Cory Siskind
My company just had its best quarter ever. As its founder and CEO, I am proud to say that I wasn’t there for most of it.
I had a good excuse, though: I was on parental leave raising my first child. Since starting this company, I had not taken more than one week off, which included marrying my very patient husband. When I tried to schedule a sales presentation the same day we had our civil ceremony at City Hall in San Francisco, he rolled his eyes.
Needless to say, I was anxious about taking time off. Baking that little muffin was no easy task and I was not sure how I would respond when she was earth-side. But I wanted some proper time off and the opportunity to get to know her and myself in this new role.
I reached out to several of my investors, asking them to connect me with CEOs who had taken parental leave and was introduced to several male CEOs who sheepishly told me they only took a week or two.
I finally got a lead on a CEO who had taken some time off, but to no one’s surprise, she was too busy to talk to me. Fair enough! However, I did get great advice about taking leave while leading a company. Here are a few things I’ve learned:
Tell people you will be taking more time off than you intend to
You will want to tell people that you will be emailing from your hospital room and taking calls while nursing. “You’re not really going to be able to step away,” many people told me.
My wise friend and investor from Mindset Ventures, Jules Miller, advised, “Tell everyone you are going to take 12 weeks, and if you want to come back earlier, great. But you never know what this experience will throw at you.”
She was right. When my daughter was 28 days old, our house flooded. We had to pack up everything and move three times in three weeks. Because I had not fully recovered, I threw my back out from the moving and could not even hold my baby. I was grateful to Jules for her sage advice and the flexibility to truly check out and get my life together.
Prepare, plan and step back
We’re moving out of the founder-centric phase and becoming a company that’s ready to grow and scale. Leading up to my maternity leave, we had weeks of planning sessions outlining, benchmarking and validating our milestones for our next round of investment.
We mapped everything from the product roadmap to sales goals and hiring plans. As an early-stage company, we were new to this level of planning, but this was an excellent opportunity to mature our process and give everyone a sense of purpose and direction in my absence.
Of course, we wouldn’t have had our best quarter ever without an incredible executive team. I learned that the key to taking time off successfully is to hire well, plan well and then let go.
Set up your communication structure well in advance
Andrew Chang, former COO of Paxos, helped me set up a detailed communication structure for when I’d be away. It involved our VP of Operations aggregating information from all the teams in a dynamic document on a weekly and daily cadence.
My team could reach me on Slack for medium-level requests, via text for urgent requests and through my husband (again, he is patient) if I had not responded to an urgent question. Luckily, we did not need this last option. This tiered and distilled communication system allowed me to check in or out as much as I felt necessary.
I also found it helpful to take phone calls only. I didn’t need to worry about my hair sticking straight up on video. Also, it’s helpful to ramp back up slowly over weeks rather than all at once. It’s also a good idea to allow yourself to watch the worst trash TV during a midnight feed without feeling guilty. It is OK not to have the energy to listen to podcasts on investing, watch documentaries on AI or read business strategy books. Hello, Love Island!
What was the worst advice I got? At a conference, someone from a rival security company observed my eight-month-pregnant belly and told me to make sure my husband got enough sleep. You read that right. He said I was basically screwed, but if my husband got enough sleep, he could be productive during the day. The idea that my husband and I would share parenting duties did not occur to him. I’m back at work now, but my husband is still out on his 18 weeks of parental leave and handling midnight feeds like a pro.
Taking time off is a personal decision, but it should be just that: a decision. It’s an option for everyone, even CEOs. While it required extensive planning and communication, I was able to recover and get to know my new, adorable, squishy, pet human. I am grateful to my executive team, investors, aforementioned patient and supportive husband, and myself for being able to both lead and temporarily take some time off.
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