An Inside Look at Informal Mentorship at DuckDuckGo

The DuckDuckGo Team

As you may know, Girl Develop It (GDI) HQ works on a fully distributed team. So do our friends at DuckDuckGo, the internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. We asked our network of chapter leaders, representing over 60 chapters across the United States, to ask the experts at DuckDuckGo anything and several of them wanted to learn more about mentoring.

The following conversation between DuckDuckGo team members Ali Greene and Lily Rouff, gives an inside look on the informal mentorship opportunities that exist at DuckDuckGo. Read along and learn some of their strategies for becoming an effective mentee and mentor.

Left: Bill Connor + Ali Greene, People Ops. Right: Lily Rouff, Daniel Davis, + Azad Abbasi, Social Media.

Ali Greene is the Director of People Ops at DuckDuckGo. In her role with the company, she oversees the overall employee experience, working from a variety of countries around the world.

Lily Rouff is a Social Media Strategist at DuckDuckGo. She engages users through social media efforts and works from the USA and Mexico.

Ali: I love that we’re here to talk about mentorship, especially with Girl Develop It. GDI is an organization that’s known for stellar hands-on learning programs that really help people break into tech. DuckDuckGo, on the other hand, puts a lot of onus on people learning through doing and making mistakes. What’s really cool here is that both formats work — with either approach, anyone can create a valuable mentorship opportunity. And so, we’re going to dive into ours today. Before we go too far into the topic of mentorship, Lily, do you want share a little bit more about DuckDuckGo?

Lily: Definitely. DuckDuckGo operates a search engine alternative to Google at, and offers additional apps and extensions to protect you from Google, Facebook, and other trackers no matter where you go on the internet. We’re a remote team with employees all over the world. Coming from a traditional office setting, the biggest change I’ve noticed at DuckDuckGo is the open communication and transparency in our work.

We’re encouraged to question assumptions, and one another — that’s one of our core values.

I was speaking with Bill Connor on the People Ops team, and he said that this can lead to helpful conversations with team members at every level. He added, “I’ve worked with so many teammates that have a passion for helping others and sharing knowledge, which has been the best part of the culture at DuckDuckGo for me.”

That accounts for a lot of how we work together. Everyone asking questions and inserting ourselves into projects that cater to our interests and strengths. It is not the hierarchal structure I’ve previously encountered throughout my career, which is fully intentional.

Ali: Our founder and CEO, Gabriel Weinberg says,

“The fastest way to learn is by deliberate practice, where you try things just out of your comfort zone, and you have someone by your side coaching you, pointing out in real time what you’re doing right and wrong. Mentorship can help fill that coaching role.”

This is a format where a lot of the responsibility falls on each individual employee, instead of a formal mentor. When you start working at DuckDuckGo you become the driver of your own future — personally and professionally.

I use this metaphor at DuckDuckGo, that mentorship is a “Hub and Spoke” model where the employee is the Hub, encouraged and empowered to own their own career development; it allows the employee to seek out mentorship in a way that’s meaningful. The different leadership roles that we have, or spokes, are able to offer an employee slightly different levels of support, in terms of the content as well.

Those include Project Advisors, that oversee specific projects, Career Advisors who help employees navigate their careers at DuckDuckGo, and Functional and Objective team leads that influence cultural and strategic leadership in the company. We’ve been talking a lot in theory though. Lily, as someone newer to the company and experiencing this for the first time, do you want to discuss what this has meant for you as a mentee?

Lily: Absolutely. Something you touched on, the “Hub & Spoke model,” really resonates with how it feels to be a mentee at DuckDuckGo. In a more formal structure, a “mentee” sounds like a passive term.

But at DuckDuckGo, getting the most out of your relationships with your advisors comes from proactively asking questions and communicating ideas and areas of interest.

Even though we have our designated Project and Career Advisors, it’s always encouraged for employees to reach out to colleagues and ask questions. I’ve found distinct value in speaking with various people at DuckDuckGo. My Career Advisor, Daniel Davis, acts as a true mentor for me, providing not only technical insight into my role and responsibilities, but also sharing tips on navigating through the organization. On the other hand, Olivia Haas, someone I don’t work closely with on projects, has provided me with insight about being a woman in tech and how to navigate that, which has been new for me in my career.

Ali: That’s great! And how do you, as a mentee, ensure you have a productive conversation?

Lily: A lot of preparation and a lot of thinking goes into it. I review everything on my own before meeting with both my Project and Career Advisors, to make sure that I’m clear on the tasks at hand and have sorted out questions to ask ahead of time. It makes our time together valuable and gives me the opportunity to drive the conversation.

I believe the relationship is a two-way street. Your mentor can shine the flashlight in the right direction, but your relationship is most valuable if you explore the path they’ve illuminated on your own.

Your mentor doesn’t have all the answers. With that idea in mind, it’s also important to highlight that a lot of people at DuckDuckGo have the opportunity to work as both advisors and advisees, mentors and mentees.

I was speaking with someone who falls within that category. Diana Chiu, who works on our Partnerships & Finance team, had some interesting thoughts on working in both roles. She said, “I find there’s a good deal of knowledge sharing from both angles.” Career and Project Advisor roles have given her the opportunity to leverage her strengths, grow others, and share perspectives on projects. On the other hand, as a mentee, Diana is also able to gain insight from her Career Advisor.

Ali, as someone who also has one foot on each side of the line at DuckDuckGo, could you talk a little bit more about your transition from mentee to mentor?

Ali: What really resonates with me from what Diana said is the term knowledge share. Being a mentee and mentor is about sharing information and helping people get a new perspective. It helps instill confidence to move forward in a certain direction.

There is something really moving about passing down confidence in oneself through mentorship.

The term, “Imposter Syndrome,” comes to my mind when I think about being a mentor. I’ve definitely had experiences in my career where I’ve felt this. I was questioning: have I gone through this experience enough times to really trust my own judgment or to back up a recommendation? Am I actually a subject matter expert here? There’s this anxiety that comes when you are a mentor for the first time. The anxiety lessens for me when I take that informal, knowledge sharing approach.

I remember times when I was growing into my next role, taking on challenges where the probability that I would fail was higher than the probability I would succeed. Knowing I came out the other end having learned something made me realize my importance as a mentor.

Lily: I love the outlook that as a mentor you’re able to imbue the confidence you’ve found in yourself into those you are advising, and vice versa; using those relationships to solidify your authority in yourself. That’s really powerful. How do you ensure, as a mentor, that the relationship is valuable for both parties involved?

Ali: I like to understand the goals the mentee has. Simply asking why me, why now, why this?

From there, it’s really about setting expectations, active listening, and opening yourself up to hearing the mentee’s experiences and challenges they’re going through.

As a mentor, it’s important that you are able to draw on and share your own experiences, explaining what worked well for you in the past, and what obstacles you’ve had to overcome. Weaving in personal stories instead of direct advice works for me, it allows the mentee to have a conversation around what other approaches might make sense in their situation.

The other thing I really like about being a mentor is what you said earlier about illuminating a path to take, not always through direct advice. I like to rely on open ended questions — why, how, what. Why did you decide to take approach A over B? Why did you decide that this was the most influential communication technique? How did you navigate that approach? How else could you have handled this situation? What would have been a successful outcome? What did you learn from this? What will you do next time? Those types of questions really let people have room to find the answers themselves.

Lily: I’ve definitely found it useful to have those types of questions posed to me. Sometimes you need someone else to step in and ask you the questions you should be asking yourself. We talk about getting “unstuck” a lot at DuckDuckGo, meaning if you find a road block in a project, your advisor can help you find a workaround. This line of questioning effectively breaks those blockers down. I find, as a mentee, that this really provides a sense of accomplishment. Do you have any last thoughts on how the GDI community can find mentors within their own careers, especially if they don’t have a system like this in place?

Ali: One thing that doesn’t get talked about that frequently is the idea of peer mentorship. At DuckDuckGo, we do a great job of cross-functional knowledge sharing through informal mentorship because of the Hub & Spoke model. For people that might not be in companies with similar outlets, or for people that are navigating new pathways in their career and maybe don’t have someone to lean on, I would say that peer mentorship can also fall informally into your personal network.

I have a peer network I have spent time cultivating including People Ops people at other remote companies. We talk through shared experiences, swap resources on trending topics and new tools, and ask each other questions. That’s been a really cool and unique way that I’ve been able to create mentorship opportunities for myself outside of work.

Lily: It is that exchange of information that can happen anywhere, whether in your own company, or among peers with similar experience. Thanks for sharing!

Ali: Thank you!

Interested in a Career in Tech?

DuckDuckGo is currently hiring for a Senior Mobile Application Developer, Backend Roles, People Ops, and more. Visit DuckDuckGo’s website for the latest job listings or find one of the 60+ GDI chapters near you and sign up to take a class to start your journey into tech.

GDI empowers women through coding, confidence, and community. Visit our website and follow us to learn more about our accessible, hands-on classes across the US.




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