Taking Parental Leave as a Startup Founder

You are a startup founder. You recently learned that you or your partner is pregnant. Congratulations!

Start planning how you'll take your parental leave now.

You run a company, which means you work incredibly long, hard hours every week. Even when you are not sitting at your desk actively working, part of your brain is still grinding away at the problems your business is facing. Have you ever taken more than one consecutive week off? For many of us (before the prospect of parental leave), the answer has been "no."

There have been many Twitter flame wars about how many hours-per-week are appropriate in workers in Tech and for founders. Let's leave that aside because this is about your growing family, and about your team.

You need and want to take parental leave. The first weeks of your child's life are an amazing blur. If this is your first kiddo, you and your partner (if you have one) are about to cross a threshold with higher stakes than anything you've done before (yes, including your company). You will be rewarded with a brand new wonderful relationship with your child, and getting to know them as their personality emerges. It's also a period of the most erratic sleep you've ever had (unless you're a combat veteran). It takes time, and likely some tears, for you and your partner to get your bearings again. Parental leave is that time.

Unfortunately, many founders don't believe they cannot take leave out of fear that the company will break while they are away.

You've built a great team - trust them.

Yes, we have all seen and heard the founder glory stories. As a group we seem to be very fond of seeing ourselves on 30-for-30 lists and on cover stories. But this founder worship overlooks the fact that you are one person.

Don't believe your own hype as a solo-executor: you have built your team so that the company can scale beyond your own abilities.

There are a few reasons founders think they cannot take parental leave (or that they need to keep it super short):

• Important things will slip through the cracks
• The team won't know what to do
• The company will slow down

• Your investors will be angry or won't understand

These are valid concerns - but you can solve for them. One of the graces of learning there is a kid on the way is you have 7-8 months of time to plan ahead and set expectations!

Here's how, step by step:

Step 1: Decide who will be in charge while you are on leave

The most important part of parental leave is that you actually... leave. That means you are not engaged in the day-to-day decision making.

To feel comfortable with that you, your team, and your other stakeholders (investors, customers, etc), will want to know who is making the decisions.

This is especially true if you are CEO: who will be the final say in unclear decisions? But it is also true if you are in another typical founder position: if you are CTO, who is the engineering team going to report to in the interim? If you have a pretty flat org chart, there still needs to be a clear and declared handoff of your current responsibilities and deliverables.

When it comes to tapping in a new leader, I was fortunate to have my cofounder available for that. Andy and I started talking about the new reporting structure about 6 months before executing it, and told the team what was coming about 2 months ahead of time. One benefit to pregnancy being a 9-10 month timeline is that you have time to plan: use the time wisely!

Sanity Check: There will be decisions made while you are away that will be different than the decisions you would have made. That is ok!

As Reid Hoffman (founder of LinkedIn) has commented on the need for speed in startup decision making, and the tradeoffs from that speed:

"In order to move fast, I expect you’ll make some foot faults. I’m okay with an error rate of 10-20% — times when I would have made a different decision in a given situation — if it means you can move fast."

This is especially true when the typical decision maker (that's you) is out of the room. Give your team the autonomy they need to keep moving fast!

Step 2: Plan your roadmap and priorities well in advance

The first step in the plan is to know who is going to be executing it (see above). This takes you most of the way there.

But you also need to equip your #2 with everything they need to be successful in their new chance to step up. This will give them and the team they are managing the confidence to keep executing.

Whatever you use as your normal planning process, make sure you stretch those plans out farther into the future where possible.

One of the unique aspects of an early-stage start us is, to use Seth Godin's analogy: there is no map. It's the founder's job to make the map. To do that, they need to understand how to use their compass and their wits.

In startups, this compass comes from an intuitive sense of the market and the problem you are solving. That intuition is built over time through lots of engagement with customers and stakeholders.

Frequently, your team doesn't think of it as their job to be way-finders (that's your job). They are good at executing based on the map you build for them. So while you are away, leave them with a map of their immediate surroundings (this is your planning). And make sure your #2 is capable with a compass by looping them into all of your decision making processes well in advance of your departure.

For example, knowing that I would be taking leave around February/March of 2022, I made sure Andy was in every board meeting and every significant decision conversation since August of 2021.

Step 3: Communicate and over-communicate

This is admittedly the step I continue to need the most improvement. It is very easy to forget how often you need to say something in order for folks to hear and internalize what you said.

As Jeff Weiner, CEO of Linkedin remarked in an interview:

"A friend of mine once paraphrased David Gergen, saying on the subject of repetition, 'If you want to get your point across, especially to a broader audience, you need to repeat yourself so often, you get sick of hearing yourself say it. And only then will people begin to internalize what you're saying.'”

Making sure everyone knows their roles and responsibilities - and how those may have changed - while you are on leave is a key ingredient to success.

And again: use the lead time you have (in most pregnancies) to make sure all of your stakeholders know what is happening and what the plan is: I made sure our Board knew what the plan on well in advance of our execution of the plan.

Sanity Check: Your investors, if they are investors worth having, will back (and encourage) your decision to take parental leave.

There are several reasons your investors will be in your corner:

1. They want you to be successful over the long-term. Your investors are helping you run a 10+ year marathon, and that means partnering with you throughout many phases of your life. For you to pilot a successful outcome for them, they need you to have a home-life that is happy and healthy as well so that you approach your work from a position of strength, love, and support. (Example: Claire Díaz-Ortiz stepped in as interim CEO to help one of her portfolio company's CEOs take parental leave.)
2. They want you to set an example for the company. The fact of the matter is, you need a good parental leave policy if you want to be able to recruit top talent. That can be hard in a startup, but it's an investment worth making. It is also much different to live those values than to just give them lip service: by taking leave yourself, you demonstrate that your current and future employees will be able to do so as well. (Example: Gary Tan said exactly that when parental leave was a hot Twitter topic last year)

In my personal experience, it was the investors on the Board that encouraged me to take my leave more seriously and completely. I originally was planning to take a two weeks off, followed by 3-4 weeks of part-time: Mike Troy (Geekdom Fund) and Ben Nahir (Elevate Capital) convinced me to take my full leave completely off.

Your team is going to do great: enjoy the time with your new family member

I had all of the anxieties and neuroses I expect most founders do when it came to taking parental leave.

My team crushed it while I was away.

We had our best sales month in the history of the company while I was on leave (and it was not obvious that would be the case before I left).

Trust your team to have your back and they will.

Congratulations again: this is going to be a crazy whirlwind of joy and tears. Best of luck.

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