10 Common Challenges First-Time Managers Face at Fast Growing Startups

Blog 7 - 13 Common Challenges First-Time Managers Face at Fast Growing Startups

10 Common Challenges First-Time Managers Face at Fast Growing Startups

Have you ever considered how being a first-time manager of a fast-growing startup has many similarities to driving a car?
Just as learning to drive requires acquiring new skills and adapting to a dynamic environment, becoming a manager demands the same level of agility and adaptability in a rapidly evolving startup landscape. From navigating the twists and turns of team dynamics to accelerating toward growth milestones, the similarities between these journeys are striking.
In this blog, we’ll dive into the 10 common challenges first-time managers face at fast-growing startups and equip you with invaluable insights and practical strategies to steer your team toward success.

1. Leading Remote or Distributed Teams

Picture yourself taking an exciting trip abroad that includes a road trip. You will have to learn to drive in a new country quickly as you tour the countryside, making numerous stops in multiple cities along the way. Everything there will be different and not only will you be unfamiliar with the layout of each city, but all the road signs, traffic patterns, and local rules will also differ. Similarly, leading remote teams introduces a new landscape with its own set of challenges, such as coordinating across different time zones, utilizing virtual collaboration tools effectively, and fostering strong team communication without the benefit of face-to-face interaction. Both experiences require honing your instincts and utilizing strong emotional intelligence skills, all while staying focused on the road ahead, and adjusting your approach to ensure smooth navigation.

Unlike bigger and more mature organizations which often have an existing global or national footprint and are used to working across different locations and time zones, leaders in startup organizations who work in a remote or hybrid model have to start from scratch and adapt their routines and processes to create a fair and inclusive environment for all their employees.

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2. Balancing Workload and Priorities

Imagine yourself leaving your downtown office after a long day of work. As you sit in your car, ready to head home, you approach a bustling street. A stream of fellow office workers is making their way out too, while pedestrians cross the road towards the nearby parking garage. With cautious precision, you maneuver across several lanes, to make it to your turn. Patiently navigating slow traffic, you encounter a few red lights that further slow you down. Finally, after a series of brief stops and starts, you triumphantly merge onto the highway heading home.
Similarly, as a new manager, you’ll face a multitude of responsibilities, deadlines, and competing priorities that require careful navigation. Just as a skilled driver knows when to accelerate, brake, or change lanes to reach their destination safely, an effective manager must adeptly juggle tasks, delegate responsibilities, and make strategic decisions to achieve team goals.
New managers will be required to maintain focus while remaining adaptable with the ability to swiftly assess and respond to changing circumstances.

Most new managers at startups are responsible for both IC tasks and management work which many experience as a tricky balancing act. In addition, startup employees tend to wear many more hats and more ambiguous and faster-changing roles and responsibilities than employees at bigger corporations. Considering these different demands, leaders at startups need to quickly learn how to prioritize their own work and help their team get clear on their ever-changing priorities.

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3. Skillset Upgrade

Just like upgrading your vehicle from a bike to a car requires a change and significant upgrade in skillsets, the same is true when upgrading from an IC role to a leadership role. Remember learning to drive, sitting in the driver’s seat for the first time, with your hands on the steering wheel at 9 and 3? To drive confidently, you need to master skills such as maintaining control, observing road conditions, making quick decisions, and using your signals and speed control to drive safely with other cars around you. Similarly, as a new manager, you must learn new leadership skills like communicating, decision-making, delegating, and giving feedback to guide your team through the fast-paced startup environment. This requires practice, self-awareness, and a commitment to continuous improvement.
Many new managers think that they’ll be fine in their new role and that they’ll figure it out as they go. In essence, they are saying “I’ve never driven a car but that’s not a big deal. I’ll learn how to drive a car when I use it to get to work on Monday.” We would all be scared of that person on the road.
The smarter way to learn how to drive is to get training and someone more experienced sitting next to you to help you get started. The same is true when developing leadership skills. Getting training and support early on makes a huge difference. In startups, this is often overlooked due to the high demands on work output and fast growth. However, chances are high that the new managers struggle and make life unnecessarily hard for their direct reports.
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4. Fostering Innovation and Maintaining a Startup Culture

Have you ever thought about the fact that people have different types of vehicles based on where they live and what they do for a living? If you live in the north, you will likely have snow chains for your tires. If you live in the mountains you will likely have all-wheel drive vehicles. If you live in the country, you may have a truck for pulling livestock trailers, and if you live near a beach you might have and Jeep with no roof and no doors. Depending on the terrain, weather conditions, and purpose, you would choose a different vehicle.
Similarly, as a new manager, you are responsible for choosing the best vehicle for cultivating an environment that encourages creativity, forward-thinking, and a sense of entrepreneurial spirit within your team. An effective manager must adapt their leadership approach to the situation they’re in.

It can be a difficult balancing act for managers in a fast-growing startup to foster innovation while maintaining the startup culture. No doubt, there are many startup characteristics that lead to its initial success, and those traits are important to maintain as the startup grows. But as time goes on, it may be difficult for managers to continue moving the company forward, embracing growth and change, while still maintaining that initial magic feeling of being a startup.

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5. Handling Conflict and Difficult Conversations

Picture yourself driving on a busy road, encountering scenarios where you need to respond to aggressive drivers, merge into tight spaces, or handle unexpected detours. Similarly, as a new manager, you will inevitably face conflicts within your team or difficult conversations with employees, stakeholders, or even superiors. Just as a skilled driver remains calm, communicates clearly, and seeks resolutions to keep the journey smooth, an effective manager must approach conflict with a level-headed mindset, practice active listening, and engage in constructive dialogue to address concerns and find mutually beneficial solutions. Both endeavors require emotional intelligence, the ability to de-escalate tense situations, and the courage to have honest conversations.

Many first-time managers at fast-growing startups often find themselves all of a sudden in a leadership role because the team grows suddenly. Because of the rapid growth the startup experiences, they may skip leadership training. But that’s a big and costly mistake. For example, new managers often struggle with handling conflicts among team members or giving tough feedback because it’s the first time they have to do this. It’s important to be properly equipped with tools that help these types of conversations go smoothly so that it creates more synergy not decreased efficiency and disengagement among the team.

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6. Managing Burnout and Employee Well-Being

Just as driving requires maintaining a steady pace, monitoring fuel levels, and recognizing signs of fatigue, managing burnout and employee well-being demands a similar level of attentiveness and proactive measures.
Imagine yourself on a long road trip, where you need to ensure a comfortable driving environment, take regular breaks to rest and recharge and stay mindful of your own energy levels to avoid exhaustion.
Similarly, as a new manager, it is crucial to create a supportive work environment that promotes work-life balance, recognizes the signs of burnout, and prioritizes employee well-being. Just as a responsible driver knows the importance of maintaining their vehicle and avoiding fatigue to ensure a safe and smooth journey, an effective manager must prioritize self-care and support their team in managing workload, setting boundaries, and fostering a culture of well-being.
Both endeavors require empathy, proactive measures, and the ability to recognize the signs of burnout or stress.

As a new startup, there are often countless tasks that need attention all at one time. This can create a sense of overwhelm for many, especially a first-time manager. Not only do they face the challenges of managing their own burnout but they also have to prioritize the well-being of their team amidst the fast-paced and demanding startup environment.

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7. Navigating Organizational Structure Changes

Imagine yourself driving through a busy city with intricate road systems, interchanges, and detours. Similarly, as a new manager in a fast-growing startup, you’ll encounter shifts in reporting lines, departmental restructuring, and evolving team dynamics. Just as a skilled driver relies on maps, GPS, and road signs to navigate complex routes, an effective manager must rely on organizational charts, communication channels, and a clear understanding of roles and responsibilities to navigate structural changes successfully. Both endeavors require an ability to quickly grasp new hierarchies, establish connections with key stakeholders, and align team goals within the revised structure.

Organizational structures at every company are dynamic and fluid, always changing and evolving. However, at a fast-growing startup, the organizational structure will not only change faster, but those ripples of change will permeate throughout the smaller teams stronger. Imagine a marketing team of three people that loses a team member due to personal reasons. Not only will all those duties need to be reassigned to the remaining 2 members, but the manager will also be faced with attracting and hiring a new member of the team while trying to retain everyone else. During periods of leadership transitions or restructuring, it’s important to maintain employee morale and keep expectations realistic when it comes to workloads.

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8. Balancing Short-Term Goals and Long-Term Vision

Just as driving requires focusing on immediate road conditions while staying mindful of your ultimate destination, managing short-term goals and long-term vision demands a similar approach. Picture yourself driving towards a scenic destination, where you need to navigate through various landmarks, intersections, and turns. Similarly, as a new manager, you must strike a balance between accomplishing short-term objectives and aligning them with the long-term vision of the startup. Just as a skilled driver manages the immediate challenges of traffic and road signs without losing sight of their final destination, an effective manager must prioritize short-term milestones while ensuring they contribute to the overarching strategic objectives. Both endeavors require foresight, strategic thinking, and the ability to make calculated decisions that align with the long-term vision.

With so many projects requiring the manager’s attention, it is key to find the right balance between achieving short-term goals while aligning the team’s efforts with the long-term vision and impact of the company. It’s important for new managers to know which tasks and projects will align with both and not be a distraction. In addition, it’s important to recognize that timing plays a key part here as well; knowing which fires to put out at the right times and which ones to let burn temporarily is a critical piece of managing a high-performing team in a fast-growing startup.

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9. Developing Effective Communication Strategies

Just as driving requires clear and concise communication through signals, horn honks, and following traffic rules, developing effective communication strategies as a manager demands similar skills of clarity, active listening, and adapting to different communication styles. Imagine yourself driving on a busy road, where you need to use turn signals, make eye contact with other drivers, and react to their cues to ensure a smooth flow of traffic. Similarly, as a new manager, you must communicate expectations, provide feedback, and foster open dialogue with your team members and stakeholders.
Just as a skilled driver adjusts their communication style to be assertive, yet respectful on the road, an effective manager must adapt their communication strategies to different situations, individuals, and cultural contexts. Both endeavors require empathy, the ability to articulate thoughts clearly, and active listening to ensure effective exchange of information.

It is imperative that messages are conveyed with clarity in the startup phase because time is of the essence in order to grow quickly. New managers need strong verbal and nonverbal skills in order to ensure clarity, transparency, and efficient information flow within the team and across the organization. This not only means that the team has to be cohesive but that the manager needs to equip them with tools that help them communicate effectively. This doesn’t just mean with email or messaging apps. Using project management tools, such as ClickUp for example, can expedite the communication of a team on a project and allows the manager to give direct feedback each step of the way.

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10. Managing Limited Resources and Budgets

Just as driving necessitates optimizing fuel efficiency and budgeting for maintenance expenses, managing limited resources and budgets demands a similar mindset of efficiency, prioritization, and strategic decision-making. Imagine yourself behind the wheel, conscious of the fuel gauge and mileage, ensuring you reach your destination without running out of fuel or overspending on gas. Similarly, as a new manager, you must make prudent decisions when allocating resources, balancing competing demands, and maximizing the value derived from the available budget. Just as a responsible driver plans routes to minimize fuel consumption and considers cost-effective maintenance practices, an effective manager must assess needs, explore cost-saving opportunities, and make informed choices to optimize resource utilization. Both endeavors require foresight, creativity, and the ability to make trade-offs while keeping long-term sustainability in mind.

One of the biggest challenges a fast-growing startup may face is the limited resources and budgets. New managers must make strategic decisions to maximize the impact of available resources, drive growth, and be prepared to do so quickly and efficiently. Being able to make sound decisions without overanalyzing them or suffering from analysis paralysis plays a key part in the success of the managers’ ability to keep the project and organization moving forward.

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In Conclusion

While there are many parallels between being a first-time manager in a fast-growing startup and the automotive world, the main theme that remains true is that both demand the acquisition of new skills and the ability to adapt to an ever-changing environment.
There will be times of accelerated growth and quick decision-making, slick maneuvers, and unexpected detours. But any new manager who is willing to remain agile and adapt is destined for success.
And just like we seek help to learn how to drive a car, it is imperative that we get support and guidance when learning how to lead.

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