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NOTE: Applications are now open for the next Ceiling Breakers cohort, starting in February. Admissions happen on a rolling basis and will close mid-January.

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KEY HIGHLIGHTS

🥳 Introducing Ceiling Breakers

🕯️ Why inspired Holly to start her coaching initiative

🔗 The link between a growth mindset and leadership 

🧩 Characteristics of a growth mindset

🔭 Understanding the larger context of work

✊🏿 How the BLM movement galvanized uncomfortable conversations

🧑‍🏫 The power of leadership coaching

👔 There is more to work than work

🤹🏻 Skills are only a fraction of what makes up work

⛔ 3 obstacles faced by underrepresented communities in the workplace

🙃 How people overcorrect to battle stereotypes

👬🏾 Why having a like role model is linked to adopting a leadership style

🌿 One leadership style doesn’t fit all

🗣️ How to deal with the negative inner voices

🧺 The wide buffet that is the coaching space

📚 Reading about leadership doesn’t prepare you for a trigger moment

☯️ Below the line vs above the line leadership

👀 How coaches encourage a different perspective

🦋 Work and life are both impacted by deep personal changes

🧑‍💻 Why coaches from the same industry understand issues better

➿ The two-fold advantage of group coaching

🧱 The importance of building a community

💪 How to embrace your diversity as a strength

💬 Hearing others’ stories builds empathy

📝 How it is possible to learn from observing coaching in practice

KEY QUOTES

The effect of BLM in everyday life

But our world changed in 2020. The Black Lives Matter movement really got me to have more honest and open conversations with people around me about race and gender and identity and topics that I used to dance around for political correctness or for the fear of accidentally offending someone. And what I realised is that there’s a much broader systemic issue faced by all the underrepresented groups.

In our own ways—people of colour, women, LGBTQ and immigrants—all have experienced conscious and unconscious bias. It’s a larger issue here versus if we improved our communication skills then everything was great, but it’s a systemic thing that we all are very familiar with, and we all know the feeling of being the “only” in the room. 

Being the “only” in the room

I’ve talked to a few black engineers and engineering managers. They mentioned being the only black engineer, and not to say the only black engineering manager, in the room. And how is that feeling? We just don’t necessarily always see a C-level executive being people like us.

Theories of leadership in practice

I love to read about leadership and growth. I used to think that I know a lot of this stuff, but realised that it is one thing is to read books and intellectually understand something; it’s another thing is actually at the moment of being triggered, of frustration, or confusion actually. It quickly changed how I feel and how I react, and be effective at the moment, and actually have that with us.

Questions that trigger epiphanies

At one point, I was struggling because there are just so many of those requests. And I see my team working so hard and working over time, so I was worried about my team. And then the story I had is not every request actually justifies the effort that we were putting in. So I talked about this with my coach, and then she asked one question: “Holly, were you being open and curious? Or were you being self righteous?” 

I was like: Oh, I was asking people to justify these requests. I was being self righteous, versus being open and curious to learn how this actually drives the impact. I would stay on the surface level versus actually working with a person to understand what they’re trying to drive; and how do we actually create a creative solution. Not necessarily just to take the request and do it, but also think about the best ways, the most creative ways to achieve that goal. Just one sentence: my whole attitude changed.

The trap of correcting a stereotype

For example, someone from the pilot programme mentioned that: “Oh, I never really fully embrace or accept my Asian American identity. I try not to let people notice that I’m Asian American. I want to fit in; I want to just be one of the people, and hopefully they can treat me the same.” In order to fit in, we deny our identity and who we are. And where else does that denial show up in our lives? Yeah, even recognising all these denials that we give ourselves, I think there’s implication on a lot of other areas in our lives.

FULL TRANSCRIPT BELOW

Shamanth: I’m very excited to welcome Holly Chen on The Mobile User Acquisition Show. Holly, welcome back. 

Holly: Thank you so much for having me again.

Shamanth: Absolutely. You know, the first time I found our conversation very fascinating, just because you described the inner workings of what, to many people is a very complex project. 

And today, we’re going to talk about something completely different. And certainly this, I would say, can be a topic that, in many ways can be more impactful and certainly more critical than many aspects of growth marketing itself, just because it is foundational to our society, and foundational to how we work. So I’m excited and thrilled to have you back here today.

Holly: I’m really grateful for you to provide me this opportunity. It’s actually the very first time I talk about the project publicly. And I’m excited to chat about it, and appreciate the time.

Shamanth: Sure! So we are going to talk about Project Ceiling Breakers. I will say that’s a very cool name—I don’t say cool in the sense of ‘cool’, but cool in the sense of very strikingly appropriate. So tell us about Project Ceiling Breakers and what inspired it. What were some of your own experiences that led to it?

Holly: For sure. So Ceiling Breakers is a group coaching and community for underrepresented leaders. We are working with women, people of colour, LGBTQ and immigrant leaders, primarily in tech to start, where our goal is to help more underrepresented leaders to become senior executives in our organisations and drive change in our society. 

How was it inspired? I am surprised that I started it myself. You may ask: “Oh, you are a marketer, you’re a growth advisor. Why are you spending time on this totally unrelated thing? And why are you doing this?” 

Shamanth: Yeah. 

Holly: In hindsight, when I was asked, what are the key characteristics I look for in a growth marketer hire, one of the characteristics I usually talk about is the growth mindset, and the ability to actually not give up and to be persistent after failures. Because growth marketers do a lot of experiments, and they need to be comfortable with ambiguity and really test out things, even when the hypothesis is wrong, or the experiment didn’t go as they planned, and they need to keep going. 

So that growth mindset, and that mindset of learning from failure is really critical. So that ties very well with leadership. I think we talk a lot about the content of growth marketing, which is how do you do channel optimization? Or how do you design experiments, but we don’t necessarily always talk about the context: the context of how we work; how we collaborate with cross functional partners; how we put our work in a bigger context. And the context piece is really about leadership. So that’s a big component of who we are as growth marketers, as a whole person. 

In terms of the story, I’m originally from China, and I’m an immigrant. I came to the US after college for grad school, and I stayed ever since. I still remember some of the political turmoil as I was growing up. So I was told from a very young age, by my parents and grandparents: “Don’t get involved in political or social activism because it’s going to be useless and dangerous.” And I’m still not a citizen, so I can’t vote. So I had this apathy to political and social issues around me, and really just was focusing on my own personal professional growth. And that’s all really what I cared about. 

But our world changed in 2020. The Black Lives Matter movement really got me to have more honest and open conversations with people around me about race and gender and identity and topics that I used to dance around for political correctness or for the fear of accidentally offending someone. And what I realised is that there’s a much broader systemic issue faced by all the underrepresented groups. 

In our own ways—people of colour, women, LGBTQ and immigrants—all have experienced conscious and unconscious bias. It’s a larger issue here versus if we improved our communication skills then everything was great, but it’s a systemic thing that we all are very familiar with, and we all know the feeling of being the “only” in the room. 

But what I realised is that the first step is really talking about it. And the next step is to do something about it. So I thought about my role in this whole thing and a few threads in my life started to emerge: the coaching that I received at Slack; the conversations I had with friends who really care about the issue; and the coaching and leadership training I was receiving from the proactive Chinese Institute at CTI. So all the threads sort of just naturally merged together and Ceiling Breakers as an idea came about.

Shamanth: Yeah. So, in many ways, it was born out of your own experiences and your own realisation that there’s just more to working than work, if I can put it that way. It’s certainly about what’s happening in the wider society that directly impacts how many of us experience work. Certainly immigrants, certainly underrepresented minorities: they experience work differently. And if we just think work is the sum total of communication skills and analytical skills, that is a very incomplete picture.

Holly: Yeah, I think my tendency before was saying: “What’s wrong with me? These are ABCD skills that I need to learn and get better at.” And I didn’t put the situation in a bigger context and understand what is going on. On a global level, why is this happening? So at least having taken a step back and looking at the issue, not only in the moment, but also in the context.

Shamanth: Certainly, certainly. I’ve been in situations where I’ve totally missed the broader context. And I’m like: “Oh, all of this doesn’t matter.” But it does, because we are a part of that big macrocosm. 

To switch gears a bit, given that you’ve noticed in your own experiences, the forces that were impacting underrepresented leaders; underrepresented people from even getting into leadership roles. What did you notice as being some of the specific challenges that underrepresented people face in the workplace that are hurdles between them and executive roles?

Holly: There are a few things. 

One is how do we become conscious about unconscious bias? Unconscious bias: Typically, it is not the intention of the person to mistreat us or discriminate against us. There’s actually a larger societal and cultural background to it. But it does happen. 

For example, some of the stereotypes for the black community is that they are aggressive and angry and loud. Some stereotypes for Asian community is they are analytical, and they’re detail-driven, but they’re not leaders. How we react to these stereotypes sometimes is that we’re really trying to correct that stereotype, or we’re trying to fit in, and in our process of doing it, we may over-correct. You may see an Asian person become overly loud, just to correct that stereotype. And that’s also not necessarily authentic and effective. So how do we actually act in that context of a stereotype? How do we react to it at the moment? 

So that’s one and two is a lack of role models and community.

I’ve talked to a few black engineers and engineering managers. They mentioned being the only black engineer, and not to say the only black engineering manager, in the room. And how is that feeling? We just don’t necessarily always see a C-level executive being people like us.

So what is actually the leadership style that we want to have that’s authentic to ourselves and effective? So what’s working for a white male being outgoing and sort of the classic societal image of a great leader may not actually work for a petite Asian female that’s really grounded and introverted. So how do we cultivate that role model and the community, where we can see the various different types of leadership styles and know that there’s no one model, and there’s multiple models that work for us. How do we learn from other people like us, their stories, and from the community? 

I think the third thing I want to talk about is the saboteurs that show up in all of us. All of us have the imposter syndrome and the self critical voice; especially for growth-minded people or driven people that we work with in tech: that voice, that imposter syndrome is pretty strong. So how do we work with that when that shows up? 

I know I have a strong stickler sort of saboteur. So a stickler is someone who really just wants to be perfect with everything. How do I make the best decision with all the information I have, so that I don’t fail? And that sometimes is not the right way or the most effective way for me to be as a leader, because as a startup, as a company, you need to move fast in making decisions with incomplete information. So how do we actually work with all these characters in our mind, acknowledge them and work with them to be a full person?

Shamanth: Certainly, and a lot of these forces are much stronger. And certainly, the experience of an underrepresented person is very different from someone that is expected to succeed, or a white male person that has the sort of privilege and experiences to not confront these exact problems in this manner. 

And you did allude, Holly, to how your own experience receiving coaching at Slack was one of the ways that you noticed the potential for change—not to put words in your mouth, but I think that what you meant. And to the extent you’re comfortable sharing, can you speak to what was the impact you saw in yourself that coaching could have? And broadly, what you see is the change that you expect to engender with the program Project Ceiling Breakers, based on your experience?

Holly: Yeah, I’m really grateful for the executive coaching I received at Slack. They provide coaching to managers, and I was also part of this diversity inclusion programme where they provide executive coaching. 

Coaching is a very segmented space: there are the coaches who charge $50 an hour, and there’s coaches who charge $1,000 an hour. And there’s a wide variety of styles, and experience from the coaches. And I was pretty lucky that I worked with some amazing coaches that I believe are at the top of their fields, and really helped me to look at things from a different perspective. 

For example,

I love to read about leadership and growth. I used to think that I know a lot of this stuff, but realised that it is one thing is to read books and intellectually understand something; it’s another thing is actually at the moment of being triggered, of frustration, or confusion actually. It quickly changed how I feel and how I react, and be effective at the moment, and actually have that with us. 

If you read ‘Conscious Leadership’, they talk about being below the line, being defensive and being closed, versus above the line, which is open and curious and wanting to know more. Of course, I want to be above the line. But oftentimes, I am below the line when the issue comes up. One of the primary benefits for me is really to help me create that new neural pathway of looking at things from different perspectives. Amazing executive coaches are so masterful and so sharp; sometimes even just one sentence, and one question. And I’m like: “Oh, my God, how did you know?!”

Shamanth: Is there an example that comes to mind?

Holly: Okay, so here is an example. My team is growth marketing, digital marketing. We actually serve a lot of the cross functional teams, who all want to do campaigns: like we need to drive more registrations for this event, or we need to get more traffic for this article, etc. 

And because there’s so many incoming requests by multiple teams, and my team was quite small at the time, we couldn’t really handle all these requests. So we have this request form, which everyone filled out to tell us more about the project and tell us about the impact of these projects and drives. 

At one point, I was struggling because there are just so many of those requests. And I see my team working so hard and working over time, so I was worried about my team. And then the story I had is not every request actually justifies the effort that we were putting in. So I talked about this with my coach, and then she asked one question: “Holly, were you being open and curious? Or were you being self righteous?”

I was like: Oh, I was asking people to justify these requests. I was being self righteous, versus being open and curious to learn how this actually drives the impact. I would stay on the surface level versus actually working with a person to understand what they’re trying to drive; and how do we actually create a creative solution. Not necessarily just to take the request and do it, but also think about the best ways, the most creative ways to achieve that goal. Just one sentence: my whole attitude changed. 

Shamanth: Yeah, and somebody that’s experienced and nuanced can pinpoint exactly what might be going on. I can certainly see that, and I’ve certainly had some experience with advisors, coaches and mentors that have been just as perceptive. So I could definitely see how that can work out. 

And you spoke about coaches that are at different levels, and it being a very segmented space. You spoke of what a very experienced coach might do. You also spoke about the people that are less experienced. So somebody that’s less experienced, but still good, what might they focus on that may not necessarily get to the most critical aspects of what’s going on?

Holly: Coaching has different styles: there’s life coaching, there’s executive coaching, and leadership coaching. And they’re converging, we can’t separate work and life, and the change you drive deep down as a person is going to manifest itself in both work and life. 

I think a new coach, who’s in training—aka me, right?—I may need some sort of formula. And I need to think this is the style of coaching that I may be able to do. Initially, let’s identify the topic and your perspective around it. And then I would help the client to explore different perspectives. And then we come to a conclusion and action, like accountability. 

So I would need structure and formula to make sure that I was effective, versus a master coach, like Anjani and Grace—who we work this—they’ve been doing this for 15, 20 years. They have hundreds of formulas or frameworks in their mind where they already worked into just how they are as a coach. And they don’t need to rigidly follow the right structure, but, at the moment, what’s the most appropriate framework for this person. 

And then two, I always appreciate coaches, who have worked in similar environments as me. So if someone has worked at rapid-growth tech startups, they have gone through that high stress during that process. Or have held chief HR officer roles, and they understand what we’re going through. So when I talk about an issue or a challenge, they know because they experienced it, and they “broke the ceiling” or climbed the ladder. So they have the context, it is easy; versus someone who has no experience working in tech, it may take them a while to really understand what I’m going through.

Shamanth: Yeah. And I would imagine the same is true of coaches having some sensitivity to the experience of underrepresented people, women and/or minorities. Certainly somebody that’s been the only one in the room or at least had enough experience in dealing with situations like that, I imagine can be more powerful in actually helping support people through change. 

So with Project Ceiling Breakers, considering that the programme is specifically tailored to underrepresented folks, how do you think about tailoring the executive coaching experience to reflect the fact that these folks’ experiences are probably not mainstream folks’ experiences? How do you think about that in the structure of the programme itself?

Holly: There are a lot of training or coaching programmes that cater to everyone. And I feel there’s really a gap in addressing the experiences of underrepresented groups. And our experiences are different from everyone. 

First of all, that feeling of loneliness and isolation is real. And so often, we’re the only one in the room that looks like us. So we don’t necessarily have the community that we need and want to support us. And because, not everyone has the context of what we’re going through, that sense of community is so important. 

And two is a common empathy and understanding of the shared experience across different underrepresented groups. How I am reacting to something may help you in your exploration. Being in an underrepresented group does shape the narrative we hold about ourselves, and there’s something powerful in recognising and accepting who we are. 

For example, someone from the pilot programme mentioned that: “Oh, I never really fully embrace or accept my Asian American identity. I try not to let people notice that I’m Asian American. I want to fit in; I want to just be one of the people, and hopefully they can treat me the same.” In order to fit in, we deny our identity and who we are. And where else does that denial show up in our lives? Yeah, even recognising all these denials that we give ourselves, I think there’s implication on a lot of other areas in our lives.

Shamanth: Certainly, certainly. And having a coaching programme that really offers the space to acknowledge and recognise these parts of ourselves, in a setting that is psychologically safe for underrepresented people, I think that can be very meaningful. 

Another aspect of Ceiling Breakers that I’m curious about is that it is a group engagement. And I understand your coaching at Slack wasn’t in a group setting. So why the group format?

Holly: Actually, I did have a few group coaching experiences. And what I realise is one-on-one coaching is really good at going deep for that person for a particular issue, or dig deep into a particular challenge. And that’s amazing, very impactful, transformative. 

What I got from the group coaching is—I got that benefit of coaching and I got a community. I have a renewed level of empathy for the people in my circle. 

I had all these stories of people who grew up in this country have all this privilege: they know the language; they don’t have to learn English as hard as I have to; and they have all the school networks; and they have it made for them. But actually… and I heard some of the really impactful stories of how being the only Asian kid or only black kid in the school and that sense of being the other. And how painful that was. 

I was like: “Oh, wow.” I grew up in an environment where I was the majority. I had no idea, this is why people are going through. You just have so much empathy and appreciation for people around us. And that level of empathy, appreciation will help you as a leader, as a manager, working with your team and working with your cross functional partners. That’s the more utility side of things. But as a person, that level of care and love is going to manifest in other parts of your life as well as other relationships who have. 

Then seeing too, how other people are reacting to unconscious bias and how they respond is very helpful for me. So even when the coach was coaching someone else, and I was observing, the issues that people raise are typically very connected and similar. It’s typically like something I have also experienced in my life. So observing that, it gave me that mutual perspective: if I experienced some similar things, then how would I react? 

So it is not only about the person who’s receiving the coaching at the time, but it’s also about all of us, and how we connect to each other.

Shamanth: Yeah, it sounds to me like knowing that we are not alone can be just very powerful, in a lot of these experiences. And this sort of coaching experience, who is this not right for?

Holly: So Ceiling Breakers in particular is geared towards people who are mid-career and who’ve already worked in companies for five years and plus, and already on the way to becoming leaders. We want this programme to help mid-career people accelerate their careers and become executives. 

There are two programmes: one programme is for people with 5 to 10 years of experience—managers, senior managers, directors—to help them to become you know, VPs and SVPs. And then there’s another senior leaders group, who are typically people with 10 to 15 years experience and who’re already directors and VPs, where they’re on the verge of breaking the ceiling, but they may have noticed that the ceiling has started getting closer and closer. How do we actually help those folks to become CXOs in our organisations. 

So Ceiling Breakers is really geared towards people who’ve already worked for 5+ years. So early career professionals, with under 5 years, are not a great fit. There are a lot of other programmes that cater to that group. 

Also, I would say, if someone is not interested in self discovery and in depth personal work; and someone who’s looking for quick fixes, rather than sustainable solutions, and to go beyond addressing symptoms. There are a lot of online courses, and you can intellectually learn a lot of things. Ceiling Breakers and then coaching actually goes really deep into who we are as a person, with our identities and with the voices in our head. And sometimes it can stir up things. So actually it really needs someone who’s open and vulnerable, and being able to say I’m willing to look into sometimes the darker places in me, and that’s where I grow, that’s my edge to become a stronger leader.

Shamanth: Indeed, indeed. It sounds like what’s really important to get any benefit out of an exercise like this is the ability to introspect and just be open to listening and hearing things about yourself. That may not be the most pleasant to find out. And, as you said, those are the dark places; that’s where the edge of growth lies. 

Holly, this has been very insightful to me. Certainly, because this is a topic and theme that’s close to my heart, because I do see in the world, a lot of instances that you speak of where underrepresented people—minorities, women, people of colour—have significant opportunities to really step up into leadership positions. I saw some of the feedback from your pilot session, and it definitely was amazing. And I’m excited for all of the work you’re doing. 

This is such a good place for us to start to wrap. But before we do that, can you tell folks how they can find out more about you, Project Ceiling Breakers, and anything else that you think they should know? 

Holly: Yeah, go to ceilingbreakers.us. to check out the programme. The next cohort starts in February next year. We’re right in the middle of reviewing applications and doing interviews. So I really hope that many of the growth marketers can apply. I have some amazing mentors and advisors who’re also part of the programme and also from the marketing perspective. 

We’re going to host, not only the coaching program, but also a lot of the community events: fireside chats with executives, topical workshops and community social events to help you really connect with other underrepresented leaders and create that sense of connection and the network. So I hope many of the listeners will check it out and benefit from it.

Shamanth: Absolutely. We will link to the program. Is there a deadline that people should be mindful of?

Holly: I would encourage folks to apply sooner than later, because we’re reviewing applications on a rolling basis. And the program starts in January, early February. So probably we’ll wrap things up, at the latest mid-January. So apply early.

Shamanth: Cool. Great. And we will link to that just as well. Excellent. Holly, thank you so much for taking the time to talk to me today. It was certainly a pleasure to talk to you, as always. Thank you so much for being on the show.

Holly: Thank you so much, Shamanth. I really enjoyed talking to you and with everyone.

A REQUEST BEFORE YOU GO

I have a very important favor to ask, which as those of you who know me know I don’t do often. If you get any pleasure or inspiration from this episode, could you PLEASE leave a review on your favorite podcasting platform – be it iTunes, Overcast, Spotify or wherever you get your podcast fix. This podcast is very much a labor of love – and each episode takes many many hours to put together. When you write a review, it will not only be a great deal of encouragement to us, but it will also support getting the word out about the Mobile User Acquisition Show.

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Thank you – and I look forward to seeing you with the next episode!