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An interview with Sherry Yang, Engineering Lead
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In conversation with Sherry Yang, Engineering Manager

Venue.sh
Venue.sh
30th April, 2024
In conversation with Sherry Yang, Engineering Manager
Venue.sh
Venue.sh
30th April, 2024

Described as both ‘distinguished’ and ‘successful’, Sherry Yang is leading the way on flexible management, enabling everyone to flourish in their own way.

Sherry Yang
Continuing our exciting series of leadership interviews, we delve deeper into the heart of Venue.sh.
As a company, we are committed to not only revolutionizing software development but also to keeping the human connection at the core of our work.
Our series of interviews offers a unique perspective into the leadership within our team, their passions, communication styles, and the stories that have shaped their journey.
Following on from our chat with Mike Maheu, GM and Co-founder of Venue.sh, next in line is a leader who has been instrumental in driving the vision forward, Sherry Yang.
For more than a decade, Sherry has strived to make the technology sector more inclusive and dynamic. Now, as Engineering Manager at Venue.sh, she has the opportunity to apply her ethos of pragmatic and diversity-centered leadership to push both our platform and the sector forward.
We talk about what that looks like in practice, how her own experiences shaped her approach, and what has her excited for the future.

Sherry, what's your leadership style?


I don't have a specific name for my leadership style. I like to say that my style is customized based on the person that I'm managing or leading, or even the team's culture. This is mainly because there are a lot of frameworks out there that ask leaders or managers to execute their leadership style in a certain way, whereas I don't believe it's transferable from team to team or person to person.
So, I customize my leadership style based on the individual's personality. I've found that my style has evolved over time, and I learn from each individual, applying what is suitable for their needs.
I find this approach most effective because it doesn't force someone to become something they don't want to be. It also provides them with a structure to guide them towards a specific path they are looking forward to.

I think about a sports team, like a team with one coach and multiple players. Would you say your leadership approach is to adapt to the team's dynamics to manage them effectively, rather than expecting all players to adjust to your style?


Yeah, that's a very interesting analogy.
So, I'm rewatching 'Ted Lasso', and I find my leadership style is somewhat similar. It varies for each individual, but as a team, we have a strategy. There’s an episode about special drills for tricks that the team can perform, and we’re the same. There are certain styles that work uniquely for our team.
I think that is something we adhere to, even with agile and scrum methodologies implemented within the team.

That's challenging, isn't it? Because the players could potentially all have very different personalities. And to some extent, you probably want those different personalities. How do you balance the time you spend with individuals versus driving the entire team towards the goals, meeting your boss's needs, implementing the right strategies and so on? How do you balance your personal time with your leadership style?


I am open to having regular one-on-one meetings with my direct reports based on their needs. There are team members who prefer more frequent meetings than others.
For me, the level of touchpoint really depends on the individual. It's more about their needs, and I find that the key to balancing my leadership style and scheduling meetings with multiple engineers is understanding the bigger picture.
I have to balance and prioritize Mike's needs with our organization’s vision as well as TAG’s (The Adaptavist Group) vision. So, I think that being mindful of that makes it easier for me to deliver a consistent message throughout the meetings I have with individuals.

I read that you were recently described as ‘distinguished’ and ‘successful’.


I chuckled when that came up, and posted about it on LinkedIn. It's a very academic way to describe me, and I am not an academic person. I'm not decorated with, you know, Masters and PhDs. So, it was surprising for me to be introduced in that way.
If I were to look inwards... I don't feel like I deserve those titles.
Externally, I am presenting myself as a successful, distinguished person. I genuinely care about mentorship and sharing my resources with others, especially underrepresented groups. So, my story and experiences as I share them with the world can be seen as a success story.
I believe that there are times when I may impact people in ways that surprise me. And when they write a comment about their experiences with me, I'm just like, 'Wow, I did that.'

Is that a recognition of success for you? Are you at a point now where you think, 'I am being recognized as a leader. This is something I've always wanted, and now I can move forward and reach that next level, whatever that might be?’


That's an interesting question. As an immigrant with Taiwanese parents, I grew up with high expectations – always, always high expectations. “You can be better. You can be better.” That's the mentality I was raised with – that I can always improve.
That made me feel like I had to prove myself and seek other people's approval earlier in my career.
But I think most recently, I have recognised that I am defining my own success. I feel strongly that as long as I'm true to my values, then I am doing what's right for me. I don't need other people's approval. And often, there are comments that make me feel really good about myself, reassuring me that yes, I am on the right track.
Imposter syndrome is a phrase that's frequently tossed around, and I dislike it because I don't consider myself to have a syndrome, nor am I an imposter. But sometimes, I do doubt my performance and my value.
Owning the work I do is important, as is showing up as a woman in the communities I'm part of.
Take being an Ambassador for Google, for example. Having like-minded women in the community who echo my sentiments, and vice versa, is empowering. We encourage each other to be the best versions of ourselves, and it has been very rewarding.

So those comments… do they go in your KitKat box?


I used to facilitate a workshop called '#IAmRemarkable'. We’d write 'I am remarkable' statements - both professional and personal - to recognize our accomplishments. I would partake and stash them away. Then, every time I felt, perhaps, a slight doubt about myself, I would refer to that box of my own writing. The reminders of my own accomplishments help me feel better about myself.

You attended an event 10 years ago called the HTML500. In the last 10 years, what's changed at events?


I think my knowledge has evolved because I was initially overwhelmed. That was probably one of the first large events I'd ever attended. Now, when I show up at a large event, my focus is more on giving than receiving. When I listen to people on stage, I can relate to them because I am probably just as knowledgeable as they are. Therefore, I often learn from the small tricks they employ and the outcomes they provide as a resource.
Reflecting on my first event, I was there in awe, eager to meet like-minded people and learn alongside everyone else.
And networking was a new experience for me. That was probably my first time learning how to network with people.

You represent underrepresented groups, and it seems like you organize these communities and events as one way to help. What changes have you observed, from an event logistics perspective, since that first event? Has the attendee makeup changed? Has the culture of the events evolved? And if they have changed, do you take a little credit for that?


Do I take credit? Yes, to some extent. I mean, am I part of the change? Yes.
Am I creating an impact? Yes. So, should I take credit? Perhaps. Yes.
Over the years, the makeup of tech conferences has definitely changed, but it really depends on the topic. Now that I am in DevOps, this is a new community that I am getting involved in, and I'm not sure about the diversity makeup in the DevOps community.
I am used to seeing more male representation than female in tech in general, especially in past conferences. That's more typical of general tech.
At these major conferences, they are encouraging underrepresented groups to show up. They are encouraging a diverse lineup of speakers on stage so that they can inspire more people and encourage them to build relationships.
Representation matters, and that's really what these large forum conferences can provide. So, if you've only ever read technology books by a male author, you never really grasp the concept of what that’s like from a female author's perspective. I really appreciate it when a male engineer highlights this difference because they care. This allyship advocacy happens a lot at TAG – I don't think I've ever experienced that in any other forum or team.

You mentioned role models… How do you define a role model?


When I think about role models… if you were to use generative AI to create a painting – the image would be blurry. It's like this invisible or imaginary role model has constantly changing features.
I wouldn't say it’s any one person. It’s a composite of many things, many people, and many resources that I've read. Historically, there are so many people whose work I've read or from whom I've received support over the years. I look up to them, and their faces are all different. They don't all look one way or the other.
Just as my leadership style is tailored to the person I'm with, when I'm receiving resources and knowledge, I'm also very open in terms of a funnel. Sometimes I listen to biased speakers, and sometimes I listen to people who can inspire the general public. But you have to hear the story from both sides to really understand what is “right” or “wrong”, and to truly understand the topic, understand where they are coming from.
That sort of builds my role model in a way that it's hard to define, like, what's the first and last name of this role model? I don't really have one. I have many different role models.

What's one thing that has impressed you lately?


Lately, I’ve been doing a lot of recruiting. So, my immediate thoughts are about the talent pool - it’s impressively diverse, for sure.
A few years ago, I had significant concerns about the knowledge or talent gap for the positions I was hiring for. Now, I'm interviewing candidates who are so well-qualified for the work that the competition is fierce. It's impressive! Impressive interviews, impressive CVs, and impressive people.
I was telling my team that everyone I've interviewed so far speaks at least more than two languages.
The education system is supporting the technology industry from the ground up. And that's crucial to really close the gender gap. I was genuinely concerned about hiring for a specific role. I was anticipating the pool to be filled with the stereotypical software engineers. But I'm seeing so many different types of engineers with diverse backgrounds. And I truly appreciate that.

You spoke on a panel recently, and afterwards you provided three of your top tips. I'm going to summarize the top tips:
  1. Success is subjective
  2. Fundamentals matter
  3. Collaboration is key

How is success subjective?


Because everyone's definitions of success are different, just like how everyone's role model is different.
If you were to ask me if I'm successful, I would say it depends. It depends on my definition of success at the time. If my definition of success is to represent women in tech at a global level, I would say, I'm successful. You can find my name and face all over the internet in discussions about women in tech. So yes, I am successful in that regard.
But if you were to ask me if my definition of success is becoming a leader for an international and innovative technology company, influencing hundreds of engineers in their vision and putting forward the right strategy, then I would say, not yet.
I would encourage everyone to reassess their definition and not be daunted by other people's success stories, because your definition of success should be different from theirs.
That's why I was surprised when someone called me successful and distinguished because I feel like that is very subjective. I can present myself as a confident, impressive, woman of color in tech, but that doesn't mean that I am at the success level I aspire to be at just yet.

Before you were put in a leadership position, what did you think about leadership? What did you think it was? And how has that changed now that you have been recognized as a leader?


Before becoming a leader, my understanding of leadership was from an authoritative perspective. However, after stepping into a leadership role, I quickly realized that I'm working with people, not objects. I can't force change.
If you force your team to become something they don't want to be, just to suit your preferences, it’s difficult to build a long-term, enriching relationship. Especially when it comes to professional and personal growth – there just won’t be any.
Now that I'm actually in a leadership role, I have more empathy towards the people that I work with than before. I used to think: Yeah, just listen and do the work. Never ask questions. That’s probably because of my background, as I was brought up in a more authoritative environment.

How can one person make change in the tech industry? Can individuals make a difference?


If I were to tell you the software development way, it would be iterative through feedback loops. So it's very agile and probably the only way that I know how to implement change is to try and to review and to improve.
Individuals can definitely make a difference. The open source community usually starts with individual projects and the projects evolve over time with community support. Software solutions nowadays are pieces of these existing solutions put together.

Is there anything that you wanted to highlight about your leadership style?


Leadership has been a growth journey for me. I would say it came naturally because I wanted to share my vision with a larger team or group of people.
Over the years, I've learned that I have to be a human being and let others know that I am human too. I can open up many paths and enable numerous possibilities for the people I manage. But I'm also human.
I also have people to report to. So, over the years, humanizing leadership has been a significant learning experience for me.

Great, thank you for your time today!


Connect with Sherry on LinkedIn.
This interview has been lightly edited for brevity and clarity.

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Venue.sh
Venue.sh