• Chris Barbin

The Lieutenants -- When Radical Candor Meets Radical Compassion

The next Lieutenant in our series is Yamini Rangan, Chief Customer Officer at HubSpot. I had the privilege to work with Yamini during our early days of Appirio, where she held multiple roles including a year stint as my head of development and Chief of Staff. This was long before she started running the show at companies like Workday and Dropbox, both of which she helped to take public. I have always admired her honesty, humility, intellect, and unique ability to dive into the details without losing sight of the big picture. In this Q&A she talks about her journey of self discovery as a leader, how to create a safe environment where ideas thrive, and why data is the greatest neutralizer of emotion.

How would you describe your leadership style, and how has that evolved over the years?

I think my leadership style falls into two parts - setting a high bar and providing a nurturing environment for teams to get there. Setting a high bar comes from wanting to be a high performer myself. When I look back at how I was raised and how I motivated myself, it was intrinsic. I rarely compared myself to anybody else. I just wanted to be better at whatever I was doing. As I became a manager and a leader, it was about having high achieving teams.


As a leader, you have got to believe in people...to give them a safe environment where what they're learning from the process matters as much as the end results.

Part B was a necessary addition to my leadership style later on. I drove myself and my teams crazy by setting too high of a bar, and not providing a safe enough environment where they could learn, fail, grow, and adapt. As a leader, you have got to believe in people. You've got to back people, and give them a safe environment where what they're learning from the process matters as much as the end results.


Was there a catalyst in your career where you realized the importance of this piece?

Yes, there was a moment six years ago that was really my turning point. My team and I had rolled out a very successful sales kickoff. I thought we had done a spectacular job, but then I got my 360 performance feedback and I could not recognize the person in that review. It said things like "she's too tough," "has too high of standards," "doesn't have time and patience for anybody that is learning," "cares too much about results and not about the process of getting there." I was shocked. It was incongruent with who I was as a person. I'm compassionate. I love animals. I cry at movies. I would do anything for the people I care about, and I just couldn't recognize myself in that feedback.


So what did you do?

I took the feedback and did something about it. You can either say, "this is my job, my job is operations, my job is execution, my job is getting things done, so that's what I want to be." Or you can say, "you know what? I'm going to rewire myself." You can change a job, change the boss, change the company but the hardest thing to do is to change yourself. If you don't change, the feedback is going to follow you.


You can change a job, change the boss, change the company but the hardest thing to do is to change yourself. If you don't change, the feedback is going to follow you.

But I decided I was going to rewire myself in a way that was still authentic to who I am. I'm never going to give up keeping that bar high, but I also wanted to nurture and inspire others. Doing that rewiring in a way that doesn't break you isn't easy. The first thing you do is beat yourself up completely. I went through this period thinking maybe I should become an individual contributor. Maybe I'm not set up for leadership. Maybe the job I've taken is not the right thing. Then you realize you have to have compassion for yourself.


It takes a little while for you to find your own railings and your authentic self, especially as a female leader in a male-dominated sales environment. My true nature was being compassionate and giving in relationships, and I needed to find that balance. A leadership journey is like climbing a mountain without a top. I've planted a pole somewhere, but I'm not at the end.


A leadership journey is like climbing a mountain without a top. I've planted a pole somewhere, but I'm not at the end.

You have been a great lieutenant in some of the most recognizable companies in Silicon Valley. What are the characteristics or values you see in great lieutenants?

The first thing is their ability to execute and operationalize. Great lieutenants are typically working with people who have a great vision, but sometimes visionaries can't be bothered with operational details. A lieutenant has to have the ability to get someone's vision, and then translate and operationalize it so teams on the ground can execute that vision without breaking. They have to be comfortable moving between that 10,000 foot and 1,000 foot view.


What happens when you have a different opinion than your leader? How do you know which battles to pick, when to push back, or how to manage conflict?

The great thing about growing up in operations and then getting into sales is you know the importance of data. In God we trust. Everybody else bring data. Data is a great neutralizer of emotion.


Data is a great neutralizer of emotion.

I try really hard not to come in biased about a decision. You can have a hypothesis, but you make better decisions if you start with data and try to put your biases aside. Say you're making a decision about which countries to enter or leave - this is one of the most emotional decisions a company can make. Every company wants to grow but then you wake up and find yourself in 35 different countries with all of them pounding the table for investment. They want a data center, language support, localization, a country GM. These discussions are very emotional. Data can support the decisions and conversations.


The second thing, which is even more important, is to understand the context around decisions. If you have five people, they might have all different views, coming at the same problem from five different angles. Say someone draws a line and asks "what is that?" If you tell me it's a number, I'll say it's a one. If you tell me if it's a letter of the alphabet, I'll say it's an L. If you tell me it's an uppercase alphabet, I'll say it's an I.


Start with data and then understand the context of the different stakeholders involved. Doing both will help you pick the right battles, and hopefully, win more battles than you lose.

As a Lieutenant, the biggest job I have is to understand different people's perspectives. Going back to the country expansion example, if you're talking to the CEO and he says he loves Japan, that he's always admired businesses that have grown in Japan, and he spent 10 years in Japan, trying to pick a battle as his or her lieutenant and saying "No, no, no, pull out of Japan," would be suicidal, and not necessarily the right thing. Just don't go there. Start with data and then understand the context of the different stakeholders involved. Doing both will help you pick the right battles, and hopefully, win more battles than you lose.


How do you go about creating a safe environment where it's okay to take risks and fail?

First, you have to be deeply vulnerable as a leader. I share my 360 reviews with my team, literally every word of it, and make it clear that I am a work in progress. I think when you create that level of vulnerability, others feel like they can say the same thing.


I share my 360 reviews with my team, literally every word of it, and make it clear that I am a work in progress.

The second thing is how you react to failure. If you give someone a big initiative and they fail, they're waiting to see how you react. If your reaction is "I'm going to take this thing away from you," then you're not going to create a safe environment. Instead you should ask, "what did you learn from this?" "What are you going to do differently next time so you don't repeat the same mistake?" You don't want to be soft and allow people to make the same mistake 10 times and not perform, but you can create an environment where people can make new mistakes. Be deliberate in your interactions. Whether you're moderating a larger group discussion, or in your own leadership meeting, let people know they can say anything with complete candor and it's going to be treated with respect.


Radical candor and radical compassion go hand in hand if you want to create a safe environment.

Earlier in my career, I was radically candid, but it didn't come with radical compassion so it just landed as someone who is super direct and brisk. Radical candor and radical compassion go hand in hand if you want to create a safe environment.


Are you a customer-first, team-first, or financial-first kind of leader?

Customer first hands down. The one thing that I believe every company has to orient for is solving for the customer. Once you get that built into the DNA of the company, employees know exactly what their purpose is. They have a sense of how to make decisions. And if they make the right decisions, the financials work out right.


In SaaS companies, this is especially true. We are answerable to our customers every month because we have monthly contracts. Every month our customers vote for us with their pockets, and every year they vote for us when they renew.


Have you always been customer-first?

Earlier in my career I was probably more of a financials-first kind of person because of my analytical and operational nature. Plus my jobs oriented me to look at the bottom line a lot more. Working for companies over the last decade that were primarily in the SaaS business has completely changed my view. And my primary bearing is all customers.


Is being a CEO something that you aspire to? If so, why? If not, why not?

No. I've never aspired to be the CEO. I love go-to-market. It took me a while to figure out what I wanted to do with my life, and it's been a process of negation rather than knowing exactly what I wanted. I started as an engineer and knew I didn't want to be an engineer, so I went to business school. I thought I wanted to come out of business school and go into financial services, but 9/11 happened and I found myself in sales.


It took me a while to figure out what I wanted to do with my life, and it's been a process of negation rather than knowing exactly what I wanted.

Now I look back and I know I love being in marketing, sales, and customer success. I like being that analytical right-hand person navigating a really large ship. I found my passion. I guess never say never though, because honestly, if you would have asked me 20 years ago if I wanted to be chief customer officer of a publicly traded company, it wasn't even in my realm of thinking.


© 2019 by Chris Barbin. All right reserved.