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This blog post has been turned into a more usable format over on my Checklist page. Give your business a healthcheck and make sure you know what aspects of IT you need to have thought of. Or contact me and I’ll help you through it.

You’re just starting out, you have your business plan and you’re trying to make sure you have everything in place to make your business successful.

Or, maybe you’re already all set up and you’ve been running your business for a few years but you know that you’ve been winging the technology side of things because it’s never been your thing.

Or maybe you’ve even had some kind of technical failure or data loss and you want to make sure your tech stuff doesn’t let you down again.

Whatever your situation, the last thing any business needs is to be held back by something as mundane, yet essential, as technology. I want to help make sure you have thought through everything you need to make your business fly, not limp.

As a small business leader, the more time you have to focus on your business, the better. Getting each of these systems set up properly – whichever ones are relevant to you – should save you time and stress, especially if you have someone who can help you get it done. Know any good IT people?

I’m not affiliated with any of these recommendations currently. If I add any affiliate links later I’ll make that clear in the text.

Where does your data live?

If the answer is ‘on my laptop’ or even ‘on a portable hard drive’ then you need to consider ways to keep that data safe. You should never have data in just one place, especially not if that place is a single portable computer or disk. By data, I mean documents, financial records, invoices, whatever files your business depends on.

Every disk will fail eventually, and it’s always best to assume this will happen at a bad time. 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).

Data Sharing

The other thing about where your data lives is this – if your business grows, or you take on a virtual assistant, 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.

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. Your Excel spreadsheet on your laptop with names and addresses of your customers is not particularly secure. 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 and relating to 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.

A word about business process

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 your business processes. 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.


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. First, how professional you seem, and second, how easily you can work.

If you’re using a ‘home’ email system, your email address will be something like [email protected] – or if this is literally your personal account, [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 is to have an email address that at least mentions your business.

Also, you’re shooting yourself in the foot if you have everything coming into the same account. 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 as you do actually answering work email – and just as bad, you’ll end up answering work email in bed when you check your personal mail. Finally, even if you set up that forwarder, clients will get mail from [email protected] and think… who is this guy?

At the very minimum (and I’d always recommend going further than this), you should have a separate Gmail or email with your business name in it, and avoid checking personal mail while you work.

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.


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.

Would a live chat window on your website help you get business? Something like Crisp or Purechat have web plugins that will let web visitors chat with you to ask questions about your services.

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. Plus, these will help with your data protection compliance.

Customer Relationship Management (CRM)

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.


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.

For photographers, I’d definitely recommend Light Blue, which can manage your whole photography business – financials, bookings, appointments, the works.

Client feedback

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 lets you make sure that you keep comunication 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.


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 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. They 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.

Customer-facing IT

Do you provide any IT for your clients? For example, does your hotel provide wifi to guests, or have a computer in the lobby for people to use? Do you have iPads for visitors to your shop to find out about your offerings? If so, you’re going to have to consider how to manage security and maybe even device tracking. You may need a bespoke service to help you charge 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 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.


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.

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).

Back end management and team communication


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.

Project and task management

If you have a few people working for you, how do you coordinate projects or other shared work? You could consider a project management platform like Asana, Trello or Basecamp. You might need a simpler task management service like Wunderlist. Or, if you’re going in the direction of a full collaboration platform anyway, features of Office 365 can be used for this too.

Team chat

When people hear ‘team chat’ as a concept, they usually first assume that this is about wasting time or 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, 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. The best ones integrate with all the other stuff you’re using, and let you voice and video chat with your teams as well as using text chat. Even just between 2 people, this can change how you work for the better. It’s hard to see how in a short paragraph 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.

IT support

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 setting 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?

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, 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. I plan to post more details on most of this stuff so that you can get a head start on getting yourself going, but if anything here has made you realise that you might need some hands-on help, drop me a line on [email protected] and I’ll see if I can get you going.