Founders Need Feedback




In the latest episode of The Clarifier, host Angie D’Sa interviews Christina Sass, founding partner of Dive In Labs and co-founder of Andela. Tune in to learn:

  • How to productively analyze feedback
  • Key challenges faced by founders
  • Why your context matters 
  • When to empower your team and let go

[Full Transcript] 

Angie D´Sa  00:05

Welcome to The Clarifier. In this episode, I interview Christina Sass. Christina was co-founder and president of Andela, a pioneering marketplace connecting international developer talent with meaningful work opportunities. Today, Andela is valued at over a billion dollars. Christina co-founded the company because she knows that talent is evenly distributed, but opportunity is not. Her personal mission was to connect high-potential talent in Africa with opportunities across the world. For her, it was a calling, not a job. And she had always believed that others appreciated her moral imperative until she received feedback that her peers on her executive team did not.

Christina Sass  00:48
You assume that this thing can only scale with you. And there is a really beautiful freedom to, like, if we’re doing this right, everybody gets layered.

Angie D´Sa  00:58

I invite you to listen to this episode if you are grappling with feedback that challenges your perception of yourself or your strengths. Christina shares an intimate story of learning to see herself through others’ eyes and learning that context matters. Okay, welcome to this week’s Clarifier. This week, today, we have Christina Sass on the show. Wait, Christina, correct me once and for all because everybody I know calls you Christina “Sass.” And every time you introduce yourself, it’s pronounced “Sahh-ss.” So tell us what it is.

Christina Sass  01:32

Okay. So my father came from Germany, the correct pronunciation is “Sahh-ss.” That said, everyone who knows me before and after a certain period, my nickname is Sass. And so it’s very, yeah, it’s like a beloved nickname. And I’m perfectly fine. Most people, it’s there is no Christina or anything else, it’s just Sass. And that’s totally fine, too.

Angie D´Sa  01:57

It is hard not to associate you with the feisty, effervescent connotation of sass.

Christina Sass  02:05

And then there’s the whole SaaS company, you know, as an S, which gets misspelled all the time. Like we used to have a joke meme at Andela, “Andela is a SaaS company,” you know, so many different versions of it. I’m perfectly fine with either one.

Angie D´Sa  02:20

Oh, my gosh, levels on levels, turtles all the way down. Sasses all the way down. So you mentioned Andela. For our audience, Christina was co-founder and president of Andela, which is a pioneering marketplace connecting international talent, developer talent with meaningful work opportunities. Today, Andela is in over 175 countries with a network of over 200,000 technologists. And for those keeping score, it’s a unicorn, valued at over a billion dollars. For people who haven’t heard about Andela, can you tell us a little bit about the company?

Christina Sass  02:55

Absolutely. We started out in 2014 to take advantage of the incredible talent pools. We began in six countries in Africa, starting in Nigeria, which is still kind of the mothership of the company. I had been working there for about the last five years, with the MasterCard Foundation. We were marrying what we were learning in cutting-edge ed tech in the US with these incredible talent pools. So yeah, we launched in 2014 in Lagos with a pilot. We put out a job description that said, “Do you want to be paid to be a world-class software developer?” At that time, the name Andela didn’t even exist, and we didn’t even have a landing page. We received over 1000 applicants for that pilot. And then we put more rigor behind it, explored specific feeder systems for software developers, and for our second cohort, we got over 2500 applicants. We used a logical reasoning and problem-solving test based out of Canada. The owners of the company called us and said, “What the hell is this job description? You guys are crashing all of our servers. We’ve never had this many people apply to one job. By the way, you have 48 candidates in this pool that we would consider to be in the top 2% of IQ in the world.” That was a crystallizing moment. We quit our day jobs and launched on an epic journey to prove that brilliance is evenly distributed, but opportunity is not. We sought out extraordinary talent and made matches with those who desperately needed that brilliance. Today, as you said, we have a massive talent pool of several hundred thousand developers, we’re in many more skill sets than before, partnered with over 200 companies, including many large enterprise-level companies, and have talent from over 130 countries. It’s been an unbelievable ride.

Angie D´Sa  05:10

There’s a lot to dig into there. As you know, this podcast is not just about sharing the journey but diving into the moments of hard-won learning and personal growth in the journey. So we’ll get to that in a minute. But I want folks to know what you’re up to today. Today, you’re serving as the chair of Andela’s Advisory Council. When you’re not doing that, how are you spending your time?

Christina Sass  05:36

Yes, I am launching a new fund called Dive In. I spent the last several years as an enthusiastic angel investor, given our talent business, I met incredible tech talent and other women founders, and started investing. Eventually, I began referring every founder I was close with to my executive coach. My co-founder, Jeremy, and I worked with Jeff Hunter and the team at Talentism. Before Angie joined full-time, we had been working with Talentism for years. I attribute a lot of our ability to deeply understand ourselves and scale the company to that coaching. So when I took a step back to figure out what’s big enough, what am I uniquely qualified to do, and what can I wake up and do every single day for five years, I decided I wanted to work with incredible founders building unique social enterprise companies. We provide extensive coaching to help them scale their teams. That’s one part of what I’m doing. I also chair our alumni network at Andela, which now has over 3,000 technologists globally. They are achieving incredible things, starting companies, graduating from Harvard Business School, and one of them is even the COO of the Malala Fund. They are truly amazing individuals, and I’m honored to chair the alumni network.

Angie D´Sa  07:16

I’m glad that our listeners can get a glimpse of how brilliant and impactful you are in your career. Because I don’t know if you know this, Christina, but I was so impressed and intimidated by you when we were first introduced over two years ago. I prepared for an hour for our 30-minute first intro call. And here you are today, having agreed to be on my podcast.

Christina Sass  07:49

Well, now the tables have turned, and I prepare for all of my calls with you, Angie. But I also hope that didn’t last long. Because I do feel like one thing I’ve learned about myself is that I love being fully engaged with founders and others, and just diving deep into their worlds. That requires trust, and you just have to trust quickly and get right in there. So I hope that intimidation didn’t last long.

Angie D´Sa  08:18

One of the things you did that I really appreciated is that you were generous with sharing what you learned, not from reading books or listening to podcasts but from going through the experience. That’s what this conversation is about—giving you the space to share what you’ve learned, especially the parts we don’t typically hear about when founders share their stories. My aim is to help listeners understand what it’s like to be the leader of an organization and go through those moments when you realize you need to do something differently, see yourself more clearly, and shed the narratives about yourself and others. So today, you’re going to talk about a challenging period in your own growth, when you realized something you previously thought was a strength might not be. Can you set the scene for us and describe where you were in your career and what was going on at Andela?

Christina Sass  09:41

Absolutely. Part of the founder’s journey is continuously learning about yourself as the background behind you shifts constantly. At the time of my most painful learning, Andela was rapidly scaling. We started in Lagos and quickly had about 200 employees there. We expanded to Nairobi, Kenya, and I led those expansions as well as into Uganda. 

We quickly found ourselves in six countries in Africa with incredible leadership in each of those countries, along with a growing group of customers in the States and a growing group of investors. At every single new round that we raised, there was an enormous amount of pressure and complexity. Jeremy Johnson, my co-founder, and I were undergoing individual coaching and co-founder coaching. As part of that journey, we were constantly looking at whether we were optimized for what the company needed right now. Were we in roles and responsibilities that made sense and had the greatest impact on the company? Frankly, were we in roles that were not serving our employees and our investors?

Angie D´Sa  11:31

I want to pause on that for a second because I think for many people on the outside of a company or a startup, there might be a hidden assumption that if you’re the CEO, you’re the CEO, and you’ve got to do what CEOs do. At the time, I think you were the Chief Operating Officer, and there were responsibilities you had to wake up and do. So you woke up and did them. I think what I hear you saying is that part of the founder’s journey was regularly asking the question: “Are these responsibilities I hold well-suited to me because of who I am and because of what it takes to do them well at this new scale?”

Christina Sass  12:13

Yeah, that’s right. Many founders wake up and are too deep in it to have that reflection. This is a gift that our coaching gave us. There were times when things weren’t going well and there was too much friction, prompting us to feel responsible for asking that question. For myself, in my role, we grew very quickly to large numbers. It became a central question for me. The goal now is to scale from 2000 developers to 10,000 developers. Quite obviously, from an external perspective, it made more sense for someone with experience in scaling a specific talent pool. I also realized that I was more suited to zero-to-one situations, thriving in chaotic environments. However, I wasn’t as skilled at managing HR systems across multiple countries or creating equitable processes. Some of it was due to a lack of self-awareness, and some was because I couldn’t simply stay up all night researching and become proficient at it. So, for sure, this was a significant part of the journey.

Angie D´Sa  13:56

Okay, so we had an unanticipated break when all my audio input failed. But we’re back, and what was clicking for me as you were speaking is that the onslaught that founders face can make it difficult to step back and visualize a different way of deploying yourself. Even giving yourself the space to ask that question can feel like a luxury, and that luxury or necessity was afforded to you through coaching and working with Talentism. Some factors necessitating the reevaluation of how to deploy oneself include changing contexts. The larger the team you’re managing, the more diverse the demands, which may render your previous strengths ineffective. People also change over time, including what they are compulsive about and what provokes fear. You shared the experience of receiving written, documented 360-degree feedback as part of your Talentism coaching. This prompted you to reconsider something you previously thought was a strength. Can you tell us more about that?

Christina Sass  15:36

Sure. We did Founder 360s, which were both painful and awesome. Looking back, the implications of those feedback sessions were gifts, but in the moment, they involved a lot of painful learning. One key aspect that stood out to me was my perception of my ability to receive feedback. In previous roles, I had received feedback that I was good at it. However, in the 360-degree feedback context, I was ranked as very good at receiving feedback from people who reported to me, but not good at receiving feedback from my peers in the C-suite. Initially, this experience was painful and confusing. Over time, with reflection and learning, it unlocked many insights for me.

Angie D´Sa  16:51

Why was that feedback painful, and what did you make of it?

Christina Sass 16:57

Well, I think that many times when you receive what appears to be conflicting information, you tend to think those people are wrong, or they simply don’t understand. So, in my initial reaction, my belief was that I’m either good at receiving feedback, or I’m bad at it. It greatly oversimplified things. Receiving hard evidence turned out to be an excellent way to acknowledge, “Okay, you’re definitely not seeing this clearly.” There’s something to be learned here because you have clear data from one group that is different from another.

For me, what this ultimately meant was that it was in one specific area, let’s say, problem-solving. I was certainly well-known on the Adela senior team as a strong advocate for our software developers and the potential in Africa. The common thread between this and other roles was being a voice of moral clarity and strength, emphasizing what should and ought to be done, and aligning with our purpose. This approach had worked well for me in many cases.

However, what became abundantly clear to me in this 360 feedback was that it wasn’t just rubbing my peers the wrong way; it was unproductive. What I was experiencing in team meetings was something I believed was crucial but was, in fact, a threat. It was integral to our purpose and how we approached solving the problems we faced. Instead of presenting viable solutions, I came across as preachy and judgmental, which didn’t yield positive results. It didn’t make people care more about what I wanted to convey; instead, it turned them off. So, this experience was a valuable learning opportunity. Still, my main takeaway was that if I could step back and approach the goal differently, I had several other choices besides insisting in a morally superior manner. There were alternative methods that were actually more effective at achieving the goal. So t here’s a lot there. Please let me know which aspect you’d like to explore further, but that’s what I took away.

Angie D´Sa  19:38

Well, first, let me say thank you for sharing that because I can imagine that, you know, there’s a vulnerability required to say, people saw me as preachy or judgmental, and I appreciate that you’re willing to go there. But I would love it if we could slow it down a little bit because what I’m hearing is somebody who’s really had a lot of time to think about what they learned from the data, what it meant about them, and how they might approach their goals differently. I want to bring folks on that journey with you. So here’s what I heard, and tell me what it felt like as we went through this. So I’m hearing you say that you were somewhere in the middle of your career, and you had been told repeatedly that one of your superpowers is rallying people and teams around a mission, in a way that’s led by a moral imperative. You’re not afraid to say, “This is what’s right, and that’s why we should pursue it.” At Andela, this was about putting developer talent first and recognizing the potential of African technologists that was being overlooked, and what you could do to change that. I think I’m hearing you say that when you received written feedback, indicating that using that superpower, the thing you knew to be your superpower, was actually ineffective with your executive team, that at first felt confusing. Using Talentism’s language, when our brains experience something that feels counter to what we believe and what we know to be true, we feel that confusion, and we start to tell a story. Sometimes it’s about “they’re idiots,” and sometimes the story is self-doubt. I think I’m hearing you say that in the first instant of getting that feedback, maybe what started to pop up was that they just didn’t get it, some version of “they’re idiots.” Then, through grappling with it, you opened up to explore the feedback a little more. Can you tell us about that? What did it take to open up and explore what you could be missing?

Christina Sass 21:51

I would say for sure, absent time and space to think about that feedback productively, I definitely went to a place of “they just don’t get it.” I think a lot of founders feel that way – you hire people, so how could they possibly orient to what you care about so deeply? In this case, I inserted that my role was to pound the table and tell everyone how important this was. And absent that, it could be lost, or I’m the only or most important voice for that. I think those were narratives I told myself.

What the evidence allowed me to do was say you can’t just say it’s two people or one person with a differing opinion – now you have an executive team of five and four of them are saying this. That is a super majority. It made me realize I hadn’t been in a dream world – there was clear evidence from my own team that I received feedback well. So what was different about this team?

I parsed apart that my job was to inspire and orient my team to the mission. This executive team were also my peers – it didn’t matter why the feedback rubbed them wrong, it was stopping our shared goals. Stepping back allowed me to get curious and ask more questions. I realized I had somewhere pissed off and offended colleagues by making them feel judged or that their opinions weren’t as important because they oriented differently.

The company growth came when I said in many instances I have a choice – what I feel I should do is dig in and pound the table because I fear something big is being lost. But from a business perspective I stopped doing that. I started asking what is my goal and am I the best messenger? Are there other voices or data we could use to make the case? That allowed me to elevate others with different skill sets. It expanded my tool belt powerfully to think what is the goal and how else could we achieve it, not just insisting my way was best.

Angie D´Sa  25:41

What I’m hearing from you is that in environments where you had built the team, you had set the tone, you were the boss that everyone looked up to, it felt very natural for you to lead with this burning passion, this moral imperative, this moral compass. And your experience was people appreciated it. You got into environments where everybody had their own function, their own thing that they cared about, their own goal that they were pursuing, right? We see this on executive teams all the time between sales and product and engineering, and everyone’s got their own goal. And not only did you have your own goal, but for you, there was this righteous pursuit around it. And I think what I’m hearing you say is when it felt like people were dismissing that, that almost felt threatening, like, guys, don’t, don’t lose the thread, this is the most important thing for us to be doing. And I think I’m hearing you say that going into that protection of the thing you cared about most ended up actually being detrimental in some ways. Detrimental to your relationships with your peers on the executive team and detrimental to actually getting people to see the thing you cared about. All because of the way it was coming across. Because of the almost protective and defensive thing that was happening. 

Christina Sass  27:01

Yes, exactly. We could do a whole podcast on this, and you should. When you really enter into an executive role, a true executive role, it’s not you representing your team, that is your team. That’s your new team. And I was like, I don’t need to defend to these people. I did, in fact, have to look at all of their cares and responsibilities and look at all of us as achieving some big goals together and giving and taking based on each other’s goals. I think it’s hard for founders to be like, we actually share accountability and responsibility. And so when you tell me that, that thing that’s core to our mission you can’t execute on, or we can’t afford it right now. That’s not just a place for me to double down, I have to figure it out. There is just a different calculus to make. So I think it definitely helped me realize, and orient to the senior team in a different way. And then look at this thing that I’ve been given. The lesson was not, hey, you’re you’re just bad at feedback universally. The lesson was context really matters. And that thing is a useful skill set in some contexts, and not useful in other contexts. It’s a more specific tool than you thought you thought it was a universal tool. And it’s not. So rich with learning.

Angie D´Sa  28:33

Yeah, I was about to ask, how did that change your action? How did it change your orientation to your team of peers on the C suite? I think I’m hearing you say, rather than thinking about how to protect the thing I cared about, when it felt like it was under threat, I started to ask myself, what is the shared goal that we have? Because if I just double down on the message I’ve been sending, I’m actually alienating others, and I’m losing the opportunity to reorient to what is the thing we actually share? What is the thing we’re going after together? And so I think that that’s such a hard thing to do. What you mentioned the dopamine hit, what let you go there to go from sort of that protective? Look, my ideas, I know my idea is right and important to what could I be missing? And how can I convey what I’m thinking in a way that connects for others?

Christina Sass  29:33

Yeah, so I do think I had to sit back and have somebody help me make sense of these two or three different instances when I just came in full force with this. Did it actually achieve your goals? And looking at that, the answer was no. So I had to step back and say, this is stopping you from achieving your goals. Now, what else? What else can you do differently, and what could you put in the middle there? Some really beautiful things started to happen. As I said, it’s like, you know, we had people on our exec team that were extremely data-driven. If there was just a way for me to say, we’ve actually been collecting this, let’s look at it together, and have the data tell the story. That lacked controversy, whereas me being the messenger did. There were a lot of beautiful things that happened when I was like, what is the goal? If my goal is to have people consider how does this choice affect developers in every choice that we make? What are the multitude of ways to do that? To prove that? What are the voices around the table? When you have that feeling of fear, what is truly at risk? And work backward from there. Look at what are the other ways to achieve it? So, I can think of so many different… I’ll tell you a really cool thing that came out of this was, in our early days, we spent quite a lot of resources to bring a gifted filmmaker all the way to Lagos to tell some of the key stories around why we were doing it. Obviously, I viewed myself as central to this exercise, and how we would shape it. But we just ended up not being able to be there; we had to be at something else. I was in a total threat state about spending money on this right now. And I just let go. I was like, you’ve hired very qualified people. Tell them the essence of what you know, what is the problem you’re trying to solve with this, and let it go. To this day, if you’re curious, go online and Google “This is Andela.” There’s a piece that consists of short clips of our software developers in Lagos reading out our company’s value statement. I watched it before every single speaking role. It’s the greatest piece. It was because I just let the team do their thing. I was in a total threat state about that. And I had to be there; it wouldn’t be the same without it. But different skill sets came out, different abilities came out. We created this beautiful thing because I let go and let people solve that problem in a different way.

Angie D´Sa  32:19

I’m hearing you say that when I don’t need to be the person front and center and when I don’t have to win my way, beautiful things can happen.

Christina Sass  32:30

Yeah. And it’s, you know, I think that we go back to our conversation at the very beginning, you assume that this thing can only scale with you. There is a beautiful freedom in realizing that if we’re doing this right, everybody gets layered. If we’re doing this right, we keep adding new levels of specificity and skill sets. We bring different things to it. It’s a constant exercise of letting go and taking on new stuff, but letting go of others.

Angie D´Sa  33:01

I was going to ask you for your words of advice for founders who might be grappling with exactly this challenge: how do I deploy myself, and how should I change that? People are giving me feedback, and I disagree with it. But I think you’ve already answered that question.

Christina Sass  33:18

Yeah, I mean, if I were to summarize. I think it’s part of why I’m doing what I’m doing now, there are patterns of challenges for founders. It feels like you’re alone. It is the first time you’re experiencing this, and it’s the first time you’re building this, but there are patterns. One is joining an executive team and really sharing power with that executive team and feeling like they don’t orient to your baby in the same way that you do. We’re here. There is support. There are things that happen in that phase where you can see yourself more clearly and you can move through it. That was just news to me, that that was a knowable thing, that that would be a point of friction, and that there were tools and skill sets that I could build upon to get better at it. I feel that way for a lot of phases of company growth. It feels very lonely. It feels like you’re the only one experiencing it, but you’re not.

Angie D´Sa  34:10

Yeah. Well, thank you for that, Christina, and I know you have to jump, and I appreciate you being here.

Christina Sass  34:15

Absolutely. It was my pleasure, Angie. Thank you.

Angie D´Sa  34:17


This episode has been updated since its original upload on 9/14/2023 to better reflect the standards of Talentism and was reuploaded on 9/22/2023.

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