There’s probably no better person to write this list of tips than me. That’s because I’ve had to tell two jobs I was pregnant, for the same pregnancy.

Why did this happen? I had to tell my first job I was pregnant when I felt comfortable doing that, and then a week later, I got a new job offer. I started that job, and then had to tell my new boss I was pregnant!

There’s a lot to consider when you have to figure out when to tell your boss and your job that you’re expecting. It’s one of the hardest topics that comes with pregnancy, because of how your coworkers might judge your ability to work, and how your boss might decide to replace you while you’re on leave.

Regardless of these challenges, here’s a list that should help you figure out when to tell your manager or your team at work that you’re pregnant. Next, I’ll also discuss how to do it.

When to tell your boss you’re pregnant

As you’ve probably learned thus far in your pregnancy, every pregnancy is different. On top of that, every job is different, and of course, every manager, supervisor and boss is pregnant.

Here are the things I considered about when to break my news, because there’s truly no “right time” to tell your work or job that you are expecting.

When you can’t hide the baby bump any longer

If you work in person, chances are you’re going to start “showing” at some point.

For me, in my first pregnancy, this was baffling late in the game. I was wearing non-maternity pants (just up one size) up until my fourth month of being pregnant and in month five, I started wearing maternity jeans with loose non-maternity shirts. I was also biking to my office in Brooklyn, just under two miles each way.

No one would’ve ever guessed I was pregnant, especially because the company hadn’t gone out for drinks any time recently!

I finally made the move and decided to tell my job I was pregnant in late July, which was into my fifth month already. After breaking the news, I started wearing tight clothes that didn’t require me to hide the baby bump any longer, even though it was small!

If you’re having morning sickness and need accommodations

While I didn’t have morning sickness (just nausea on a few occasions) in my first trimester, I have plenty of friends who had debilitating morning sickness and other first-trimester symptoms.

If you have nausea, insomnia or other medical symptoms, it may be best to privately tell your boss in confidence that you are pregnant, for logistical reasons. This may help with some understanding if you need to nap due to exhaustion or sleep late due to a night of bad sleep, and more.

If you have a medical need and want to be transparent

Some women come down with medical situations early in pregnancy, and while this was not me, I’m sensitive to this as a matter of fact. If you need to go for frequent testing or frequent doctor appointments, it may be helpful to let your boss in on the secret of your pregnancy so that you’re excused from business trips or meetings.

If you really need to start planning for your leave and replacement

I started planning for my leave well into my third trimester, with a robust thought-out plan and frequent meetings with the two coworkers who’d be taking over my duties.

If your job is a higher-level position whereby multiple people will be taking over for you and tons of advance notice is key, you might want to tell your boss earlier than others that you are expecting. Together, you can make the planning happen.

Helpful Tip

Regardless of all my maternity leave planning, I was laid off while on maternity leave, and I recommend reading about it!

If you can’t come to the office anymore

If you work in person, whether in a hybrid role, full in-office role or on-site role, your pregnancy may affect your ability to commute, for any number of reasons. If your pregnancy is going to be affecting how you may need to work remotely, your boss may appreciate earlier notice than later notice about your pregnancy. Truly, it is up to you!

Things to consider about letting your work know you’re pregnant

So many women, including myself, lose sleep over the fact that telling your boss you’re pregnant is one of the most stressful things you may have to do in your life. Giving away that you’re pregnant can lead to all sorts of worries, from being treated differently, to being judged for taking time for parental leave.

When I told my boss and all my higher-ups that I was expecting, I felt like a flip had been switched, and you may feel this way, too. As if all the things you can’t do while pregnant wasn’t enough of a change!

Pregnancy discrimination

Pregnancy discrimination is real, and of course, it is illegal, but at the end of the day, it is hard to prove. I found that the article from What to Expect describes it well, and it was a big player in my decisions to conceal my pregnancy when I got a new job while pregnant.

People treating you differently

I was very lucky in that no one really treated me differently at my first job, when I told everyone at 5 months pregnant that I was going to become a parent (yay!). In fact, the colleagues who already had kids were over the moon and overjoyed for me, and one of them almost cried when I told him. It was so sweet!

At my second job, the one where I started at 6 months pregnant and gave birth while at that job, I felt a little more tense in telling people. I think it’s because I hadn’t known them as long, and once I told them I was pregnant, I became the “pregnant coworker” and they had to figure out how to deal with that.

I hope that you don’t get treated any differently, and I think I learned that I much preferred being pregnant around people who knew me really well and were happy about my news, rather than coworkers I had just met who barely knew me.

Being able to connect with other parents at work

Once I had broken my news and had my pregnancy out in the open at my new job, I started connecting with other coworkers who were parents! I joined the #parents Slack channel, and even posted, “Let me know your best advice for having a newborn!”

At least 15 people chimed in, and it was nice to see the voices of coworkers who were also parents, because at times it felt like so many of my colleagues were younger and didn’t understand what I was going through. This was one of my favorite things about being pregnant, and was a positive light when I had rib pain and back pain.

How to tell your boss you’re pregnant (Tips and advice)

Here’s where you have to do what is comfortable for you. Everyone has a different communication style: some women are straightforward, and some are less direct communicators. Depending on where your boss is located, you may break the news in person, or by phone or by video meeting.

Here’s how I told my boss I was pregnant and here are a few tips to keep in mind.

What I did to break my news

I broke my news first to the CEO at the small startup I was working at in the first two-thirds of my pregnancy. I was close with pretty much everyone at the company, and felt that I should tell the highest-level executive first, just to be fair and considerate. I also came up with a strategic order of executives I’d tell, and then colleagues on my level.

I asked the CEO for some private time in a meeting one afternoon, and he and I sat down together to discuss the “things” I wanted to chat about in private. I talked first about my growth at the company, and how serious I was about leadership, and then I said, “And I should tell you, I’m five months pregnant.”

Of course he said congratulations and that it was great, as he was expecting a child that summer as well. Next, we jumped right into the logistics: maternity leave, covering my position, expectations about preparing for leave and then returning to work. It was business.

Talk about taking leave

Lucky me: I had two opportunities with two bosses to discuss my taking maternity leave. At my first job, I would’ve been the first person to take maternity leave at the company, ever. The company was young, the employees skewed even younger, and there was no formal policy about accruing parental leave nor taking it.

So, I put down my expectation, was told what I could expect (it was going to be New York State leave, paid at 66% of my salary for 12 weeks) and that was it.

At my second job, it was more complicated because I would not have been at the company for a full year before taking leave. Instead, I was under the impression that I’d be receiving the minimum paid parental leave time of 8 weeks, and accruing additional leave time for “months worked at the company.”

Helpful Tip

Be SURE to discuss parental leave policies and square everything away before giving birth! I cannot stress this enough, as people anywhere can be disorganized and your dates can be misconstrued. Make sure to put the dates and info into the right hands, and confirm twice.

Discuss your replacements and return to work expectation

Things can get a little complicated once you’re looking for who will take on your work while you leave. It might be anywhere from your colleague, who could take on your entire workload, to two colleagues who could split it, or a new hire completely who will cover for you at a bare minimum and then move into a different position when you come back.

Whew, that was a lot! The bottom line is that all of these logistics take a lot of preparation, especially if your boss wants you to hire someone new to be your replacement. It can be helpful to start early.

Put everything in writing and hit Send

After the conversation with the CEO and other leadership, I wrote a group email that formally announcement pregnancy and my due date, and the fact that I would be on leave starting around then, give or take.

I also stated that at that moment, we were figuring out my leave, but I noted the approximate timeframe for my parental leave and an expectation that my job would be there for me when I returned.

Create a parental leave plan

While I never got around to creating a maternity leave plan at the job I gave my pregnancy notice to around 5 months, I did have to create a maternity leave plan for the new job, because I was soon to give birth.

I think my maternity leave plan was the single biggest accomplishment I had at the job I got when I was six months pregnant. It was almost nine pages, and outlined every responsibility of mine, and who would be responsible for it in the months I was on leave.

It also put into writing my expected dates of leave, based on my due date, and my approximate return-to-work dates. Lastly, I put both my due date and my leave dates into Google Calendar and made “invitations” to send to my boss and immediate team, so that they could reference those details.