Student Maid Founder Kristen Hadeed Isn’t Afraid of Mistakes

November 05, 2017 | Filed in: Your Career

Kristen Hadeed knows the value of a good blunder. Her new book, Permission To Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong, chronicles her journey from inexperienced founder of a startup to seasoned CEO and author who credits her mistakes as much as her successes for making her who she is today. She started her company, Student Maid, (which offers cleaning and concierge services) as an undergrad at the University of Florida, and still employs largely college students to this day. Read on for her thoughts on leadership, managing millennials, and staying true to herself at work.  

On being a born entrepreneur:

I was always really interested in business, and I was also very bossy as a kid. My parents created an environment at home where, anytime my sister and I wanted to do something, they never said it was impossible. When I was six, I had this idea to start a babysitting service. I made these flyers, and every word was spelled wrong. I asked my mom if she would drive me around to hang them up, and she did. I came home and I waited by the phone, and of course no one called—but that was just one example of how they encouraged us.

On having the courage to screw up:

When you’re leading a team of people, there’s pressure to make sure everything goes well. You feel like you have to make people feel safe and secure, and like you’ve got it all together. It’s hard for a leader to admit “I failed,” or “I don’t have the answer,” or “I need help.”

If the leader of an organization isn’t somebody who talks openly about those moments, it creates an environment where no one else wants to talk about it, and then people don’t ask for help when they need it—which ends up hurting the team.

On building a business as a millennial hiring millennials:

If you look back, with every new generation that comes into the workplace, there’s a change. It’s always different. I think that what shaped the millennial generation more than anything is the technology that we use. We grew up building relationships behind a computer or a phone, in a world where everything can happen pretty instantly. That’s why I think we sometimes expect the raise before we really deserve it. The environment has made us expect everything to be instantaneous.

The average person stays at a job for four and a half years, but for millennials, it’s about half that. With social media and technology, you can now see where your friends are working and how happy or unhappy they are there, and it creates restlessness. But I also think everyone wants to feel valued and supported and significant, and in that regard, I think millennials are no different than any other generation.

I’ll do talks sometimes at companies and they’ll say, “Can we have all the millennials in one room and then everyone else in another room?” Why? Why can’t we all be together? I think this is part of the generational divide.

On cultivating flexibility at work:

When I was running Student Maid, I came to realize that my weakness is executing. When you think of somebody running a company, you think, “Oh, they must be really focused. They must really get things done.” That wasn’t really true for me. I started focusing on the areas where I was strong, and asking for help in areas where I was weak. And now at Student Maid, we have official roles, but they’re very loosely defined. In order for it to work, the environment has to be one where people feel comfortable saying, “I’m not good at this. Can I do something else?”

On keeping employees engaged:

For a long time, I was so convinced that there was some kind of interview test you could give and you would be able to know for sure if somebody was really into the business and into the work. Now, I think you just have to be direct with people and say, “Look, I am going to invest a lot of time and resources in you. And you’re going to invest a lot of time here. If you’re not excited about this, I would rather talk about it now than in a month or a couple of months.” That way, you’re also setting the precedent from the very beginning that this relationship is going to be really honest.

On encouraging female leadership:

Leadership is not your rank on the totem pole. I think that you can lead the people who work around you, and create an amazing environment and culture, without necessarily being the boss or CEO. What matters is action: If you feel like there’s a problem, speak up. Act quickly to fix it if you mess up—it’s okay, you’re going to learn from it.

I also think that there’s pressure, especially for women leading big teams of people, to have it all together and be perfect. I wish more women leaders would come forward and share what really happens behind the scenes, and the mistakes that everyone inevitably makes. And I think many women are naturally more empathetic and better at being vulnerable, which is a critical piece of leadership.

On self-presentation:

I think you have to feel confident in your clothes: whether you’re at work, giving a speech, or doing an interview. And you feel more confident when you feel comfortable with what you’re wearing. When I first started my business, it was hard working with other students: I would think “What do I wear? I want to be relatable.” I found myself wearing jeans, or sometimes even gym clothes, at work. And then I thought, “Wait a minute, this actually isn’t what I would normally wear.”

It’s most important to feel like yourself, to be authentic and stay true to who you are. In those moments when I don’t, I’m usually upset with myself, and then I don’t do my best.