Nicole Glaros: Build Psychological Safety for High-Performing Teams

[00:00:01] Hello and welcome to My Biggest Lesson, the show that brings you the key learnings from the most influential founders, executives, and investors in the Colorado tech community. My name is Adam Burrows. And I'm Chris Erickson. Together, we are the co-founders of Range Ventures, an early stage venture firm based in Denver. You can find out more about what we're up to at range.vc. Our guest this week is Nicole Glaros. Nicole has been a fixture in the Colorado startup

[00:00:30] scene for many years as an operator, board member, investor, and mentor. She most recently served as Chief Investment Strategy Officer at Techstars, where she helped grow the portfolio from 10 companies to over 2,500 and from 300k to over 750 million assets under management. Nicole Glaroszzi Hey, Nicole, thanks for joining us today. Nicole Glaroszzi Thanks for having me. I really appreciate it, Chris.

[00:00:58] Nicole Glaroszzi Yeah. So we're going to get to your biggest lesson. We're going to talk about it before we get to that. I would love our listeners to learn a little bit more about your background and then also want to talk about Colorado Tech, given your extensive experience in the ecosystem. But before we go there, if you could share with our listeners what your career has been and what you're up to now. Nicole Glaroszzi Yeah. I got my start actually as I was getting a master's degree in sports psychology. I realized that I wasn't going to be able to pay off my

[00:01:27] student loans with a career in sports psychology at the time. And so I did what any classically trained human performance professional would do is I started a tech company. Like it's somehow that made sense at the time. And I ended up doing fairly well. And that's sort of how I sunk my teeth into entrepreneurship actually come from a long line of entrepreneurs. My father's an entrepreneur. His father was an entrepreneur. But that's how I kind of got interested and excited about early

[00:01:56] stage tech. The first company that we started actually created a very early platform, a very early e-commerce platform before e-commerce was even a word. This is like in the late 90s. Anyway, the company did fairly well and put a lot of cash in the bank for me. And then I tried a couple more startups after that, that both sort of failed miserably. And I blew through the earnings of my first, the sale of my first company. And then I became very fascinated with

[00:02:21] what makes entrepreneurs tick. And so there's a lot of, there's a lot of parallels between sports psychology and entrepreneurship. The athletes and entrepreneurs are wired very similarly. And then I've spent the better part of my career really working with mentoring, investing in early stage companies. So most recently I was at Techstar, an organization called Techstars when I joined. There were roughly 10 companies in the portfolio. And by the time I left, we had over, we had

[00:02:50] invested in over 3,000 portfolio companies and doing a new 500 investments every year. And I raised a bunch of venture funds along the way and I sit on a bunch of boards. So today I still work with early stage companies. I do a little investing. I run an early stage program for startups that focuses on the key drivers of performance and I sit on boards. So I have this weird background of scaling operator, but I come at it from a human performance angle and I've probably worked with,

[00:03:20] I don't know, like it's hundreds in the hundreds, mid hundreds of companies at this point. Long background in tech and long background in venture and, you know, it's been fun to watch the ecosystem here grow too. Yeah. And one of the other places we'd like to talk about too, before we dive into some of the stuff on your biggest lesson, a long experience with Colorado tech in general, right? Would love to

[00:03:44] hear how you sort of, when, when you moved here and sort of what tech was like then and how it's changed and what it looks like now versus then. Cause I think you have a really unique perspective on how this ecosystem has evolved. Yeah. I moved here in right after Y2K, January of 2000. And there wasn't really that much of a tech ecosystem here. There were companies, it was very disjointed and there wasn't a real like solid

[00:04:11] community yet. And I would actually say Colorado was still very much a cow town. Like Denver was very small. It wasn't really on anyone's radar yet. Boulder, while it was growing, attention on Boulder was kind of growing, but it was still also very small. And, and the community was really just a bunch of people that sometimes sit high. Right. And, and now we just see this, like you could fit everybody in the tech community in a room. And they, like I said, they all knew each other and

[00:04:40] shake hands, but like, there wasn't really any motion to like really bring the community together. Today, that's really different. We have, I mean, I don't even know how many seed funds, do you know how many seed funds? A dozen, two dozen here? Not quite two, but yeah, we probably have about a dozen early stage funds, either fully located here or principally located here. Yeah. So there, back then there was maybe two funds and they were all later stage funds,

[00:05:06] nothing in the early stage, right? Now there are coworking spaces, there are startup activities, there are programs, there are like LinkedIn groups and Slack channels and like everything that you can really do to, to come together. And so the focus on bringing the community together and really helping provide resources for early stage companies is night and day different than it was in 2000.

[00:05:30] And it's, and it shows, right? The number of investments that are in this state has absolutely grown. Not only the number of investments, but the dollars that are invested here have absolutely grown. The number of startups that are starting here are growing, right? And so somebody once said that it's a 20 years journey and every day that 20 years starts over again, and that's true. So like, I can imagine what it's going to look like 20 years from now, because 20 years ago, it was very, very different. Yeah.

[00:06:01] Yeah. That's, that's absolutely amazing. And you've had a front row seat to all of it, which is incredible. And not just a front row seat, but actively involved in a lot of it as well. You know, before we get to the lesson, you've seen a bunch of different companies here. You've seen a bunch of different industries, things come and go. Are there any either companies or industries in Colorado that you're particularly excited about? Do you think were uniquely? Yeah. You know, we sort of touched on this a little bit before we started, but I think the

[00:06:30] industry that I'm most excited about here in Colorado right now is actually quantum. And everyone else is going to tell you AI, and I'm going to sit here and say it's quantum, maybe not everyone else, but a lot of people will say that it's AI. And while I think AI is really interesting, its ability to sort of achieve its full potential probably relies on quantum's ability for it to achieve its full potential. And the amount of funding that's going, federal funding that's going into quantum in the state right now, the national labs that are focused on it, the number of companies

[00:07:00] that are focused on it, the talent that's here around quantum. While elements of quantum are still very theoretical, I actually believe that Colorado has the talent in order to make that a reality, which is going to fuel all kinds of other industries. And so we're keeping a close eye on quantum here, because there's just a lot of development and a lot of dollars flowing in, federal dollars to help develop that ecosystem. I completely agree. And I agree. I think I would probably say AI, if asked at the surface level,

[00:07:30] but you're right, the potential of AI will be unlocked, right? If quantum achieves its full potential, right? And if that happens, back to your earlier point about a 20-year cycle, we do those two things. The world is going to look so amazing, different 20 years. From now, both of those achieve their potential. So watch what you say on AI, right? Because our AI overlords are... I always thank Alexa whenever she sets a timer or tells me the weather outside.

[00:07:56] So let's shift more to you and specifically to your career, right, Nicole? You've seen a bunch of companies. You've worked with a bunch of founders. You've been both an investor. You've run your own company. I imagine you've learned dozens, if not hundreds, of important lessons in your career. But we'd love to hear, what's the most important lesson that you've learned in your career? How did you learn it? And how does that influence how you operate today?

[00:08:20] It's hard to boil it down to one thing. But if I had to boil it down to one thing, I would say building psychological safety is bar none one of the most important things you can do to achieve maximum performance from people. And there's a bunch that goes into that, but I'll tell you the story that's related to it. So early on in my career at Techstars, and Techstars was still this very nascent company, and we didn't have all the people and investments

[00:08:49] that we'd had. I was running the Techstars Boulder program, and we had the companies, and we also had a group of mentors. And we also had our investors, so a group of investors. And I had an email address for each one of those groups of people. I had mentors at techstars.com and lps at techstars.com and companies at Techstars. And at this time, I think my daughter was, I want to say she was six months old, and she didn't sleep through the night until she was probably

[00:09:18] almost four. So I wasn't sleeping, and I was working, I was, you know, sleeping in two hour increments. And I was also working about 80 hours a week. And so between those two things, I was massively sleep deprived. Once a week ish, I used to send an email update to the mentors and the LPs. I would send an email to the LPs because they were partners with us, right? They owned a percentage of all of these companies, and they were really partners with me. And a lot of them were

[00:09:44] really big influences on me, right? So I used to give them the like true dirty, what was going on. And I used to call the email, the good, the bad, and the ugly. And I would walk through everything in that email, like what was working in the program, what wasn't working in the program, what company was companies that were really excited about and why, and what companies were really struggling. And then what we could do as an LP base, as a partnership base to really help those companies.

[00:10:08] But I was raw in it, right? Then I would send a sort of watered down version of that email to the mentors, basically saying, hey, here are the things that we could use help with. And here are the companies that could use your assistance. It had mostly the same information, but a little less strong. Well, one night I was coming home. It was like maybe midnight. I was driving back from the office to my house. I was totally sleep deprived. And right before I had left the office, I had sent the

[00:10:36] email update to mentors and then a separate email to the LPs. Well, I'm in the car and I'm driving. And then I'm thinking, did I send the right email to the right group of people? Now here's why this was challenging because at the time we had a company that was in the program whose founder was also a mentor. And so I thought, did I send the LP email to the mentors? And I started to panic. I'm driving.

[00:11:06] I pull over. I pull up my email. And sure enough, I had sent the very raw, very unfiltered LP email, all of the mentors, which also meant it went to a company that was in the program. And I just, I mean, again, sleep deprived, all the things, right? So I basically burst into tears. I'm like, that's the end of my career. And I sent an email to David Cohen is the founder of Techstars

[00:11:31] and Brad Feld, who's also one of the founders. And I said, I'm sorry, I messed up. And here's what I did. And you will have my letter of resignation in the morning. Like I did not expect to survive that. And I got a phone call 35 seconds later. Now remember this is like at midnight. I got a phone call like 35 seconds later from Brad and he was just laughing. And he said, what are you kidding me? That's the best thing you could have done.

[00:12:02] And told me all, he asked me, he's like, did you say anything in email that was untrue? And I said, no. And he said, okay, well, so maybe you're a little harsher than you needed to be, but if everything you said in email was untrue, you're probably going to get more engagement out of that email than you ever have before. And you have actually given everybody really clear marching directions on how to solve it. Right. He's like, letter of resignation, not accepted,

[00:12:29] go to sleep. And I mean, I was like shaking. I was so saddened by what I had done, the mistake I had made. And also like what the repercussions were that that would be in the community. Like I thought I just burned every bridge and everyone was going to hate each other. Right. It unfolded exactly the way that Brad had predicted. Like I had more engagement from the mentors than I ever had before. I did have to talk to the one founder slash mentor because his company was mentioned and it was

[00:12:56] mentioned in the ugly category. And we had a real heart to heart conversation about that. I apologize profusely, but I also said, but these things are true. There's a bunch of things I learned from that, which is number one, if somebody messes up, you're not going to fire them because you just paid for their education. And why would you like release them to a potential competitor to take advantage of that education? You just paid for that. So you should embrace this person wholeheartedly

[00:13:26] because they will not only never make them a mistake again, but I guarantee that like nobody that works with them will ever make them a mistake again. But also when you create an environment where you allow people to fail and then you have their back, they're much more willing to come to you when things are messed up so that you know how to deal with it and address it. But also they're less fearful from taking risks. They will take more risks that push the boundaries more because they know that

[00:13:54] as long as it's done in a good faith, they still have a job, right? And when you're in this sort of high growth, high performance environment, you need to be pushing your envelope. You need to be walking the line. You got to like push right up against what the limits are in order to figure out like how far and fast you can go. And so it's like, I put it in this sort of psychological safety category. There's a lot of research that's been done on this topic. And at the time I didn't have

[00:14:20] the words for that. That was still kind of a new concept in leadership development. But in looking back, oh man, like I try to build a lot of trust with the people that I work with now so that they do feel comfortable taking risks and they will come to me when something isn't working. And then together we can figure out how to sort through it, but that allows them to like really push against the envelope. And also when you forgive somebody and you sit next to them as a partner rather than an accuser,

[00:14:50] it just builds loyalty and it builds trust in ways that can't be mimicked anywhere else, right? And so one of my biggest lessons was always make sure that I'm building psychological safety with the people that I work closely with so that they trust me and that they know that they can push the envelope and it's okay as long as it's done in good faith. And then when stuff doesn't work, which happens all the time, we solve it together, right? So they're not in an alone,

[00:15:19] they're not hiding it, right? Which often makes it worse. One thing also sticks out to me about that story, which is incredible. I think we can all relate to sending an email to the wrong person, right? At the wrong time with it is, you know, even before you had that conversation and Brad called you back, you know, you proactively sort of felt safe or felt the right step to own up to what happened and said, this happened, I did it type of thing. So even before you

[00:15:47] had that conversation, I think reinforced it. I think you were already a bit in a place where you felt that that was the right step to go do, right? Which maybe doesn't even exist in most organizations too. Well, to be clear, I couldn't hide it. It was an email that went out, right? And so I don't actually know what I would have done and if it's something I could have hidden. Yeah. But this is one of my points about sort of building psychological safety, because if I could have

[00:16:15] hidden it, maybe I would have, at which point it would have made it a lot worse. Like it could have done way more damage than I had done without the partnership and support of how to handle the situation. And so like when mistakes happen, you kind of need all the brains at the table. How are we going to make the best of the situation? You can't do that on your own when you're freaked out. And so what I was going to ask is, you know, two things, you know, both, you know, then and after, right? What are things, some things you've seen that companies or leaders can do tactically?

[00:16:44] You know, someone who's listening, one or two things they could take away and go do immediately within their current companies that they have to increase the likelihood they get that type of reaction engagement that you just talked through. And then second, is there anything that you've seen done well sort of in interviewing or hiring to screen for people that both will be proactive in the way you were and also want to create that environment too? Because I imagine there's both

[00:17:11] management and hiring practices that lead to doing this well. Yeah. So maybe on the first question, what are things that like, what tactical things can leaders do today? The two things come to mind, right? One is control your face. And what I mean by that is when somebody comes to talk to you about a problem that they're having, you need to control your reaction to that person. And so sometimes just taking a deep breath, even that can be really scary to somebody. So I think just like working on like, hey, it's going to be okay. We're going

[00:17:40] to figure this out together. I don't know what the answer is right now, but I'm really glad that you came to me. Thank you for coming to me. Wow, that must be really scary for you. Let's figure out how we can tackle this problem together rather than like, you did what? Right? And so that's working down. And then also working up and down, you need to ask for forgiveness when you have done things wrong. And it's very okay to say something like, hey, listen, I've made a mistake and I'm

[00:18:07] really afraid to admit this right now, but I'm going to do it anyway because I need your help. And when you do that, you disarm the person that you're talking to, even if it's your board or your lead investor or not your board, your executive leadership team. You're talking to the team that reports up to you. That conversation is super powerful because you're actually creating the example that you want other people to follow. And so you have to do it both directions. You have to

[00:18:33] learn to own your mistakes and you can soften the blow by saying, I'm nervous about telling you this because it's bad, but I need your help. That softens almost every conversation and also just controlling your face when people come to you. So those are a couple of tactical things. And then I think on the hiring side, on the hiring side, it's harder because it's what people do in moments of stress. And so yes, okay, an interview might be a moment of stress, but it's probably not extreme

[00:19:01] stress. Like if you've done something that puts your job on the line, that's definitely different than like answering question interview. I mean, you can ask questions like, what was the biggest mistake that you've ever made and how did you handle it? But like people are sort of prepared for those questions, right? So one thing that you can do is ask that question, but then make sure that you're getting references and that you're tying the story that they're telling to the reference and that you

[00:19:27] then check with the reference to make sure that's true. And so one thing that I always like to do is just say, hey, talk me through one of your big mistakes. Okay. Which role was that in? Who was your manager at the time? Are you okay if I reach out to that manager and ask that question? And man, it's really interesting how stories change when you sort of ask that sequence of questions. And then the people that have done it are like, sure, no problem. And you call a manager,

[00:19:55] the manager's got most, you know, 80% of the same story, which is a good ratio. But the ones sort of hem and haw, well, I don't think the person's there anymore. Or yeah, I don't know. You know, those are the ones you kind of doubt for. Well, Nicole, thank you very much. I think that this is a really important lesson, especially in startups where more things go wrong than go right. And it's, I think, how you navigate those and get to the right as quickly as possible, which is often addressing the wrong as quickly as possible and moving forward. So where can our listeners follow

[00:20:25] what you're up to today with your, with your new projects? Oh, geez. I published two places. One is on my blog, nearly Nicole.com and the other places on LinkedIn. Nicole, where else on LinkedIn? You can find me in both of those two places. Cool. And we will update our listeners if you all of a sudden start a TikTok account. So Nicole, thank you so much for joining us and for everything you've done for the ecosystem. Yeah. Thanks so much, Chris. Really appreciate it.

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