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10 Small Business Growing Pains & How to Solve Them

Your company has growth goals. But is it prepared to handle the growing pains?

Business growth is the focus of so many company goals but the very idea comes in only a few forms:

Sales growth. Profit growth. New products. Traffic or audience growth.

These are what most think of when they discuss growing the business, but they’re far from the most important factors. Not only do they contribute to company growth, but also help to maintain it.

Most inexperienced business owners never predict what happens to the business’s structure when they achieve those growth goals. They plan for growth in the spreadsheets but not with their personnel.

Or operations.

Or product creation, launching, distribution.

Or employee growth paths.

Or even benefits.

Growth naturally leads to hiring more people. Most don’t think more people are an issue unless they run out of office space. But your increase in personnel can quickly become the crack that causes the dam to break.

You need very different processes as a company of 5 than of 50. It can lead to challenges most CEOs don’t consider, and definitely don’t plan for.


Proactivity vs Reactivity in Business Growth

A lot can tank a business. Mismanaging funds, a lack of good marketing, and general systems failures are among the top. But something that’s arguably more important is your mode of operation.

Is it proactive or reactive?

Reactive businesses wait for the problems to arise before they solve them. Their leaders grin and crack the old, “we’ll cross that bridge when we get there.”

But what happens when the bridge is already destroyed when you arrive?

You’re not going anywhere.

Proactive businesses think holistically about goals, including the problems that can arise as a consequence of each. Making more sales doesn’t sound like an issue until you can’t fulfill them. You’ll end up with unhappy customers and negative reviews that impact the company long-term.

It seems obvious that you’d focus on being proactive. But the majority of businesses operate in a reactive state.

And unfortunately, being reactive isn’t the worst thing that happens when it’s your mode of operation.

What’s worse is that this then becomes the expectation for your team.

Your team operates as their leaders do. If the top isn’t focused on pre-mortem discussions that prevent challenges before they arise, neither will the rest of your team. You’ll end up with an entire business of reactivity.

But all hope is not lost. You can turn the ship around no matter how strong the winds are pushing you in one direction. It just might take more time and effort.

If you’re getting ahead of the problems though, these are the common business growth pains and solutions to right the ship again.


Common Small Business Growth Pains & The Proven Solutions

Don’t ignore the problems holding your business back just because they might seem too big to fix. Most often, fixing a few will make it easier to solve the rest.

If you’re new to the business ownership world, write these down and reference them when you’re setting goals.

1. Siloing

In the early days of a business, people end up wearing multiple hats. The finance guy is also the HR guy and the marketing guy is also the sales rep. This is beneficial most of the time because each part of the role can help enhance the other. Working as a sales rep will offer insight into how to market more effectively to the types of people who buy.

But as your business grows, jobs become more defined. Employees end up fitting more specifically in a single department.

While it often seems like a logical move to organize the business, it can lead to something called siloing. This happens when certain departments work only within their department and the communication outside of it halts.

When that communication breaks down, like between marketing and sales and customer service, you shoot yourself in the foot, and slow down progress.

The Solution:

If it’s not hurting the business (and in fact, helping it), maintain some split roles if it’s what that person wants. At a minimum, make sure you have representatives from other departments present during strategic meetings. This way, they can offer insight necessary to avoid these silos in the first place.

You can also set up your project management software to include cross department collaboration in order to get thoughts and feedback about how one initiative will affect other parts of the business.

2. Disorganized Project Management

More sales. More products. More staff. It all usually involves more projects happening simultaneously. When your business is small, there are both fewer projects and fewer people involved. Communication can be handled with a short email, text, or DM, in these cases.

If there’s no intentionality as you grow to manage these projects, you end up with staff working out of email and texts and DMs, or whatever other communication software you adopted. Not to mention the task management system you end up using.

It can get messy quickly. It can lead to burn out even faster.

The Solution:

Use a project management software that can do it all in one and save on costs—including the cost of distraction and decision fatigue.

Look for features like:

  • Internal communication
  • Client access (for agencies or freelancers)
  • Project creation and organization
  • Simple to-do lists or Kanban boards
  • Document folders inside the software
  • Easy to navigate interface for faster onboarding
  • Minimal features that do the job

3. Reduced People Management

More people requires more management or those with more experience. It’s often harder to lead larger teams and continue to nurture growth, offer feedback, and maintain the relationships necessary to work well together.

The quality of how you develop talent becomes the quality of your business.

If systems aren’t in place to manage those people—including for communication, projects, and time off—it becomes problematic for growth.

The Solution:

Take into account your managers’ experience and skill set when growing teams. Are they able to handle the influx of one-on-one development and managing projects at the scale you’re growing to? Do you need to hire a department Director after your team surpasses a certain size?

Don’t make hiring plans without determining at which team sizes you need to reassess your manager’s needs. A general rule of thumb is no more than 10 direct reports per manager. Of course, figure out what works for your business and managers.

Set a benchmark for this in your business growth plans and respond. You can even build this into your to-do list hiring template so it’s never overlooked.

Example of hiring to-do list in Basecamp with a list item dedicated to determining the needs of the manager or director.
Example of hiring to-do list in Basecamp with a list item dedicated to determining the needs of the manager or director.

4. Company Goals Take Longer

It’s easier to keep three people rowing in sync than 25. A goal that might have been simple and easy to get the entire company behind at one size won’t work as you grow. Meaning, you’ll find it harder and harder to hit the same targets at the same rate.

The Solution:

Create a single project that everyone in the company has access to on a daily basis. Label it “Company Goals” and even pin it to the top (if your software allows) so it’s always in view first thing when your team logs in to work. Then create to-dos or buckets for each department where that department’s primary goal will live. From there, each individual can have goals within that area to help accomplish that team goal.

In Basecamp, it would look like this:

STEP 1 - Create a new project and label it “Company Goals”

Step 1 in creating a Company Goals project inside Basecamp.
Step 1 in creating a Company Goals project inside Basecamp.

STEP 2 - Click into “To-Dos” and make a new list for each department

Example of creating a to-do list for each department inside Basecamp.
Example of creating a to-do list for each department inside Basecamp.

STEP 3 - Fill in the list details to include the team’s goal and end date you’ll accomplish that goal by

Examples of including Teamwide Goal and End Date in to-do list details inside Basecamp.
Examples of including Teamwide Goal and End Date in to-do list details inside Basecamp.

STEP 4 - Create individual to-dos within each department list with their goals to accomplish the main department goal.

Example of creating individual goals that help achieve the department goals inside their respective to-do lists with Basecamp.
Example of creating individual goals that help achieve the department goals inside their respective to-do lists with Basecamp.

STEP 5 - Have everyone pin that project to the top of their dashboard by clicking on the gray pin icon so it’s top of mind every day

Pinning a project to the top of your dashboard inside Basecamp project management software.
Pinning a project to the top of your dashboard inside Basecamp project management software.

5. Losing Sight of the Vision

Your business has a purpose. You created it for a reason and your team should not only be aware of it, but bought in. Shared purpose can hold your company together through tough times of no growth as much as it can inspire during times of rapid growth.

Knowing why you’re doing what you’re doing is vital, especially as you grow. Oftentimes, this gets lost in the day-to-day, resulting in default modes, lack of innovation, and lost passion that can be the driving force of growth.

The Solution:

Your purpose should drive your business decisions. Does that product ultimately serve your purpose? Is that feature in line with your customer promise?

With every project, include the purpose along with the project details so it’s top of mind whenever someone views the project and clicks into it.

Example of editing a project description to include the purpose inside Basecamp.
Example of editing a project description to include the purpose inside Basecamp.
What the project details purpose statement looks like for the project from the dashboard view inside Basecamp.
What the project details purpose statement looks like for the project from the dashboard view inside Basecamp.

6. Systems That Can’t Handle Demand

It’s one thing to oversell products without the means to fulfill the demand. It’s the same to overload your internal systems that can’t handle the workload. Taking on too much work because of a lack of foresight is a huge business growth pain.

If you’re a social media marketing agency, promising too many graphics, videos, or other designs without budgeting the resources (time, capacity, funds) can sink your ship. This is in addition to potential timeline crunches and needing to communicate the state of projects with clients.

The Solution:

Know your team’s capacity. Make sure, as a leader, you’re not just assigning to-dos and projects without checking in with your team to understand what it takes to complete. And make sure you have a way to keep your clients up-to-date about the status of a project. It will save you from needing to field a ton of questions or sit in on time-wasting status meetings.

In Basecamp, you can give clients access to both projects or individual tools like to-do lists and kanban boards to cut down on client communication and keep them updated on progress.

Options to share to-do lists with clients or keep it private to the team inside Basecamp’s software.
Options to share to-do lists with clients or keep it private to the team inside Basecamp’s software.

7. Hiring & Growth Paths

As a new business, your focus is primarily on getting the work done and hiring for whatever role you need next. A big growing pain companies run into is when they lack a path for your employees to grow into.

Long-term retention is a huge factor in how well your company grows. The longer someone has been with you, the better they know the business, its customers, and your systems. They’re typically more loyal and tied into the business’s purpose and values.

But if you want to retain employees, you need a growth path for their position. If an entry level digital artist wants to become a brand manager and you’ve failed to both recognize that and create a path to develop them into it, they’re more likely to gain experience at your company and then leave when the time comes. This is costly in many ways.

The Solution:

Plan for it. In your business plans, create a future org chart. If you have business growth goals, they’ll require more people. You have to imagine what that will look like when it comes to personnel, as well as when you want to hire for those additional roles.

This will help you plan for capacity, LER, and overall direction of the business.

8. Outdated Onboarding Systems

It’s easy to forget how much your company has grown and exactly what that includes when you’re on the inside. A big growth problem for businesses is outdated onboarding practices.

You’ve hired new people, which is great! But your onboarding systems can’t be the same as when you were a small business. There’s much more to your company, which means a lot more to learn.

When your onboarding is poor, you have unprepared employees. They’re slower to get up to speed and therefore, slower to reach a level of quality work. Instead of getting what they need initially, they’re left floundering to learn systems, not sure who they can go to for help, and might even enjoy the job a lot less.

The Solution:

Get feedback about your onboarding from your new hires. Spend the time necessary to understand how it went and if they’d recommend anything to improve the system. Most often, they’ll have the best input because they just went through it.

From here, update your onboarding systems (and review them) with each new hire.

You can easily do this by creating a to-do list template for onboarding with a recurring item listed first for “review onboarding template” to make sure you’re prioritizing keeping it up to date.

To do this, navigate to your to-do lists, click “+ New List” and then “Use a to-do list template”. Then scroll below your existing templates and hit “Manage To-do List Templates”. Click on the onboarding template you want to edit and adjust as needed.

Where to find the option to Manage To-do List Templates in Basecamp.
Where to find the option to Manage To-do List Templates in Basecamp.

9. Interpersonal Relationship Challenges

In general, business owners tend to fixate on company culture.They attempt forcing it into what they really want, instead of allowing it to exist on its own. But there is cause for concern when your business grows and interpersonal relationships slip.

With small companies, it’s easier to maintain friendships. Communication is easier when there are only a few people to talk to. Larger companies have a harder time maintaining communication, and more people often means more strangers.

It also means more opportunity for conflicting personalities. Of course, diversity in the workplace—especially in the way people think and operate—is a strength. This growth pain arises when a lack of communication and non-work related conversation leads to conflict.

This is even more true in a remote-only company. Not seeing faces makes it easy to dehumanize your coworkers, boiling down their humanness to a name on a screen. If there’s conflict, there’s often fear and stress, resulting in a lack of creativity and productivity.

The Solution:

Find a way for your team to keep in touch with each other in a way that’s not only for work. This can look like a specific channel for chatting about sports, food you’re making, movies and TV you’re interested in, and other life occurrences that lead to bonding.

Use a system where your team can at least see each other’s faces with profile images, too.

In Basecamp, we do this with Chat rooms within projects. It’s a place to connect and converse in a random and fun way.

10. Excessive Workloads

In the early days of businesses, the idea of “hustling” is common. In order to get off the ground and move from a startup to a secure business, it can mean long days and work-filled weekends. If your business isn’t careful, this cultural expectation can remain long after it’s no longer needed.

At some point, you have to work smarter, not harder, not longer.

At some point, your startup is no longer a startup.

The Solution:

Don’t get sucked into the startup mentality. If you already are, gain some perspective.

In Rework: Change the Way You Work Forever by Jason Fried and David Heinemeier Hansson, they discuss the idea of a startup and what it means:

“The truth is every business, new or old, is governed by the same set of market forces and economic rules. Revenue in, expenses out. Turn a profit or wind up gone. Startups try to ignore this reality. They are run by people trying to postpone the inevitable, i.e., that moment when their business has to grow up, turn a profit, and be a real, sustainable business.

Anyone who takes a ‘we’ll figure out how to profit in the future’ attitude to business is being ridiculous. That’s like building a rocket ship but starting off by saying, ‘Let’s pretend gravity doesn’t exist.’ A business without a path to profit isn’t a business, it’s a hobby.”

The solution is to recognize that you’re a business. Businesses can’t run on hustle culture and no plans. Expecting that every single one of your employees can dedicate the bulk of their lives to running your business is completely unrealistic, just like trying to push out your plans for profitability to an unnamed someday.


Business growth can come with a lot of ups and downs. The downs can easily be offset by sound logic and planning for all the facets of growth.

Want to keep a handle on your business and its growth? Consider the all new Basecamp.

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