Ask Me Anything: Lenny's Newsletter Edition

An expanded look at some of my AMA answers

Aug 15, 2022

Last week I participated in a Lenny’s Newsletter Community AMA, where fellow Lenny Community members were able to ask me questions about career development, product management, and more. In the spirit of sharing and amplifying knowledge, here are some of the questions I was asked, along with my responses. (They have been edited and expanded for clarity.)

Lenny has built such an amazing community, and I'm proud to have been able to contribute to it. If you haven’t yet signed up for his newsletter, make sure you do.

PRODUCT MANAGER CAREER ADVICE

Q: What advice do you want to share with new PMs to not spend too much time focusing on the wrong things?

A: Determine what's a good use of your time. Too many times I see PMs want to be in every conversation or meeting to get context on what is going on. Remember, you need to choose what you focus on carefully because for every single thing you say yes to, you are implicitly saying no to something else. Focus on impact. Always be asking yourself, “Is this meeting going to help serve my customers or improve my product?”

Q: What daily routines/habits would separate a good product manager from a great product manager?

A: Dogfooding, using data, and understanding user research. Those who know their customers and products inside and out have a huge advantage over those who just have a surface understanding of the customers' needs. PMs who have deep customer empathy identify with the customers and feel their pain points. If they are not the target customer, they will seek to learn from them, whether through focus groups, follow-me-homes, or ride-alongs. Seeing how someone uses your product, and the love/hate relationship they have with it, is illuminating.

Q: What steps can PMs and designers take in teams / environments that feel chaotic and disorganized to ensure that they can still contribute quality work?

A: A good PM is also an excellent project manager, culture-carrier, and cheerleader. Having clear team norms, touch points, and processes is important. For example, for one team that needed more connection, we held daily 15-minute scrums during their three-month sprints. We would keep that up until launch, then move to a bi-weekly cadence. It was a matter of putting basic processes in place until they no longer needed them.

Things feel chaotic when there is no rhythm, no clear process. Remember, "process" doesn’t have to be a dirty word. It can help to have a forum to organize without overwhelming the team with micromanagement.

Q: What advice would you give to someone who wants to make the leap from a mid-level PM to a manager (Group PM, Lead PM)?

A: Make a plan and tell your manager. We often wait for a promotion to come, but being proactive will get you to what you want faster. Instead of asking, “Will you make me a manager?” say, “I would like to become a people manager. I am passionate about helping others succeed, and I have been mentoring and coaching junior PMs for X years. What is the distance between where I am and getting the opportunity to manage? What are the skill gaps we can work on?” This way, instead of making it their decision, you are enlisting your manager to come alongside you and help you grow.

Next, really invest in the skills you need. Mentor junior PMs. Take on an intern. Learn about performance reviews. Shadow a manager. Demonstrate that you are proactively preparing and ready to grow into the new role.

Q: You mentioned in your podcast with Lenny that the best product managers are folks who can walk into a room with zero context or preparation and say something intelligent that can align with the people in the room. How does one hone that skill? As a fellow introvert, how did you build that skill as you went up the ranks?

Treat speaking up like a skill you can learn. Have metrics and milestones. Set goals that you can achieve, such as speaking up twice per meeting. Then start measuring the quality of your comments. Consider joining Toastmasters or a mentoring circle so you can get comfortable speaking in a room full of trusted colleagues. Then expand from there. I speak more about this to introverts like myself in this post.

Q: What advice would you give to someone who wants to make the leap from a junior PM to a PM?

A: Create a plan. You want to get to X role by Y date. Figure out the distance to your goal. Talk to PMs who are at a higher level. Get one of them to be your mentor. Once you have that in place, start talking to your manager about:

Things you need to demonstrate
Skill gaps you need to fill
The scope you need to have
Space on the team or company for you to advance (some companies have limits on levels)

Your next step is to document your progress. Follow up with your manager and show them how far you've come. Ask for their feedback. This process may feel arduous, but it can be freeing to know exactly what you need to do and execute in order to move forward. I talk more about promotions in this article.

GENERAL CAREER ADVICE

Q: What advice do you have for someone planning out a career? I aspire to have a trajectory like yours and would like to know what opportunities you sought, mentorship, and anything one might not think to ask.

A: Be intentional. PM your career like you PM your product. In Product Management, you create goals, metrics, milestones, and a roadmap. But how many PMs use those things for their own careers?

Set goals for two years, five years, and ten years. Then, every year, check whether you are getting closer. A PM I know once said she wanted to be a CEO by the time she was my age. But she was still a mid-level PM at her company. I explained the steps (get to manager, then become a manager of managers, then a VP, then a GM, while joining a board) that are needed to make it to CEO. She realized she had to make a change or she would never get there. She took another, more senior job, became a manager, and now she is on her way. As a bonus, she is being compensated more as well.

Q: What's the one piece of advice, wisdom you have received, and/or "best practice" that you think is bad?

A: "Stand your ground." Sometimes that is the right answer, but sometimes it's not. Standing your ground means never giving way, and that can lead to burning bridges. Instead, open yourself up to new ideas. Be curious, and allow yourself to grow. I hate how we call politicians who change their minds “flip-floppers,” rather than praise those who honestly allow themselves to grow and evolve their thinking as new information comes in. “My way or the highway” never works out well in the end.

Q: In recruiting, I often have the impression that women are underselling themselves and men are overselling themselves. Being aware helps to close the gap a bit, but what else can a recruiter do or say to close the gap even further?

A: It would be unfair to overweight women’s communication of their experiences and underweight men’s. We know on a macro level that these imbalances are there, but not on an individual level. (Here's an interesting study on this topic: https://news.harvard.edu/gazette/story/2020/02/men-better-than-women-at-self-promotion-on-job-leading-to-inequities/)

One useful thing I found was to dig deeper. I heard many women say, “We worked on this project with X outcome," rather than, “I led this project with X outcome.” Think about how those words come across. This is a small semantic difference, but it can be crucial. When someone gives a vague response, try asking them, “What was your role in the project?” This may get you a more precise and useful answer, no matter the other person's gender.

One thing recruiters should remind all candidates to do is to speak more precisely about their roles and their impact. This is not self-promotion. Rather, you are helping the interviewer evaluate and understand your skill set and experience.

MENTORSHIP ADVICE

Q: On the topic of mentorship circles that you discussed in the podcast with Lenny—do you have any suggestions or specific tactics on how to start one of these internally within a company that has worked well for you?

A: When they created LeanIn Circles at Facebook, they were an incredibly powerful way for women to connect across the organization. I've been a part of three of them over the past ten years: two at work and one outside. Later, the company created mentoring circles for PMs. This informal network ended up benefiting the company because it fostered loose ties between groups through individuals who worked on different products.

Having company support is not necessary, but it can be helpful if you want to maintain and scale your circles over a long period. Learning and Development can help you here. In fact, a group of us reunited about a week ago to reflect on how far we've come and continue our allyship and friendship.

ON BEING CEO

Q: What do you think are the most unique aspects of the culture you've built at Ancestry, and can you talk about the impact these pieces have specifically had on your team / the business?

A: Ancestry is a 35-year-old company, and it has always had a strong culture of meaning and mission. As I did my listening tour, I realized that the frustration most people had was not with the company, culture, or mission, but with the speed of decision-making and execution. So we worked to change that together. We called it “unlocking and unblocking.” We created a new process to more quickly escalate issues, get to resolution, and align priorities. This resulted in us shipping to customers 50 percent faster.

Q: How do you manage to keep your cool despite such frenzy around? I can only imagine how many things you have to deal with as a CEO on a daily basis.

I remember speaking to someone who said they used to get into shouting matches with their manager. I just can’t fathom that. I have never yelled at anyone at work. I only lose my cool when my kids push my buttons (kidding, sort of—Jonathan, Bethany, and Danielle, if you are reading this, I love you, but please get your chores done). Seriously, though, I have a rule.

The way I see it, there are two buckets:

Things I can control
Things I can’t control

I think about the things I can’t control, and then I set them aside to focus on what I can control. Doing that gives me a lot more mental space. Focusing on doing ensures you are not always in your head, ruminating.

GENERAL HIRING AND WORK ADVICE

Q: Your career and achievements are impressive. I am a big fan. What can be one actionable piece of advice to amplify your impact at work (more impact, more influence) without overwhelm or overwork?

A: Don’t look at communication as self-promotion. Look at it as amplifying your impact. Decide what accomplishments are important and get the word out. Whether through weekly newsletter updates, all-hands, or posting wins, find the right cultural touchstones for your team and focus on those. Don’t focus on volume; focus on impact and reach.

BUILDING MARKETPLACES

Q: We are currently doubling down on word of mouth (NPS) in a C2C Marketplace. Any advice/direction to maximize these efforts?

A: Make your customers your best word of mouth.

For sellers: Find ways to help them share their listings.

Make it a part of the listing flow to post on social media.
Give them a discount if the buyer comes through their link (affiliate).
Create a “storefront” so they want to make it their home and share it with others.

For buyers: Make it easy for them to discuss their discoveries.

Many people shop C2C with their friends or family. Make it easy to message using WhatsApp, Messenger, or text.
Create an affiliate program.
Suggest they share their purchase if they are happy with it.

Q: You mentioned in your inside story of Marketplace that you were "terrible at selling the idea" of Marketplace for five years. What do you think was holding you back from successfully selling the idea, and do you have any advice on selling big new ideas internally?

A: I tried a few different things to get my idea out there—Hackathons, pitches, strategies—but I never got much traction. Part of it was that I was looking at the world from such a different vantage point than everyone else. Growing up with limited resources as a child of immigrants, shopping at garage sales and church rummage sales was a huge part of my life. I was an avid eBay power seller before 2000, and I was also the only “mom PM” at Facebook. There were only four women PMs at the company when I left the product team, and six PMs when I hired numbers seven and eight (both moms!). At the time, I struggled to break through, but as more people became parents, it got easier and easier to tell the story. Part of it was that I had changed, and part of it was that the environment had changed.

During those five years of selling my idea, I also built up the credibility and experience I needed to craft my message better. My work colleagues knew my track record for delivering products. I slow-dripped the idea for Marketplace whenever I had an audience until it was the right time. When it was, all the work finally paid off.

After having been in the tech industry for over 20 years, I have learned a lot. My goal is to share that knowledge so you too can grow your career and find the right trajectory. The industry has changed somewhat since I started, but it's still so important to be your authentic self, amplify your impact, and learn what you can and cannot control. These skills will take you a long way.

I hope that by reading these responses from the Lenny’s Community AMA, you are able to reflect on and apply some of the information to your career and work. If you have any questions or comments, feel free to reply to this email or leave me a comment.

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