
Leap Academy with Ilana Golan
Nextdoor’s Bryan Power: Turning Big, Scary Opportunities into Career-Defining Success | E59
Thu, 05 Dec 2024
Known for seizing “big, scary opportunities,” Bryan Power has defined his career by embracing risk, adapting to change, and staying focused under pressure. After turning down a promotion at Google for a new challenge at Square, he quickly realized he was in over his head. But it was in facing that discomfort head-on, that he experienced his most significant growth moments. In this episode, Bryan joins Ilana to discuss the importance of tackling challenging opportunities, the practices that lead to career growth, and his unique approach to leadership. Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments. In this episode, Ilana and Bryan will discuss: (00:00) Introduction (00:22) His Journey to Silicon Valley (01:31) Big, Scary Opportunities that Drove His Growth (03:45) Bryan’s Annual Growth Reflection Ritual (05:29) Transitioning from Google to Square (08:40) The Weight of Leadership in Today’s World (10:18) How COVID-19 Impacted the Way We Work (12:37) The Pros and Cons of Remote Work (16:52) Why Adversity Makes the Best Leaders (20:05) How Bryan’s Background Influenced His Success (22:46) Bryan’s Secret to Landing Your Dream Job (25:57) Key Skills Every New Leader Must Master (29:54) Building Trust in Your First 90 Days at a New Job (34:41) Nextdoor’s Success in Digital Community Building (39:37) Career Lessons Bryan Wishes He Had Learned Sooner Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments. Bryan has a proven track record of building and leading high-performing teams across North and South America, Europe, the Middle East, Australia, and Asia. His expertise extends to board-level work, where he has developed executive compensation strategies, company-wide cash/equity incentives, and benefits programs. Connect with Bryan: Bryan’s LinkedIn: www.linkedin.com/in/bryanpower Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: What big, scary opportunities shaped Bryan Power's career?
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I don't want a job where I'm thinking by myself.
I really experience success as a we, not an I. Brian Power, he leads the people team in Nextdoor, but before that, Chief Human Resources Officer in Yahoo, Square, Google.
Chapter 2: How does Bryan reflect on his career growth?
I was lucky enough to join Google. I joined Square One as a startup. Both of those opportunities, I just felt like it was more than I was going to be able to do. I get an extra push from needing to figure things out. But I think everyone wants the success, but you have to go through the level of challenge you haven't dealt with before to really feel that come through.
Chapter 3: What challenges did Bryan face transitioning from Google to Square?
When I'm looking for leaders, I really try to just pay attention to
If you talk to different professionals, they're thinking I would love to maybe work with some of these really cool companies. How do I even get in?
I think people underestimate.
Brian Power, he leads the people team in Nextdoor. But before that, Chief Human Resources Officer in Yahoo. Before that, Square, Google. You just pick all the cool companies, Brian. What helped you really climb up the ladder in all these amazing companies? Brian, thank you for being on the show.
I think if you go all the way back, I was also a dot-commer. I came to the Bay Area in 1999, and that was a really inspiring time in tech and in Silicon Valley. And I think I learned at an early age to try to chase down and lean into really challenging opportunities, probably a little more than I thought I was capable of.
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Chapter 4: How did COVID-19 change the work landscape?
Tell me more. I mean, you came before me. I was still back in Israel. So that's fascinating how you maneuvered the whole dot com.
I was really young. I was 23 or 24. And so I was grateful for to be exposed to like the super high bubble of the dot com where you kind of look back on it now and see that change was going to take longer than people thought it did at the time. But this period of massive change was clearly in the air, particularly in San Francisco in 1999.
Chapter 5: What are the pros and cons of remote work?
It kind of reminds me similar of the feeling around AI today where people are not totally sure what exactly it's going to look like, but clearly something massive has really shifted.
You then ticked a lot of the companies that people would love to be part of, like Google, Square, Yahoo, Nextdoor. Like you tick a lot of boxes and you managed to also climb up to leadership in those amazing companies. What do you feel helped you?
It looks better looking backwards than it does in the moment. I was lucky enough to join Google. They had just gone public. This is now almost 20 years ago in 2005. And it was certainly a darling of Silicon Valley, but it wasn't like the mega corporation that it is today. And I just didn't anticipate the... journey that I went on there and everyone who's worked there has went on.
And even Square, you know, I joined Square One as a startup and I can't say we all thought it would play out the way that it was. We were certainly optimistic, but it just succeeded more than even we anticipated it was working there. Both of those opportunities, and this has been consistent really with all of the
the jobs I look at or teams I seek to join, I just felt like it was more than I was gonna be able to do. That choice that you're scared or stressed that you're gonna be able to achieve something, I've found for me personally is a better choice than taking something where you know you can do it.
It's actually, for me, a better choice to manage the stress and anxiety or feeling like you don't know what to do because you're probably going to figure things out as you go versus look for creating an opportunity where you're kind of boxed into a safe or a small position. It doesn't enable growth the way the big, scary opportunities do.
So you go for the scary then.
Well, I think whether it's a small company, like a startup or a bigger company, I've found I'm personally energized by not really knowing what to do. And that I get an extra push from needing to figure things out, whether that's personally... or at the company level, that brings a lot of energy and attention to whatever problems are in front of you.
And again, like many of us, I've also been in environments where I haven't been as challenged and I found the demands on you drop and then the growth can slow and you end up doing different things.
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Chapter 6: How can leaders build trust in their first 90 days?
Because for me, the best growth has come from periods of real adversity where the instinct is to leave and to quit and to give up or to try something else. And it's when you really push through those steep challenges that you experience personal or professional growth at a totally different level.
And I absolutely agree with that. And I love how strategic and intentional you are every time to reassess. Is there a certain story that you think you can share of adversity or a challenge that actually lifted you and grew you from there?
I'll go back in time because I'd been at Google for about eight years and I had an offer internally for a new assignment that was exciting. This is now 2011 or 2012. So again, a really long time ago. And just to reorient what was going on then, that was three years after the major economic crash of 2008, 2009. and it was an incredibly fertile landscape in tech.
This is when today's dominant tech companies, Uber, Airbnb, they were all 100% startups. Pinterest, Dropbox, Square, kind of the list goes on. And Google at that time was really a major player, and I had this internal opportunity, but I decided, you know, I think I kind of want to try a much smaller startup and see what I can do. There were other things.
I was in New York at the time, and I was interested in coming back to California. But anyway, fast forward to I ended up working at Square and it was really difficult to go from Google at that time was just such a rocket ship that I don't know. And this is common.
A lot of Google, a lot of my experience is you got to underestimate the tailwind the organization provides for you when it's really on this path of success. And so Square was the first time where I felt my personal, at the time I was leading recruiting and Square was going through a leadership transition where we really needed to bring in a lot of new leaders.
And, you know, that was my responsibility. Just like a be careful what you wish for moment. I had got this challenge where if I didn't do my job, the company was really going to feel it. And I'd never felt personally that level of stress before where if I failed, everyone around me was probably going to fail. The chances would really go up.
What I learned in that moment was I'd been stressed about myself and my own job before, you know, or my manager or my team. But I'd never really worried about company level stress for a long time because, again, Google was on this run. And so I had to learn to deal with these different aspects of stress.
And I remember the moment of being like, well, hey, do you want to just bail out or do you want to do what you signed up for? And so that began a few month run where we really rebuilt the leadership team at Square. I should say the next iteration of leadership is Square. that ultimately took the company public and really took it to new heights. And so I got that direct feedback I was looking for.
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Chapter 7: What lessons does Bryan wish he learned sooner in his career?
There's a lot of things globally that are making people really anxious and it just feels more than normal. And so what I think that means is a lot of people turn to their company as the thing that they feel like they have some sense of impact or control on.
And so many people expect their organization is going to make their day-to-day better because of the fact that so much outside of their day-to-day world professionally is scary and intimidating and stressful.
And so that means leaders who have a tough enough time trying to go from A to B on your company level goals are also being asked to help people through this macro level stress problem, which fair or unfair is increasingly the expectation for a lot of people that their work is what's going to get them through this. Their professional identity is going to be a source of strength for them.
And so they look to leaders to really fulfill that. And that's very difficult, just given what is important to so many different people, how to play that role. in their day-to-day lives. So I definitely worry about that. I think that the nature of work has changed so dramatically since the COVID-19 pandemic four years ago.
in what people expect out of work, what it means to have a job, what it means to go to work or do work. All of these things have just been disrupted in a way that it's very hard to think about the last disruption at this level of the work experience going back decades. It's really been seismic. And I think people are still really sorting out what that means.
And so in the heart of your question, what I worry about, a lot of the big plates that just going to work and doing are built upon have really been moving around. So that makes it almost like three-dimensional chess of how to figure out, just to get your work done as a company, you've got to grapple with these other external factors that are really significant.
So tell me more about these COVID challenges. I think we see a part picture. We see the remote work. We see other things. But I want to hear more, Brian. What are you seeing?
I think that one thing we learned, and I've been at Nextdoor the entire time. I started here two years before COVID. So my whole post-COVID, during COVID experience has been with Nextdoor. The only thing I felt really confident in, if you go back to 2019 and 2020, when we were really in the throes of lockdown and pre-vaccines and just the unknown,
was that a lot of people were quick to declare victory on what work was going to be, whether that was everyone's going to be fully remote, this is the future, or no, no, no, no, remote was just a fad, you got to get back. Like everyone just having these declarative statements that they knew, that was the only thing I knew was wrong, because it's just too seismic, it's too disruptive.
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Chapter 8: How does Bryan assess and hire future leaders?
You can usually think about it. If the team's big enough, company's big enough, there's someone where you're like, I just don't get it. Go make a relationship with that person because they will get just as much out of you in your way. And that can help buffer you from the stuff that's either uncomfortable or confusing or unknown that's very natural to them.
Because it's probably the opposite is true. The things that come very easy to you will probably be harder or more confusing for them.
So one of the things that we're seeing a lot in Leap Academy is when somebody joins a company, lands a role, and now they want to prove themselves. They have that famous 90 days or whatever you call it. What would you say to people that are coming in? I mean, you don't want somebody to just immediately change everything because they didn't even learn anything.
What would you say is some of the more important things for them to really understand? Like somebody that is joining next door, what should be the first few months?
I'll give people two, and this works for leaders as well as anyone joining a company that I think are significant.
The first is really around three or four weeks in, you almost have these night vision goggles where you can see the company, the culture, their processes, their way of doing things in this incredibly visceral way because your brain is actually working in overdrive because it's in a new environment. Your limbic brain is charging to make sense of this world.
So you're actually accessing like way more juice than you normally would. And a couple of weeks in, you kind of actually start to understand it, but you haven't yet assimilated. And so your ability to really share reactions over like what is this company is profound three or four weeks in around that timeframe. Not your first week, everything's too new.
Not two to three months in because you've kind of started to settle in. But like a month in, you can just share incredible observations. So as a... People leader, like I really seek out these new higher observations a month in because they can really confirm or educate on what you think your company actually is. And they have no agenda. They're just like, wow, this is really interesting.
I've never seen this before. This really stands out. This is so cool. Those are like the observations I think are really powerful. And that can help your onboarding. You know, you're letting people understand maybe something they didn't appreciate that's so different because they've been here now for four or five years. It's just become... their day-to-day.
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