Jul 29, 2021 · 45m · 20vc
20VC: A Masterclass in Leadership and Scaling Companies: The Decisions only the CEO Can Make, The Secret To Talent Acquisition and Retention and How To Find The Unscalable Things that are Fundamental To Scale with Christa Quarles, CEO @ Corel Corporation
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In this episode of The Twenty Minute VC, host Harry Stebbings interviews veteran tech executive Krista Quarles, CEO of Corel Corporation, to explore the mechanics of scaling organizations, building complementary executive leadership teams, and navigating corporate culture. Quarles shares lessons from her tenure at Disney, OpenTable, and Playdom, offering actionable insights on CEO decision-making, executive talent evaluation, and maintaining personal resilience.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 21.4% of the talking time here. How this is scored →
Harry as informed peer 2.2 Guest teaching 2.6 Guest disagreement 0.1 Harry pushing back 0.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:32 Krista pushes back on corner-cutting framing
Krista openly re-frames Harry's question on cutting corners by asserting that she is a corner cutter by nature and intentionally hires detail-oriented deputies to balance herself.
Hardest push from Harry ▶ 18:12 Harry introduces mentor challenge on cutting cornersHarry brings a structured counter-perspective from a mentor, challenging Krista on distinguishing between acceptable and unacceptable corners to cut.
Biggest teaching moment ▶ 9:53 Breakage points framework at different employee scalesKrista educates Harry with a clear organizational breakdown showing how companies predictably break at 50, 150, 500, 2000, and 10000 employees based on Dunbar's number.
Harry holds his own ▶ 26:24 Harry cites Krista's exact tweet on plate removersHarry demonstrates deep research and alignment by quoting Krista's exact tweet on plate adders vs plate removers to frame the executive delegation topic.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Krista Quarles's Entry into Tech and Early Career | 1 | 1 | 0 | 0 | Harry welcomes Krista warmheartedly and asks a broad career question about her entry point into tech. Krista details her background transitioning from investment banking to startups like Playdom. | |
| Leadership Insights from Disney and Bob Iger | 2 | 2 | 0 | 0 | Harry asks how her four years at Disney shaped her leadership principles. Krista shares insights on watching Bob Iger handle global diplomacy alongside granular product debates. | |
| The Craft of Leadership Across Organizational Scales | 2 | 4 | 0 | 0 | Harry asks what the craft of leadership means across scales. Krista outlines her framework on exponential company breakage points based on team sizes and Dunbar's number. | |
| Fostering Innovation, Ambition, and a Failure-Tolerant Culture | 2 | 3 | 0 | 0 | Harry asks how to keep teams ambitious when the CEO is not in the room. Krista explains her OpenTable experience where she had to make it unsafe to avoid taking risks. | |
| Doing Unscalable Things and Recognizing Market Timing | 2 | 3 | 0 | 0 | Harry inquires about determining how long to test new initiatives before cutting them. Krista discusses doing unscalable things for scale and recognizing market timing externalities. | |
| Balancing Leadership Traits and Finding Complementary Number Twos | 3 | 2 | 1 | 1 | Harry brings up a mentor insight regarding corners you can vs cannot cut. Krista candidly owns being a corner cutter by nature while surrounding herself with complementary detail-oriented executives. | |
| Resiliency, Overcoming Setbacks, and the 'Stuck' State | 2 | 3 | 0 | 0 | Harry asks how Krista rebuilds after setbacks and what being 'stuck' looks like. Krista reflects deeply on psychological safety, amygdala responses, and overcoming unsafe work environments. | |
| Plate Removers vs. Plate Adders and CEO Core Decisions | 3 | 3 | 0 | 0 | Harry references a tweet citing Krista's concept of plate removers vs plate adders. Krista explains delegating operational issues and identifying the three decisions only a CEO can make. | |
| Evaluating Executive Talent and Aligning Strengths | 2 | 3 | 0 | 0 | Harry asks how to evaluate whether a stretch executive has been pushed too far. Krista uses a psychological perspective, emphasizing aligning individual joy and strengths rather than forcing apples to be oranges. | |
| Effective Board Engagement and Managing Board Dynamics | 3 | 3 | 0 | 1 | Harry asks about managing board dynamics and handling board members with persistent pet peeves. Krista shares advice on board context retention and using curiosity sessions to address concerns. | |
| Quick Fire Round with Krista Quarles | 2 | 2 | 0 | 0 | Harry conducts a fast-paced quickfire round covering books, tech reflections, rich people myths, and advice. Krista provides articulate and humble responses throughout. |
Statements from this episode (22)
Quarles: Playdom Was Second to Zynga in Social Gaming When She Joined
“Sitting on the sidelines, armchair quarterbacking, as we say in America, and I was like, I want to go play the game, and so the only way to do it here is to just go to a startup, and so I went to a small gaming company called Playdom, and we were second to Zyn…”
Quarles Forfeited Her Investment Banking Bonus to Join Startup Playdom
“I dove in, I gave away a giant bonus that I was going to get in my old banking world to go join this company. Cause I like, I was like, screw it. I'm just going to go. And I didn't get paid my bonus that year. I left in December and I was going to get paid it …”
Quarles: Bob Iger Context-Switched Between High Diplomacy and Product Details
“He had this Incredible ability to one day, like, conduct high-end diplomacy for Disneyland Shanghai, and then the next day, debate the finer points of The Sims with me, and I was like, how is this possible?”
Quarles: Disney Acquired Playdom to Understand Shifting Consumer Media Habits
“When we sold Platum into Disney, a lot of that was, hey, consumers are spending different amounts of time with different types of media. We gotta understand this, and I think that was Bob who leaned in”
Quarles: 150 Employees Is a Company's Most Significant Scaling Breakpoint
“Companies tend to break at 50 people, because it's like, you used to be able to just get everybody in the room, and like shout at them, or put them in a Slack channel, and tell them what to do, and you knew every single person, and you could direct everything …”
Quarles: Playdom Reached 150 Employees Without an HRIS or Written Policies
“And this was exactly what happened to me at Playdom. Like we hit one 50 and like pretty, you know, all the software that's helped companies grow, but like we didn't have an HRIS. It was like in somebody's like spreadsheet on Excel or we had never written a pol…”
Quarles: Culture Is How Employees Make Decisions When Leaders Are Absent
“Culture is how people make decisions when you're not in the room, and increasingly, you're not in more rooms as the company gets bigger, and you have to really adjust and figure out how that transition is going to go.”
Quarles: OpenTable Ran on an Old Microsoft On-Premises Database
“When I got into the company, we were at a point at which the software that we had inside the restaurant was an old Microsoft on-prem distributed database, like not in the cloud.”
Quarles: OpenTable Failed to Give Its Product Away Free in Palo Alto
“We picked a street in Palo Alto and I said, give it all away for free. I said, I don't care. Don't charge anything. I just want to see if we can get a hundred percent of the restaurants on the street. And what was interesting was they came back and we literall…”
Quarles: OpenTable Pay Would Succeed Today Due to Modernized POS Infrastructure
“Had that launched now, it'd be wildly successful because you think, see food delivery businesses and other things like that have changed the paradigm of what point of sale looks like in a restaurant, but we were just early.”
Quarles Hires Detail-Oriented Executives to Offset Her Corner-Cutting Style
“I am a corner cutter by nature, I'd say. In fact, I've surrounded myself with, like, iDotters and T-Crossers. So that they keep me safe sometimes.”
Quarles: Asking Who Would Make a Great Number Two Reveals Candidate Weaknesses
“One of my favorite reference points Questions to ask is who would make a great number two for this person? And what that reference question is getting at is like, you know, of course it's like sort of quote unquote weakness, but nobody can spike along every di…”
Quarles: A CEO Operates Three Months Ahead of Their Organization's Perception
“My time equals zero is always, like, three months before it hits everybody else, so I have to recognize, like, they're just seeing this for the first time. You've already been processing it”
Quarles: Remaining Stuck Is More Dangerous to Performance Than Falling
“I think that's the most dangerous place for anybody to be is the stuck state. Falling, fine, all right, I know what I'm dealing with, you know, ugly truth, fine, bring it on, let's go, let's, now I know what to do. It's that, that moment before you let yoursel…”
Quarles: CEOs Distracted by Delegable Tasks Limit Company Growth
“The other critical thing is understanding which decisions only you can make as the CEO. Many other decisions can be delegated. Many other decisions can move down the ranks. There's certain decisions that Only you can make. And one of the reasons why this is im…”
Quarles: A CEO's Unique Duties Are Mission, Team, and Board
“Brand mission, you know, kind of purpose of the company, the people of the company. And then really the third thing would really be, you know, kind of how we interface with our board. How are we Driving forward that conversation. You know, I can't put my, you …”
Quarles: Early-Stage Executives Rarely Scale Past 50 Employees
“So the person who was amazing with From zero to 50 often can't take the next leap. Some people can. Some people are purple unicorns and they can ride the ride.”
Quarles: Executives Waste Energy Trying to Change Employees' Core Nature
“So like I've often said, I was like, if you're an apple and I need an orange, I can't make you become an orange. I can make you a juicier apple. That's great, but I can't actually make you be an orange. And so it's not personal. And so the kind thing is to say…”
Quarles: Board Members Lack Operational Context and Retain Very Little Data
“These people show up You know, five times a year, or maybe a lot more often in some VC board that they just simply don't have the context. In fact, somebody gave me this advice early on. They said, don't underestimate how little your board retains.”
Quarles: CEOs Must Directly Address Recurring Board Member Pet Peeves Immediately
“To lean in with curiosity, and then to not let it repeat, though. I think it's kind of like a stuck state, back to that other part, is if you just let them, like, keep asking every meaning, and you just don't hit it on the head, you're gonna be frustrated, the…”
Quarles: Wealthy People Falsely Attribute Success to Skill Over Luck
“Oh my God, like, there's just so much more capable. Like, it's not luck that I'm just really that much better than everyone else. I think that's the goalie. I think understanding the importance of preparation, meeting opportunity, i.e. Luck, that's an importan…”
Quarles: Employees Must Prioritize Self, Family, Then Company in Strict Order
“You know, one of the things I say in my company, like, you know, it'll often happen, like, somebody's going to a funeral, or somebody's mom gets cancer, or a kid gets sick, and I will say to them, you know, like, self, family, company. Always in that order. Be…”