Small Business IT Checklist

Here’s what I think a small business needs to address when thinking about their IT, data and processes. The smaller the business, the more likely you as the business leader has to deal with the IT – confident or not. And the bigger the business, the more likely you have enough important IT to warrant having someone look after it for you. Either way, I can help. Contact me if you want any more information on any of this. I’m not affiliated with any of these technical recommendations. Any affiliations I may make later will be clearly marked in the text.

Here’s the overview:

  • Where you keep your data, how it’s backed up, how easy is it to access it for your staff, and how easy is it to lose or leak
  • The various ways that you communicate with your clients
    • Email
    • Website
    • Newsletters
    • Customer Relationship Management (CRM) database
    • Invoicing and Payments
    • Client Feedback
  • How you manage any technology that you provide directly to clients, e.g. wifi access, an accessible computer, etc
  • How you communicate with and manage your staff, track your inventory and manage your projects
  • Who can help you set up and manage your IT systems

Where Does Your Data Live?

If the answer is ‘on my laptop’ or even ‘on a portable hard drive’ then you need to consider other ways to keep that data safe and accessible to the people who need to work with you on it (and only those people). By data, I mean documents, financial records, invoices, whatever files your business depends on. You should never have just one copy of your data, especially not if that place is a single portable computer or disk.

Keep your data safe - Backups and Cloud Storage
Every disk will fail eventually, and it’s always best to assume this will happen at a bad time. Businesses that lose their key data don’t last very long. What if you lost your unique designs, your financial records, your client records? And with them, the only copies of your kids when they were babies?

Your data needs to live in at least 2 places, and ideally in 3. I would advise you to have at least a local backup (like Apple’s Time Machine or other equivalent, on a hard drive you keep plugged in to a computer) and a cloud backup (to cover you if someone or something steals or destroys the computer and backup drive together). Dedicated cloud backup solutions like Backblaze, or cloud file sharing systems like Office 365, G Suite and Dropbox allow you to keep (multiple) local copies and the cloud copy, and have other benefits besides. It’s not worth chancing it with one of the most important assets you have.

Share your data with colleagues and clients - Cloud Data Sharing
If your business grows, or you take on a virtual assistant, or you already have other staff – how will anyone else help you work if your laptop is where all your files are? Traditionally this would have meant setting up some kind of server, but now I’d always suggest a cloud collaboration suite like Office 365 or G Suite. At the very least you will want something like Dropbox for your files, even if you don’t want the other features of a full suite. The free version will get you going if you don’t have a lot of stuff.

Using something like this will let you share your files with whoever you need to, and will also mean that you can access them and work on them from multiple devices yourself. It’s worth it just for that, to be honest. Bonus points: cloud storage counts as an additional location for keeping your stuff backed up.

Don't leak sensitive information - Data Protection
You have an obligation to keep your customer data secure. Cloud services have people whose job it is to work out how to do that, although you will also need to play your part in this. Your Excel spreadsheet on your laptop with names and addresses of your customers on the other hand is not particularly secure. It’s worth thinking about, at least. I’m not a data protection expert but I know that you don’t want to be the one who leaks customers’ personal details to the world.

How are you communicating with customers?

Most of your IT systems relate directly to your customers in some way. Email, website, Facebook, a CRM system, invoicing…. Each part of the process can either enhance or worsen the customer experience. At the same time they each have an impact on your own speed and effectiveness, and even your own sanity. With all this at stake, it’s worth getting the pieces right.

Think about how you work - Business Processes
Before you think about technology, you need to know and understand your business processes. That is, think through the various building blocks from attracting clients through the various stages of communication, agreeing the work, supplying the work, invoicing, tracking payments, following up past clients, and so on. Maybe draw a flow diagram.

No electronic system will magically solve your needs if you don’t understand what you’re trying to do from end to end. But when you know the flow of information within your business, you can plan out the various forms your data needs to take and what systems you could use to store and manage each stage.

Appear Businesslike - Use Professional Email Addresses
Do you have a separate business email? Or are you trying to do everything from your personal Gmail or account? There’s a couple of issues to consider here. The first is how professional you appear.

If you’re using a ‘home’ email system like Gmail but you’ve created a ‘business’ email address, it will be something like [email protected] . Worse, if this is literally your personal account too, it might be [email protected]. The thing is, if you’ve got a professional website at, you’re aiming to show people that you’re a slick, real business that can be trusted. Your crazy email address can let you down here. The absolute minimum is to set up a forwarder from an email address on your website’s domain – [email protected] – that goes to your other email. That will at least let you put something professional on your business cards and ads, although when you reply, you’ll still be sending from your normal address, so that’s why the other minimum requirement is to have an email address that at least mentions your business. Otherwise, clients will receive replies from [email protected] and think… who is this guy? What happened to

The best solution, of course, is to have a proper email mailbox tied to the same domain as your website, so you can send and receive from a professional account. This also keeps your business email all in one place. Check with your hosting company whether there is a simple email package available, and then compare this with suites like Office 365 and G Suite to see if you would be getting better value there. As it happens I can help you get this stuff set up if you need it – either the whole process or just helping you out if you get stuck.

Split Home and Work - Use Separate Email Mailboxes
The second issue to consider about your email setup is how easily you can work.

You’re shooting yourself in the foot if you have everything coming into the same account – home and business. When you sit down to do a day’s work, your attention will be pulled away from important things to… whatever else you get in your inbox. Newsletters, offers, Facebook notifications, friends, and so on. You’ll spend as much time trying to get back into work mode every few minutes as you do actually answering work email – and just as bad, the flip side is that you’ll end up answering work email in bed when you check your personal mail.

At the very minimum (and I’d always recommend going further than this), you should have a separate or Gmail email with your business name in it, and avoid checking personal mail while you work. This helps solve the work/life balance issue, but not the professionalism one.

As before, the best solution (which fixes both)is to have a proper email mailbox tied to the same domain as your website, so you can send and receive from a professional account and keep your business email all in one place. Again, check with your hosting company whether there is a simple email package available, and then compare this with suites like Office 365 and G Suite to see if you would be getting better value there.

Make Web Updates Easy to Do - Website
I’m not a PR or web design person, so I can’t help with your message, how it’s presented, or what it looks like. But I can ask you this: is your website easy to manage? Can you add news or blog posts to it simply? Can you make basic tweaks to page layout yourself, or do you always have to call your designer? If your website doesn’t let you make most changes yourself, you’ll either let it stagnate and never post content, or you will be paying your designer a lot of money. This is the minimum you should expect from your site. If you’re still stuck with an old static site that you can’t edit, it’s time to look for something else. Luckily, you can get this quite inexpensively from WordPress, Squarespace, or similar, which can get you going until you need anything more complicated.
Give Your Customers Instant Contact - Web Chat
Would a live chat window on your website help you get business? Depending on your line of work, people looking to make a decision might be helped by instantly chatting to you or your team. Crisp and Purechat along with many others have web plugins that will let web visitors chat with you to ask questions about your services. If you’re not available, you’ll still get a web enquiry. It could make the difference between a sale and… not a sale.
Keep Customers Informed - Bulk Mailings and Newsletters
If you need to communicate with many people at once, how are you doing this? Do you clunkily mail merge from an Excel spreadsheet into Outlook? Or could you use an online service like Mailchimp or Constant Contact? Anything you can do to reduce the manual steps you have to take to get something looking good and self-managing will save you time – and as a sole trader or small business leader, your time is the most crucial thing you have. You can get people to sign up themselves without any manual intervention and because they help you deal with unsubscribes and bounced emails this will all help with your GDPR and data protection compliance too.
Understand and Develop Your Client Relationships - CRM Systems
How do you keep track of your customers and potential clients – how you’re doing with developing them, what you last said to them, and any sales pipeline you might be taking them through? You might need a CRM system, which used to be expensive, but there’s now a few free ones out there that suit small businesses. HubSpot is one of them – free, but with a lot of features if you want to set up a full sales pipeline and lead management. You can track your communication with contacts at a company or individuals, decide who is at what stage in the buying process, and get insights into how well you’re converting potential clients into sales or deals. Pretty powerful stuff, and worth a look if you’re serious about understanding your clients.
Automate Your Finances - Invoicing Systems
How are you keeping your financial records and managing your invoices? If you’re still doing this manually, you will really save a ton of time by trying a cloud-based system like AND.Co (which is free) or Freshbooks, which will track your expenses, quotes, invoices and payments, as well as sending reminders to late payers so you don’t have to spend time on that. Some will integrate with certain bank accounts to help track your real income and expenses so all you have to do is assign them to the right client or project. Some will track time and let you convert that directly into invoices. You can even set up subscription-based invoicing where you charge a regular fee to a credit card and automatically send a receipt.

When it’s tax time or you want to see what invoices remain unpaid, there’s a ton of reports that will help you see what your financials are doing. A spreadsheet would take a little longer to set up and doesn’t have a team of people working on new features while you sleep!

Manage Your Photography Business - Invoicing and CRM
For photographers, I’d definitely recommend Light Blue, which can manage your whole photography business – financials, bookings, appointments, the works. Standard workflows help you to manage each booking and not leave out crucial steps like sending contracts or asking for deposits and balance payments. Reports help you see what kind of shoots bring in the most profit and, as with any financial system, lets you report out your turnover, expenses and net income for tax returns.
Get Customer Reviews and Opinions - Client Feedback and/or Helpdesk
Some of you may make a product that reaches enough customers that you want to have a place to get product feedback or even provide a helpdesk service for your product. Cloud services like UserVoice or Zendesk can be helpful for this. I’ve learned from my experience running an IT department that splitting feature requests or user help tickets away from your normal email and into a dedicated help system lets you make sure that you keep communication going until it’s resolved, rather than losing customers’ requests in the sea of your email. This can mean the difference between a pleasant support experience and making a customer angry because you’ve forgotten about them.

There are also services out there that can pull in user feedback or queries from your Facebook or Twitter channels and help you to manage them with your other requests.

Get Money From Customers - Card and Other Payment Processing Systems
How do you take payments? Do you have a point of sale credit card device? Do you use Paypal or Stripe to process online payments? You may or may not know that there are rules (called PCI DSS rules) about how you can take and process credit card details – for example, you shouldn’t type credit card details into your computer (other than your own card details – that’s at your own risk) or store them on there in a file. The assumption is that bad guys can probably get into your computer if they want to, and companies that process card details have to have a lot of security. Your payment providers have this security, so they can store and manage credit card info. You rely on their PCI DSS compliance to keep your customers’ data safe. That’s no good if you then keep a list of credit cards and addresses on your laptop. There’s probably no good reason to be doing this, but if you are, it’s time to stop.

If you don’t have a credit card machine, and think you might want one, luckily that market is becoming a lot easier and cheaper. Devices like iZettle and SumUp pair with your mobile to allow card payments on the go. Not taking cards can be the difference between an immediate sale and a ‘well, I’ll think about it’ in many lines of work. If you’re selling goods at a market and you only take cash, a potential buyer who would be able to hand over a card on impulse might pass you up if they’re short on cash. They might love what you do, and then never get around to coming back or searching you out to buy later.

All these services take a small percentage fee for each transaction of course, but it is worth weighing up what extra sales you may make by having this available.

Secure Your Wireless Environment - Providing Guest Wifi
If you provide wifi to members of the public, there’s a few things to consider. First is – change the admin password on your router. If you’re running a B&B in your house, and people are connecting on a normal wifi router, those things have the default username and password printed on the bottom. A nosy person could log into that and change the settings, locking you out, changing the wifi password, or whatever they wanted. You’d have to factory reset and set the box up again.

You may need a bespoke service to help you charge for or automatically assign WiFi use, if that’s not just going to be a guest WiFi password on a sign. And if you are just a B&B it would be worth finding out if your WiFi router has a guest WiFi mode. Orange in France, for example, now supplies routers with this feature, which will keep guests from being on the same network as your own computers which hold your business data. Many home wifi routers now include this function. As always, if you need a hand finding it, I can help.

Also, change the network name and password to something professional-looking. The default network name and password will be almost gibberish, and you want clients to know which network is yours and easily be able to type in the password without help.

Never open your wifi up completely (no password). Doing this means that the signals going over the air are completely unencrypted and can be seen by anyone sat outside your house – they can record information you send and know what sites you’re browsing, what information is sent back and forth, and so on. (HTTPS on websites makes this a little better, but I still think using an open wifi network for anything serious is like shouting your bank card PIN out loud whenever you use it).

What Do You Need To Do Behind The Scenes?

How you manage the stuff at the back end – the stuff the customer doesn’t see – can be just as important as the customer-facing parts of your business. You can provide great customer service and have no idea whether you have items in stock, or take a long time finding them, leading to late shipments. You can be a great designer but have no organisation when it comes to keeping track of where you’re up to with the various projects you have going on. You can have all the right people working for you but have no joined-up way of making sure that everyone knows what’s going on as your company grows and deals with new challenges. How are you managing your team, your projects, your inventory?

Keep Track Of The Stuff You Sell - Inventory Management
If you hold stock, an inventory management system could come in handy. Spreadsheets will eventually get too unwieldy to manage. There are some decent free programs and cloud services out there that can help you track what you have and where you have it. If you have a lot of different items in different places, it may be time to manage this professionally rather than on scattered pieces of paper or spreadsheets.
Manage Your Work - Project and Task Management
If you have a few people working for you, how do you coordinate projects or other shared work? As a sole trader, your trusty notebook could well be enough – until you lose it or drop it in a puddle. Then you’ll wish you had somewhere in the cloud that you could bring it back from. But as soon as you are trying to coordinate work with 1 or more other people, your notebook is definitely holding you back.

You could consider a project management platform like Asana, Trello, Monday, or Basecamp. You might need a simpler shared task management service like Wunderlist. Or, if you’re going in the direction of a full collaboration platform anyway, the Planner feature of Office 365 can work for this too.

Revolutionise Your Team Communication - Team Chat Workspaces
When people hear ‘team chat’ as a concept, they usually first assume that this is about wasting time, or they can’t see why you’d ever want to do that when you have email. I can tell you that team collaboration apps like Slack, Microsoft Teams (both as a free standalone workspace and part of Office 365) and Hangout Chat in G Suite can really change how your team functions, cut through the email overload, allow people to get quick answers to things they’re working on, and make it easier to keep all the discussion on a particular topic in one place.

Best of all, whether you use one of the productivity suites (Office 365 or G Suite) or not, there’s always a free option to try. Both Slack and Teams have stand-alone free options. The best ones have great integration with all the other services you’re using, and on top let you voice and video chat with your teams as well as using text chat. Mobile apps let you do all this internal communication from wherever you need, linking to files and other notes that you need to carry on the discussion. Email, compared to that, is just a messy place full of too many messages.

Even just between 2 people, chat-based workspaces can change how you work for the better. It’s hard to see how in a short few paragraphs like this but in my experience, email as an internal communication method is a disaster, both for all-company news and for team collaboration. As it takes a little bit of getting used to, you might get more out of it with some professional help, or at least plan to spend some time working with it before you start to see the benefits. But once you are really working with it, you won’t miss your overloaded email box. Keep that for communicating with customers and suppliers, and watch the mail volume drop. Sound good? Get in touch and I’ll help you work out how to get started. I prefer Teams, but Slack has a very large following as well. You could just try one out yourself.

Who’s Running Your IT?

Finally, and potentially the most important – who can you call on to help you with your IT when you’re in trouble, or when you want to set up something new that will move your business forward? As the business owner, do you spend a lot of your time struggling to set all this stuff up and trying not to throw your computer out of the window? Why not get someone else to do that for you? I mean set it up, not throw it out the window. You can do that yourself.

Have you ever wasted an entire day doing something that you know someone more experienced could have done for you in an hour? We’ve all done that. Often it’s not until afterwards that you realise that it would have been cheaper and easier – and by then the time is already wasted.

The problem is that we don’t think of our own time as an hourly rate. You should really work out what your own hourly or day rate is, and then you will be able to see whether paying for a service will be worth it.

The CEO or business leader has a unique role in a business. There are a lot of things only you can do. If you spend too much time doing things anyone can do, you’ll have no time for the critical decisions and strategy you need to move your business forward.

Delegate as much as you can. Keep less in your head and more written down in systems or procedures someone else can follow for you. And hire contractors you trust to have your business in mind, not just their own.

I personally work as if I was your own personal IT department – just smaller. You can’t probably hire a full-time IT person yet, but you can contract one in on a regular support agreement, working on whatever you’d task an IT staff member to do, from user support to configuring your cloud services. I’ve had clients from a couple of hours a month all the way to 3 days a week, and I also work on a project basis to get new systems set up and make sure you know how you want to use them.

What's Next?

I hope this has helped you get an idea of some of the IT questions small businesses need to answer. You can do a lot of this stuff yourself, but unless you love this part of the job, why put yourself through it?

If anything here has made you realise that you want some hands-on help, click this button, send me a message, and I’ll see if I can get you going.