Episode 260 Transcript:

0:00:00 – (Ramona Shaw): In today’s episode, we’re diving into a big career shift that’s often underestimated. It’s moving from a large enterprise to a smaller business or a startup. Let’s dive in. Here are the two questions this podcast answers. One, how do you successfully transition into your first official leadership role? And 2 how do you keep climbing that leadership ladder and continuously get promoted? Although the competition and the expectations get bigger, this show, The Manager Track podcast, will provide the answers.

0:00:31 – (Ramona Shaw): I’m your host, Ramona Shaw. I’m on a mission to create workplaces where work is seen as a source of contribution, connection and personal fulfillment. And this transition starts with developing a new generation of leaders who know how to lead so everyone wins and grows. In the show, you’ll learn how to think, communicate, and act as confident and competent leader you know you can be. Welcome back to this episode of The Manager Track podcast.

0:00:57 – (Ramona Shaw): Today’s episode is for any leader who’s feeling a bit off balance after making the leap from a large org to a smaller company or a startup, or for someone who might be considering making that shift again from large to small, or if you are managing someone who has gone through that shift and you realize they’re having some challenges with adapting to the startup environment. So in this episode we’re going to unpack the cultural, psychological and even the operational shifts that make this transition hard or easy, depending on how you look at this.

0:01:38 – (Ramona Shaw): The goal is really to explore a bit more of what is this shift about and what do people need to keep in mind in order to be successful. You’re going to hear real world examples, what startup teams really think, and hence the mindset shifts that can turn frustration both on their end and on the leader’s end into success or even fulfillment. Now, the reason why I chose this topic for today’s podcast episode is because I have, over the course of the last six to 12 months, worked with several people who’ve made that switch.

0:02:12 – (Ramona Shaw): I’ve also worked with startup teams where individuals on those teams have made that transition and are now trying to adapt to the new reality that things are very different in a scrappy startup environment than they used to be, and the kind of friction that comes up as a result of that, both on again their end as well as the team or their direct supervisor or leader. So imagine you’re a VP at a large company. You probably have a big title, you’re a vp, therefore you have probably a bigger team or enough resources to plug into to help with your work, and you likely have plenty of infrastructure that you can leverage and use from technology and tools such as CRMs, from resources and other teams that are dedicated to help for certain projects or in certain situations, to processes, established protocols, a culture, personal resources that you can tap into to get help, be this in HR department, learning and development programs and so forth.

0:03:21 – (Ramona Shaw): Now you decide, okay, this is all good, but I would like to get a little bit closer to the action and really drive impact or I am kind of fed up with the bureaucracy of it or the politics of the big company. I want to build something, you know, I want to be part of a team that builds something. And so you decide to make the leap to, let’s say, a 50 person startup. And in your first few weeks you realize that you are the one handling your own onboarding.

0:03:50 – (Ramona Shaw): There’s no nice onboarding checklist. No one prepared the laptop for you and introduced you or gave you even a training on how to use the different tools on it. No, you probably had to go speak to it to get the laptop, to get access rights, you had to go figure out what are we using for which processes, and then you had to figure things out yourself. That’s typically how this happens. Not that that’s necessarily the best way to go about it, but typically the onboarding process at that level hasn’t been fully flushed out or institutionalized where that would all be set in place. There’s a lot of taking on things on your own.

0:04:29 – (Ramona Shaw): You might also find yourself together with your team in the midst of a fire drill because of a bug on the app for your product or whatever that might be that no one’s ever seen before. No one knows where it’s coming from. The person who wrote the code is no longer with the company. And so you’re all just kind of diving in, trying to figure out what happened and how to rectify it. Or you might find yourself being dropped to a customer call where someone says, hey, I can’t take that call, please talk to them.

0:04:59 – (Ramona Shaw): And you, you barely got 20 minutes to read up on the customer and why this call was set up, but you just have to wing it. You might not have a nice fancy slide deck prepared, but you’re making things up as you go. That is typical startup life. It can feel messy, it is messy, it can get overwhelming. And you’re often find yourself in a situation where you have to be resourceful, figure things out that have nothing to do with what’s on your job description.

0:05:25 – (Ramona Shaw): Now, in large organizations where we have established departments, specialized roles, if you need a legal review you call the legal team, you want a competitive analysis, you find the strategy or the research team and you get them involved. If you need to hire someone, you get HR to kick off the hiring process. But in startups, none of that is possible usually right. Everyone is expected to figure things out on their own and to do so fast.

0:05:54 – (Ramona Shaw): And therefore a lot of the leaders that find yourself in such situations feel a little bit shocked or overwhelmed at first. And it’s not that they intellectually didn’t know that that was going to happen. Most of the leaders I speak with in this transition, they knew what they were going to get themselves into. They left their other job behind because they wanted exactly that. But knowing something and then experiencing it, those are often two different things.

0:06:20 – (Ramona Shaw): So yes, you might have known this is what’s coming, but once you’re in it, it can still feel overwhelming, it can still feel really challenging. Especially when you realize that the rest of the team may have never worked at a big org. And so they don’t even know what they’re missing. They don’t have that reference point that you have. So this idea of like, why do we need a process? We don’t need a process, not a problem culture and us being scrappy, that’s the process.

0:06:48 – (Ramona Shaw): And so you having a reference point of what it could be, what it has been for you, and now seeing the disconnect while everyone else seems to just like raise their eyebrows at you of like, what are you talking about? It’s not a big deal. That is often sort of the frustration of like, I don’t get why they don’t get it. And specific on this one. When it comes to people leadership, this may involve the lack of performance review processes, calibration discussions, not having clarity on who gets promoted or what are the salary guidelines. Everyone and every leader is kind of figuring it out on their own and they all have their different approaches.

0:07:26 – (Ramona Shaw): And so you may feel like, well, that’s not fair, that’s confusing. Why aren’t we all on the same page? How come this one team is so generous and everyone seems to be an outperformer? And then on my team, I’m really doing sort of a very proper fair assessment on their performance. And then I’m being very resourceful and appropriate with the budget and realizing that not everyone operates this way can be the hard part here.

0:07:54 – (Ramona Shaw): Similarly, not having a learning and development budget or additional resources to support your team members can be challenges that leaders who made that transition, if that’s you, then be you have to figure out as you find yourself in this new role at a startup. So that was one. The second one common challenge is that there isn’t any title based power. So yes, you might be the most experienced person in the room, you might be the one who had or still have have the biggest title.

0:08:26 – (Ramona Shaw): But that doesn’t automatically mean that people will follow your lead. So in bigger organization there’s often sort of this hierarchical understanding of who gets to make which decisions. What is appropriate to bring to whom do we they’re going to follow the chain to bring something upwards or to get attention on an issue. But at a startup, everyone just talks to everyone. Your direct report may have a conversation about what’s going on on your team with the CEO without you knowing.

0:08:55 – (Ramona Shaw): And to the CEO and to that team member, that doesn’t seem like a big deal at all because why wouldn’t they Talk? It’s only 50 people, we all talk all the time. But if you come in with that understanding of the hierarchy, you might feel like someone intentionally caught you out of the loop and went behind your back to talk to the CEO. And then that can break trust, if that’s how we interpret the situation.

0:09:17 – (Ramona Shaw): So in addition, working with your team, if your role in itself or your title doesn’t inherently mean you have more power, then people may question or challenge your decisions and they ask why they have to do what they have to do. They may provide a lot more pushback than you used to in your past roles. So that’s the second challenge. The third challenge I often pick up in those conversations is that conversations are casual.

0:09:50 – (Ramona Shaw): Everything is informal. Decisions happen over slack or over coffee or over dinner. There are no formal decks, no official sign off procedures. There’s no way to track who decided on what and who’s been communicating what. And are we the right channels, the right timelines to communicate information? And so the challenge people, leaders often have here is that it seems like a complete lack of rigor, lack of accountability, and it can feel really hard to keep up and track what’s been done by whom before they or you joined the organization.

0:10:32 – (Ramona Shaw): So to summarize this, I remember talking to a leader who moved from a global consulting firm to a fintech startup and he said, oh my gosh, Ramona. It’s not just humbling, it’s completely disorienting. And I think that brings it to the point. It is humbling on one hand because you realize how much you started to rely on all the resources that a bigger organization has. But then it’s also so Disorienting because you find yourself like having to assess the environment because you realize that you have to operate very differently in this type of environment.

0:11:08 – (Ramona Shaw): Yes, you have expertise and experience and knowledge and skills that you will transfer into this role. But that’s a pretty siloed perspective if you look at it holistically, how you leverage those experiences and skills and whatnot. That new system is going to have to be very different. Now for most leaders, once they get past that initial friction, which by the way, can, it’s not a matter of weeks, this is typically a matter of months, or if not even half a year to a year.

0:11:40 – (Ramona Shaw): But once they adapt to the environment and start to embrace it, they then actually get to that place where they feel a lot closer to the action. They realize they have a lot more autonomy, things can go faster, they make more decisions, they have real impact and they can see it day to day. And that is where the fulfillment kicks in. And at that point people will say, no, I’m so glad I made that transition also.

0:12:04 – (Ramona Shaw): Now I know, and now I know what it is like to work at a big organization, to work at a startup. And in the future, as I, you know, map the path for the next few steps, I will have a lot more awareness and tools and knowledge and skills in my backpack, so to speak, to be smarter about. When do I transition from a small company to a bigger one or mid sized company for what positions and when? The key though, to get to that place where you start to sense that fulfillment in the current role in a startup really lives and dies by your mindset.

0:12:44 – (Ramona Shaw): So I want to talk about six critical mindset shifts that will help you adapt to the startup environment. And again, you might think, okay, that’s, I get it, I can intellectually understand it. Intellectually understanding it and actually doing it and seeing the effects of it day to day are two different things. So if you’re in it and you’re struggling and you know what’s going on, know that this is normal, it takes some time.

0:13:13 – (Ramona Shaw): Some of these mindset shifts are not overnight switches. Like we have to actually go through a bit of friction and struggles in order to evolve and develop a mindset that’s a lot more effective in a small work. Okay, first one is you got to let go of that corporate identity. If you’re coming from a big company, chances is that you had some status there, right? You had a network, people knew what you were doing, you were respected, maybe you had a team, a budget, the title, all of that in this startup none of that carries over. You’re literally coming in as a new person.

0:13:48 – (Ramona Shaw): And very often, unless you’re very senior, most people aren’t that impressed by your old title. They want to know, what can you do right now and how will you lead the team themselves? How are you going to benefit them? That is what they’re going to look for. Not how successful were you at your past role. That’s what got you in the door, and that’s why they’re giving you a chance. But now that you got to prove yourself in this new situation, so letting go of all the successes from the past and realizing you have to now earn their respect, it doesn’t automatically carry over.

0:14:23 – (Ramona Shaw): That will likely make you a bit more humble and open to listening to what’s really going on. If you show up constantly talking about, this is how we did it in my past org, that’s likely not going to fly so well. So think about your experience like a set of tools that you bring with you. It’s not about recreating what you had. It’s just about offering ideas when they’re useful and leveraging the tools that you have in order to make real change happen.

0:14:54 – (Ramona Shaw): For example, hey, here’s something that we’ve tried before. Do you think this could help here? That shows humility and like, an understanding that just because it worked in your past rule may not work here. So you’re not coming in saying, like, oh, here’s how we’re going to do this, here’s how is this is supposed to be? No, it may not. The the things that this larger org now has is not what it had when it was only 50 people.

0:15:20 – (Ramona Shaw): Right? There’s a time for everything in an organization. So coming in with that awareness and it all starts with letting that old identity go and really embracing the fact you gotta earn the respect in this new role all over again. The second one is self sufficiency is now your superpower. You’re going to be doing things you probably haven’t done in years. Maybe it is as simple as booking your own meetings or building your own slide decks or writing your own copy for something, or as simple as submitting your own expenses.

0:15:53 – (Ramona Shaw): Right. It might feel like a step back of like, oh my gosh, I had an assistant who do that, or we had a tool that would automatically read the expenses. Now I have to manually take pictures and submit them in a spreadsheet. If we let our ego get in the way and we feel like this is a step back, then that’s going to Be challenging because it really isn’t. It’s just about doing the job differently and building new muscle, so to speak.

0:16:19 – (Ramona Shaw): A leader that I know once said that in their second week at a startup, they negotiated a contract, prepped a company wide presentation and onboarded an intern all in one day without any help or additional team members supporting her. And that seemed to be crazy to think about just month before. But now in this startup environment, that’s just how it’s going to go. And that’s what they had to do. You have to be self sufficient and get through the work that is sort of that scrappy get it done mindset. And that’s what makes you valuable. That’s often what startups really are looking for.

0:16:58 – (Ramona Shaw): The third mindset shift is speed over perfection. If you like things polished and perfect, startup life might stress you out because things often work really fast. Mvp, soft launches, beta testing, ship it, learn, iterate. It’s not that quality doesn’t matter, it totally does. But speed is often a strategy to survive. And I’ve heard Lita say, you know, I used to spend weeks refining a deck and now I get it to 80% and I just send it and refix it on the fly.

0:17:33 – (Ramona Shaw): So that shift away from perfection to progress is a big game changer. And if you feel like, oh, I can’t let that go, I also got to prove how good I am. And so everything needs to be perfect that the team or that senior leaders see. For me, in that startup environment, you might actually hurt yourself because it’s going to slow you down and you might be perceived as not adaptable and not fast enough, or of making things too compliment, complicating, delaying decisions and so forth.

0:18:05 – (Ramona Shaw): Okay, so now the fourth mindset shift is input over authority. So you might be used to being the person people defer to, but in a startup, everyone’s expected to contribute regardless of their title. So if you’re surprised if a junior developer pushes back on your strategy again, that can get difficult because it’s often not personal. It’s usually not personal, it’s just how these teams operate. And so the best thing that you can do is to listen, to really listen.

0:18:37 – (Ramona Shaw): Like this one founder who once publicly said that their most impactful hire was a former VP who spent their first weeks just absorbing, asking questions, understanding the rhythm before then quietly dropping a thoughtful idea in slack and inviting feedback and how much he appreciated that approach and then encouraged all these other new hires thereafter to adapt a very similar approach in their 3,069 new plants.

0:19:05 – (Ramona Shaw): That’s how to lead without the ego. So not coming in trying to prove yourself, but really coming in trying to listen and seek the input versus relying on authority. Okay, moving on to the fifth one. So in that big org that you’ve worked, there may have been innoprents five year strategic plans. There’s the big vision statement, that is the mission. All these different pieces are in place and what you might find in a startup is that A planning is really flexible and it can shift really quickly, B we might have not even found product market fit or that all is still a bit evolving. Or maybe you’re in a situation where you realize, hey, we’re totally pivoting what we thought based on external factors such as technological advancements or economy.

0:19:54 – (Ramona Shaw): Imagine a time when sort of OpenAI first released its first ChatGPT model and how many companies you had, you know, their strategic plans and had that all mapped out, suddenly looked at this and realized, wow, if we continue to do what we’ve been doing, we’re going to die within the next 12 months because ChatGPT can totally replace what we plan to do. So they had to all get back to the drawing boards and figure out what is now their value add angle where everyone has access to Chennai through a tool like ChatGPT.

0:20:27 – (Ramona Shaw): So with that in startups things shift really fast because there’s like that single focus on often a single product versus large organizations who have multiple revenue streams, multiple ways that they want to progress. So your priorities, let’s say in January, might be completely irrelevant by April. And that can be frustrating, especially if you’re someone who loves long term planning, stability, clarity and clear focus.

0:20:55 – (Ramona Shaw): But this is also the chance where you can say okay, how do I practice being more agile? Where are we heading and why are we heading there and what does this mean for us now versus okay, what have we already locked in and how are we going to execute on what is already been decided? So really shifting and becoming a lot more involved in assessing the direction of the organization and the team as such.

0:21:22 – (Ramona Shaw): So the most effective leaders in such situations build flexible frameworks. They focus on pivoting where needed, sort of shorter term planning cycles and so forth. They adapt their working model to adjust to the required flexibility. And then the last point, we can’t really leave this one out. It’s that whole work life blend, not necessarily a balance. Oftentimes startup life doesn’t fit into sort of a 9 to 5 box.

0:21:52 – (Ramona Shaw): You might have late nights during crunch time, you might also take a long lunch or hit a midday workout without anyone really batting an eye. And you know, multiple times I have people say I used to, you know, always leave the office at 4:30 to pick up my kid from school. I might have, you know, opened my laptop again and worked for an hour or so after that. But typically that was it. And I would hardly ever work on a weekend unless I had to travel.

0:22:18 – (Ramona Shaw): But now in the startup environment it’s just expected that everyone pulls longer hours and the rhythm is completely different. That means not only do you and your sort of whole holistic life need to change a bit, but also it’s often that other people in your life might be impacted. Let’s say a spouse or children or family or friends who see that you now are running on a different schedule. And if you’re unprepared to handle that and start to feel resentful when you’re asked to stay late or when it’s just expected and you don’t really get a thank you for it, then that can starts to feel frustrating. And again this resentment builds up which is not helpful.

0:22:57 – (Ramona Shaw): So you really have to figure out what works for you. Some startups really celebrate this work life blend and boundaries and are really clear. We do not slack anyone after 6pm we do not slack or email people on weekends and whatnot. That is something that you would want to evaluate obviously in the interview process, not that you land there and then you realize, oh shoot, I wasn’t aware how much work and how many hours might go into being successful in this job.

0:23:25 – (Ramona Shaw): Okay, so let me quickly recap the six shifts that we talked about. The first one was let go of your corporate identity. That’s a thing of the past. You’re re establishing your the respect and your agency and authority here. Second, self sufficiency is now your superpower. Third, speed over perfection. Fourth is input, like asking for input over authority, especially early on. The fifth was being flexible to planning to pivot fast, but also spend a lot more in setting their direction for your team.

0:23:58 – (Ramona Shaw): And then the last one was really understanding that work life plan what that looks like and mean for you. Okay, now let’s talk a little bit about what startup teams might expect from you. So startup teams want your experience, but they don’t want you to recreate that corporation you just left. They’re usually not bringing you in because they think, oh, that corporate experience is really useful. Unless that is explicitly stated where someone may say, hey, we’re bringing on a VP of finance in order to systematize our processes, in order to prepare us for maybe another fundraising round. And we have to get our stuff together. So we’re bringing you in because we want you to take as much from your corporate experience and apply that here.

0:24:46 – (Ramona Shaw): But if that is not explicitly stated or agreed on, then oftentimes they’re getting you because of your skills and your experience, not because they want you to recreate what you’ve left. Because founders and even, you know, often these startup employees, especially the early ones, they’re often looking and making sure that they’re not hiring people who over complicate things, who this the current team’s scrappy solutions who need to have processes for everything and always think that their way and the way that big, big orgs do it is better just because they see it work elsewhere.

0:25:26 – (Ramona Shaw): In another conversation with the leader, someone said to me along the lines of them having hired a pretty senior leader from a big org who then spent their first month or six weeks or so trying to implement a three step approval process for expenses. And he said, we were like 20 people at the time. And I got that. That seemed to be the smart thing to do and we needed to make sure that not everyone was just, you know, using their credit cards for God knows what, but it was also just an overkill.

0:25:57 – (Ramona Shaw): Not only did everyone sort of hated and disliked the fact that they had to go through this three step process because it didn’t fly with us. The culture is all about autonomy and everyone was being really resourceful because we didn’t have a long Runway. We had to be really careful with our money. So it almost felt like we were no longer trusting team members that they would be resourceful and caring about the money that they spent. Because now we’ve asked them to get to go through this approval process so that, you know, it was overall a good intention to help us systematize, but it was totally the wrong thing at that time.

0:26:33 – (Ramona Shaw): If you look at that example, and it may sound like an extreme one and such an obvious one, but those things happen all the time where someone comes in and they think, oh, this is what the company needs because obviously we’re trying to get bigger and grow, so this is important, but it’s not at all what the team values. So again, this goes back to this idea of really looking for input, really listening, really trying to adapt and embrace this new environment versus coming in with a lot of assumptions.

0:27:02 – (Ramona Shaw): And in addition, leaders who operate well are those who go into the trenches, they communicate really clearly and often they are nimble, they can quickly pivot, they have respect for the existing culture and systems, but they also call out what they recognize and see as potential blind spots. They ask a lot of questions to their team. Their share their expertise through collaboration, not through commands.

0:27:32 – (Ramona Shaw): And they fully acknowledge what’s already working or why something has worked so far and why that was a good thing before suggesting changes. So it’s like the respect for what the team has already done before coming in and labeling something as crap. So before we wrap up, let’s call out the frictions and the typical things that come up. The typical complaints are, my gosh, I used to have so much support, so many more resources at hand.

0:27:56 – (Ramona Shaw): Now I feel like it’s all just dependent on me and it feels really heavy on my shoulders. One second one there’s so much ambiguity. Everything is constantly changing and I don’t have much clarity of where we’re going. Yes, things change fast. Like consider that a challenge. Like it’s going to strengthen you in some core leadership skill. So instead of resisting the change, really practice how to engage with those kind of moments of pivoting.

0:28:24 – (Ramona Shaw): Speaking of how to deal with all these specific challenges, I want to highlight five quick strategies for navigating this transition into startup really, really well. First of all, quick wins. Build trust. So find something small but meaningful that you can improve. Again, don’t try to implement a whole new process. Find something small and meaningful. It could be as simple as streamlining a messy onboarding process or doing something to improve, password sharing or whatever that may be.

0:28:55 – (Ramona Shaw): Create one small routine. Could be a daily standup. It could be introducing shared documents. It could be having a one page business plan or strategy that you review with a team on a regular basis. Don’t drown the team in too much structure and too many new changes and routines. Start with 1/3. Teach others by modeling behaviors Instead of telling people, here’s how we should be running a project. Just run one well and let people see what you’re doing and let the results speak for themselves.

0:29:33 – (Ramona Shaw): If that’s actually what’s working, they will naturally adopt and learn through observation. Fourth one Practice open communication. So use Slack or whatever collaboration tools are out there to communicate. Hold Q&As for people to ask for you to have a dialogue with what’s working, what isn’t working. Be as transparent as you can be in order to build trust fast and to solicit feedback. You want to know what other people see, what they like, what they don’t like. It’s not that you need to listen to all the feedback and make all the changes suggested, but it is signaling that you’re curious to hear their inputs and that you’re taking feedback well.

0:30:13 – (Ramona Shaw): And then the fifth one Just respect the chaos and even embrace it. It can be tempting to try to clean everything up and make it all good so that you can feel more calm and in control. But in early stages, some of the chaos can be productive. It means things are growing and evolving. So if that’s what the team is used to, just let that be for a moment and focus on something that matters a lot more than that.

0:30:39 – (Ramona Shaw): This transition overall will likely test you, but it will also grow you. And I’ve seen this over and over again. Religious go through it. They embrace the friction, they struggle, they get frustrated, but they come out on the other side and they realize how much more adaptable they’ve become and how much wider their perspective says and how to go about certain problems. And that’s a wrap for this podcast episode. If you work with someone who is thinking about making that career shift, or someone who’s in the midst of it or has done it, please share this podcast episode along and and if you are looking for a sounding board, someone who can help you lead effectively in a new environment, that is what executive and leadership coaching is exactly here to do.

0:31:23 – (Ramona Shaw): So check the show notes for a link to schedule a strategy call so we can talk about what that would look like for you and how coaching can significantly increase how well you do through this transition to make it as likely as possible for you to be successful, to have a team and senior leaders who trust and respect you. And with that said, I wish you a productive and successful rest of your week and we’ll see you next time. Bye bye. If you enjoyed this episode, then check out two other awesome resources to help you become a leader people love to work with.

0:31:54 – (Ramona Shaw): This includes a free masterclass on how to successfully lead as a new manager. Check it out@archova.org/ Masterclass the second resource is my best selling book the confident and competent New Manager. How to quickly rise to success in your first leadership role. Check it out@archova.org/books or head on over to Amazon and grab your copy there. You can find all those links in the show notes down below.