If you told me two years ago that I’d be able to take an extended leave from our business to spend time with my family, I would have never believed you. Now, I’ll be doing just that.
I know, too well, the fears, stigmas and worries entrepreneurs face when hoping to take parental leave and start a family. I hope sharing my and my team’s story will support changing and challenging this lived reality.
I wanted to share how we as a company prepared for this moment because it not only allowed me to start a family but also be excited for this next chapter for Sampler.
Getting the right leadership team in place
Over the last two years, one of my primary focuses as a leader has been hiring, nurturing and promoting the right people to join our leadership team. A good leadership team is instrumental in making effective strategic decisions and driving those strategies in your leadership team’s respective departments. If I have learned anything over the years, it is that hiring the right people can bring the dreams you never thought possible for your company to life.
Before having a formal leadership team in place, I had way too many direct reports and was too involved in the company’s day-to-day. I could have never dreamed of taking some extended time off at this point.
Now that I have the right support in place:
- Most of my time is spent on strategic planning and key decision making
- Very little of my time is spent on managing the details that ensure my business runs
This was my goal, and I worked towards this separation over the last two years. I wanted to ensure that Sampler’s day-to-day operations wouldn’t be impacted by my time away. If you’re planning to build a family in the future, laying this kind of foundational leadership will be key.
Finding the formula for success that will work for you and your family
Once you start preparing your leadership team, the next step is to talk with your partner and/or loved ones about what will work well for your family.
My husband and I don’t have family nearby and we’re both very busy entrepreneurs. We thought about getting child care, but we also live in a small downtown condo that during the pandemic has been our office, home and everything else in between. We decided that we didn’t feel comfortable with options outside of our home and the more we discussed it, the more I realized that it meant a lot to me to take some time off, especially after seven and a half years of running a fast-growing company.
I discovered how important it was for me to just spend quality time with our soon-to-be new son. I couldn’t imagine myself missing those sweet first few milestones and I decided I was going to take a leave. These are decisions that we, as entrepreneurs and leaders, are allowed to make for ourselves – even though we are too often told otherwise.
You are not alone, talk to your network
I talked to a few friends who were CEOs, founders, executives when they had their first child and they shared different perspectives. After speaking to them and doing some thinking I made a decision that I would take a total of six months.
My formula for success
During the first month, I’d be fully off and I’d slowly re-integrate to check-in one day a week. That day and another day per week, my husband would be taking time off to enjoy daddy and baby time. This is our formula for success. I’m sharing it as an example, but yours will be completely different. Whatever it is, remember that you are absolutely entitled to it, you do not have to make it happen alone and you’ve earned it.
Creating and communicating your formula to success clearly, often and early
I felt (now and then) so lucky to have such a supportive board and team, but I also understood that telling them the CEO was going to be less available for six months with short notice would raise some questions. That’s why I thought it was so important to share my plans clearly, often and early. I wanted to give a good amount of heads up to everyone, but also to explain how the business would continue to operate.
By giving me and my team lots of time, I was able to show and discuss my plan often and regularly with different stakeholders from different areas of the business. This allowed me to discover gaps I wouldn’t have noticed on my own and ensure the plan was understood across the company.
Here is how I created my formula to success:
What am I responsible for?
My first step was to think about all the things that I am responsible for. I even did a fun pie chart which showed my average week:
What can I automate?
From there, I looked to see what I could automate or assign ahead of my leave.
For example:
- Supporting our finance team to template our investor reporting so they can fill the report monthly without needing me to go through a highly-manual review
- Working with the leadership team to template our bi-monthly leadership meetings and to get in a cadence of shared ownership so that everyone is preparing content ahead of time to ensure a productive discussion.
- Accelerating some of my key initiatives and assigning owners for those that I knew I wouldn’t get to. This meant hiring a few extra people including a people operations manager a little faster than we’d anticipated.
Review the plan with your leaders
Once both my personal and business plans for the leave were established I reviewed the plan with my leadership team. I told them the good news one by one, it was summer so we were able to do so on a nice patio (pre-COVID-19). Being one-on-one allowed me to answer their questions and reassure them with the plan I had set. In a consecutive meeting, we reviewed the plan all together and many of them offered up help, solutions and feedback to make the plan even stronger.
Bring in your board
From there, I picked up the phone and told our board. I was scared at first that they would be worried. That perhaps, they’d ask me to find a replacement CEO or something funky but they were all so excited for me and they were insistent that I take time. All of them made me feel trusted and simply suggested we review the plan I had set at the next board meeting.
At the next board meeting, the leadership team and I outlined the plan. It included a few new roles to off-load our VP of operations so that she could support my leave more actively, as well as new reporting and leadership team routines that would help keep me up to speed and involved effectively in planning.
Sharing your news with the greater team
I shared the news with the leadership team and the board a little earlier than I wanted to share with the team. I thought about how much can happen in the early months and I couldn’t bear imagining having to share having suffered a loss more broadly. Once we felt that the pregnancy was progressing well, we finally shared the news with the team. Everyone was so excited! It was really such a special moment and I was excited to go through this journey with everyone.
As a small company, we had coincidentally just recently set-up a parental leave policy as another teammate was expecting a child and I was really proud to tell everyone how important I felt it was that everyone takes advantage of this benefit. I hope that me taking the time for my family will inspire others on the team to do so if they choose to build a family. Just like I did with the board and the leadership team, I outlined a plan and reassured everyone that we wouldn’t skip a beat.
Prioritizing your time up until your leave
By now, I was past the horrendous first-trimester. I was, unfortunately, one of the women who suffered from bad nausea and extreme fatigue in the first trimester so I couldn’t wait to get back to my ‘regular self’.
I’ll be honest, in the first three months, I took full advantage of the pandemic work-from-home lifestyle and took several mid-day naps to try and feel like half a human during important meetings. I kept telling myself that it was okay to take it easy on myself and that when the first trimester would pass I could get back to the full schedule.
If you or someone you know is going through this, be kind, there is a human being growing inside of someone! That’s a lot of work!
Just as the books said, the second trimester came about with a huge surge of energy. I was feeling great and ready to tackle my to-do-list. Because I knew that the five-ish months left at work would fly by, I immediately created a priority project list and started removing things from the list that did not require me. That means I spent a ton of time critically thinking about how to effectively delegate responsibilities.
Making time to listen, listen, listen
During that six-month period, I also spent a whole lot of time listening to the team to ensure I wasn’t missing anything on my priority list. Was a team having communication issues or was everyone clear on what their key priorities were? I wanted to know it all.
One of the tools we already had in place was pulse surveys that are really good for receiving anonymous feedback from the team. But, I wanted to go one step further. I wanted to ensure I was hearing directly from every single team member. Even if they had recently joined the team and could tell me about their onboarding process or they’d been with us for a longer period of time and could tell me about how they felt their evolving role and responsibilities.
I decided I would have at least a 30-minute Zoom coffee with every Sampler team member within a six-week period.
You have no idea how much I learned. I got to:
- know every single person a little better. In so many cases I identified strengths in them I had not known about. For example, Charlotte Crawford who had just joined us had done a ton of diversity, equity and inclusion work in the past and she brought up something we could tweak in our product to make it more inclusive.
- to identify some important information, which inspired some new projects I knew I needed to tackle before my leave. For example, strategies to dismantle information silos that were starting to develop as we are growing so fast.
- find some key smaller company functions to address that were beyond the scope of my leadership team
I am so thankful that I was able to do this. I left these meetings overwhelmingly confident that my ‘first baby’ was in the best hands possible and with the most talented team.
Sending your thanks
March 11 was my official last day and the team put together the most amazing virtual baby shower for me. I am so thankful for how they showed their support as I prepared for my leave. But I am even more thankful because they put their full hearts and smarts into our company every day. For that reason, I will be able to take this special time.
Don’t forget to thank your team for making this possible. I’ll be forever thankful to Sampler’s for giving me this opportunity.
I decided to write this post because I was looking for something like this as I was starting to think about how to get prepared to start my family and I couldn’t find anything. I hope my story helps in bringing you peace as you start preparing for a whole new type of ‘startup.’
