Office Hours: 4 Ways To Be an Intentional Mentor
Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.
Mentoring done right is an enriching part of your career. As a two-sided relationship, you have both an opportunity to seek out mentors who provide knowledge and counsel and to be one yourself, and each of these exchanges has its benefits. Neither, however, should be forced to fit within the classic construct of mentorship, that of a seasoned veteran taking a green employee under her wings. In fact, sometimes mentorship is the opposite.
I owe much of my early career success to what I learned from mentors, but I also owe some of my more recent strengths and knowledge to my mentees. Our evolving workplace and technological norms means mentoring can happen in all sorts of ways, and if you're intentional about mentorship you can be both a mentor and a mentee throughout your career — and, importantly, learn from both roles. Here are four principles that guide my approach to intentional mentorship:
1. Learning Is a Two-Way Street.
Mentorship isn't and shouldn't be one-sided. If it's a drain on your time and you're a busy person, odds are you'll run out of time for it quickly. I always try to find something I can learn from those I mentor. On the outside this may sound a bit selfish, but it actually works to both our benefit. We feel like we're trading value, which inspires confidence in your mentee and emboldens them to ask for real help and guidance when they need it without feeling like an imposition. As a mentee, you might think at first glance that you have less to bring to the table because you typically have less experience. But look closer; you usually have something you take for granted that is immensely valuable to others.
Some of my most memorable and impactful mentees include my Pacaso colleague Whitney Curry, who, as Zillow's first social media hire, taught me the magic of Twitter and Facebook and put me on my path to being a social CEO; years later, Whitney hired Kat Parra, who to this day continues to help me figure out Snapchat and TikTok to stay current in my social footprint. I've provided career counsel to both of these pros over the years, but they've taught me a lot, too.
Recently, another former colleague of mine from Zillow, Racquel Russell, joined Bird's Board of Directors. Racquel comes from a political background and over the years has taught me so much about how government really works; to this day, I still use her as a resource, asking her opinion on whether I should donate to a campaign or what she thinks the chances are for a piece of legislation passing. In return, I've been a resource for her on career development and joining boards. We both benefit from our relationship, and because of that we're emboldened to ask for what we need from one another.
2. Broadcast What You Know.
A couple of years ago I wrote about how to "hack" mentorship and build your own perfect mentor by following leaders and other professionals you admire. As I said, mentorship doesn't have to fit into that (increasingly uncommon) archetype of being taken under someone's wing. Over the years I've followed the lead of Jeff Weiner on people management, Sheryl Sandberg on building thought leadership, Warren Buffett on shareholder communication and Jeff Bezos on communicating priorities. I don't really know any of these people, but the internet and all of their self-published or publicly available content makes it so I don't have to.
Much of the reason I am constantly teaching publicly through my podcast and blog posts is that it enables me to mentor others in this anonymous way. I'm hopeful that the advice and perspectives I post help others navigate career hurdles, whether it's figuring out how best to manage your first team, how to grow your startup or how to take your company public. I share the things I know because others have shared them with me, and I want to continue to feed into that virtuous cycle. You, too, can do that easily. If you're a great writer, tell others your formula and some keys to your approach. As I said earlier, you probably take your strengths for granted; others won't.
3. Speak Up — With Candor and Kindness.
Dara Khosrowshahi, now the CEO of Uber, was one of my first managers in my career. As a summer analyst 25 years ago at the investment bank Allen & Company, I learned from Dara (then a young associate) how to value companies and build financial models. He taught me how to become an expert on Lotus 123 long before there was Excel or Google Sheets. But Dara also taught me another incredibly valuable piece of advice: Don't wear suspenders to the office. I'd mistakenly thought Hollywood accurately portrayed Wall Street; Dara kindly corrected me and saved me from repeating that faux pas.
Often the role of the mentor goes beyond subject matter expertise; it's about teaching mentees decorum — how to act and behave in certain situations. It may feel awkward for you as the mentor to teach when presented with awkward circumstances, but take it from suspender-wearing Spencer — they will appreciate your help more than you realize.
4. Invite Others Into the Room.
Though there are always reasons for closed-door conversations on sensitive topics, there are often exchanges that would prove valuable opportunities for your mentees (or mentors!) to listen and learn. I am eternally grateful to one of my first mentors — my dad's friend, Fred Rosen, the legendary founder and longtime CEO of Ticketmaster. In 1990, Fred invited me as a know-nothing 15 year old to his executive offsite at the Four Seasons Biltmore in Santa Barbara. He let me be a fly on the wall for two days of intense management meetings with the leadership team at Ticketmaster. Looking back on that experience now, I probably only understood a small fraction of what was discussed, but it was an extremely impactful moment in my life which set me on a path towards my business career. Some kids visit the baseball Hall of Fame in Cooperstown and decide they want to be a baseball player; I was invited to the leadership offsite of a big company and decided I wanted to become a businessperson.
In my early 20s, my mentor Andy Snyder at Goldman Sachs taught me how to behave among company clients and CEOs simply by including me in meetings where I was able to soak in knowledge by watching their interactions. Greg Lee and Bruce Evans at Goldman Sachs would generously invite me into their offices and use speaker phone when negotiating M&A deals so I could listen and learn. In my time as CEO of Zillow, I often pinged junior members of my team to hover around and listen to strategic discussions among our senior leaders — in part because I wouldn't have to explain it to them later but also because it helped them see how we debated and worked through scenarios that would decide the fate of the company.
Our acceleration into a virtual environment can either hinder or help these opportunities, and the difference comes down to whether those of us in the room are intentional about inviting others to join. Our virtual meeting rooms have no capacity, but they're also not easily dropped into (you don't have people passing by as you do in physical offices). If you're sharing knowledge or having strategic (but not confidential) conversations, consider taking advantage of our virtual environment to invite others in.
Though the methods of mentorship may be changing, mentorship itself remains as critical as it's ever been for career development and personal growth for junior team members and seasoned leaders alike. We're all pressed for time, and mentoring often drops on the list of priorities, but if you find ways to engage in it — intentionally, through small actions within your existing schedule — you'll gradually find that mentoring becomes second nature and a lasting habit.
Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.
Match Group and Tinder CEO Spencer Rascoff
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