Loose watercolor rendering of data screens, photo by Hal Underwood - PeriPakroo.com

If you’re like most small business owners, you fantasize about “streamlining” and “automating” a lot. Like, a lot. The yearning for streamlined nirvana is especially strong in solo operators at early stages of growth, either right before or during the period when you first hire a contractor or employee. As soon as there’s even just one other person on your team, having systems in place becomes essential.

There are loads of great tech tools to solve business needs — but choosing and implementing technology can be a real challenge, even for tech-inclined folks. The time it takes to learn about existing software and platforms is daunting, and if you don’t take action on what you’ve researched within a short amount of time, a lot of what you just learned becomes obsolete and you have to start over again. The worthy goal of getting streamlined can feel like chasing rainbows, and it’s common to feel frustrated or downright demoralized during your quest.

Doing this work is undoubtedly resource-intensive, but the payoff can be huge.

To use tech effectively, it’s important to put appropriate time and thought into the systems you want to streamline; research the available options; make a decision and implement the technology within a defined timeframe; and train your team on the new systems. Doing this work is undoubtedly resource-intensive, but the payoff can be huge. Tools like accounting software, point of sale (POS) systems, project management software and customer relationship management (CRM) software are often the backbones of successful businesses. The sooner you invest in developing key systems, the sooner you’ll reap the benefits.

To give you an overview of the types of software and tech solutions out there, here’s an excerpt from my book The Small Business Start-Up Kit.

From The Small Business Start-Up Kit, Chapter 12:

Bookkeeping Software

Bookkeeping software is so powerful because it automates the process of generating financial reports, such as cash flow projections and balance sheets. If you take care to enter and categorize your income and expense records regularly, you can easily crunch that data and answer important questions about your business such as how much profit (or loss) you’re making, how much you’re spending on certain expenses, or how much money your customers owe you.

QuickBooks is by far the most popular bookkeeping software; it offers products for different sizes and types of businesses, including an online version that stores all your information in the cloud, making collaboration with a bookkeeper or accountant easy. Another option for businesses at the small end of the spectrum is Quicken, which focuses more on personal finances but offers a Home & Business version with plenty of features for small operators.

When choosing bookkeeping software, pick a product that offers the features you need, keeping in mind the information you need to track and what reports you need to generate. For instance, if you need to manage multiple categories of inventory  and must regularly deal with returns from retailers, the software and the version you choose should make it easy to enter and categorize inventory and to generate reports, such as a yearly summary of returns by category or by a particular retailer. QuickBooks offers dozens of add-on products, including many industry-specific applications to help you manage certain kinds of businesses, such as restaurants, retail, or manufacturing.

Finally, make sure your bookkeeper and accountant can work with whatever software you choose. Virtually all financial management professionals work with the various QuickBooks products.


A spreadsheet is a document that allows you to store information in rows and columns, making it easy to sort the information in different ways. For example, a spreadsheet containing information about your clients could have column headers of “First Name,” “Last Name,” “Business Name,” “Business Address,” “Business Phone Number,” and so on, with each row containing that information about one of your clients. If you had 50 clients, you’d have 50 rows of data, and you’d be able to sort the list by first name, last name, business name, or any other of the columns.

Beyond sorting, a big power of spreadsheets is in their ability to do mathematical formulas. This makes them particularly useful for doing budgets, project estimates, and projections. (To track actual income and expenses you’ll be better off using bookkeeping software, as described above.)

For example, you could use a spreadsheet to cost out a landscaping project, entering individual expenses in separate lines: Dirt; Gravel; Weed barrier; Plants; and so on. You could define one cell to display the sum total of all the individual expenses, so when you tweak individual line items the total will be automatically updated. Using a spreadsheet in this way makes the budgeting process much easier and faster than if you had to manually add together the expenses each time you made a change.

In essence, a spreadsheet is like a mini- database, which is software for managing lots of pieces of information. (Databases are discussed separately below.) Like databases, spreadsheets allow you to do mathematical formulas and functions, as well as sorting and filtering of text data.

To do sophisticated or complex formulas, sorting, or filtering, you’ll probably want to go with a true database that will typically have more robust reporting functions already built in and require less manual customization. For example, you could easily customize a client and project database to create a report showing what clients were signed in a specific year, with a list of projects you completed for each of those clients, sorted by the total amount of project fees. You could track similar information with a spreadsheet and create a similar report, but it would typically take considerably more work to do so. In addition, if you have a lot of data, using a database is preferable to scrolling through hundreds of lines of a spreadsheet.

If you don’t use databases for whatever reason—perhaps your business needs are simple, or you can’t afford to buy and customize a database at the moment—spreadsheets are a great alternative. They’re cheap, easy to use, and quite powerful for a wide variety of applications. Besides budgeting and job-costing, they can be great for tracking project hours or maintaining client or vendor lists.

The most common spreadsheet software is Microsoft Excel, which you might already own as part of a Microsoft Office package. Another very practical option these days is to use Google spreadsheets, which are cloud-based and allow multiple users. For example, a small sales team could use a Google spreadsheet to manage its list of prospects. Whenever a sales person contacted a prospect, she could enter the encounter information into the Google spreadsheet, which would automatically be visible to all other members of the team (who could also edit the spreadsheet).

Point of Sales (POS) Systems

Generally speaking, a point of sales (POS) system is a system for tracking and managing retail sales and inventory. This is typically a computerized cash register system that handles each sales transaction as it is made; calculates the sales total and any sales tax; tracks inventory by SKU (stock-keeping unit) and automatically updates inventory databases; and generates detailed sales and inventory reports.

POS systems vary widely in the hardware and software they use; hardware often includes a computer and terminal or an electronic cash register, a bar code scanner, and a credit card swiping machine. A recent development is the use of a tablet plus a swiper, along with software like Squarespace. The software varies in the complexity of the information it can track and report. You’ll typically integrate the POS software with your bookkeeping software so that sales are automatically recorded into your books.

While QuickBooks and other bookkeeping software offer some inventory management functions, POS systems generally allow for more advanced management and reporting. More complex POS systems can manage inventory across multiple stores. Many POS systems are tailored for specific industries such as hair salons, medical offices, grocery stores, or restaurants.

To find the right POS system for your operation, start with some online research. It’s not hard to find discussions on forums among business owners sharing their good and bad experiences with various POS systems.

Project Management Platforms

Service firms, consultants, and freelancers can often benefit from using project management software. Platforms such as Notion, Asana, Trello, Basecamp, and Slack help with a variety of details involved in managing projects; depending on the platform, management can include coordinating project team members, sharing files, sharing calendars and schedules, tracking billable hours, managing different billable rates, tracking project expenses, and invoicing clients. Freelancers often find the time-tracking and invoicing features particularly useful in automatically preparing professional-looking invoices, based on hours and billable rates entered into the system.

Each project management application will have a particular focus or strength in certain features and be less strong in others. Choose an application that handles the aspects of projects that will be important to you. Find out from other business owners (either directly or by reading comments online) what they like and don’t like about the software. Typical features include:

  • scheduling, including shared calendars
  • budgeting and estimating projects and components
  • time tracking
  • billing and invoicing
  • establishing different rates for different types of work
  • file sharing and document distribution, and
  • threaded messaging and

Project management software can be integrated with your bookkeeping software if the two applications are compatible. If you plan to integrate these applications, confirm compatibility before purchasing.

Most project management software is pretty affordable. How you pay will depend on whether you purchase and install software, or use an online version. Overall, yearly costs start at around $100 for small businesses with just one user. Larger businesses and multiple users might end up paying a few thousand dollars a year.

Appointment Scheduling Software

Scheduling is a huge time sink for many of us, and it only becomes more of a burden the busier you get with a small business. If earning income from client meetings is a part of your business model, emailing back and forth with potential clients to find a time that works can be a huge drain on your productivity. Similarly, scheduling meetings with partners, collaborators or other business associates can eat up a lot of time and emails.

Enter appointment scheduling software. Apps like Acuity Scheduling, Calendly, or TimeTrade allow those who want to meet with you to book with you—and pay, if applicable—online. You set available times in the system, and the calendar will be accessible online to people you choose; typically you can provide your contacts a scheduling link, or embed your calendar at a “Scheduling” page at your website. When appointments are booked you’ll get an email notification. Brilliant!

Consultants, lawyers, massage therapists, salon stylists, and anyone else who relies on client bookings should consider using one of these online appointment scheduling apps. Rates range from $10 a month to $50 per month or more for multiple users, and will be well worth the operational efficiency even if you book only a few clients per month.

Customer Relationship Management (CRM) Software

Customer relationship management, or CRM, software helps a business manage potential and existing customers with the general goals of finding and retaining customers and reducing marketing costs. It started out as a tool to help salespeople—often a sales department—manage prospects, accounts, and territories, including tracking the types of outreach and communications that had been made to individual contacts. Today, CRM has grown into a more comprehensive strategy for managing customer service and marketing efforts.

CRM software is essentially a database that contains key information about current and prospective customers. From a sales point of view, the CRM application should identify the best prospects and provide key information about their needs in order to help the sales team turn them into paying customers. The CRM database can also support customer service operations by including all information that may help a representative effectively assist the customer, such as what products or services were purchased, details of previous service calls, warranty expiration dates, and login information for the customer’s online accounts.

Data in a CRM system can also be helpful to marketing departments in identifying trends and evaluating the popularity of the company’s products and services. This in turn helps the marketing team develop marketing campaigns and messages.

As with other types of business management software, CRM software can be integrated with your bookkeeping application, depending on compatibility. If integration will be important for your business, make sure your choices are compatible before purchasing.

A popular CRM application for larger businesses is SalesForce, which can be integrated with QuickBooks. Other reputable products include SAP CRM and SugarCRM. For smaller operations, ActiveCampaign and ConvertKit are well-regarded. Most of these applications have different versions, some installed and some cloud hosted, with a wide variation in cost. Very generally speaking, a basic version for a small or one-person company might cost a few hundred dollars per year; a large company might spend tens of thousands of dollars a year for robust data functions and multiple users.

Customized Databases

Boil them down, and much of the technology we’ve been talking about in the sections above are essentially databases. A database is simply software that helps you manage information, such as clients, vendors, products, parts, employees, and more. Bookkeeping software is really nothing more than a database that has been customized to handle financial information; CRM software is essentially a database that’s tailored for customer data.

When your business has complex tracking or reporting needs that can’t be handled by an off-the-shelf solution, you might need to create a customized database from the ground up. With database software like Filemaker Pro or Microsoft Access, you can customize a management solution to handle your data and generate reports to suit your unique business needs.

Of course, customization from scratch comes with costs. While purchasing database software isn’t terribly expensive in itself, hiring a consultant to customize it for you can easily run into the tens of thousands of dollars. You’ll also need to maintain the database, such as making changes as needed and dealing with bugs and problems, so you’ll need a maintenance budget of probably at least a couple thousand dollars a year, maybe considerably more. Make sure there’s not an off-the-shelf product that could meet your needs—likely at a significantly lower cost—before committing to the expense of a customized database.

Tip: Ask your bookkeeper and other business owners what software they recommend. Talk to people within your network who might know of industry-specific applications with features customized for your type of business. A bookkeeper can also help you set up the software and show you how to use it. You can usually test-drive these applications at their websites or with a trial version of the software.

If an industry-specific application for your type of business is not available, QuickBooks offers several different versions to meet the needs of all sizes and types of businesses.

The Small Business Start-Up Kit is available at your local, independent bookstore. Mega-retailers carry it too. 

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