Dear Bossy #3: I'm pregnant, when should I tell my boss?

Dear Bossy,

I’m pregnant. it is kind of early in my first trimester. I haven’t told anyone at work (just our close family). I know that after the baby is born I don’t want to go back to work full time and I may not want to go back at all. When should I tell my boss I’m pregnant and when should we talk about my returning to work?

Baby Bump in Boston


Dear Baby Bump in Boston,

Congratulations! So excited for you. Big life change coming at you. This is a great question and one I think most women who have children grapple with. Here are my thoughts for you.

I wouldn’t tell your boss about the baby until mid-2nd trimester. Lots can happen in your first trimester and you don’t need to share this news so early. Once you are solidly in your 2nd trimester you will definitely start to show and I would disclose to your boss about your baby and your due date. That said - if you are suffering from any first trimester health issues that require some workplace accommodations, then I would tell your boss sooner. But if you are managing just fine right now, then keep it your business for a bit longer.

I assume you are a woman of child bearing age, so your boss (male or female) has probably already made the assumption that you are going to get pregnant some day. So the news you are having a baby shouldn’t be a huge deal or a big shock. When you are ready to tell your boss, I’d focus on the due date, the maternity leave policy and making sure there is a plan in place to cover your workload while you are gone. More time for the team to plan is good, so don’t wait to start this conversation for too long.

However, I feel very strongly that you should not plan beyond the maternity leave with your boss right now. You don’t know what adding a baby to your life is going to be like and I wouldn’t make life plans that far in advance in collaboration with your boss. You should make all these decisions together with your family (partner, etc). My suggestion is to plan for a regular maternity leave, taking advantage of whatever policies your workplace has to give you. You do NOT need to start negotiating about part-time or not returning at all right now. Give yourself the full pregnancy and maternity leave to make these plans known to your boss.

Again, most bosses, make assumptions about women and babies. They assume some aren’t coming back or aren’t going to be as engaged when they do come back. So instead of tipping your hand about that - tell them you are planning on coming back on xy date and at full time.

Then once you’ve made up your mind about what you want for your family (once the little one has arrived), you can begin the negotiation process with your boss. If you are planning on not returning at all, you still want the maternity leave coverage and benefits through your labor/delivery and post delivery phase (this stuff costs a lot of money) and you may have a better sense of your availability and needs once you know about this kid and your needs.

If you decide you want to return to work in some part-time capacity, this is a different negotiation and depending on your workplace and flex time policies it may be hard or easy to have that conversation, but I’d wait until you know what you want.

I have one other piece of advice I give to ALL women who want to have families and have jobs and I stole it from Sheryl Sandberg - lean in to your work before they know you are pregnant and/or before your maternity leave. Get the raise, the promotion, the interesting project before you depart. If you do want to come back to work right away or later, you want something interesting to come back to. Don’t assume you will be less engaged or less productive and don’t let your boss assume that either. Get the raise and if you leave, you will have little more in your pocket for your time with your family and if you decide to go back to work you will have a higher salary expectation.

Good luck with the pregnancy. When you are on your maternity leave and decide what you want to do, write back and we can talk about the negotiation!



Dear Bossy #2: I'm a teacher and want a new job

Dear Bossy

Quick note. I’m a teacher. have been for 20 years. I’m about to walk into a ed-tech career fair. Any advice??

Thanks for any advice

Teacher in NY

Dear Teacher

20 years as a teacher - you have experience. My advice

be upbeat - no one wants to hear how burnt out you are as a teacher or what little shits your kids are or how this new generation is lazy. Keep it upbeat and positive.

Remember your experience - you have 20 years of experience. Anyone building an EdTech solution would be lucky to have you. You know what actually works in the classroom and with learners. Lots of this will translate.

I truly believe that anyone who can get up in front of students and get their attention day in and day out can do anything. You got this!

- Bossy

Dear Bossy - my new advice column

I have been called bossy my whole life.

I take it as a compliment.

I’ve decided to share some of the advice I’ve given (and been given) over the years about being overworked, always on, dealing with co-workers, re-org’d (again), poor performance reviews, changing managers, downturns, promotions, crying at work… and share it in all in an advice column format.

Let’s learn from each other.

Please send me your letters at

On International Women's day 2019 - Give me the effing ball

Abby Wambach - Barnard Commencement May 16, 2018

Abby Wambach - Barnard Commencement May 16, 2018

If you haven’t heard Abby Wambach’s Commencement address at Barndard College on May 16, 2018, you should. Watch it now.

As a speaker/coach/consultant to women in business, It makes good business sense to raise up more women into positions of power across industries. There are many barriers to women’s success, but none are insurmountable.

Here are a few goals I challenge each business leader and executive team to adopt in 2019

Promote more women

The pay gap is also a promotion gap. Don’t be fooled. Women are passed over for promotions. We aren’t seen as leaders, we aren’t given chances and we are paid less when we do get the job.

Women in the Workplace study 2018, McKinsey & LeanIn

Women in the Workplace study 2018, McKinsey & LeanIn

According to the 2018 Women in the Workplace study from Mckinsey and LeanIn, “The two biggest drivers of the pipeline are hiring and promotions, and companies are disadvantaging women in these areas from the beginning. Although women earn more bachelor’s degrees than men, they are less likely to be hired into entry-level jobs. At the first critical step up to manager, the disparity widens further. Women are less likely to be hired into manager-level jobs, and they are far less likely to be promoted into them.

in 2019 - I challenge CEOs and business leaders to see potential in your women. Raise them up. Pay them well. Promote them to leadership. Your women are a competitive advantage.

Stop keeping mediocre men in management positions.

Bad managers are bad for business.

According to the HBR article “Why do so many incompetent men become leaders,” “The truth of the matter is that pretty much anywhere in the world men tend to think that they that are much smarter than women. Yet arrogance and overconfidence are inversely related to leadership talent — the ability to build and maintain high-performing teams, and to inspire followers to set aside their selfish agendas in order to work for the common interest of the group.” Women make great leaders.  Can you afford to keep that mediocre man in place when you know how much it will cost you?

The real productivity killers - Jerks.

The real productivity killers - Jerks.

In 2019 I challenge CEOs to scrutinize your under-performing managers. Bad bosses are costing your business. And right behind that mediocre male boss is probably a set of competent and talented women ready for the job.

Believe women

Whether we are talking about sexual harassment, abuse, toxic workplaces, bad bosses…it is time to believe women. Women have been disadvantaged and assaulted and humiliated and de-humanized for long enough.


The brave and powerful Dr. Christine Blasey Ford testifying against Kavanaugh.

When an employee tells you they have been harassed or mistreated at work, believe her. The all too common story of the woman complaining to HR and getting no support replays over and over again in our companies. Remember Susan Fowler taking on uber or the big payout google gave to its exec after accusations of sexual misconduct. We can and should do better.

In 2019 I challenge CEOs and Boards to believe women, trust women, support women and remove toxic managers, and build cultures of zero tolerance for harassment of any kind.

As Abby Wambach said “Women, wolfpack, be united, storm the valleys together, and be our salvation.”

3 tips for negotiating more in 2018

I had the honor of being up for an award at the PDX Women in Tech Holiday party last night in Portland, OR. And was invited to give a 3 minute lightening talk. 

In case you missed it, here are my 3 Tips for Negotiating More in 2018

  1. You can't get what you want if you don't know what you want
    • and Money isn't everything
  2. You don't get what you don't ask for
    • Someone else is in your bosses office asking for that promotion right now
  3. Stick with it. No may be just the beginning.
    • If your boss says yes right away, you didn't ask for enough

Here are the slides

What are you going for in 2018?

My Favorite Negotiation in the Movie Hidden Figures...and there are many great ones in this movie

Women in the workplace too often face a double bind between being perceived as likable vs being seen as competent. Push too hard for your idea and you may get what you want, but you'll be called a bitch or be labelled "too aggressive." Help out a colleague or keep quiet in the meeting and in your next review you may be given the feedback that you "don't have leadership qualities." 

In the tug of war between being aggressive and appeasing, women often find they can't find the right way to advocate for their ideas and their own career trajectories.

That is one of the reasons I loved this scene in Hidden Figures. If you haven't read this book, read it. You will be inspired by the African American female NASA Engineers who were smart bad ass women that did the math behind the scenes who sent men to the moon and dealt with extreme racism and sexism in the streets and in the office. And the movie does an amazing job of bringing these stories to life on the big screen.

Want to watch a black woman navigate an extremely tough negotiation? Check out this clip:

Here is one of the smartest engineers - called a "computer"-  initiating a negotiation about "being in the room" where key decisions are made that impact the inputs to her calculations. Here are they key features of this masterful negotiation. 

  1. Find the person who has power - her immediate supervisor is racist and sexist and clearly threatened by her smarts and talents. Don't let a manager like that stand in your way for too long. Find a way to skip level to their manager, where the power/decisions are made.
  2. Bias may be less overt now, but biased people are not likely to help you out - so don't waste your time with biased people, you are unlikely to change their mind.  If you can point out their bias in a non-threatening way, do so, otherwise, find allies who can help you and assume your success may teach them a lesson in the end. 
  3. Make the negotiation about the success of the team, not your success - in order for NASA to send a man to the moon, Katherine needed to be in that room. This wasn't about Katherine getting a raise or about getting recognition or about a corner office. This was about the performance of the team. It is hard for a manager to argue with something they know they need, in this case, quicker results. Connect what is good for you with what is good for the team and your ideas will become more strategic and important to your boss. 
  4. Use what you know about the person you are negotiating with to get them on your side - Katherine knew that her boss was under tremendous pressure to get these numbers, get this right and get a man on the moon. He had no time. She picked this moment well. The hallway, a split second decision, sometimes that is when you get the yes. 

Walking the tightrope between being likable and being competent can be exhausting. Don't let it wear you down. Don't let feedback on your style hold you back. Pushy, aggressive, demanding, abrasive - these are all gendered terms that are used to subtly disadvantage women. 

If someone says "don't get so upset," when you are getting animated about a topic at work, as Katherine is about being in the briefing room, keep your cool and stay focused on the goal. You can be passionate and pushy and right all at the same time. 

Equal Pay Day - Closing the Wage Gap

Research from BLS 2014

Research from BLS 2014

Today, April 4, 2017 is EQUAL PAY DAY.

What is Equal Pay Day, you ask? It is a day where we as employees, employers, advocates, policy makers and concerned citizens can focus our attention on the wage gap that exists between white men and pretty much everyone else who works.

The wage gap has very real consequences for women and people of color for what they earn for equal work compared to men. 

Want some concrete tips on what you can do to personally make a change for yourself, or others, today?



The system has a pay imbalance built into it. Women are promoted less, paid less and given fewer opportunities. Don't wait for someone to take care of it for you. Negotiate for yourself for a new salary, for a new role, for a total, a promotion, whatever you need. Here's a great article from Entrepreneur today with some good tips. Contact us to talk about your own negotiation or bringing us into your company to teach important negotiation skills to your women. 


Be an ally

Whether you are in management or aspire to be in management - see something, say something. If you have a co-worker who is doing a great job, go out of your way to let her and her boss know about it. If you see a co-worker not being heard, amplify her voice. More voices together are powerful. Vocal allies can often say something for or about us that we can't say about each other. Read about the Women of the Obama White House who amplified each other's voices in meetings: 

Support businesses who support this cause

More than 300 businesses are offering a 20% discount today as a protest #20PercentCounts. See the full list here at And that isn't limited to retailers. Last year Salesforce spent 3 Million to close the gap between what women and men make.


Need more tips? (as if we aren't busy enough?!?)

 Here are 10 things HuffPo says you can do to dismantle the wage gap. 



Diverse and inclusive cultures: What are you waiting for?

I can’t say that I was shocked to read the recent Uber scandal from a female engineer, Susan Fowler. But, I was sad to see Uber’s CEO and Board say they were “shocked” by these allegations.  The actual quote from Uber CEO in an all staff email was “abhorrent and against everything we believe in.”

Too many tech startups hide behind a series of excuses about why discrimination and bias persist in their companies. A common excuse is "we grew so fast". Another is “I didn’t know this was happening.” The truth is - it is your job as the CEO/Management team/Board to know, especially as you expand the company beyond your core team. Who you hire, promote, and reward sets the tone for your company and actually demonstrates “what you believe in.” But most Management Teams and Boards aren’t asking the right questions and aren’t committing to changing their own diversity and inclusion practices.

As a collective group, those of us at tech startups aren’t doing very well. Our leadership teams, our Boards and our VC firms are all woefully un-diverse and the pace of change is inadequate by most standards. Creating an environment where a female engineer is harassed and her complaints are ignored my HR and management repeatedly is intolerable and we need to turn our shock and outrage into actions and concrete commitments to change.

Why is this problem so intractable? I believe the main issue is that Boards, VCs and Leadership teams aren’t holding themselves accountable. Enough is enough.

Here are 5 actions you can take right now to change what your future looks like as it relates to diversity and inclusion:

1. Know your diversity numbers

You cannot manage what you don’t measure. Let’s start measuring our numbers, across departments, before we become Google and Facebook. It is a quick chart, trended over time, of Gender and Race/Ethnicity by department. Add in attrition rates by those same demographics, because this can be an early warning sign that you haven’t created an inclusive culture where diverse people can thrive.

As you put your next Board packet together – put this slide in there and commit to having a conversation about it with your leadership/Board team.

Inspired by:

2.   What training can we afford?

Commit some resources (stage appropriate) to provide training for your managers. If you are a 10 person company bootstrapping, you don’t have a lot of resources, I get it. But if you are a unicorn growing like a wildfire, you do. Divert 2% of your food/snacks budget to training for managers on a regular basis. Smaller staff = smaller training budgets. If you wait until you are Uber size, you better have bigger pockets. Lawyers and crisis management teams cost a whole lot more than trainers.

3.   What does our Team and Board makeup say about our commitment to diversity?

It starts at the top – Diversify your Leadership team and Board. Make every effort to recruit people of color and women into your company and into Leadership and Management positions.

You will be in good company – many other tech companies are vying for the same executives you are, so be prepared to woo them with your commitment to diversity, inclusion, what role they will play in helping you get there. Be honest about where you are and where you want to go and why you need them. 

One founder I know of a tech startup that had a successful exit says that if he had it to do over again, he would start with a diverse Leadership Team from the get go. Let’s not continue to make his mistake over and over again – if you are starting out or just at the onramp of your growth curve, make this one of your goals this quarter. You can’t expect to have a company that values diversity if you don’t have any diversity making decisions at the top.


4.   Do we truly believe that diversity is worth investing in?

A core problem with many of the Leaders and Boards and VCs today is they aren’t on diverse teams themselves. Silicon Valley Bank just released some new numbers for how many women are in VCs and on Management teams and the numbers are not great.

Here’s another diversity breakdown of top VC firms. If you look at these teams, it seems like diversity is a nice to have, not a business imperative. But it does matter and research is clear that diverse teams outperform non-diverse teams on all measures of success. Remind yourself and your company of the business outcomes that come with diverse teams. Not sure what those are or don’t really believe them – educate yourself. It is well documented that diversity improves the bottom line.


5.   Can we afford to do nothing this quarter?

Maybe it doesn’t feel like the right time. For most of us in tech startups we live quarter to quarter with very little wiggle room to lose focus. I’ve been there (I am there today). If that feels like your story right now, do a thought experiment about what it is costing Uber right now in the eye of this storm.

Can you afford to be the next Uber or Tesla? Think you won’t be as stupid as Uber? Maybe not, but without a diverse team building and shipping your products, you might miss important market segments and features that are important to your customers. Remember when Apple launched the Apple Watch without a period tracker when a large share of their potential market would have a period in her lifetime?

Without diverse teams you can’t continually ship products that appeal to your customers, unless you sell only to bro-grammers.


Is this a turning point for the tech industry to focus more on diversity and inclusion? I don’t know, but I do know, each company can do a few things on a regular basis to make a big difference for their own culture and team and chances of success. What are you waiting for?

Need more ideas for what to do to tackle diversity and inclusion at your own startup?




Nevertheless, she persisted

I watched my son's 7th grade rec basketball team win a tough match this weekend. And the MVP of the match was most definitely the only girl on the whole court. This girl was consistently fouled by the same big 13-year old dude on the other team. And she kept at it. Drawing fouls, heading to the free throw line and sinking her shots. 

What was astonishing to me were a few things:

  1. How tenacious she was - she kept driving to the hoop through 9 dudes - fearless and tough.
  2. She kept drawing fouls. She would take it strong to the basket no matter who was in her way. And she landed on the ground a lot. But got right back up again.
  3. She was clear headed enough at the free throw line to sink almost every shot.
  4. Only girl out there. And I've watched them all season and she is the only girl in an all boy basketball league. #Fierce
  5. Finally, and this is the best part, as she was walking to the free throw line for the 4th time in a row, she looked straight at the guy who kept fouling her on the other team and said "that's 4 in a row, 5 and you foul out." Loud enough so he could hear it, but not so loud that the ref heard. She was definitely not intimidated by him. And you know what, he fouled out pretty soon after.

What I love about this is her perseverance.

I was an athlete as a young woman and I credit my coaches and teammates for teaching me how to be good on a team and how to perform under pressure. And wouldn't you know it, there is a body of research that ties business success to experience with sports and especially for women. A 2014 study by EY Women Athletes Business Network and espnW found that 94% of C-suite women participated in sports at some point in their life, the majority having played at the collegiate level. And all of these studies point out that sports teaches communication, problem-solving, confidence and resilience, which are critical drivers of business success as well. You can read more on the study here

But this story isn't really about sports. It is about perseverance. Whether you are negotiating for a raise, dusting yourself off after a layoff, being the sole voice of dissent in a room of yes men, launching your own business or jumping back into the workforce after a hiatus - DRIVE TO THE HOOP LIKE YOU MEAN IT!

Image source:  This is a Book  by Demetri Martin

Image source: This is a Book by Demetri Martin


Because the road to your goals is long and winding. And your persistence will be the difference between making it or missing out.

I love seeing passion in my co-workers, in people interviewing for jobs and in people who want to "pick my brain" over coffee. Your tenacity can be infectious. Everyone I know who is successful in their own career is a fighter and playing to win. Don't let someone else hold you back, don't let failure define you. Get back up, get out there and fight for what you want.

This is especially true in negotiations. When you are negotiating for yourself at work, you are often raising a problem or issue to your manager. This is not easy and sometimes you can be seen as the problem. Women who negotiate are often penalized more than men. But that shouldn't stop you. Be prepared, have data to back up your ask, have allies, and most importantly, be persistent! No may be just their opening position.

You do not have to be a Senator from Massachusetts to persist when you are being denied. You can be a girl on a basketball court or a female in the boardroom. And your drive and passion is powerful. 


This post is dedicated to all the teammates and coaches I've had the pleasure to play sports with over the years. From junior high basketball and softball, to high school field hockey, lacrosse, and basketball, to college Ultimate frisbee, to my triathlon buddies, and my most recent old lady Futsal league!

From you all I've learned teamwork, collaboration, hard work, tenacity, losing with grace, what it feels like to win, how to get knocked down and get back up again and most importantly how to persevere. Thank you!

Girl Interrupted

We've all had those meetings where you say something and no one responds, the conversation moves on, and later on in the same meeting someone else takes your idea and everyone responds positively to it. Don't you hate that? 

I really do. 

I've been thinking a lot about this phenomenon lately. For us women in the workplace, this is not all in our head. It is well documented, here and here and here and here. Men mansplain, they talk over you, they take your ideas, they dominate meetings. And this can erode our self confidence and how we are seen by our peers and our boss. I hate to say it, but it can hurt your career trajectory. 

There are several concrete things that an organization can and should do to try to stop this habit from forming or for tackling it once it is in full swing. These include: 

  1. Make a no interruptions rule. Period. No interrupting while someone is speaking. Post it on the walls of your meeting rooms.
  2. Make sure everyone has time in the meeting to speak - go around the table or call on people who haven't shared opinions. 
  3. Provide unconscious bias training for all staff (and make attendance mandatory).
  4. Mix up meeting formats to allow for different personality types and styles to shine. Meetings don't always have to follow the same format - try card sorting exercises, white boarding, pair people up to generate ideas in teams. 

I've worked at places with some or all of these practices in place. Beyond organizational support, a very important component is also what you are going to do about it. You will be in a meeting (likely often) where your voice isn't heard. You need some strategies to try out and see which work for you and your company culture. Here are some I've used in my own manterrupted episodes (credit to Jessica Bennett for that phrase).

Find an ally
If the interruptions are epidemic where you work or always perpetrated by a few lone wolves, you can try to find an ally. Best allies for this are men who have some power in the room, but another woman can also be your wing woman here. The goal - have a signal that you can use to let them know you have something to say or that you are having trouble being heard. They can then jump in and say "Sarah has an idea we should listen to" or "I want to hear what Kelly has to say."

Be Subtle, But Take Credit Back
I hate to say it, but sometimes people don't know they are being obtuse and you have to point it out. Jump in right after the person restates your idea and say "Jeff, great idea, that is what I was trying to say 10 minutes ago. I'm glad you brought it back up. Here's my take on it." Maybe Jeff won't pick up on it, maybe he will. Either way, you are back on the board. 

Be Direct, Privately
Sometimes you have to nip this in the bud, directly. After an especially egregious meeting, take Johnny aside and tell him what you are observing. This can be awkward. Hopefully you have a good working relationship and mutual respect with this co-worker and he will hear what you have to say. At the very least, it may make him think twice in the next meeting. You can even try to make him an ally. Suggest he helps you get your ideas across in the next meeting!

Lobby for your ideas
Oftentimes decisions are made in side conversations or in smaller pre-meetings. If you are having trouble getting your ideas heard in a larger setting, nail the pre-meeting politicking. Have one on one meetings with key decision makers to plant seeds of your ideas with them. Ask for their support in the larger meeting. 

Pick your battles
Sometimes this is not the hill you should die on. If you find certain meetings or certain people just can't be changed, mix it up. Either start skipping these meetings, de-emphasize the importance of these meetings in your mind, follow up the meeting with key points in an email or find other ways to drive your agenda without fixing this problem. I have found sometimes sitting quietly speaks volumes.

What strategies have you employed to deal with being interrupted at work? Share your tips.