Best Practices for Startup Leaders According to Leadership Coach Orianne Gambino

Orianne Gambino: Hi, my name is Orianne, and I am a leadership coach and writer on mindset and leadership.

Spyros Tsoukalas: Welcome to the Growth Mentor Podcast. I’m a big fan of leadership coaching. So I’m excited to learn from you today about all the exciting things that you do. So, would you tell us something that we don’t know about startup leaders?

Orianne Gambino: Yes, happy to. So, I think at startups we talk a lot about the growth that the company goes through. But what we don’t talk about is how startup leaders within like a year or only a few months, go through a tremendous amount of growth themselves and within their role. We kind of know and understand that leaders in startups have roles and responsibilities that evolve really fast, but we don’t really talk about it. And what it means. If you look at like a regular corporate setup, when someone gets a promotion, they get promoted every two years, every three years, maybe every one year, if they’re like super high performers. And when they get that promotion they have time to adjust and adapt. And startup leaders or startup founders don’t really have that luxury. So they need to move really, really fast. Despite going through a lot of change internally, if that makes sense.

Spyros Tsoukalas: I could talk about that for hours. Thank you for highlighting it. So being a startup leader, what are the potential obstacles or major blocks that you might face?

Orianne Gambino: So many? There’s so I think it’s like very much that growth, that’s kind of like creating a lot of friction. Because they don’t really have time to adapt to their new role. The number one block they may have is not adjusting fast enough to that to their new responsibilities. Because everything is going so fast, they don’t really have time to pose, regroup and decide, okay, what is my new role look like? It’s kind of happening to them, and they need to figure it out as it goes. And so the lack of time is number one. The second one is impostor syndrome because they’re moving so fast and moving from one role to the other so fast Sometimes they were doing sales, and then all of a sudden, they become manager of a team of sales, and then head of sales. They’re figuring things out as they do it. And so they face a lot of maybe self-doubts that they can’t really show because they need to be moving really fast. And then the third one is clarity, and communicating things clearly. When you’re growing very, very fast. And if you think of like anything in your daily life, like if you’re driving a car if you’re going super fast, you don’t really have time to process all the information and communicate things clearly. And I think a lot of startup leaders struggle with this. It’s like they know where the company is heading five years from now. But communicating the goals that are happening in the next six months or in the next year is much more difficult because it keeps on changing.

Spyros Tsoukalas: Have you observed any relation between all these quick transitions that you mentioned last important point impostor syndrome experienced because of those to be related with any type of like, burnout? In my experience, I have burnout a couple of times because of all this effort, especially mentally and psychologically to adjust to all these new challenges. So have you seen any? Have you seen that?

Orianne Gambino: Yes. 100%. If you think about it, imposter syndrome is good. It means that you moving in, which means that you’re growing and it means that you’re challenging yourself. But the downside of imposter syndrome is that it puts a lot of pressure on yourself. And if it takes over, it turns into anxiety, potentially depression, and a lot of fear. And then when your work is driven by fear, especially in a fast-paced environment, then you like you just keep on running towards burnout. And any comes down to like not having time to pause or not taking time to pause in a context of growth. We assume that if we pose we’re slowing down or even kind of going backward when actually pausing is what gives you time to then take a massive lift, and avoid burnouts. So definitely kind of like imposter syndrome can mentally drain you and lead you to burnout.

Spyros Tsoukalas: Been there done that. So, having interacted with, I guess, a few hundred or even more people, what mistakes do you see startup leaders doing?

Orianne Gambino: So not pausing to reflect is one, not really taking the time or not getting support. I’m kind of like preaching for coaches. But it’s very true like having a coach or having support. And someone that can help you check in weekly, bi-weekly, or once a month. If you don’t have that type of support, you go through burnout much faster, or you don’t have clarity. And as a consequence, you don’t communicate clearly. I think a second mistake is not communicating clearly goals. And assuming that people know where we’re going, leaders in startups like they have a 360 view of what’s happening and where the company is heading. Employees of the startups don’t. And so employees don’t understand why everything is moving so fast, and everything is changing all the time. They work towards a goal. And then all of a sudden, they’re being told actually, this is not the goal anymore, we’re going to be doing something else. And oftentimes, leaders struggle to communicate that, in a way that makes the employee feel empowered, and that makes them feel understood. And that makes them understand what’s happening with the company. And like it’s not just startups it’s also scaled up. I’ve seen this, in many big tech startups like Airbnb, and Google, like you see this happening a lot where the leaders don’t really communicate what’s happening in a way that’s digestible for the rest of the team. And then another mistake that we can see is around hiring. And so that’s very much for smaller startups that are moving really fast. When they hire, at month five, they have very specific needs. And usually, those people can’t fit those needs for 12 or more months. And so that’s kind of like a mistake that a lot of founders and leaders do if they hire and then don’t know how to either stop working with that person or help them evolve into a new role. And as leaders, because they are evolving into a new role every two months, every three months, or every six months, they kind of assume that employees can do this. And maybe they don’t give either the rights report or a way out for people.

Spyros Tsoukalas: That’s really interesting. I have seen people going through that. And it’s a challenge mentally as well. I think both coaches, mentors, and even mental health support can be very helpful in along this journey. So, let’s say that a leader realizes that and starts doing steps toward a positive direction to improve or to fix sad challenges. What tips do you have for startup leaders around leadership matters?

Orianne Gambino: I think it starts especially with employees, it starts with understanding what your employees want. Very often actually, on Growth Mentor, I’ve talked to a lot of new managers and the number one advice I give them is to sit down with all of your reports, and understand what their five-year plan is on a personal level. And this is going to do two things, it’s going to help you know how to distribute to them work that actually makes sense for them and help advance their career, it’s also going to help you influence them better because if you know that they’re working towards X goal, then it’s much easier to give them tasks that make sense with that and convince them to do it and get them motivated to do it than if you just give them a task just because so really understanding your employee and where they’re going and where they’re heading is super helpful. And the same if you need to, like some employees, especially in startups, they only like small startups. After a series B or C, they want to leave because they want to go back to like something smaller. So if you understand that and know that then you also know how to place your employees and when also to say goodbye or to give them a promotion.

Spyros Tsoukalas: How can they sharpen their focus? Because that’s like giving all these transitions that we mentioned earlier like focusing and not getting lost in this labyrinth of things to do is challenging. How do you manage that?

Orianne Gambino: Two things. You start with why? You always ask yourself, why are we doing this? And you see this in the company all the time like you see projects happening. And then eventually after two months, and someone’s like, Okay, but why are we doing this again? And no one can answer it. And it’s crazy because you’re using resources to do this. And so if you ask yourself, like, why are we doing this? And if is this serving our goals, then you keep a better focus. And then creating those moments of space. So be it with a coach, be it with a mentor, or on your own? Having moments where you actually reflect on like, okay, what are we doing right now? Because what happens sometimes is that we kind of like to get stuck on one idea. That’s the what are the how, and not the why we are doing something. Like, yeah, if like, if you want to eat, and you’re so sure that the only way to eat is grocery shopping. If you don’t stop and reflect on it, then you may be missing out on the fact that you can also I don’t know, like get take out or go to the restaurant, like it’s a silly example. But that’s the idea. And then if you’re stuck on the grocery shopping, you’re missing all the other options. And then your mission is to go to the grocery store instead of feeding yourself. Does that make sense?

Spyros Tsoukalas: Yeah totally, totally. How do you recommend people attempt at least to find balance with their time? Because time management is a serious challenge in this journey.

Orianne Gambino: Um, I think that depends very much on the personality of the person. But kind of like planning things and putting in the calendar time for personal things, is super important. If it’s not on the calendar, it’s not going to happen, right? I remember I had a colleague at Airbnb that started training for Ironman and he was telling me he was training because he was putting the training slots in his calendar. And that time that I thought I could never free, because now it’s on my calendar, I’m freeing it anyway. So, I feel like planning is the number one thing. And then ask yourself, like in this week, tomorrow, again this week, next week, like what happens if I actually don’t do this, we oftentimes create a fixed sense of urgency, because it makes us feel safe and in control. So kind of questioning this constantly is a good way.

Spyros Tsoukalas: Been there done that as well. So, I have another broader question in the context of things that leaders can do to support themselves or their teams. So we are approaching a roadblock, there is a major block, whatever the kind, like could be a strategic problem could be a matter of capabilities or skills. Like, is there a mindset that you use to face challenges?

Orianne Gambino: Yes. Like, there are a couple of things. The first one is to, again, go back to the why, like, why is this a roadblock? And how is this going kind of like against our goal, like how solving this is gonna go into our goal? And the why and like, I know I’m like, if you read what I write, if you talk to me, like why is always like my number one question. But I think it’s so important, because otherwise you build solutions that are not solving the like, you build solutions that you think are solving the problem, but they are not like solutions for what you want if that makes sense. And so kind of like thinking about, Okay, why are we doing this, what is happening right now is super, super important. And then brainstorming and trying to find ideas outside of what you know how to do is also super important, especially in the context of a startup, we need to be constantly innovative. Sometimes that means bringing in other people that can give you a completely different perspective. So being open to a completely different way. What I like to do when we kind of like problem-solving is okay, let’s not be realistic. For starters, let’s find solutions without thinking about whether or not they’re realistic. And then you take the solutions, and then you break them down into a realistic solutions. Have you done this before?

Spyros Tsoukalas: Well, I like the 70% done is better than 100% perfect mindset. So that’s the way I approach personally some challenges. I’m trying to pull through it as much as I can and then I seek help.

Orianne Gambino: Yeah, not looking for a perfect solution.

Spyros Tsoukalas: I was honest, earlier when I was saying I have been there and learned that because I like the mental aspect of work and all these things I have spent so much time trying to learn and understand what’s happening, and why do I experience what they experience? But that’s a topic for another episode. So, the last question for the day is, what’s the role of technology in all this?

Orianne Gambino: It’s a lot of support. Actually, technology is like a game and is such a powerful tool for leaders. On so many levels, right for typical organization stuff. So having your calendar, having reminders. You could even set up like for your mental health, you can even set up reminders of like, have you drink enough water today? You can track how many steps you’re taking, or how many activities you’re doing with your Apple Watch or like, whatever. So that’s one, and then there are more and more apps that are helping leaders become better leaders online. And I think that’s like super, super helpful, like two minutes tips that you can get or like apps like Growth Mentor, or like a way to kind of like, communicate and get constant information and train yourself constantly. So I think, yeah, technology is supporting leaders more than ever.

Spyros Tsoukalas: Orianne, thank you for joining the Growth Mentor Podcast today. This was a really interesting topic, and I think many, many people in the startup world face those challenges. So, thanks for sharing your insights.

Orianne Gambino: Thank you.