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3 tips for CEOs planning to take parental leave

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3 tips for CEOs planning to take parental leave

February 20, 2023
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Cory Siskind is the founder and CEO of Base Operations, a threat intelligence software company based in Washington, D.C.

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:

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.

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

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