Andrea Ippolito: How to Bind Your Team With Friendship and Trust

Richard:

To support this podcast, visit my website kasperowski.com. Hey Andrea, thanks so much for joining us today. How are you?

Andrea:

Not too bad, very excited to be here. Thanks for having me.

Richard:

It’s a pleasure, it’s a pleasure. Is there anything else you would add to that introduction? I totally invented that description of SimpliFed. I kind of invented that description of you. What else would you add to that?

Andrea:

Yeah, well, with SimpliFed, you know, our mission is to allow every family to feel good about being their family. We start working with parents during pregnancy and we provide 100% virtual baby feeding and breastfeeding support, no matter how you feed your baby or whatever your goals are, whether that’s formula feeding, breastfeeding, combo feeding, breast pumping, whatever it is. And we work with health plans to get that fully covered. Under the Affordable Care Act, it is a covered benefit. Not a lot of people know that. And so we work with health plans to get our model, which is up to six appointments starting during pregnancy, and then further providing support postpartum. We work with health plans to get that fully covered. So it’s just been a real honor to serve families. A tiny bit more about my background, biomedical engineer by training, worked in the medical device industry. I went to grad school at MIT where my research was for the Chairman that Joint Chiefs of Staff on how to implement and scale tele behavioral health systems of care for service members faced with posttraumatic stress. Co-founded my first company out of MIT called smart scheduling that eventually was acquired by Athenahealth, I was a product manager at Athenahealth, and then went to the federal government where I was a presidential innovation fellow based of the White House Office of Science and Technology Policy. My appointment was at Department of Veterans Affairs, had an incredible time there. And then I joined the faculty at Cornell in the college of engineering. And I also had my first daughter when I was a faculty member there. And that’s what motivated me to found SimpliFed.

Richard:

Whoa. very impressive. And okay, we have a common connection, at least at Athenahealth. I didn’t know that you were connected with Athenahealth, that is so cool.

Andrea:

Yeah, we’re big fans of Athena.

Richard:

Now this podcast is about teams and I like to talk to, I like to talk to people about the best teams they’ve ever been on in their lives. So you have a small and growing team right now at SimpliFed. We could talk about that team. We could talk about whatever team you think is the best one of those you’ve ever been on in your life. And it could be a work team. It could be a not work team, any group of two or more people aligned with a common goal. That’s one definition of team. So any one of those. What’s the best team you’ve ever been a member of in your entire life?

Andrea:

Well, I have a couple of different answers to this question. So right now I am obsessed with our SimpliFed team. And one of the reasons for that is we all have that common mission and vision to allow every family to feel good about feeding their family. And we’re incredibly values-aligned. That’s so important. Whenever you’re working on a team that you share the same values, you understand what your mission and vision is, but we’re also a team of working parents right now who respect that. And after the pandemic, during the pandemic, depending on how you want to frame it, it’s been particularly hard for parents. And I love being on a team with other families because we all have just deep empathy for when someone’s sick or when someone’s going through something. And it’s hard to separate personal and professional life, especially when you are a parent. And so that’s something that’s really, really important to me. Other teams I’ve been a part of that have been my favorite are ones that you feel comfortable raising problems. And we know that is a core tenant of successful teams is having that psychological safety to feel comfortable raising problems and identifying problems. And so that’s something with the SimpliFed team I love as well. And so it’s really, it’s really critical for any team.

Richard:

For sure. I want to dive deep into one of these teams. Should we talk about SimpliFed or a different one?

Andrea:

Yeah, let’s go with SimpliFed.

Richard:

Okay. And I’m sorry. I keep slightly mispronouncing it SimpliFed, SimpliFed, SimpliFed.

Andrea:

You got it.

Richard:

As you reflect on the SimpliFed team, if you could describe the sensation within yourself of what it feels like to work together for you. Is there a single word? What one single word could you use to describe what it’s like to work with the SimpliFed team?

Andrea:

So one of the words that comes to mind is proactive. I really, really appreciate how the team is always activated and proactive. So what do I mean by that? So we need to always be ahead of the game and thinking about how we can serve families and understand their goals, understand their needs, understand their pain points and the situation right now in baby feeding is that there’s a crisis right now. There’s tremendous baby formula shortage. And our whole model is inclusive, whether you’re formula feeding, breastfeeding, breast pumping, et cetera. And so one of the key words that comes to mind is proactive. And that’s so important, ’cause we need to be ahead of the game and serving our families. And to me, that’s a sign of a very healthy team. Those that don’t need to be told what to do. They just do it because it’s the right thing for the people you’re serving.

Richard:

Right. And that’s in my experience, anyway, that’s easy to do when you’re all aligned on what you’re doing together when you all have that shared goal, shared division. How did you come about getting that shared vision together?

Andrea:

Well, our team all at baseline shares similar values, and that’s something that we really look for when we’re bringing on new team members is do you align with our values just, and how you are as a human being? So full stop. Like that is so critical. Secondly, is we vet for that during our interview conversations and you know pretty quickly who’s aligned with that and who’s not. But third and it’s going, you don’t need to be a parent to be on our team, but we find that those that have lived experience with the pain point we’re solving understand it more and they get it more and we all bring our own lived experience to whatever we do. But that has been particularly important because when we identify a small, medium or large, or, you know, nationwide issue such as what we’re seeing with the formula shortage is that if your values are aligned you have that shared mission and purpose, you know what your mission and vision is then frankly, you have a lot of those key aspects that are really critical for activating teams and being ahead of the game. So it’s something that we actively look for and I hate to use the word test, ’cause we don’t do any, you know, test during the interview process, but it’s something that you know when you see it very easily.

Richard:

Yeah, for sure. For sure. Now how do you know that this is such a great team, this SimpliFed team. Subjectively, how do you know this is a great team?

Andrea:

So one of the things that I look for during the interview process, but then I’m always very, very closely monitoring is that point of, are you comfortable disagreeing with someone? Are you comfortable raising a problem even when it’s incredibly uncomfortable to do so? And so when we’re in these pretty intense conversations, tackling a really gnarly complex issue, what I’m always looking for as the leader of the organization is are we actively disagreeing with each other, especially around complex things. And that might sound counterintuitive, but if you are willing to disagree with a team member healthily, in a thoughtful way, it means that you are actually going further faster. And that’s something that’s really, really, really important to me. And so one of the specific questions that I ask any new team member that comes on is can you share a time where you disagreed with someone in authority and how did you approach it and what ended up happening? And being able to raise issues that perhaps could be detrimental to your organization or not, or they could be small or minor, is so important to any organization, especially organizations like ours that are in healthcare.

Richard:

So let me ask you, then. You’re the leader of this organization. Can you give an example of a time that somebody disagreed with you about something, disagreed with you about something and how they shared that with you and how they handled it, and how it all turned out?

Andrea:

Yeah, I mean, all the time, you know, one of the things that we’re always trying to grapple with is how do we approach communications, especially during this time of crisis. And so one of the key questions that we were talking about is, you know, how do we explain what we’re doing and how do we explain what we’re doing in a way that isn’t like health plan speak or like insider talk. And so one of the things that we have those disagreements on in very healthy way is like, how do we communicate what we’re doing that’s in compliance with health plans, but also explaining in a way that means something to a parent, right? That maybe isn’t from healthcare or has that background. And so we were having this really thoughtful, but intense discussion a couple weeks ago that I’m like, that’s coming to my mind right now. And we were disagreeing as a team. And like at one point, like when I was getting more intense, I said, just so everyone knows: everyone is doing their jobs right now. Like you are saying something that you are 100% right from the health plan perspective, you over there are saying exactly what we need to be saying in terms of engaging parents. So well done everyone. Everyone is saying exactly what stakeholders they represent. Now let’s figure out a way to move forward. But this is exactly a sign in my opinion of like what everyone should be saying. And if one of those stakeholders wasn’t saying what they’re saying then to me, then that’s a huge red flag or yellow flag as a team that holy moly, they don’t feel comfortable speaking. And we need to fix that.

Richard:

What is it like for you, you know, maybe in a previous position when you were disagreeing with somebody in authority, what subjectively, what was that like? And objectively, what did you do?

Andrea:

Yeah. So we’ve all been in those situations where you have either to appear maybe a leader or manager disagreed and been shut down. And when you are shut down and maybe it, especially when I was a more junior, it took more guts to disagree and then to be shut down, it takes the air out of the room and then you don’t feel comfortable speaking. So I can think of plenty of meetings where I raised an idea and people said, no, that’ll never work. And you’re like, all right, well, I’m done here. I will not be contributing the rest of the meeting because, sorry, like, and so, and it’s maybe like pour on me just to shut down, but that safety to raise ideas. And it’s not that all ideas are good ideas. That’s not what I’m saying, but there’s a way to disagree with someone, or there’s a way to say no, but still allow people to feel part of the conversation. And so all ideas cannot be enacted. You can’t bloom a thousand flowers all the time, but that’s what I mean is that there’s a way to disagree with someone and use like the improv speak of don’t say, no, that’ll never work, or yes. Oh, the worst is yes but. But there’s a way to say and, you know, have you considered that still allows people to feel comfortable contributing?

Richard:

Yep. Yep. So cool. I giggled because I was just teaching this two days ago. Yes and versus yes but what does that say-

Andrea:

Exactly.

Richard:

Are there any other subjective senses of how the SimpliFed team is one of the best teams you’ve ever done with?

Andrea:

Yeah, I mean, we’re just all like activated and-

Richard:

What does that mean?

Andrea:

For better or worse.

Richard:

Activated.

Andrea:

What I mean by activated is, and some people might see this as a bad sign. And so this is one of those things that different teams approach, different cultures. So we’re all parents. And so I have two daughters that are four and one, and my one year old has had RSV this past week. And there are times when, like I need to go prioritize her and her health. I need to take her to the doctor in the middle of the day. And we try to create a work environment that’s very much like appreciated and respected. And so what I mean by activated is that we are constantly supporting each other through those times and our kids are in the shot. We welcome kids in the shot. We’re happy to have that. And when you, especially, I don’t want to be gendered here, but especially for moms that is so critical. And unfortunately it is a bit gendered in this day and age still moms are often default parent, not always, and we should create more societal infrastructure. So that mom isn’t always the default parent. And what do we mean by that? Universal childcare support, paid parental leave for both parents, all those types of things, but our team is activated and, but we allow for flexibility to still be a parent. And so when it’s 2:00 AM and I’m up with my daughter, feeding her, you know, I’ll be on Slack, cruising around and other people would disagree with that approach by the way of turning in. But you’re activated and you can turn off your notifications to not receive anything. But for me as a parent, having that ability to make, take a couple hours to go deal with my kid in the middle of the day, but then be wired in later is just and having that flexibility of being able to work when it works for me. That’s how I refer to activation.

Richard:

Okay, cool. Yeah. And that totally makes sense. I’m sort of a solo entrepreneur and I’m sort of always working and sort of never working, right? All at the same time. So I totally get what you mean. You have important things to do during the day, take care of your daughters.

Andrea:

Yeah. And you get more out of people that way. And that’s the thing that people don’t understand in the whole, like nine to five, be at a desk in-person, you’re going to lose some pretty great talent that way. And so if we can create those flexible work structures, you actually get a lot more empowered workforce.

Richard:

Yeah. Yeah. Okay. Now, how about objectively? What are some, what are some, what are things that somebody outside of this SimpliFed team would notice about the team that goes into their greatness?

Andrea:

Yeah. So one thing, and, you know, I’m an engineer, so this isn’t as quantitative as I would like it to be. Although we should, like in reflection of this question, we should have some more quantitative metrics to measure this. You can measure psychological safety as one example. And that’s something that we aren’t currently quantitatively measuring just subjectively measuring, but objectively, what I can share is that, you know, you hear right now of people like companies that are just having a really hard time hiring. I might eat my words in a couple months now, but at this moment in time, we do not have that problem. Like we have hundreds of applicants. And the consistent thing that we hear from people when they’re applying is that they love what I just described about how we have that flexible work environment. I don’t want to put any of our team members on the spot, but we all have our unique needs. For me, I have a four year old and a one year old and my husband’s a physician and he’s on call a lot. And so there is, you know, he can’t bring a baby into surgery with him. So sometimes I have my little sidekicks here with me as the CEO of the company. And what we’re seeing from the community that are applying for jobs here is that we all have our own unique story. We each have our own unique needs. And especially with working moms and creating that flexibility. And again, I don’t want to be gendered. And I hate like as a CEO company, when everyone talks about me as a parent too, but nonetheless, it is a part of my life, a very important part. But when you create those flexibilities, then you are going to just get the best talent. So objectively, what I can say is we are getting hundreds of applications for each position, which allows us to hire the very, very best. And my peers at former institutions are not seeing that. And so that’s something that we’re really proud to see is that our culture at our team is resonating with people externally as well.

Richard:

All right. All right. Now how about, I don’t know if there’s anything. Well, let’s see, you’re sharing the story. You’re sharing the story about this kind of flexibility, which is part of what’s bringing people, and bringing all these job applicants to you. Are there any, what other concrete behaviors do you all engage in together that help make this team so good?

Andrea:

So we are 100% distributed team. So when you are 100% distributed virtual team, you need to have strong communication channels. And by the way, we have not perfected this. Like, we are always, always iterating and learning on this, but we do a lot of the distributed team norms that are now very commonplace, but like three years ago, weren’t very commonplace. So we have a daily huddle right now, and that’s great. And then we’re all on the phone. Sometimes audio, sometimes video, whatever works for that person. Also, we have Slack and we have protocols and SOPs around Slack usage and creating transparency there. And that definitely helps. Third, we have our 30, 60, 90, and we used objectives and key results. And our KPIs are, you know, embedded within our key results. And so we have all of these different tactics that keeps everyone very, very focused. We also have things like weekly performance review meetings, and we have all hands meetings that are now happening monthly. That’s a new iteration. So I’ll let you know how that goes, but we create these internal team infrastructure and communication channels. And what I want to very much highlight that’s so critical for our team is asynchronous communication. And that’s, you know, what slack is fantastic for. But that’s something that is super important for our team to create those flexibilities that I mentioned earlier.

Richard:

Yeah. Now, what do you notice as differences between synchronous and asynchronous communication? Yeah, everything about it. What do you notice? What are the benefits? What are the drawbacks? Everything.

Andrea:

Yeah. So synchronous is great, quick answers, but you know, we’re on phone calls the whole day and we’re serving families. And so we can’t just pick up the phone all the time. We’re not often just like sitting at our desk, able to pick up the phone. So for us, asynchronous communication allows us to frankly move a lot quicker because not when we’re on the phone, speaking with a family member, but you can multitask, right? And I know, it’s not, it’s a bit of a dirty word, but the ability to communicate asynchronously and especially via Slack on your phone, if you need to answer a quick question, just matters tremendously. And that’s been very critical to our team’s success.

Richard:

All right. So if you could give advice to listeners and viewers for how they could get some of this goodness for their own teams, what would you tell people? What advice would you share?

Andrea:

So one piece of advice is be okay with trying something other than throwing it out the window after a couple weeks or a couple sprints, if you work in a sprint model. And you got to give it a try. You can’t throw it out immediately, but you also have to be ready to change quickly in a reasonable amount of time. And don’t just keep doing something to keep doing it. And, you know, meetings is a perfect example of this. Like meetings is something that you can just like, keep it on your calendar and it will forever just live there and, you know, and it won’t die. And so feeling comfortable to make stuff more productive. And that’s something that we’re always learning and iterating through. Like the operating rhythm that I just describes is something that has taken us a while to get here. And no doubt it will look very different in three months. And so we’re always iterating based on the needs also as our team grows and our team has different needs. And so the biggest thing is don’t be afraid to throw something out that isn’t working.

Richard:

All right. All right. Is there anything else you want to add? Anything about you, the company, random other advice, anything at all?

Andrea:

Yeah. I mean, it’s actually really quite simple understand what motivates people and then make sure that based on what motivates them, that they’re getting out of their work environment. And by the way, we’re all, again, always learning there. The other thing is that in this, again, sounds obvious, but the teams that know each other socially feel more comfortable disagreeing with each other. And there’s actually studies to prove that. There was this one study of operating room culture. And when the OR team, you know, whether it’s the surgical tech, the nurse, the surgeon know each other socially, they are more willing to point out issues. And patient safety is improved and you see less errors. So I love that example. and it makes sense, right? If you feel comfortable and friendly with someone, you’re more willing to say, yo, that didn’t go super well. Or, ooh, you really shouldn’t use that word. And one of the things that we’re always trying to do, especially after a big meeting, maybe with a house plan or a partner, is like immediately after we ask, hey, how could I have done that better? And it’s sometimes very painful and you have to have a mindset that’s willing to receive that feedback. And you know, that this is one of my flaws is sometimes my mindset is not ready to receive feedback. And so I’m always trying to improve upon that and actively seek feedback and give people permission. Not that they need permission, but just to invite them, to give me feedback, because it’s so important that you’re always learning, iterating and improving, and that’s something that I’ve learned along the way.

Richard:

Yeah. Awesome. Awesome. Well, Andrea, thank you so much for joining us today. I really appreciate you sharing your time with us. Thank you.

Andrea:

No, thanks so much for having me and excited to share the great work that we’re doing at SimpliFed. So thanks for the opportunity.

Richard:

Oh, it’s my pleasure. Oh, one last question. If anybody wanted to get in touch with you, is there a way to do that?

Andrea:

Absolutely. So you can DM me in @andreakippolito on Twitter, or you could email me, andrea@simplifed.us.

Richard:

All right. Great. Thank you so much, Andrea. And listeners and viewers, remember to support this podcast. Visit my website, kasperowski.com.