Living in the “and”
The last few weeks have been some of the hardest we’ve ever been through as a team.
I recently made the extremely difficult decision to transition Amanda’s role—Chief of Compassion—out of our business. With Amanda’s encouragement and permission, she and I decided to collaborate on this blog post and share this news with you together.
This post is about the “and”: How it’s possible for something to be so hard and so compassionate at the same time. How it’s possible for something to feel so difficult while also being the most caring decision for Amanda, me, and our team. How it’s possible—and human—to go through an experience that can evoke such conflicting emotions and for multiple truths to exist in the same breath. And how building a human organization really makes it possible to live in that “and” together.
Before we talk about where we are now, I want to back up a bit and share Amanda’s journey with our company and all that she has meant to us.
Amanda started at Student Maid seven years ago after she responded to a Craigslist ad to answer phones. The moment I met her, I knew there was something so special about her: Amanda has a natural gift for connecting with people and making them feel cared for. Because of that, she quickly worked her way up to become our Chief of Culture and played an integral role in developing the culture we became known for at Student Maid.
Some of Amanda’s greatest accomplishments as Chief of Culture include creating our Ambassador Program (a paid internship program for our students to learn about business), revamping our Guidebook to reflect our more human culture (the Guidebook was our version of an “employee handbook” that felt too rigid and strict at the time), and our Incentive Program (which she designed to inspire students to take ownership of their growth). She met with our students one-on-one to check in on how they were doing at work and outside of it; she conducted interviews and helped us hire team members who would bring our culture to life; and she led compassionate accountability conversations with our students to help them reach their potential. Most of all, Amanda kept our culture intact—and she did a huge part of this remotely before remote work was as popular as it is today. When we hired her, Amanda was very upfront about the fact that she dreamed of moving back to the Pacific Northwest, and a couple years into her employment, she achieved that dream. Even with virtual barriers, she was able to keep Student Maid’s culture strong, which is a huge testament to the kind of leader Amanda is.
In 2021, when we made the decision to transition Student Maid away from cleaning and go fully toward the leadership development space, it meant that Amanda’s role needed to drastically change because the business had drastically changed—especially now that we no longer had a team of students working with us. We went from being a team of hundreds of students during our peak times to a team of five (including Amanda and myself). Our needs on the culture side of the business just aren’t the same with our smaller team. Plus, going into the transition, our culture as a leadership team was already extremely strong because we had been building it together for years. Knowing we didn’t have a need for Amanda’s Chief of Culture role, I started to look at other areas in the business where Amanda would be able to contribute.
At the time of the transition, I was really struggling with integrating my life at work and my life outside of work. Personal and work tasks were piling up because of the demands of leading a business, and it would often leave me feeling overwhelmed and not at my best at home or at work. I presented Amanda with the idea of a new role, which would include helping me with various tasks so that I could be at my best, supporting other members of the team with similar taks, helping me integrate my life and work on my calendar, partnering with me on existing cultural initiatives for our leadership team, and eventually growing into more of an executive support role as the business continued to grow. Amanda decided she was in, and together, we gave it our very best go. After a few months, Amanda landed on a name for her new role, which is honestly the coolest title we’ve ever had in our company: Chief of Compassion.
Amanda has made such a big impact on me in her time as Chief of Compassion. She has made me feel loved and cared for on really hard days; helped me think differently about my calendar; helped me plan celebrations for milestone anniversaries for our teammates; helped me get a handle on my overwhelming tasks; and inspired me to be a better human and leader with her consistent “can do” attitude. She’s helped me pinpoint where I need the most help, and I have so much more clarity and self-awareness now than I did when she started in this role. And with that clarity, I’ve started to recognize something very difficult.
On our team, we are really big on aligning roles to people’s sweet spots—the place where strengths and motivations meet. The idea is that work is more fulfilling and energizing when you are working in your sweet spot. Working in your natural strengths prevents you from feeling like you need to stretch or overextend yourself on a regular basis, and working in areas where you are motivated allows you to feel that “spark” inside.
Amanda and I have very similar sweet spots, which is a huge part of why we love working together. Our strengths and motivations most definitely lie with people, relationships, and culture. We approach our work in similar ways and get energized (and drained by) very similar things. The difficult reality is that, despite trying our absolute very best to make it work together, I have recognized that this role is not in Amanda’s sweet spot. Nor is it in mine, which is ultimately the reason I have a need for this role in the first place. Keeping Amanda in a role that I know isn’t her sweet spot means I am putting her in a place where she will continuously need to stretch. And even more than that, it means that Amanda’s superpowers are not being used to their fullest potential. But what made this realization even more difficult is that there isn’t another role in our business that will allow Amanda to use her strengths to their fullest and make the kind of impact I know she is capable of having.
If I’d had this realization 10 years ago, it would have gone very differently. I would have ignored this hard reality, neglected my true needs and the needs of the business, and continued to create experimental role after experimental role for Amanda so that we could continue working together. I would have done that because I feared losing and hurting people—and to be honest, I still have that fear. But the thing is that that approach was not responsible leadership on my part, and it got us in a lot of trouble. It led us to hold onto a team larger than the business could sustain and played a huge part in why our company went into debt years ago. By continuously creating roles to keep people on the team, I thought I was being a caring leader, but in reality, I was hurting my company and everyone in it.
Today, I approach hard decisions very differently. I look to our values, which are Courage and Compassion. And while I want so badly to keep Amanda on the team because I love her endlessly and we have been working together for seven years, I had to ask myself: Is keeping her on the team really a Courageous and Compassionate choice? The truth is, it’s neither. It’s not Compassionate because I know that Amanda will continue to stretch to fit this role because she cares about me and our business. Keeping her in a role where she is stretching is preventing her from working in her sweet spot, which ultimately hurts her, me, and our team. And it’s not Courageous to ignore that reality just because it’s difficult and sad and I love working with her.
And so . . . that leads us here.
Here is a place where, even though it’s so incredibly hard, we are letting Courage and Compassion lead the way. That means running toward this together, having open and honest conversations, stepping outside of our comfort zones, rallying around Amanda to help her find a new role and organization that she will love and where she can have the greatest impact, taking care of Amanda financially so that finances are a nonissue and she doesn’t need to rush into her next step, and holding space for our feelings—especially those of Amanda—as we ride the emotional rollercoaster that comes with difficult moments.
What is most important to Amanda—and to all of us on our team—is to be authentic and to show the human side of our business. To show that it’s not always rainbows and butterflies and that we have difficult moments as a team, too. And most of all, to show that while this decision has been absolutely heart-wrenching and devastating for each person on our team, it’s also been beautiful and compassionate, and we are taking the very best care of each other humanly possible.
In all of it, we realize that the “and” is possible. That’s the message we hope you take from this blog post.
It’s possible to be courageous and compassionate.
To make a difficult decision and take care of someone.
To be devastated and know there are beautiful moments ahead.
To feel that something is hard and right.
To experience loss and gratitude.
To be so sad that there is an ending and be so comforted by how caring that ending can be.
And the only reason that “and” is possible, I think, is because of the trust and relationships we have worked so hard to build. This is the power of a human organization. It gives you the foundation to weather even the most difficult moments together.
One of the most important things Amanda shared with me in collaborating on this post is that she wants you to know that she feels the “and,” too. That it really is possible to go through an extremely difficult time while still feeling cared for and knowing that something beautiful is waiting for you on the other side. In her own words:
The last few weeks have been SO hard. It’s been filled with moments of devastation and tears . . . AND it’s also been filled with love, support, and many moments of knowing this feels right. I’m so grateful for Kristen and our team . . . that we acknowledge there is an AND. That I can go through the hardest moment of my career (arguably my life!), feel the feels, and also feel so loved and supported. It almost doesn’t sound believable, right? But it’s true!
I wanted to collaborate on this blog with Kristen because like she said, I want everyone to know that the AND is possible. But after more reflection, it’s also to encourage others to embrace difficult decisions even when they feel hard and know that there will also be good on the other side. I don’t think I would have made this decision on my own—not because it isn’t the right one, but because I love our team so much and I know that our company is so amazing. I’m grateful for the high level of trust we have so that we can say the things that are hard to say and encourage one another to be in roles where we thrive. That’s what we teach others to do, and so even though it’s hard, I’m happy and proud that we are practicing what we preach.
I’m going to miss working with Kristen and the team so much! To be honest . . . that’s where most of the tears are coming from. I’m excited for the future . . . to find a new environment where I can use all of my strengths and make my biggest impact. Yeah, it may have a few unknowns, but we’ve created a plan that makes me feel safe and secure! Reader, we want you to know, and I want you to know that the AND is possible. It’s hard, difficult, and sad AND I feel loved, excited about my next chapter, and I know my team has my back.
This is definitely not a goodbye for us. Amanda is and will always be one of our dearest friends, and we are absolutely committed to helping her find her next step. In addition to covering her financially far after her role ends in December, we are actively pursuing positions for Amanda where she can harness her superpowers and make the kind of mark she’s made on our company. And while we don’t know what that next step looks like just yet, we do know that the organization that gets Amanda next is really freaking lucky.
If you are reading this and think that you might have a role for Amanda in the people and culture space of your organization, of course we would love to hear from you. (We’ll be honest, though: We have some pretty high standards! This is our Amanda we’re talking about!)
Thank you for giving us the space to share this with you. Thank you for making us feel safe to share our happy times and our hard times. And a special thanks to Amanda for encouraging me to write this post and to show what it means to be human.
Big hugs from all of us,
