The Workup team has spoken with many small business owners over the past couple of years, ranging from start-ups to scale-ups to well-established small businesses.
What stood out was how often these owners faced the same day-to-day challenges, causing regular stress and sleepless nights. Running a business is always hard, especially with the responsibility of employees, clients, and loved ones relying on you.
Again and again, we heard about the same operational issues cropping up. Below are the five most common pain points that were identified, along with strategies to tackle them effectively.
1: "Cashflow, cashflow, cashflow. I need to make payroll each month"
Cashflow is the lifeblood of any business, but for small business owners, it often feels like a never-ending juggling act. The need to make payroll every month isn’t just a financial obligation, it’s a fundamental aspect of maintaining team morale, retaining skilled employees, and ensuring the business can continue operating.
Why is this a challenge for small businesses?
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Thin Margins and High Stakes: Small businesses operate on razor-thin margins and lack financial buffers. They don’t have the luxury of absorbing significant losses or delays in payment.
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Client Payment Delays: Small businesses rarely have the leverage to enforce strict payment terms, and chasing overdue invoices takes up valuable time that could be spent on growing the business. When payments don’t arrive on schedule, it puts payroll and other essential expenses at risk.
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Untracked Non-Billable Hours: Non-billable time, whether it’s spent on internal admin, rework, or client communication, can snowball into hours of lost productivity. When time isn’t tracked effectively, it becomes invisible to the business owner.
What can be done?
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Implement a Rolling Cash Flow Forecast: Use forecasting tools available in systems such as Xero or QuickBooks to project your cash flow for the next 12 months based on actual data and anticipated changes. (For a comprehensive guide on creating a rolling cash flow forecast, including step-by-step instructions and templates, you can refer to this great guide from Bench)
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Track Billable vs. Non-Billable Hours: Use time-tracking tools like Toggl, Harvest, or Workup to differentiate between billable and non-billable hours. This clarity helps you identify where resources are being spent. Workup will shortly be publishing a comprehensive step-by-step guide to help you manage billable vs non-billable hours.
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Accelerate Receivables: Often it is unpractical to shorten debtor payment terms, but solutions are available, such as offering small discounts for early payment, minimise time-to-invoice (watch this space for a detailed article on this in the near future!) or consider retainers or advance payments for long-term projects.
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Build a Payroll Reserve: Set aside surplus funds during peak revenue periods to cover lean months. Use tools like Wise or Revolut to automatically transfer a percentage of incoming revenue into a reserve account
Interested to know more? Read our full guide on managing cashflow effectively.
2: “Effectively using my resources can be the difference between success and failure.”
Every resource—time, money, and people—matters in a small business. With lean teams and tight budgets, inefficient resource allocation can lead to burnout, underutilisation, missed deadlines, and unscalable operations. How resources are allocated can often make or break a project, impact client relationships, and ultimately determine the success of the business.
Why is this a challenge?
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Overextension: Small businesses often rely on a handful of key individuals to wear multiple hats. This can result in team members being stretched too thin, often creating a cycle of firefighting, stress and ineffiency.
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Missed Deadlines and Client Dissatisfaction: Overcommitting resources can result in projects running late or falling below expected standards. This can damage reputations, lead to lost contracts, and even harm the company’s ability to attract new clients. For businesses reliant on word-of-mouth referrals, this can have long-term consequences.
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Underutilised Resources: On the flip side, small businesses sometimes fail to fully utilise their resources, leaving skills, capacity, or tools untapped. Whether it’s a talented team member stuck on admin tasks or software investments gathering dust, underutilisation represents wasted potential.
What can be done?
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Understand Current Resource Utilisation: Before optimising resource allocation, it’s crucial to understand where your resources are currently being used. Consider introducing time tracking tools such as Toggl or Workup to identify which tasks consume the most time.
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Use a Skill Mapping System: Consider using a skills mapping tool such as the one within Workup, or alternatives like CompetencyCore or TalentGuard, to create a detailed inventory of each team member’s skills, certifications, and areas of expertise. Align skills with current and upcoming business needs and address any skills gaps through upskilling or recruitment.
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Leverage Resource Planning Tools: Platforms like Workup, Asana, or Monday.com offer resource planning features that allow businesses to allocate future workload based on team capacity and skills, monitor project progress and provide management insights at a glance to aid decision making.
Read on to understand more about effective resource allocation.
3: “I spend more time on admin than on actual client work.”
For small business owners, every hour is valuable. Yet, too often, those hours are swallowed up by endless admin tasks—tracking invoices, chasing payments, managing schedules, or manually updating spreadsheets. Instead of focusing on delivering value to clients or pursuing growth opportunities, owners and their teams find themselves buried in repetitive, time-consuming tasks that feel like a necessary evil.
Why is this a challenge?
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Inconsistent Processes: Many small businesses start without clear, standardised processes. As the business grows, a lack of consistent workflows in place mean tasks are often duplicated, forgotten, or delayed. This results in more time spent fixing errors and filling gaps, rather than getting ahead on meaningful work. As the business takes on more clients or projects, the admin workload increases exponentially, which can be a barrier to scaling.
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Time Drain on Revenue-Generating Activities: Admin tasks don’t directly bring in revenue, but they’re essential to keeping the business running. The problem arises when these tasks consume a disproportionate amount of time, leaving little bandwidth for client work, business development, or strategic planning.
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Manual Work Increases Errors: Admin processes that rely heavily on manual input, like updating spreadsheets or compiling reports, are not only time-intensive but also prone to human error. Small mistakes, like entering incorrect client details or forgetting to send a follow-up email, can result in missed opportunities, damaged relationships, or financial discrepancies that take even more time to resolve.
What can be done?
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Standardise Processes: Creating structured workflows and templates for repetitive tasks ensures consistency and reduces time spent on manual work. Documenting workflows in Workup or Notion makes delegation easier and improves efficiency.
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Implement Time Management Strategies: Dedicate specific time slots for admin work and stick to them. Avoid multitasking and set clear boundaries between admin and client work.
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Adopt an All-in-One Platform: Consolidating project management, resource tracking, and invoicing into a single system eliminates the inefficiency of switching between multiple tools. Workup, Productive and Scoro provide seamless integration of multiple functions to support small businesses.
4: “Clients keep adding extra requests, and it’s hard to say no.”
Scope creep is one of the biggest threats to profitability. For small businesses, delivering exceptional client service is often at the heart of what they do. But balancing client satisfaction with maintaining profitability can feel like walking a tightrope. Extra requests can quickly derail a project’s profitability, especially when those requests aren’t properly managed or billed. Yet, saying no outright can feel risky, particularly when nurturing client relationships is vital for repeat business and referrals.
Why is this a challenge?
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Fear of Damaging Client Relationships: Many small business owners hesitate to push back on additional client requests, worried that it will jeopardise the relationship. They want to be seen as accommodating and easy to work with, but this “yes to everything” approach can backfire.
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Profit Erosion: Extra requests that aren’t accounted for in the project’s budget reduce profitability. The time and resources spent fulfilling these unplanned demands often go uncompensated, meaning the business is essentially subsidising the client.
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Lack of Clarity on Boundaries: Without clear agreements upfront, clients may not even realise they’re making additional requests. This lack of clarity puts the burden on the business to constantly manage expectations, which can feel draining and frustrating.
What can be done?
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Set Clear Boundaries: Establishing a transparent scope of work before a project begins prevents scope creep. Clearly defined contracts, along with pre-approved pricing for additional work, set client expectations upfront.
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Develop a Pricing Strategy for Extras: Structured pricing for out-of-scope requests ensures profitability. Bundled service packages or hourly add-on rates allow businesses to accommodate client needs while maintaining fair compensation.
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Use Project Management Tools: Tracking project changes and billable hours in Workup or Toggl ensures that extra work is documented and billed correctly. Automated notifications and approvals help maintain clarity on evolving project scopes.
5: “It’s hard to find new clients when most of my time goes to existing ones.”
Maintaining a steady pipeline of new clients is critical to long-term success. However, balancing business development with the demands of serving existing clients can feel impossible. The day-to-day grind of client delivery and operations leaves little room for prospecting, networking, or nurturing relationships that could lead to future work.
Why is this a challenge?
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The Immediate Always Trumps the Strategic: Existing clients often take priority because their needs are immediate, tangible, and tied directly to revenue. In contrast, business development feels like a longer-term activity with no guaranteed payoff.
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Feast or Famine Cycles: When small businesses focus entirely on delivering work to existing clients, they risk falling into the “feast or famine” trap. During busy periods, business development slows or stops, leaving no new opportunities in the pipeline. When existing work wraps up, this can lead to a lull in revenue, forcing a frantic scramble for new clients.
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Time and Energy Constraints: Prospecting and business development require focused time and effort—time that’s often unavailable when the bulk of the workday is consumed by client meetings, project delivery, and operational admin. This lack of bandwidth means prospecting activities are either rushed, inconsistent, or abandoned altogether.
What can be done?
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Allocate Dedicated Time for Business Development: Setting aside a fixed portion of the week for outreach, networking, and lead nurturing prevents prospecting from being sidelined.
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Leverage Marketing Automation: Automating email sequences, LinkedIn outreach, and ad campaigns ensures a steady flow of leads. Platforms like Mailchimp, Dripify, or LinkedIn Sales Navigator streamline client acquisition with minimal manual effort.
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Build Referral and Partnership Networks: Encouraging satisfied clients to refer new business or partnering with complementary service providers creates a sustainable lead pipeline. A structured referral program with incentives can further drive new client acquisition.
Conclusion
While these five pain points are common, they don’t have to define your business experience. With the right tools, strategies, and automation, small businesses can:
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Maintain healthy cash flow to cover payroll and reinvest in growth.
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Allocate resources efficiently to prevent burnout and inefficiencies.
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Reduce admin workload to focus on core business activities.
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Manage client expectations to avoid unplanned, unpaid work.
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Build a sustainable pipeline of new clients without neglecting existing ones.
Each of these challenges is explored in-depth in the linked blogs, providing actionable solutions and tools to help you streamline your business operations.
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