. We want to hire people who are passionate and that we want to get a meal with—who have diverse interests or backgrounds, but shared values. Part of our culture is a focus on balance. We’ve seen the shift with Millennials—there used to be work/life balance but now there is work/life integration. You might bring your work home at night and at the same time might go to the gym during your lunch hour. We really take that to heart.

Jobs aren’t 9-to-5 anymore, but to combat that or make it more livable, we do things like go for runs in the afternoon or make sure that we completely sign off when we’re on vacation. We want everyone to ask: How can I make sure my life is getting as much attention as my work? Keeping that in mind has made everyone feel a lot more like their work is part of their life, and their life is part of their work, and that both are really valued by everyone in the company.

This is a reprint from a series of contributed blog posts from Zendesk customers and startup founders, each sharing lessons learned along the way.

Kit Hickey is the co-founder and former Chief Retail Officer at Ministry of Supply. Since the writing of this post, Hickey has become a lecturer at the MIT Sloan School of Management, and is currently the Entrepreneur in Residence at the Massachusetts Institute of Technology. Follow her on Twitter at @kit_hickey.