How Humans Choose

Before having my son, I had to buy a stroller. There are so many strollers. Big ones. Small ones. Folding ones. Different colors. Different designs. Ones that transform. Used ones. New ones.

I needed a stroller and the idea of picking the wrong one gave me anxiety. What if I spend too much money? What if I spend too little? What if I regret buying the wrong one because of some unforeseen requirement? I was paralyzed. Of all the experiences before having a baby, this is probably the most prominent thing I remember. To this day, it still gives me anxiety.

Unfortunately, decision paralysis is not specific to strollers. In 2000, psychologists Iyengar and Lepper did a study where they sold jam in a grocery store. First, they offered 24 types of jam. On a later date, they offered six types of jam in that same display.

What were the results? The larger display attracted more interested buyers but they were less likely to buy. When they did buy, it took them longer to choose. This is also known as Hick’s Law.


Another lens through which to look at this problem is information overload. Information overload is the paradox that the more information and options we provide to our users, the more considerations they have to make, which actually makes it more difficult to make a choice. By providing users with more choices, product designers can actually make it harder on them, not easier, to make a decision and be satisfied with your product. With more possible choices, users are more likely to make mistakes and ultimately make decisions they’re less happy with.



Source: Cheesecake


Source: CodeAnalogies

The Emotional Cost of Information Overload

Hick’s Law and information overload may not seem particularly groundbreaking. Who cares if it’s the wrong jam? However, if you’re choosing from 50 Vanguard retirement plans, and you don’t contribute because you’re overwhelmed by the number of options, it could impact on your ability to retire.

Barry Schwartz, Psychologist, gave a TED talk on the paradox of choice. He alludes to this study and emphasizes the cost of too many choices. “Not only does this mean people are going to have to eat dog food when they retire because they don’t have enough money put away, it also means that making a decision is so hard they pass up significant matching money from the employer … up to $5,000,” said Schwartz.

Choice can also take an emotional toll. Imagine you’re at a restaurant, like the one we mentioned earlier. There are close to fifty items on the menu and at least 10 are something you’re genuinely interested in. After 15 minutes of consideration, you order a dish. How do you feel? How would you feel if that decision was between three options instead?

The more choices, the more missed opportunities to consider. And the more missed opportunities to consider, the more regret you feel.

How to Help People Make Satisfying Decisions with Product Design

Below are a few of my suggestions for preventing your customers from feeling the dread and confusion of information overload, based on my years of experience as a product designer at HubSpot.

1. Run weekly design critiques.

“We built a new feature. Let’s add it to the global navigation.” A teammate suggested this to me a while back.

Would our feature be highly discoverable? Yes. The global navigation is the most highly prioritized, most visible part of our entire product. Would it get a lot of usage? Because of the placement, our hypothesis is yes. Was it as important to our users as the other items in that navigation? Unclear. This was a new feature and we had no user research data and no behavioral data.

Will one more navigation item really impact our users that much?

Here’s the thing. I feel very protective of our customers. We know the majority of them work in small and medium-sized companies and wear many hats. They’re incredibly busy and it’s our job to advocate for them in these situations.

If I add one more feature to the navigation, it means I add one more decision for every customer. The same goes for any additional text, icon, button, link, color, field, or radio button anywhere in our product. It means a little more anxiety, a little more paralysis, and a little more potential regret on top of all the other decisions they have to make in their daily lives. What should they make for dinner? What should they buy mom for her birthday? Which pipe should they buy to fix the plumbing issue in their bathroom?

Our User Experience (UX) team takes pride in this value and we run weekly design critiques to ensure we hold each other accountable to changes we’ve made, and provide feedback where needed so no UX changes are being made in a vacuum.

2. Be thoughtful about how often people use your design

The truth is, we’re constantly striking a balance between limiting choice for our customers and giving them access to the things they need. Additionally, that balance varies based on how often customers use our designs.

When I designed for the content management system team, the majority of my users interacted with my designs once or twice a month. This meant that every time they went to build out a landing page, they looked at that design with fresh eyes. They had to relearn everything each time. Some forgot how to perform key actions.

In contrast, the majority of my CRM users (sales reps, sales ops, and sales managers) are in my product every single day, all day. Because they’re in my designs so often, they remember where everything is and they feel comfortable with more choices and more information. This is a stark contrast with the marketers who make landing pages once or twice a month. The more customers use a design, the more choices they feel comfortable making. Miller’s Law lays down this framework stating that the average person can only keep between five and nine items in their working memory, so I try to bear this in mind, along with my users’ professions and needs, when I’m thinking about or proposing product changes.

3. Analyze user data and feedback on a regular basis

To find the right number of choices for your design, one must look inward. Here is what I recommend:

  1. Pull behavioral data to understand 3–5 key user flows in each design. These flows should be the thesis of why your design exists. They are the critical paths for customers in this view.

  2. Get on a call or meet in person with customers and have them to walk through those key flows while speaking out loud. Include both new customers and experienced customers. How quickly can they make a decision? Do they seem anxious? Do they regret their decision? You may have given them too many choices. Are they impatient? Annoyed they have to go somewhere else to do what they need to do? Bored? Maybe you can add choices to your design.

4. Put in the work and do right by your customers

Analyzing the results can be time-consuming. It’s easy to toss a word in here, another color in there, and a feature in the navigation. What’s not easy, is reversing hundreds or thousands of lazy design decisions after your company has scaled. Don’t wait until your customers scream. Be good to them and do what’s right. Put in the work to make decision making manageable from the start and build a culture of it on your team by running weekly design critiques. Your customers may not thank you but you’ll sleep well knowing they have one less thing to worry about in their very busy, hectic lives.

Ladies, Know Your Worth

Defeated and disappointed, I opened the door to my apartment and told my partner that I didn't get the position I wanted.

"You let them talk you out of it, huh?" he said.

"... Yes." I replied quietly.

"Loey, you're so empathetic you can get caught up in what others want - even if that means sacrificing what you want. You and I know you'd be great in that role. You're completely capable and totally qualified," he said.

It hurt to hear that but I knew he was right. Not only did I let empathy sabotage my goals, I let it alter the way I thought about myself. I walked into that discussion feeling clear, capable and confident. I walked out feeling insecure and overwhelmed. That person needed something that conflicted with what I needed and instead of standing my ground, I chose to appease them and let them make the call-both about my career path and about who I was.

How were we on such different wavelengths? I've found that the bigger teams get, the more change there is and the less connected people are to each other. As a result, you tend to run into a lot more situations where people are assessing your worth and capabilities without much or any history of knowing you. You change teams. You change bosses. You change boss' bosses. Consequently, you run a greater risk of being underestimated or placed into a role or team that doesn't play to your strengths. It's crucial that you have a strong sense of what you want and that you advocate for that-regardless of what's going on around you.

Don't be deterred by others' misperceptions of you. Business will always change. Your passion, goals, and growth should not.

When I gave a talk at SheHacks BU a few weeks ago, one of the students asked me, "what advice would you give to young women who are interested in tech?" After reflecting on this discussion, my answer would be this:

Only you know what you're capable of. Don't rely on others to validate or recognize that. Be consistent and firm in asking for what you need even if it's uncomfortable or inconvenient. If people don't hear you it or if they don't give you a chance to prove it, find someone else who will.


How to connect People of Color & Queer folks without sounding like a weirdo.

A few years ago, Shane Ogunnaike, a Nigerian friend of mine was breaking into tech. He was an incredibly sharp, funny account manager at my startup and I kept thinking I should connect him to Marlon Cumberbatch, a sales director at my husband's consultancy. Marlon was from Barbados. They were both part of the tiny, tiny population of smart, funny, Black sales guys in tech. I wanted to connect them but I never did.

Here's what went on in my head:
What if Shane thinks I only think of him as a Black guy?
What if Shane thinks I'm an idiot and that I believe all Black guys should be friends?
What if I make Shane feel tokenized?
What if Shane feels even more singled out than he already feels because I call out his race?

The same thing happened to me last weekend. I gave a talk at BU and I wanted to connect two Black women-one an intern at Facebook, and the other an Insights Lead there. I sent the email and felt incredibly awkward immediately after. Did I just screw up my relationship with both of them?

Ridden with guilt and terror, I reached out to HubSpot's #pocah group on Slack (POCaH stands for People of Color at HubSpot. It's an employee resource group that was started in 2016 to give employees of color a space to share, learn, and grow at this company). 

Here's what folks had to say:

Screen Shot 2018-05-01 at 11.58.46 AM.png

My mind rushed back to my email-scanning through my words. Did include these elements?

My email read,


Hi Bru!
Loe here, Anna Lee's little sister. Hope all's well! I'm in Boston doing Product Design for HubSpot. Had a kid. Life is a little crazy but also wonderful.

Reaching out because I gave a design talk at BU recently and there was a gal there who's interning at Facebook this summer. She's a Black, Business Law major who's interested in diversity and inclusion in tech. I remembered you're at Facebook and mentioned you to her-thinking you might have some interesting insights.

Would you be down to chat with her? Let me know and I'll do an email intro. She seems awesome.

Hugs. Loe


I reflected back on the Slack conversation in the #pocah channel. Similar to David, Melissa, Ashley, and Carina, it seemed like Bru would value connecting with another Black woman in tech since there are so few Black women in tech and since there's a special camaraderie within those groups. Did I, as Ashley said, call out the elephant in the room and mention they're both Black/Latina/Cambodian/Arab/Queer instead of beat around the bush? Did I, to Valentina's point, give more context around why they should connect that goes beyond the fact that they're both the same race?

When I review these needs as a checklist, I did cover everything that was mentioned. I still feel awkward. Was I direct enough with calling out the fact that they're both Black? Was I too direct? Should I have said African American?

It seems like being different means different things to everyone. While there'll always be room for error due to the complexity of race and queer identity, it's extremely important we keep trying. Fall on your face trying to help others or glide there gracefully. No matter what path you take, you'll reach the same goal. That's what matters.

Thank you HubSpot's POCaH group and in particular, Ashley Jeffress, David Ly Khim, Valentina Mendoza, Melissa Obleada, and Carina Kurban, and Quintin Marcus for giving me constructive advice and for being open to discussion. You're wonderful humans.

Also thank you to Shane Ogunnaike for letting me share this story. His response:
"Go for it! Honored! And also like, you knew another Black dude in tech sales and didn't tell me?!"

Design Leadership and Peanut Butter & Jelly


A mentor once sketched out their ideal qualities for a design leader. 

I read through the three categories of specialization, fully digested them, and then quickly recoiled-realizing I'd fail if I had to meet the criteria. I was only one of the three things on the board. I was great with people but I wasn't remarkably strong in product vision or in refining design skills and design processes.

Was my future as a manager unattainable? Did I have it all wrong?

I pocketed my disappointment and focused on my work. A few months later, something emerged that I hadn't previously noticed.

I work really well with a Laura Mikulay, a designer on my team. We're a unique pair because we work on the CRM, an extremely complicated product that integrates with everything at HubSpot.

She's super detail oriented, focused, and strategic. Tiny design problems keep her awake at night. Nothing gets past her. She'd rather be strategizing, designing and getting things done than dealing with conflict and miscommunication between colleagues and teams. She'll tell you exactly who is working on any given feature at any given time (we have a large team). It's remarkable.

I'm different. I can't keep track of every detail. I'm more passionate about designing teams and communication methods than interfaces. I love learning about people's unique qualities so I can get everyone to grow and work well together. I have a hard time remembering everything that's going on in the product-what's behind what gate, who's working on what, and when things are due.

Laura is the peanut butter to my jelly. Where I'm lacking, she totally rocks.

Laura delegates projects to me when they're with other teams, vaguely defined, or a little random. She partners with me to define high level priorities and to move things forward with the right stakeholders. She also leans on me when we're blocked by conflict between teams or a misunderstanding around goals and strategy.

I lean on Laura when I can't remember the details and I'm worried I'll drop the ball. I send designs her way to make sure requirements are being met and larger product and design strategy remains consistent. I also rely on her when I need to know who to talk to to unblock us to clarify the direction of a cross functional project.

As Laura and I continued to crush it on the CRM team, it dawned on me that this is what design leadership could look like.

It requires a Yin and a Yang-one detail oriented, driven person with insanely deep product and design knowledge and one person who's dialed into relationships within and around the team to improve the way people grow and work together. One person to drive product development and another person to streamline the way we work- unblocking the team if there's friction.

Maybe Design leaders shouldn't be individuals who do it all. Maybe they should be unified duos that together, give Product teams everything they need.

Know Before you Grow

Some things are particularly difficult.

1. Communicating effectively and efficiently across multiple personalities, teams, and departments is difficult. 

2. Solidifying job descriptions, career paths, incentivization structures, and hiring processes is difficult.

3. Moving forward as an entire company with a cohesive business strategy is difficult.

4. Ensuring managers are qualified and supported is difficult too.

You know what's even more difficult? Not putting in the time to address these challenges and hiring more people instead.

Poor communication is amplified. Resentment around career opportunities grows. Chaotic, rogue business strategies run rampant. More managers get overwhelmed and more direct reports are misled.

If you're a growing company, consider the benefit of another body and weigh it carefully against the cost of scaling any unresolved problems you need to address. It might be worth the wait.

The Tragic Reality of Motherhood and Career Growth


As I approached my due date, I became more aware of other new moms around me.

I saw them struggle to go back to work. I saw them quit work altogether. I wasn't one of those women. I was strategic, career driven, competitive, and tenacious. I was going to return to work as a person with new super powers I acquired from childbirth and childrearing over three months of maternity leave.

Returning to work, I was triumphant and full of energy-excited to be stimulated and social after a depressing, lonely three months of maternity leave. I'd hit the ground running like I did in any job. I'd pick up where I left off with a clear path to promotion on my 2-year anniversary.

Things I didn't anticipate:
1. The high of returning to work wears off and exhaustion sets in. 
2. Returning after three months is like starting a new job.
4. Working without enough sleep is exhausting.
5. Working while breast feeding is exhausting.
6. Pumping takes up an hour and half of my day. 
7. Parenting means no more downtime. Ever. This is also exhausting.

I'd be in meetings and not know what was going on because I was so tired. I remember trying to cover it up and wondering if people noticed. I remember lugging the milk I pumped back from work and scrambling to pump when people scheduled meetings over my pumping sessions. 

The fog cleared as I stopped breastfeeding and developed a routine with my partner. Then a new slew of unforeseen things started to emerge.

I looked around and saw patterns in the heterosexual parents I knew. My partner got promoted before he went on paternity leave. So did my director of product. The majority of my male coworkers had female partners who didn't work and took full time care of their kids.

Six months later, my partner got another raise and a new job with more responsibility. I was happy for him but couldn't help but feel resentful that I wasn't moving forward too. We had always been competitive with each other and now I watched him fly past me while I was flailing, overwhelmed, and tired. Was I crazy or was there a theme of men accelerating their careers and women falling behind when kids arrived? 

Fortunately and unfortunately, a New York Times article popped up to confirm my theory in a more scientific way.

"Immediately after the first birth, the pay gap between spouses doubles, according to a recent study." 

This was all too familiar.

"The issue, in general, comes down to time. Children require a lot of it, especially in the years before they start school, and mothers spend disproportionately more time than fathers on child care and related responsibilities. This seems to be particularly problematic for women building their careers, when they might have to work hardest and prove themselves most." 

My partner and I intentionally write out and evenly distribute household chores to prevent this gap but unfortunately, I was still putting in more time for the first six months of our son's life due to breastfeeding and pumping. It was impossible to avoid. So what else could I do or could I have done?

1. I wish I lived in one place for at least a year before I had my son. I moved from Oakland California to Cambridge Massachusetts and got pregnant shortly thereafter. Consequently, I missed out on exploring my new surroundings and establishing a strong social network and rhythm in Cambridge. It definitely added an unnecessary amount of stress and isolation during my pregnancy and after my kid arrived.

2. I wish I stayed on a team or a product for at least a year and returned to that same team after maternity leave. Again-this is about minimizing change. I changed teams and products two months before leaving for maternity. Essentially, I started a new job before I left and then had to start afresh again when I returned. Starting a new job is hard. Starting a new job while sleep deprived and recovering from major surgery is harder.

Unfortunately, because of biology, it seems that women are highly likely to fall behind their baby daddies because growing, having, and sustaining a new life is a gigantic, exhausting, time consuming thing.

Is it unfortunate? Honestly-I'm not so sure anymore. Personally, I'd rather be there for my son than wear myself thin trying to keep up with my husband who had no new job, no three month hiatus, no C Section, and no six month breastfeeding duty.

Maternity Leave is not Vacation


Sand between your toes. Ocean breezes. Rejuvenating sunlight. Should you nap or drink a cocktail?

This is not maternity leave.

Like an idiot, I thought maternity leave would be a great time to reset. I welcomed the time to regain perspective on life as I gracefully transitioned to being a mom. Blissfully silent, meditative days with a precious new life. Time away from a screen. The opportunity to forget about time for months and to really reflect on what life's about. Maybe I'd start meditating daily. I've always wanted to do that.

That was not maternity leave either.

The first two months of maternity leave were the hardest two months of my life. They were like Hunger Games meets Divergent meets Inception but with a lot less action and a lot more depression.

I was held prisoner by a screaming newborn while my breasts leaked, my nipples bled, and my C-section scar ached. I had hot flashes and cold sweats. I couldn't leave the house. The pain medication made me constipated and I could feel (this is gross) a hot searing pain as the stitches held me together when I got out of bed or out of a chair.

I'd wake up to Mischa's screams as soon as I'd fall asleep and I had bouts of depression where I'd wake up paralyzed and too scared to be alone. I imagined this was how they'd torture prisoners-by beating them up, administering constant pain, and then keeping them awake until they go crazy.

While I didn't go crazy (thank you mindfulness), I did become a hint of a human being. I couldn't remember what time or day it was. I talked to a psychiatrist and forgot I called the previous week. I disappeared from my friends' lives and couldn't carry a conversation. I was the opposite of what I was before Mischa and I feared I'd never be the same.

It did get better. I was lucky enough to have a supportive partner, incredible parents and sisters, and wonderfully helpful in-laws. Additionally, I had HubSpot, a company that gave me three months (they now offer four) to recover. Despite all of that though, there are some glaring things I want to address as I see more women embark on the adventure of being a mother.

1. Having a baby (aka being gravely wounded and then tortured 24/7 for two months) is a big deal and companies need to give women enough time to physically and emotionally recover. At least four months.

2. Companies need to give new mothers' partners enough time to support their baby mamas. By giving partners short (or no) leave, companies are basically leaving new moms to fend for themselves during a really dark, difficult time. They're also perpetuating the sexist expectation that mothers should spend more time caring for their children.

3. Companies need to educate childless employees about why parental leave is necessary. I wish I had known more about what happens during the first few months of parental leave-both so I could prepare and so I could support my new parent coworkers.


A simple tune

Heavy and exhausted
She cradled the aching newborn in her arms
Rocking back and forth
Breathing silence

She exhaled a shaky melody

Don't you cry
Go to sleepy little baby

The world imploded
History filled her lungs
She choked on memories of her mother's voice
A hand on her back as she drifted to sleep

When you wake
You shall have
All the pretty little horses

Quivering throat and blurred vision
She tried her best to sing like her mother
To hold memories and not rewrite them
To fathom the magnitude
A simple tune
Sung to a new life
From one generation to the next


Strong Personalities Need Feedback Too

As I caught up with my friend today on Gchat, she voiced her frustration with a colleague who talked a lot and always had a lot of opinions. It annoyed her because she couldn't get a word in and because he always dominated the conversation.

I asked her if she felt comfortable giving him feedback on his behavior and she thought she might if she saw the behavior again (this, unfortunately, was probably inevitable).

I have a lot of experience working with strong personalities. When I say strong - I mean people who talk a lot, dominate conversations, and maybe don't have the awareness to recognize when others are annoyed, hurt, or bored.

It's really hard to give strong personalities feedback because they can be really intimidating. You feel small, misunderstood, and under-appreciated because your voice isn't heard. If you're a highly empathetic type like me, you might assume they know you're feeling this way because it seems obvious to you. You're giving them social cues by looking unhappy or disinterested.

One thing that has helped me immensely in my career is this mantra:

Never make assumptions about how people feel. Ask them.

While this is true for everyone-for me, it's especially important with people who have strong personalities. 

I was in a meeting with many people and had made a crucial decision for an important, time sensitive project. The strong personality (who also happened to be my boss) argued with me about my decision in front of everyone, said it was stupid, and then took over my meeting. 

I completely shut down. I was on the verge of tears and was seething with anger. I felt hugely disrespected. I assumed the strong personality knew they made me feel this way. Days later when they asked me why I was so quiet, I realized they didn't.

I told them I felt hurt, undermined, and embarrassed in the meeting. I told them I had a ton of respect for them and I didn't feel like they had my back. I wished they had pulled me aside to talk about the decision instead of arguing with me in front of others. They felt genuinely bad about it and it never happened again. 

I could go on and on about stories like these because during my eight years in tech, I've come across a lot of stubborn, dominant, not so empathetic people. Truthfully, it's often what makes them successful in the industry-especially in leadership.

I used to shy away from them and harbor a lot of resentment towards them. Now I love interacting with strong personalities because I see it as a unique challenge and an opportunity to help.

If you're easy to approach and easy to give feedback to, you get feedback all the time. If you're a strong personality, you're often left in the dark because people can't muster up the courage to tell you how you make them feel. It can be lonely, frustrating, and confusing.

Think of strong personalities as a psychological challenge, a monster under your bed, or a giant rollercoaster. Recognize how they make you feel but don't let that stop you from finding your socks, going on that ride, or giving constructive feedback. You'll be happier and they'll be grateful you disregarded their prickly exterior.

LinkedIn Recommendations: Your New Pokemon

Recommendations are awesome for many reasons. You feel good when you get them. You feel good when you give them. Recommendations make you look valuable and competent to potential employers and new colleagues.

Over the course of my career, I've been diligent about giving and asking for recommendations. I'd go back and read them to reaffirm my value. I also liked collecting them. They were like a currency I was accumulating as I developed my skills and grew into more senior roles over time.

After 7 years of giving and receiving recommendations, here's what I'd... Recommend :)

1. Don't be afraid to ask. Asking for recommendations can feel awkward and self indulgent. The truth is, they're really important to growing your career-especially for women (Allyson Downey, the founder of WeeSpring, argued that women are seen as more valuable if others vouch for them-vs. women vouching for themselves). Focus on the benefit of having that recommendation in your pocket as you move forward in your career and try to look past the strange feeling of asking for compliments.

2. Ask folks in a variety of roles. When people look at your history and recommendations, they want to see growth and an ability to interact with others in various situations. Are you easy to manage? Do your direct reports like you? How far is your influence? Do folks in other departments feel your impact?

3. Ask all the time. For a while I found myself scrambling to get recommendations once I was leaving a company. While this works sometimes, you often have better luck when you ask for recommendations when you're not looking. Recommenders won't feel as rushed and their recommendations may be more substantial because they're truly invested in their relationship with you (you're not going anywhere). Receive positive feedback at your job? Take that opportunity to convert the feedback into a recommendation. It's a great way to get a recommendation because it's pretty effortless for the recommender.

4. If you think someone is awesome, recommend them. Love working with someone? Admire their leadership? Did someone totally save your butt because they went the extra mile? It's cliche but it's true-what goes around, comes around. If you recommend others, they'll be more likely to recommend you. 

5. If you think someone is not awesome, don't recommend them. Is it awkward? Heck yeah it is. However-it's really important to only recommend people you know and admire. Your recommendations are an extension of your network and your reputation. If you don't have enough experience with someone or if you don't feel comfortable recommending them, follow your gut. Don't do it.

6. When you recommend, give it substance. What was the context in which you worked with them? What did they do that impressed you? Similar to writing a good resume, recommendations are stronger when they have context, an action (what that person did), and how it impacted you and/or the company. Avoid sweeping statements or recommendations that only applaud someone's character. The more you can ground that person's value in something tangible, the more outsiders will trust in and see their value.

Why you should get pregnant at HubSpot

I feel incredibly lucky.

I moved from Oakland, CA seven months ago to Somerville, MA and started working for HubSpot. In January, I found out I was pregnant with my first kid. It took me by surprise because it happened as soon as I went off birth control. I was on birth control for ten years. TEN YEARS! The human body is pretty remarkable. Turns out it's not like starting a dead car.

My plan was to be at HubSpot for at least a year before having a kid. I wasn't sure how I'd approach the subject at work and I wondered how supported I'd feel and what the culture would be like there.

I was immediately comfortable with my design team of 30 people. They were all kind, thoughtful people with a good sense of humor. The head of my department, Tim Merrill, was a dad of four. He was very open about how difficult it was to be a good parent.

My boss, Jonathan Meharry, was also a dad. His son was two and he was open about how overwhelming it was to raise even one very energetic kid with two working parents.

The week I found out I was pregnant, I first Slacked Tim to tell him the news. He was overjoyed and asked me if he could swing by and give me a hug. I Slacked Jonathan and he congratulated me too.

I shared the news with my design team shortly thereafter at a mac and cheese dinner party I hosted at my new apartment. They offered me a shot of vodka and I told them I couldn't because I was pregnant. Everyone cheered and congratulated me. I wasn't planning to share the news but something inside me wanted support if things went well but also if things fell apart. I also wanted the other women on the team to know both scenarios were normal if they ever decided to get pregnant themselves. I was going to be the first mom on a team of 30 people and I wanted to normalize it.

My greatest fear was to be socially excluded because I was pregnant. While not drinking made it difficult to go out and let loose, being pregnant actually bonded me to certain people in a way I wouldn't expect.

Suddenly the dads around me opened up more about their lives. They shared detailed, emotional stories about their wives' pregnancies and deliveries over lunch. They offered me resources like midwives, online mothers communities, and baby clothes. I felt like I was suddenly a part of a club I never knew about and I was extremely touched by how much these dads cared about their partners and their kids. 

Being a young feminist, this all seemed relatively normal to me. I expected to be treated with respect and for people to understand how hard it was to be a mom. As my pregnancy progressed, I had an experience that made me realize just how lucky I really was.

You’re going on vacation before your maternity leave? Do you even work?
You should really thank them for giving you all that time.
Be careful of what you say-make sure they don’t forget you when you go on maternity in August.

These are things I heard from my mother-in-law and my mom in the same week.

I was angry and offended. Didn't they know how hard I worked and how valuable I was? I explained that tech was different in that it wasn't about the quantity of hours you put in but the quality of your work. It was about efficiency and working smart. They weren't convinced.

I then explained that I'm in a highly valuable role and that hiring and onboarding a new person would be far more costly than giving me three months to recover. They still thought I should show my immense gratitude so I'm not "forgotten".

What I realized, after the anger subsided, was that my mother-in-law and my mom were trying to protect me. Their advice rang true when they were new moms and it could even ring true to this day. I was blissfully entitled to my support and stability as a pregnant woman at work and I didn't know how lucky I was. 

A few weeks ago, my PM, Shawn Bristow, sat me down in a meeting room to catch up.

"Oh, Loe... I can't believe it-I totally forgot you'll be gone for 3 months instead of 1. I didn't plan for that because we haven't had any moms on our team-only fathers," said Shawn.

I hesitated-feeling slightly guilty for causing him all this additional stress.

"I'm sorry-I know it's not easy," I said.

I continued, "Let me know how I can help. If I were in your shoes, even as a woman who believes in moms, I'd be stressing about losing a player on my team for three whole months. It's a lot to plan for."

Shawn cut me off and stared at me with his intense, retired fisherman, Shawn Bristow stare.

"Loe...You will never get this back again. It goes so fast and it only happens once. Just be there and be present as much as you can because time moves so quickly. If you call or email me I'm not answering-just disconnect completely. You're talking to a dad who's counting down the number of school vacations before his daughter goes to college."

He paused.

"It's four, Loe. Four," he said slowly as he sat back into his chair and exhaled.

I was speechless, in shock, and so moved by Shawn's support and by his love for his daughter. I tried to maintain my composure as I held back a few tears.

When I got pregnant, I expected to be treated with respect and to keep my job. I never anticipated having so many fathers advocating passionately for my ability to be a great mom. I'm forever grateful to Hubspot for hiring them and I'm forever grateful to those dads for taking me under their wing(s).

Special thanks to HubSpot dads...

Kyle Gieste for helping me find my midwife
Gregory Cornelius for giving me baby things
Jeff Boulter for shamelessly hustling his kids' girlscout cookies
Tim Merrill for being real about the challenge of juggling career and family and checking in on me during my first trimester
Jonathan Meharry for being a boss who encourages me to do what's best for me as an ambitious but also pregnant direct report
Jay Ciruolo for leaving work early when possible to relieve his sleep deprived pregnant wife from 2-year-old duty
Shawn Bristow for being Shawn Bristow
Christopher O'Donnell for talking about his 2-year-old at Inbound
Dharmesh Shah for telling stories about his kid on stage and in company announcements

Also special thanks to my new friends and fellow HubSpot designers Chelsea Bathurst and Quintin Marcus for supporting me through all this change and for listening to me as I navigate strange and annoying pregnancy symptoms.



Steering a Giant Ship

"Do you feel like what you do has purpose?"

"Loe-what do you think about this UI solution?"

I was asked these questions recently and my answer left the asker feeling a bit lost. 

The truth is, anything you do-whether it be UX design, product management, marketing, sales, or customer success is meaningless unless your whole team or company is bought into the same goals and prioritization of those goals. At Hubspot, it would be like 1500 rowers on a giant boat with different sections trying to forge their own paths without communicating with the rest of the ship. You mind as well jump out and swim to get anywhere.

I see this happening a lot at larger companies and the truth is, it's really really hard to get everyone to row in one direction. The larger the company gets, the longer it takes to get buy in and to execute on the cohesive plan. Just think about playing telephone with 10 people vs. a thousand people.

Example: Let's say you're Salesforce or Marketo. Your product has kicked ass and now it's huge. It serves hundreds of thousands of use cases and the codebase is, well, (in Silicon Valley standards) old. You kept building on your original code base because every new addition met the needs of your customers at the time. It was enough and a rebuild was too costly in comparison. 

Eventually you plateau and you find yourself in a position where you have to rebuild your entire codebase to survive. You can't scale on your old framework and you can't slap on some new technology because you'll break things. You have to update everything and that means migrating all of your customers and use cases onto new technology. You can't do this as an Engineering team. You need Customer Success to prepare and customers for the change. You need your Education department to help customers learn about why you're doing it. Sales needs to coordinate with you so they can adjust their pitches and prepare old accounts for the migration so it doesn't impact their renewals. Marketing needs to create new content to support sales and they'll need to update their marketing materials.

Even within your Engineering department, there's a ton of complexity. Instead of building your product one thing at a time like you did when the company was new, you're building a giant, complex product with a ton of people at the same time. And you're trying to do it as quickly as possible.

This is a more extreme example-but the truth is, this sort of cross functional involvement should happen all the time as you build and update your product. If I update the text on a page to improve the user experience and my knowledgebase team doesn't update their help articles, my design update is meaningless. If I fail to pass on this update to my entire sales team so they're prepared to demo the new UI smoothly, it's also meaningless. Not only is it meaningless, it's detrimental to the company. I'm sabotaging my team and my customers by not keeping them in the loop.

So what's the solution? I wasn't quite sure I'd have one for this post until I discussed it with Chelsea Bathurst and Quintin Marcus, two of my fellow Hubspot designers and extremely good looking friends.

Here's what we came up with:

Collaboration and communication should be a highly valued asset at the company. It should be something that's imperative to a new hire's list of skill sets. It should also be something that's measured on the individual and team level so employees are rewarded for not only problem solving and producing on their own-but doing that with their team, their department, and departments across the company. It should be equally important to the quality of that person's individual work. If they can't work with others, again, that awesome work is useless.

How to run a horrible design meeting


  • Establish no clear leader(s) of the meeting who's responsible for the planning, agenda, moderation, and outcome
  • Have extroverted, more senior men speak 90% of the time (this is a symptom of the first bullet)
  • Change the agenda mid meeting
  • Have the most vocal, opinionated people be the ones who know the least about the problem
  • Have those vocal, opinionated people come up with a "good" solution based on their own personal needs and desires (not because of user interviews or data)
  • Go into the meeting with high level business decisions unresolved so the scope and long term vision of the solution is up in the air
  • Invite ten people to the meeting
  • Spend an hour on taxonomy with those ten people
  • Make the meeting is 9-5 for an entire week
  • Do multiple brainstorming, sketching, and KJ post-it exercises with no clear follow up/resulting action plan

The Good Ones: Men Who Have Empowered Me as a Woman in Tech

There has been a lot of horrible news floating around about how women are treated in tech.

While I've experienced my fair share of sexism (pinched from behind while walking up stairs, looked up and down, etc.), I wanted to take a minute to reflect on the people - the men, in particular, who have made my work life an incredibly safe and comfortable one. I felt this way before I got pregnant. Now that I'm a mom to be, I have an even deeper sense of gratitude for my respectful, compassionate male colleagues. 

Here are the men I'm grateful for in my career:

Robert Kavaler, Senior VP and Co-Founder at Sensys Networks
Robert was an executive who walked around wearing the same Cal button down, khaki shorts, and sandals every day. His wiry grey hair was always trying to escape his head and he approached everything with a healthy dose of playfulness and suspicion.  

I started my tech career at Sensys Networks as the company's Administrative Assistant. From day one, Robert treated me with collegial respect. We'd talk about politics at my desk. A cofounder and PhD from Cal, I held Robert in incredibly high regard. When he wanted to hear what I had to say I by default, felt smart and worthy. 

David Royer, Product & UX Designer
Dave is the reason I went into design. His friends were all designers and he loved his job. I couldn't believe there was this world of thoughtful, kind people who make great money studying computers and human behavior. 

I told Dave I was interested in becoming a designer and he was immediately on board. I had no product or design experience and he helped me construct a long term action plan to break into the field. He never questioned my ability to learn and he willingly nurtured my curiosity as soon as it was detected. 

Robert Hoehn, CEO @ IdeaScale
Robert Hoehn is a free spirited hippie turned CEO. He's always laughing and adventuring. He brought me on board in my first (and possibly last?) product management role and quickly promoted me to manage the entire four person product team. I was petrified by the responsibility but I accepted it because Rob believed in me and he gave me the chance.

I attended my first board meetings and managed my first team. I managed a department budget for the first time and oversaw development processes for a 20-person team in Bangladesh. It was one of the most challenging roles I've ever had but I learned and grew a ton. It made me a better designer.

Jeff Boulter, Tech Lead @ Hubspot
While I'm only 5 months into Hubspot, Jeff has already left an impression on me. He's a dad of three and he has a ton of experience leading teams of engineers. I was intimidated by his experience level when I joined and that quickly dissipated as I worked with him and another 27-year-old female Product Manager. 

Jeff immediately trusted me and the PM-supporting my PM's strategic decisions and working through problems with us in a informative, respectful way. He encouraged my PM to lead and he never made me feel stupid or inexperienced despite his greater wisdom. Jeff made it seem normal to be a young woman leading a team and I appreciated that. It became normal for me too.

Jay Ciruolo, Senior Software Engineer @ Hubspot
Jay made my jaw drop when I joined Hubspot. I remember I was in a user research meeting with him and we were debriefing on a session we had just listened in on. There were about ten of us in the room and a young twenty-something woman was leading the session.

Jay and the meeting leader spoke at the same time. Immediately the woman apologized and told Jay to continue speaking. Jay paused and said, "no-this is your meeting, you go." I literally thought I stumbled into a different dimension. I had never seen a guy be so self aware and supportive of a woman leading a meeting. 

Jonathan Meharry, Design Lead @ Hubspot
I may be drinking the Meharry cool-aid but Jonathan has been the best manager I've ever had. He spends most of our 1:1s listening and when we problem solve together, it's always highly collaborative and rarely someone with more power telling someone with less power to do something.

He advocates for his people and he does it with finessed communication and no ego. He has also followed up with me frequently to ensure I'm getting what I need to do my job well while I simultaneously grow a human being. It's so helpful to have a manager who's also a new dad with a 2-year-old son.

Tim Merrill, Director of Product Research and Design @ Hubspot
When I interviewed for a new job this time round, Tim Merrill stood out in a huge way because unlike other executives/department heads, Tim listened. Most of the interview was listening. Since then, Tim has continued to listen and I've been incredibly touched by how compassionate and caring he is towards his people. He's an open book who cares about both good design/product and bettering the world at large.

Why are they awesome?
When I look back on these men who have nurtured my career, 6 of the 7 are fathers. If you're looking to foster healthier, more equal work environments-maybe start there? From my experience dads do it right.


The Ten Plagues of Pregnancy

Around August 17th, I'm going to birth a human.

"Congratulations!" you say.
"Awe! What a precious gift!" 
"Don't you just love pregnancy and the miracle of life?!"

No. No I don't. Being pregnant blows. Yes it was planned-but if I could have gotten my husband pregnant or grown my child in a petri dish, that's what I would have done.

Being the progressive Jew that I am, I will now present to you, the Ten Plagues of Pregnancy:

Plague 1: Hurting boobs
Imagine if your boobs were made of pure muscle and a professional boxer punched you as hard as they could in the chest. That's what it feels like when you first become pregnant. It's uncomfortable to sleep and you're walking around with tender, bruised, boobs.

Plague 2: Flaming nipples
This one doesn't need much explanation. Ok imagine every sensory nerve on your nipples is turned up way past the maximum and a slight breeze feels like an electric shock.

Plague 3: Everything you ever loved to eat or drink now makes you want to hurl
Ah, remember that lovely cup of coffee in the morning? A bowl of ice cream? A big plate of delicious brunch with crispy bacon and french toast? Now that you're pregnant, your body will be repulsed by anything you consume or think about consuming. 

Plague 4: You sleep like an old cat
If you're an active, social person, get ready to say sayonara to the waking world where you can function at work past 2pm and have a cohesive conversation with your partner at home. Growing a human is exhausting and all you can to to fight fatigue, is sleep. My partner said he missed me for two months. I was such a zombie he didn't get any attention.

Plague 5: You're freezing one moment and sweating the next
You drink a hot cup of tea and you start feeling so hot and uncomfortable you might pass out. Then you take off your sweater and start shaking because you're so cold. Your boobs start hurting you're so cold. You put on your sweater back on again and  overheat again.

Plague 6: Gas
In addition to being nauseous, in pain, sleepy, and fluctuating in temperature, you're also unpleasant to be around because being pregnant makes you fart a lot. How lovely.

Plague 7: Dizziness
You get up to go to the bathroom at night and you almost fall on your face because you're so dizzy you temporarily lose your site. You fall over in yoga. You almost fall over at work. When you grow a baby, your blood vessels expand to allow for more blood flow to the fetus. Unfortunately, your circulation suffers as a result.

Plague 8: Heartburn
Progesterone is a hormone produced during pregnancy. It also relaxes the valve that separates the esophagus from the stomach and gastric acids seep back up and cause an unpleasant burning sensation! Yay!

Plague 9: Emotional insanity
You feel really sad. You feel depressed. You feel anxious. You feel pretty good. Why? THERE IS NO REASON. Except that you're growing a human and it's making you crazy. 

Plague 10: More gas
This one was written by Peter. I haven't noticed it but apparently he has.

I will love this baby with all my heart and I've set up a stable family and life as much as I can. I won't, however, pretend to love being pregnant and I expect giving birth to be the most painful, gross thing I'll experience in my entire life. Cheers, baby. See you in August.

My People

One month into my time at Hubspot, I was struck with fear because I realized that this may be the first and last best job I'll ever have in my entire life. I wanted to hold on to it as tightly as possible - to absorb it before it slips away and becomes a memory.

Since then, I've become spoiled and more focused on the problems that exist on my team and in the company (as a natural cynic and product designer, it was only a matter of time).

Before I completely lose track of that initial feeling, I want to take note of the things that made Hubspot feel like the best job I've ever had.

1. Hubspot has values. At my first company meeting, I discovered Hubspot hired Ta-Nehisi Coates to speak at their yearly conference. If you don't know Ta-Nehisi Coates, he writes about being a Black man and a Black father in the United States. You can't have a speaker like Ta-Nehisi Coates  and feign indifference. Being someone who also cares about Black people in my country, I was so grateful I started crying at the company meeting. Hubspot was willing to ruffle feathers and lose business to stand behind someone they believe in. It was refreshingly honorable.

2. Hubspot hires people who are both sharp and kind. At almost every job I've had, someone has always made me feel small or uncomfortable. At, a woman would completely ignore me whenever I'd try and communicate. I'd try to talk to her in the hallway and she'd act like I'm invisible. It made me feel horrible and it made me incredibly inefficient at my job. At Hubspot, I've never met someone I haven't liked. Consequently, I'm a happy person, I collaborate easily with new people, and I'm efficient in getting work done.

3. Hubspot is a big company with a small company feel. Big companies get overly political and bureaucratic. Culture is often lost and you quickly become a bee in a hive-slogging through process after process to get your job done or to accomplish any HR task. You feel like your voice is lost. Hubspot has maintained an incredibly friendly, free atmosphere as a 1500 person company. There is a shared culture of getting shit done, putting ones ego aside, and asking questions. Everyone is responsive and accessible from the Head of Culture to the VP of Product. You're empowered to do what's best for your team and to lead your own charge in your own way.

4. Hubspot has great design managers. It's common to promote the loudest, most extroverted, outspoken people. Hubspot is different in that they promote a variety of personalities into management positions. My boss is a soft spoken, incredibly empathetic person. His boss (the head of our department) is a super creative, nurturing type who's always looking ahead and reexamining the way we work to ensure we get what we need. My therapist says I've never been this happy. She says all this time, I've just been looking for a good manager.

So what about that Disrupt article that guy wrote-the one that talks about how Hubspot is a frat house filled with 20-year-olds? Here is what I can say:

- I had read the article and I was skeptical about the seemingly very young people who interviewed me.
- They won me over in minutes with their smarts and lack of ego (to me, this has nothing to do with age).
- I've never experienced any of that fratty behavior in Product.

Everyone Needs a Little Help

Think of the word VP. What descriptors come to mind? What about CEO? Here are some that I usually think of:

- Powerful
- Authoritative
- Remarkable
- Smart
- Intentional
- Tough

Every time I look for a new job, I view it with an increasing amount of scrutiny. I try to work for companies that solve problems I've seen in past positions. For example, after seeing conflict and chaos render companies inefficient, I decided it was important to have focused and decisive executive leadership wherever I go.

Now that I'm headed off to another adventure (Hubspot), I realized I missed a key element in my search: I want my leaders to be self aware. More specifically, I want them to acknowledge their weaknesses and to listen to others-especially those who are strong where they're weak.

I (and I suspect, many others) have a tendency to think VPs and CEOs are somewhat superhuman. The fact is, they're not. It's a lonely, stressful job and aside from that, they can only think and act in the way that they've been programmed because they're human. A Sales CEO may tend to be naturally gregarious, outgoing, impatient, and great at communicating. A Technical CEO may be more detail-oriented, abstract in their thinking, focused, and careful. Whatever the combination, humans always lack where they excel. 

When running an entire company, it's imperative that leaders acknowledge their weaknesses and find others to balance them out. Not only does it make companies more efficient (you can execute on all left and right brain ideas instead of just one combination), it builds a more diverse culture and employee base where openness and diversity of thought is a value. And what could be better for building great products?

On to fall leaves, chowder, and snow. I'm going to miss you California.




It's the Little Things

Disruptive. Innovative. Groundbreaking. Ninjas. Unicorns. Magic.

These are common words in the tech world. Everyone wants to be big, impactful, and untouchable. It's like winning the lottery or becoming famous.

It's great to have stretch goals or aspirations that seem impossible. They spur creative and abstract thought so amazing things happen once in a while. One thing I wanted to highlight, however, is that small, meaningful things get overshadowed by these goals. While they aren't groundbreaking, they do hold a ton of value and they're easier to accomplish. They can also have a ripple effect. Here is an example of what I'm talking about:

Big Goal: Carl is a Stanford MBA grad. He wants to be a CEO so he can make a product that completely disrupts the healthcare market. He wants to go IPO and live next to Mark Zuckerberg. 

Impact: World domination.

Likelyhood: -134098632049487209874%

Little Goal: Carl is a Stanford MBA grad. He got an internship at Google. He sees that there's recurring miscommunication between his boss and one of his direct reports. He sees why they're on different pages and wants to find a process that will help them understand each others' perspective so his team's work will be more streamlined.

Impact: Happier boss, direct report, and team. Better product.

Likelyhood: 85%

Making big waves is honorable and rare. Making little waves is honorable and attainable. Make sure to incorporate them into your plan as you reach for the moon.

You Know Nothing Jon Snow

People think they're smarter than others all the time. They've worked longer. They have more experience. They're more educated. They're older. They're younger. They're more proficient in a language. They think differently.

There are many reasons for why people put themselves above others. Ambiguity and the unknown are scary and people pride themselves in knowing all the answers. It defines them and their reputation. If one belief is in question-what about all the others? Will people respect them less? Will their reputation be in jeopardy?

After seeing this, experiencing it, and doing it myself, I've come to realize that as a designer, putting yourself above others is sabotage. You create distance and mistrust and you build barriers between you and others so there's no possibility of open mindedness and understanding. You're also missing out on crucial design feedback that you clearly, for whatever reason, cannot see.

I made a promise to myself that every time I feel frustration and confusion in design, I shouldn't see it as a personal affront but a key opportunity to grow.