How Growing Teams Can Overcome Their Biggest Challenges

Growth is exciting, but it’s not always easy.  

Simple systems that worked with a small, tight-knit team likely won’t translate well when new hires come on board. What once felt like an efficient system can turn into a chaotic mix of overlapping responsibilities, missed messages, and increasing administrative work. 

Many companies underestimate the challenges that come with scaling a team. More people mean more complex workflows, different communication styles, and a bigger need for structured processes.  

So, what are the biggest challenges growing teams face and how can you get ahead of them? Keep reading and we’ll let address the biggest struggles that come with a growing headcount and how to address them.  

The Hidden Costs of Poor Growth Planning 

Scaling without structure is a recipe for disaster. When businesses don’t adapt their policies to their growing team, it can cause serious issues including misalignment, inefficiencies, and even burnout.

In fact, a study by McKinsey & Company found that companies that scale too quickly and without proper planning experience a 20% higher turnover rate than those with structured growth plans.  

Increased turnover means more time and resources spent on recruiting and training. Additionally, when employees are unclear on responsibilities, productivity drops, and costly mistakes become more frequent.  

Companies that invest in scalable systems early on tend to see stronger long-term success. The good news? You don’t need to overhaul your entire company’s processes, just a few key adjustments can make a big impact.

Common Challenges Faced by Growing Teams (And How to Solve Them)

Lack of Alignment & Communication 

Watercooler chats and lunchtime catch ups might work in a startup’s early days, but as headcount increases, relying on informal communication leads to gaps in knowledge-sharing.  

The bigger the team, the more information, and the greater the need is for communication. When your team is small, company-wide meetings are easy to orchestrate. But, as your team grows, it’s easy for information to get lost and have employees working in silos.  

Without proper systems put into place, it’s almost impossible to keep your team aligned, resulting in inconsistencies, differing priorities, and delays. A layer of complexity is added for remote or hybrid teams, who need to make deliberate efforts to communicate in order to stay on the same page. 

To prevent these issues in your growing team, we recommend setting up structured communication methods from the get-go. Employees need clear channels to ask questions, receive updates, and collaborate efficiently. Having designated spaces for different types of communication including project-specific discussions and general company-wide updates can help teams stay informed without losing flexibility. 

This includes communication tools like Slack or Teams, project management tools like Jira or Asana, and setting up recurring meetings to check in on your team's progress and encourage collaboration. Teams working in different time zones can use tools designed to improve asynchronous communication, like Hive or Loom.

Workload Distribution & Burnout  

Your team is growing and so are their responsibilities. But is it all too much?  

Periods of rapid growth can be exciting, but also stressful. It's not uncommon for leaders to put pressure on their team when trying to motivate and inspire them during pivotal moments in the company's growth. While it’s usually done with good intentions, this can often cause employees lots of stress and potentially puts them on the path to burnout.

To make sure your team is not overworked, look out for signs like:

• Employees frequently working overtime to meet deadlines 
• Rising absenteeism  
• Lower engagement levels 
• Uneven distribution of tasks 

These are key indicators that you're struggling with proper workload distribution and that your team might be headed towards burnout. To prevent this, assess areas where automation can help to lighten the load. Repetitive admin tasks like scheduling and PTO tracking can easily be done using software rather than taking up valuable time away from your employees.  

Consider implementing a performance review system to encourage conversations between employees and their managers and help to identify workload concerns before they escalate into burnout. 

Managing Time Off 

More employees mean more to coordinate, especially when it comes to scheduling. It’s easy to keep track of time off in a small startup environment, but as your growing team expands into the double digits and you grow your departments, it becomes harder and harder to keep track of where everyone is. Spreadsheets, paper forms, emails, or the good old honor system cause unnecessary scheduling conflicts that frustrates your team and delays your projects. Plus, errors in PTO tracking can lead to discrepancies in payroll, affecting compliance and upsetting your employees. 

The fix? PTO tracking software.

Automating the process helps to streamline leave requests, maintain real-time visibility, and integrate with calendars to prevent conflicts. Solutions like Vacation Tracker make it easy for teams to request, approve, and track leave without manual updates and mistakes.

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Maintaining Company Culture 

Smaller teams tend to be more tight knit. It’s easy to organize team lunches when you’re only a handful of employees. And odds are you’ll be spending a lot of time with a small group of people and collaborating closely. Plus, startup environments tend to be less formal, allowing for less work-talk and more opportunities to build friendships. 

So how do you ensure you keep your team engaged as your grow? 

Here are 3 key strategies that you can implement today: 

1. Create intentional team-building moments: Virtual or in-person, make space for connection outside of daily work. 
2. Encourage leadership transparency: Open communication from the top helps employees feel connected to the bigger picture. 
3. Celebrate wins: Recognizing achievements, individually and as a team, reinforces a positive, engaged work environment.    

Practical Strategies for Scaling Your Team Successfully   

Automating Processes to Reduce Admin Overload  

Admin work increases with your headcount, and without automation, your team can quickly become overwhelmed with repetitive and time-consuming tasks. As organizations scale, the demand for efficient workflows and streamlined processes grows. By leveraging automation, companies can free up valuable time, improve accuracy, and allow employees to focus on higher-value work. 

Automation can optimize several different parts of your business, including: 

• PTO tracking: Instead of relying on spreadsheets, teams can use automated PTO tracking tools like Vacation Tracker to manage time-off requests, approvals, and calendar integrations. 
• Payroll processing: Automated payroll systems ensure accurate calculations, tax deductions, and direct deposits without manual intervention. 
• Employee onboarding: HR automation tools can send welcome emails, collect documents, and assign training materials to new hires without requiring HR managers to do everything manually. 
• Project management workflows: Task automation in project management platforms like Asana, Jira, or Trello can help assign responsibilities, set deadlines, and track progress automatically. 
• Performance management: Automated reminders for performance reviews, feedback sessions, and goal tracking help keep employees and managers aligned. 

Setting Clear Policies & Expectations Early  

A lack of clear policies can lead to confusion, inconsistencies, and potential compliance risks. Companies should document everything from the start, including PTO policies, communication rules, and individual responsibilities. As companies grow, having well-documented policies ensures that all employees understand expectations, workplace guidelines, and their rights. 

Here are some best practices to successfully manage policies within a growing workforce: 

• Store policies in a central, easily accessible location: Use an internal wiki, employee handbook, or HR platform like Notion, Confluence, or BambooHR, and make sure all employees can access policies at any time. 
• Create clear, concise, and up-to-date policies: Avoid jargon. Write policies in a straightforward, easy-to-understand format and regularly update policies as laws change or company needs evolve. 
• Communicate policy changes proactively: Announce updates via email, Slack, or company meetings and provide opportunities for employees to ask questions or seek clarification. 
• Require employee acknowledgment: Have employees sign off on important policies and keep digital records of acknowledgments for compliance purposes. 
• Offer training: Conduct onboarding sessions to familiarize new employees with company policies and offer refresher courses for existing employees. 

Encouraging Transparency & Self-Management  

As teams grow, fostering transparency and promoting self-management are essential for efficiency and engagement. Employees should feel empowered to track their leave balances and access key company information without unnecessary bureaucracy. 

Transparency helps build trust, alignment, and accountability within a growing organization. When employees understand how decisions are made and have visibility into company operations, they feel more engaged and motivated. 

Self-management empowers employees to take ownership of their work and responsibilities, reducing micromanagement and improving efficiency. 

Here’s how organizations can encourage self-management: 

Implement self-service HR tools 

• PTO Tracking: Employees should be able to check their PTO balances, submit requests, and see team availability using tools like Vacation Tracker. 
• Expense Management: Implement software that allows employees to submit reimbursements without excessive paperwork. 
• Benefits Enrollment: Employees should be able to access and modify benefits via self-service portals. 

Promote a culture of transparency 

• Share company goals, financial updates, and key metrics through meetings, dashboards, or internal newsletters. 
• Encourage leadership to be open about decisions and strategy. 

Use shared calendars and scheduling tools 

• Visibility into who is on leave or unavailable helps teams plan better. 
• Integrate PTO tracking with tools like Google Calendar, Outlook, or Slack.

Encourage employee-driven problem-solving 

• Allow teams to make decisions within their scope without excessive approval processes. 
• Support initiatives that encourage employees to take responsibility for improving processes and workflows. 

Provide continuous feedback and check-ins 

• Regularly check in with employees to discuss workload, concerns, and areas for growth. 

By integrating transparency and self-management into company culture, growing teams can maintain agility, improve efficiency, and keep employees engaged. 

Next Steps for Your Growing Team

Every company has a plan for growth. But do you have a plan for what happens once you get there?

A growing company means a growing team. And that comes with its own set of challenges.  

We’ve summarized the biggest issues teams usually encounter and gave you some easy suggestions that you can implement immediately to prevent them from impacting your progress.  

If you have only 30 minutes, we recommend starting with implementing a leave tracking software. It’s a simple switch that reduces admin work, minimizes scheduling conflicts, and gives employees the transparency they need to plan their time off confidently.

With Vacation Tracker, your leave management system scales with your team. Whether you’re a startup or a fast-growing company, you can: 

• Customize leave policies for different locations, departments, or employees
• Integrate directly with Slack, Microsoft Teams, and Google Workspace to keep PTO tracking connected to your daily workflow 
• Generate real-time reports to track trends and stay compliant as your team expands 
• Enhance functionality with add-ons to customize the system to your team’s workflow as you grow

Instead of relying on spreadsheets or manual tracking, Vacation Tracker grows with you so managing leave stays simple, no matter how big your team gets. 

The best part? You can set it up in minutes and start seeing results right away.

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