For those of us who spend our days participating in the paid labor force, we spend a lot of our time working. Our working conditions have a direct impact on our energy and stress levels, and on our ability to navigate life outside of our careers.
For years, I accepted that relationships with c-suite executives will inevitably feel tense or strenuous, because they have to put the interests of the organization above all else. However, I’m happy to say that I now have a whole new perspective – and new expectations of my place of work.
It’s my hope that, by sharing my story, it will help others realize that they no longer have to accept stressful or toxic working conditions. There are CEO’s who will prioritize the well-being of their employees over everything. They have learned the key lesson: when you care for your employees, the organization thrives.
Last June I started consulting for a female-founded, early stage start-up. Caren Cioffi, its founder and CEO, came to me because I have 10+ years of experience in software sales, and the organization was ready to start building a go-to-market strategy. I’d like to point out that I am extremely intentional when I partner with organizations in this capacity, but from our first conversation about the arrangement, it just felt right.
It felt right because it felt different than all the other interviews I’ve had with CEO’s in the past. Instead of grilling me about my experience and the 30-60-90 plan I had built, she centered the conversation around my ability to think strategically, my ideal working conditions, and where I like to focus my time and energy. It felt safe and collaborative. I realized that it was going to work with my ever changing crazy and beautiful life.
This was my first taste of the joy you can feel working for a female CEO. When you care for your employees, the organization thrives.
Reflecting on this experience, I’ve been able to identify four key reasons why I enjoyed this working experience so deeply:
1. Room for Flexibility
I have a family which includes a 16-month-old daughter, a husband, and an incredibly active pup. I also have a coaching practice, and the desire to live a fulfilled life outside of paid work. Like so many of you, I’m constantly trying to find more hours in the day! And we are not alone in this. According to McKinsey’s 2023 Women in the Workplace survey, it is flexibility that allows women to pursue their ambitions:
One in five women say flexibility at work has helped them stay in their job longer, and avoid reducing their hours.
Caren understands this. In the past I’ve worked for leaders who verbalize their desire to support more flexibility at work, but their actions speak differently. The expectation of flexibility in the workplace falls short.
Caren is located in California and I am here on the east coast. She does not care when I work, or where I work from. Being a mom of a little one while living in a country where childcare is so challenging to navigate will make it nearly impossible for me to work “normal” hours. That is not a concern. Daily updates are not necessary, because she trusts me. Not once in nearly a year has she put any pressure on me to put in a certain number of hours in a day or week for her and her team, or asked when or where I’m working from.
Having this kind of flexibility has empowered me to produce my best work when it works for me. On some days, that’s at 5:30 AM before my daughter wakes up, others it’s during a normal 9-5 work day, and sometimes it involves picking up my laptop after she goes down to bed. The beauty of it is that it doesn’t matter when I work, and in this phase of my life, that’s what I need.
2. No Space for Judgement
Caren is both a woman and mother. She understands the mental load we carry as women and the dozens of different tasks or thoughts we are juggling at any given moment. Instead of viewing this as a distraction to work, she views it as a superpower. She encourages me to take calls with her when I’m outside walking the dog, in the car for daycare pick-up, or unloading the dishwasher. These tasks are all things that have to be done, and she realizes that we can fulfil the duties of life at the same time as being a productive member of the team. Life is fluid, and conversations about work shouldn’t be restricted to your desk.
This way of thinking has opened up a whole new world of creativity. It turns out that my creative juices flow best when I’m driving. Every day, Caren lives her life out loud. What I mean by this is that the team knows when her children have events, which colleges they are applying to, where and when family trips are planned, and so much more.
She is a shining example of someone who celebrates their life outside of paid work, instead of viewing it as a distraction from producing results. This leadership style encourages the rest of the team to do the same.
If I can’t make a meeting, or need to reschedule something because an important life event is taking place, there is no fear of judgement.
3. Scope for Vulnerability
Caren has built a culture where failure is celebrated. After every big launch we come together as a team to reflect. If things didn’t go exactly as hoped, there’s no blame or anger. We simply look at things through a lens of growth; documenting our findings and making necessary changes for next time. As CEO, Caren accepts responsibility and holds herself accountable for everything, but she doesn’t do it in a self-deprecating way. The energy around these discussions is truly rooted in her desire to learn and grow.
As a team, we are encouraged to experiment, try new things, and innovate quickly. Inevitably, things fail, and that is OK! Embracing failure has empowered all of us take big risks. A lot of them pay off, but when they don’t we feel a sense of freedom to be open and honest in discussing our shortcomings.
Unfortunately, many people work in cultures where they feel like they have to hide certain parts of themselves. They fear that by being fully human at work, they will be penalized. The reality is, bias exists and this can happen. That’s why it’s so refreshing to work for a leader who doesn’t hide parts of herself, but instead celebrates them. It’s my hope that we can all aspire to lead more like this. I want to see more employers investing in their people.
We have the opportunity to create working environments full of flexibility, zero judgement and vulnerability.
4. Connecting to The Mission
The vision for Caren’s company, AgendaHero, emerged from a place of frustration. As a mom of two very active teenage children, Caren found herself spending hours each week building, organizing, and sharing schedules. Despite all the time she was spending, she felt that the agendas she made still failed regularly. She tried to find a tool to help, but had no luck. So she decided she needed to create one.
According to Pew Research, 74% of mothers say they do more to manage their children’s schedules and activities than their spouse or partner. AgendaHero takes the stress out of managing and scheduling events, so we can all spend more time enjoying them together. It addresses the mental load of schedule management and builds in safeguards to ensure that everyone shows up at the right place at the right time. This definitely spoke to me! When I connect with a mission I find that I am more motivated and driven to work.
This experience has taught me that it is possible to find a work environment that encourages my authenticity while also meeting my needs as a busy mom. It’s just a case of raising your expectations of your workplace! Before working for Caren, I didn’t know this was possible. Moving forward, it is what I have come to expect: when you care for your employees, the organization thrives.
