We tend to think of strong teams as being held together by strong leaders. Great generals commanding their loyal troops in the thick of combat. Bold visionaries leading thousands of people to march for justice in the streets.
What we don't think about as much is their daily interactions—the little things, like asking for help in a moment of doubt, having meaningful conversations beyond work-related issues, or reaching out to a colleague who seems a bit down. All these seemingly innocuous acts serve to build trust, the foundation for any enduring relationship between a leader and their team.
In a follow-up to our interview about giving feedback, I sat down again with Kristen Hadeed, CEO of Florida-based cleaning company Student Maid, so she could tell me more about how she crafted a motivating and empowering company culture in an industry that deals with mold and grime.
Relationships over revenue
Alex: To start off with a frame of reference, how big is your company?
Kristen: We used to have 500-600 people, but it was really affecting our culture. We decided the way we wanted to grow was not by franchising, not by growing the number of people on our team, but by teaching people about our culture. In the last couple of years, we downsized. Now, our company fluctuates between 50 and 100 people.
This is something we don't talk about enough in business because we think that downsizing is automatically a failure. But downsizing can be a courageous decision to protect your culture and your environment. If you decide to downsize, you just have to think about where else you're going to make revenue.
For us it was more meaningful to teach people about our culture and to emulate what we've created. That felt more authentic than growing all these locations while sacrificing the culture we worked so hard to build.
Alex: In downsizing, did you voluntarily forgo some revenue?
Kristen: A lot of it. But it was worth it.
In a cleaning company, the only way to make more money is to do a lot more volume. Back then, we would sign contracts to clean 700-800 apartments with just five days to do it, so the conditions were already tough. On top of that you would have customers that don't treat your employees very well. When I would see my people walk through the door, I could tell they didn't want to be there. Even I didn't want to be there! That made me think, "What am I doing to people? This isn't worth it!"
When you walk into the company now, you can tell everyone wants to be there. We even have a rule that if there's a client that makes us feel like we don't want to go to work, then we're not going to work with that client. It's not worth the money.
We actually call revenue "difference dollars" now. We see money as a way for us to make a difference in people's lives. I think we really changed our relationship with revenue. What we earn is ultimately for our own people, so the way we generate it has to feel good.
Kristen Hadeed, author and CEO of Florida-based cleaning company Student Maid. Kristen and her company have been featured in several prominent news outlets (including PBS, FOX, NBC, TIME, and Forbes), and she has spoken on numerous occasions to companies about building an empowering work environment.
Photograph by Pete Longworth
The courage of vulnerability
Alex: You mentioned in part one of this interview a time early in your career when 45 people quit on you. Can you tell me more about what happened?
Kristen: Part of it was that I was very inexperienced as a leader. I didn't know what I was supposed to do while everyone was cleaning, I didn't know anyone's name—I didn't even know I was supposed to give people water and lunch breaks!
People didn't think I cared about them. Why would they, when I didn't bother to remember their names? I didn't help them carry their heavy vacuums; I didn't even check on them. I just stayed in the office all day and told people, "If you need me, I'm in here." Naturally, they thought all I cared about was money.
Also, the work was very hard. Cleaning empty college apartments is absolutely disgusting. I couldn't afford to pay people what they really deserved for that kind of work. You mix all that together, and I just think there comes a moment when you say, "Why am I doing this? I don't want to do this! I'm quitting." It took just a few people deciding that they wanted to leave; they told everybody around them, and all of a sudden 45 people were gone.
When they walked out, I remember thinking at first that they were the ones at fault. How could they commit to something and then not see it through? I had a victim mentality.
Then I started panicking because we had so much work to do. I went and found the people who didn't quit and told them what happened. I asked them for help and they had a great idea: Let's have a meeting. We'll give everyone an early paycheck if they show up, and we'll talk about what went wrong. It was at that meeting that it dawned on me that maybe I did something wrong. Maybe I was the problem.
Before the meeting I didn't really know what I'd done wrong, because when they quit they didn't tell me why they were quitting. So, I told them: "I think I did something wrong. I don't know what I did, I've never done this before, but I can tell you my heart's in the right place. I'm very sorry for whatever I did, but I need your help."
I didn't realize it back then, but I admitted weakness. I was vulnerable. I didn't have an ego. That's why they came back, why they gave me another chance.
Alex: You talk about "care" and "vulnerability" a lot when it comes to leadership, but many leaders are worried about losing face in front of their team members. How can you be vulnerable but at the same time show leadership?
Kristen: I think we've given vulnerability a bad reputation. I think we've learned to see it as a weakness when in fact it's a form of courage. People want to follow a leader who has courage.
We all know there isn't anybody in the world that's perfect, who always has the answers and always knows the way forward. That person doesn't exist. So when someone pretends to be that way, we don't trust them.
I've learned to think of vulnerability as a strength. At work, being vulnerable means asking for help. Asking for more training. Being willing to say "I messed up" and owning up to your mistakes. Being willing to admit you don't know the answer.
Tough times toughen teams
Alex: Apart from care and vulnerability, what are some other criteria necessary to build a strong team spirit?
Kristen: Trust, which you build through feedback. After that, I think good relationships are huge. People want to work with others who care about them.
Our relationships at work need to be more than superficial because we spend so much time with these people. It's important to create space for people to talk about what's happening in their lives. That involves moving away from emails and doing more face-to-face, taking more people out to coffee or lunch, building relationships slowly, asking questions that are more meaningful than "What are you doing this weekend?" or "Wow, the weather is nice!"
I also think resilience is important for a team. I define resilience as a team's attitude when facing failure or hardship.
In my company, we say that as long as we learn from it, we're not failing. What we do is we talk about it; when we mess up, we sit down, have a meeting, and ask what happened. How did we make this mistake? What will we do if this happens again?
If you start to learn as a team, you'll get to a point where you know that when things get hard, you're going to get through it. When times get tough, people aren't scared. They know that they've done this before, and they can do it again. We don't talk that much about resilience, but it's a key ingredient in a team.
Alex: On the topic of relationships, I've seen companies where a lot of people work remotely, don't really interact with their colleagues, or keep their private and work lives very separate. How do you build relationships under such circumstances?
Kristen: Our whole executive team is remote. We've learned that we are the leaders of the company, so we have to have the best relationship possible.
Every week, all of us will have a two-hour meeting. The first hour is just personal updates. We go around and every person talks about their personal life. Whatever you want to share, good things, bad things, tough things, whatever. Then the second hour is about work updates.
These meetings are huge for us because we're dedicating that time to making sure we really know what's going on in people's lives. The reason it matters for work is if somebody seems really stressed or upset, it could be because they have something going on in their life. But if you don't know that, you'll think they're stressed or frustrated with you.
Also, we do all of our meetings using video. We never let anyone have their screen turned off. It's as if we're in the office. Face-to-face is such an important thing to see people's body language, understand their tone of voice, and so on.
Then we have a general rule throughout the company that is: If it's something significant, don't text or email it. If it's something quick like "What time is this happening?" or "Where is the report?" then fine, use email. But if it's "I had this idea, what do you think?" then do it face-to-face, or at least on video.
Finally, every quarter we do something called "Development Day." We close our company for a day, we don't serve any clients, and the only goal is to help people grow. We always start with vulnerability questions that help build relationships.
Specifically, we put people in teams of three and we give them really tough questions that everyone in the group has to answer. These questions might be things like "What is one of your biggest fears in life?" "What relationship challenges you the most in life?" or "What is something you regret in your life?"
First, the leadership team answers the questions in front of the whole company, so every single person hears our answers. Then we break off into teams and everyone answers these questions with their group of three. We always start that way because we want to teach people that if you want to build meaningful relationships, you have to ask questions that have depth.
Know your team
Alex: How do you recognize that something's not right? Are there red flags or warning signs that make you think, "We have to do something to help the team at this point"?
Kristen: I look at how engaged people are in meetings. When people feel like they can say what's on their mind, they freely give their ideas and feedback, which is a sign that everything's healthy.
It's the quiet meetings that scare me. When I feel there's something wrong in that room, I will stop a meeting and say, "Something doesn't feel right, what's going on?" Then we talk about it, right then and there. Usually there's some elephant in the room that comes out, and we just deal with it.
Don't get me wrong, by quiet I don't mean someone who's quietly working at their desk. You know your team; if people who are normally very talkative and giving ideas are all of a sudden quiet, you know something's up.
Alex: What about the people who are just not very talkative in general?
Kristen: It comes down to knowing people's personalities. When it comes to the introverts in the room, I can gauge what's happening in their minds based on their body language and facial expressions. If their body language shows me there's something they don't agree with but they don't speak up, I stop the meeting and say, "Let's do a check-in, how do we feel about this so far?"
We call it being a conflict miner, someone whose job in a meeting is to look for people who are disagreeing but not speaking up.
Alex: Is that usually the leader's job?
Kristen: Not always. Sometimes we designate someone in the meeting to be the conflict miner. Usually it's not the person facilitating the meeting, because you can't be both at the same time.
Alex: It seems like there will always be people who aren't comfortable with speaking up in front of others. How do you engage people like that? Is it OK to force people to speak up in front of everyone?
Kristen: You don't want to make people feel uncomfortable, but at the same time you need people's input before moving forward on something. I put it on the person. I'll tell people we're moving forward with an idea unless someone in the room disagrees. You sometimes have to say that sort of thing.
On matters where there's some time, you can say: "I know some of you really need time to think this over and you do better when you think independently, so I want everyone's thoughts by a week from now."
This is important. I'm somebody who feeds off the energy of people, so when I brainstorm, I like to brainstorm in a group. However, what works for me doesn't work for everybody. That's why when it comes to brainstorming, I'll say, "If you're somebody who feeds off people's ideas, come to this side of the room. If you're somebody who really likes to think independently, go back to your office and collect your ideas." It's important to allow people to give their ideas in the way that works best for them.
Alex: It sounds like you really use time to your advantage.
Kristen: Yes, because some people need time to digest things.
Also, we do a lot of self-assessments. This includes things like introvert/extrovert tests, personality tests, behavior tests, and so on. Then we have people share what they learned about themselves, so that everybody understands the different dynamics in the room. If you're an extrovert, you might get hurt that the introvert never speaks up. If you're an introvert, you might get hurt that the extrovert is always in your office talking to you. We try to learn about each other's different personalities and dynamics.
Invest in people
Alex: The last topic I want to discuss is onboarding. How do you get people to assimilate the company culture that you've created? How do you get them to feel like they're part of the team from the get-go?
Kristen: It takes time. There isn't anything you can do right away to make the person feel like they're part of something that's been around for a long time. But I think onboarding starts on the first day, when they come in for the interview.
We try to make it feel like family. The very first interview is not really an interview. We give them a tour of our office and we start by telling them where we come from and what our goals are. Then we say, "If this is exciting to you, we would love to interview you. But first, we just wanted to meet you." From day one, we are building a relationship.
When it comes to training, we just launched a new training program that takes about a month to go through. We invest in people a lot during this month. In their classes, people learn about company practices like FBI, take self-assessments, learn more about who they are as people, and learn about building relationships.
We invest a lot of time in teaching people skills to become good people and good leaders. These will help them in every area of their life. We do this despite knowing they might move on. For a lot of people, it's in that first month that they realize, "I hate cleaning, this isn't for me."
By making this investment from the very beginning, we're showing people that we care. We're doing all this just because we want to make them a better person, and that speaks volumes to people.
Alex: The cynical question here would be: Is it really profitable to invest so much in people from the start, when you know you'll have turnover?
Kristen: It's funny; when you start investing in people and your only goal is to help people become better versions of who they are, all of a sudden people don't want to leave.
There's a brilliant quote—I forgot who it's by—that goes: "What happens if we invest in people and they leave?" followed by: "What happens if we don't and they stay?"*
I used to always think that your retention rate showed whether you have a good or bad culture. What I've realized is that sometimes people can love their jobs and they can still want to move on, because they want another experience, or they've got this wonderful opportunity. It doesn't mean you're a bad leader or the company is bad.
In our case, perhaps ironically, when we stopped focusing on retention and instead focused on investing in people, our retention rate became the best it's ever been. I think it's because people realized, "You care about me, so I don't want to move anywhere else."
*Although attributed to multiple people, the earliest form of this quote can be accredited to Henry Ford.
Written by Alex Steullet. Edited by Richard Ho and Michelle Adams.
Top photograph by Pete Longworth. All pictures courtesy of Student Maid.