How to automate your online booking system for small business

I love writing Guest Blogs. Sharing tips about how to make technology work for you, and your business is something I enjoy immensely. In 2018,  I wrote up a little something for Angela Henderson , from Finlee and Me, and Angela Henderson Consulting.

The blog is syndicated below:

As a business coach working with women in business, automating my online booking system was a major step forward in automating my business. I’m super excited to have Stephanie from Rocking Rose to share her knowledge about automating online booking systems for small business.

Take it away Stephanie…

This blog is about the mechanics, and some of the things to consider when setting up an online calendar booking system for professional services businesses, and specifically looking at what happens when someone comes into the first stage of your sales funnel.

In order to get the most of the tips and steps in this article, you will need to have done the below already:

  • You are crystal clear on your business purpose
  • You know your target market inside out. You know their habits, where they hang out IRL as well as on social channels. You speak their language
  • Your main content and messaging are done and ready to be pushed out into the world
  • You have already done some work around your credibility and branding and perhaps you have dabbled in social media

Assuming all the above – let’s chat about how you would automate so that someone who is just coming into your sales funnel doesn’t fall off the radar.

Learn How to Automate Your Online Booking System for Small Business

Grab a pen and paper, and list down the first few steps of your current sales funnel.

Maybe it looks something like this :

  1. 15 Min Free Phone Call /Discovery discussion
  2. Book in for Small package / Workshop
  3. CTA at workshop for bigger package / coaching

We can automate at several points just with the first step in the 15 min call booking and subsequent processes. So let’s look at the communication flow when someone uses a booking system to pick a time to speak to you.

Remember that the idea is to facilitate an easy flow of information, not to overwhelm your prospect with a daily spammy automated email – or make them feel like just a number being herded down your funnel.

So the first rule is to absolutely not put them in your list, unless they have explicitly said yes (and saying no is an option that doesn’t prevent them from booking with you).


There are a number of excellent calendar booking systems and tools to choose from, most of which will easily interface with your Google or Microsoft 365 calendar so that you can block out times when you are not available.

Some examples are Calendly,  Acuity Scheduling, as well as

The first automation step is to implement the calendar booking tool of your choice on your website.

Things to consider when choosing your calendar booking tool:

  • Does it interface easily with your current CMS or web platform
  • Does it interface with your calendar easily
  • If you’re planning on taking payments, does it offer easy implementation from a range of payment providers?
  • Does it interface ( or integrate ) to your CRM
  • Can you insert bookings into your video software such as Zoom or
  • Does it have the ability to integrate with Zapier or a similar integration connector tool?

Booking Rules

Booking rules are how your booking system knows when you allow someone in, and when to show you as ‘Not Available’.

Tip – if you can, make sure to use the ‘random’ setting in your booking system so that it randomly blocks out time for you as unavailable.

Whilst you don’t want to be completely unavailable for weeks on end, on the other end of the spectrum you also don’t want to be fully available all day long (it’s not a good look).

If you prefer to work on sales on specific days, capture those rules into the booking set up so that you don’t get booked at a time when you are doing other work.

Confirmation Emails and Texts

Once the person has made a booking, your booking system should have a template for the booking confirmation which is sent immediately.

Make sure you enable and edit this template, do not use the default.

‘Your appointment is confirmed’ wording. It will sound robotic – and people can spot the template a mile off. You want to engage this person from the get-go.

Use your own language, and style and tone in your content. Change the subject, and if you can update the template colours to match your branding.

Appointment & Booking Reminders

Use the 24-hour reminder in your tool, to prompt the person and remind them of your booking with them. Again, don’t use the default wording.

In your own words, note that you are looking forward to speaking with them, be sure to give them a chance to make a ‘graceful exit’ with a rescheduling option.

It’s far better than being stood up (even virtually) even if it sounds counter-intuitive to offer this option.

After the Booking Has Taken Place

Use the automation template to send a follow-up email at a set point after your call. (1 day, 2 days, 3 hours – think about what makes sense for the booking type, and your business).

Dig into your process a little and decide if you’re going to use the email follow-up to do one of the below:

  1. Give them a CTA or a link to a specific resource that you always talk about in your discovery calls
  2. Ask them for some feedback, if your first point of contact was a freebie of some sort

Try not to cram too much disparate and unrelated information into this email (i.e. don’t make it a ‘covering all bases’ type of email – because those look terrible) – you want one actionable step, perhaps it’s a subscription to your newsletter list, or perhaps it’s giving you a review on Facebook.

If you do find yourself trying to do too many things in the follow-up email then consider setting up specific and different appointment types that trigger different templated follow-ups. Each follow-up then has the specific wording, information, and CTA, with relevant links for the type of appointment you offer.

Payment Integration

If you charge for your bookings, or you want to take a deposit before securing an appointment  – consider implementing an integrated payment platform.

Stripe and Square are two excellent options that easily integrate to a large majority of calendar booking tools and systems.

Consider the experience of your prospect if you take deposits, and insist on a bank transfer, or you have to email them your bank details to get a payment or issue an invoice manually.

The best way to automate is to consider at each step what the purpose is of the automation and to do so in such a way that you don’t lose the human touch of your brand and business.

I hope you found this article helpful and that you too will be able to automate your online booking system for small business soon, as life will be so much easier for not only yourself but for your clients.


You can find the original publication of this article at Angela Henderson Consulting :


Angela started her consulting business because she kept getting asked in different platforms/forums for her business advice. Seeing a need for advice based on first hand experience , she took the plunge and began helping entrepreneurs and small business owners. You can find out more about Angela and her services at : 

An Australian Opportunity circa 2014

This article was written by Steph and accepted for publication to Merise Magazine,  in late 2014. It was, to the best of our knowledge never published, online or in print.

Here it is - with some slight modifications for the time between 2014 and 2018.

We hope you enjoy Steph's story of Opportunity and Growth.

I’m sitting on the train at 5:30 pm, mid September 2014, coming home from the Google Analytics User conference in Melbourne, and thinking about how I am going to write this article. That should teach me for jumping in head first to the opportunity.

An opportunity is a time or set of circumstances that makes it possible to do something.  Don't take my word for it, that's the official definition.

So, by its very definition, an opportunity is neither negative nor positive. It simply is.

It is chance to do something. A turn. Your go at taking the shot.

Opportunity does not discriminate, it does not take sides.

Getting the chance to write this article, is the result of an opportunity. One that I grabbed hold of without hesitation when I met the Merise Team at the Ladies Tea in Melbourne in early 2014.

I ponder thoughtfully that the definition of an opportunity is not about the end result, but rather about the circumstances. Getting more money into your business is not an opportunity, but helping someone in your network, that’s an opportunity. It’s a chance to do something.

It's also not a guarantee, to the disappointment of a great many humans I think.

It's an option, a happy coincidence of circumstances that enables you to

  • be something more,
  • try something different,
  • learn something new about yourself or
  • test your limits and boundaries.

And for Migrants and Saffers ?

What does this mean for migrants that land on our adopted fair shores ?

I think it’s about understanding what it means to have a fair-go. A fair-go is really the chance to take a hold of your Great Australian Opportunity.

Everyone in Australia has their "Fair-go" it would seem. Does that mean we all do well and prosper?

Not at all, because having a fair-go is not the same thing as working hard.  Australia,  in my experience does extraordinarily well at providing opportunities to more people than any other country, but you still have to work, and network, and be extraordinarily better than the rest to make a success of your career, your life,  or your business. In whatever way you choose to define that success.

So I’ve been pondering my journey since settling in Melbourne and the opportunities that have come my way.

In my whole working life, the longest I have ever worked for a company is 8 years. The longest I have ever had the same job is 5 (at that same company).

In South Africa I’ve cleaned houses, worked as a receptionist, a bookkeeper, a supervisor of dance instructors (couldn’t dance a step myself when I started) , a call centre agent, a debtors clerk, and a business analyst. All with a BSc Biochemistry under my belt.

In Australia, my CV looks a lot more stable, but that calm surface belies a far more complicated, and challenging personal and career growth curve.

I run a software company owned by 2 co-founders, and I'm not one of them. Technically, and legally not  mine, but it’s my baby nonetheless, as many other General Managers, Managing Directors and employed CEO's can relate I am sure. We invest ourselves, and our working identities heavily into these "children" of ours. Staying awake consecutive nights when we take big risks, and wondering what will happen to our team members and staff if it all goes belly up. Feeling the weight of that responsibility very heavily when our staff have families, and thinking about how much your decisions affect the lives of these newly minted little Aussie tykes.

I’ve learned to say Yes. 

I’ve learned to say No.

And more importantly, I’ve learned how I can tell in advance when each is appropriate.

I’ve learned to be discerning in my trust, and to go with my gut when there is no other data to work from.

Snakes are very pretty, and can be exceptionally hypnotic and charming before they bite, or strangle the life out of you without mercy or empathy. Life-giving wells of breathing space, and genuine appreciation are often hidden under plain unassuming facades. Don't judge a book by it's cover, sales is an art in Australia, and it's full of charlatans.

If you try to embrace Australian "mateship" without understanding it first, you’ll fall flat very quickly.

I wish that I’d been told this all of this when I arrived in 2010.

Eagerness is not always appreciated by your average small business Australian, they are a very reticent people, and if they don’t know you, you just look pushy.

Sometimes the opportunity is to be found in sitting back, and waiting.

And when the universe sends you a cryptic email wondering if you’d like to explore doing business in USA, you whip out that eagerness and energy and throw everything you have at it, in the face of enormous fear, because those are the times when the opportunity is in the YES, and you have to learn to stretch yourself.

An that is how I find myself all alone stranded overnight in Sydney en route to the USA in May 2013, fighting with an airline, and negotiating my way into 24 hours of plane hopping across the globe so I could get to my 2 week immersion in San Francisco on time.

I had a surreal moment in the middle of that night in 2013 in the Sydney Hotel, waiting for a call back from an airline. I made a wry mental note-to-self that I was having a chance to do some personal growth. This was rapidly followed by an angry admonishment to the Universe in general

“Personal Growth be damned, I just want things to work!”

It's so much easier to look back and see how far you've come, and apply an overlay of logic to the circumstances that challenge us. Much easier than seeing and grappling with the discomfort of that growth when it's happening in real time.

So I became the CEO of said company, because American Investors in Silicon Valley will not take a Business & General  Manager seriously. They want to talk to the CEO. It’s a bit like having a split personality really. CEO on one side of the globe and a Manager on the other.

What a moment that was, I think I celebrated by making myself another cup of coffee.

Celebrations do happen often in any business that I have a significant interest in, I believe it's important to mark the small wins and big. We had an apoplexy of happiness when we made it into the Apple App Store – and we got a couple of rounds of applause when we told our friends and business colleagues. It was a small win for us, but apparently far more impressive to our friends and clients than we realised.

The irony of that did not escape me,  that we had built this amazing software company over many years, with an incredible online platform, and no-one applauded until we had simple contact manager app in the App Store. When did the measure of business value become an App I wondered?

We cannot all be Steve Jobs

Moments like those bring my attention sharply into focus; snapping me back to the reality that we cannot all be Steve Jobs. Most times, us normal people need to see, pick and exploit opportunities by listening to what people want.

They may not have the words, but their needs and desires are there in their behaviour. And if you are not solving a problem, then you’re not doing anything useful, marketable and by extension, sellable.

Everything that happens to you every day when you live in Australia is an opportunity to grow.

It’s so damn hard to remember that,  when it’s 3 am and you can’t sleep because you miss your family with a pain so deep it knocks the breath out of you. It is true nonetheless.

One last lesson I have learned, is that you will be happy only when you decide that you’re going to be.

Unfortunately, it is the one lesson I cannot pass on as if it were a transferrable skill. Us migrants, we the brave that leave everything we know behind - we each have to come to our own peace and settlement of why we now live in Australia, and what it means to be an Australian from another birthplace. And we do it in our own time.

I notice the train has stopped here in 2014 - we’re at my station, so this is the end of the line for today. Only today mind you, because tomorrow morning will bring with it another set of opportunities.

What will you do with your opportunities, here in our adopted homeland?

What you need to know about BadRabbit malware

Here’s what’s important to know about BadRabbit malware - if you’re a business owner

BadRabbit is ransomware

If infected,  your computer will be locked down , and you will be extorted to pay money ( currently around $300 or equivalent in bitcoin)

There are 2 ways that it spreads

Primary infection on a network is via infected websites - it then secondarily spread through that network  via a leaked NSA exploit in Windows Operating systems ( not dissimilar to  WannaCry)

What’s that in plain English ?

You, or your staff, will most likely be exposed to it by browsing the web, and coming across an infected website - where you will see a popup that looks like you’re being prompted to download and install an Adobe Flash Update

If your computer is on the company network ( example a business with an internal network of computers ) - then the malware spreads across the network in a very similar way to WannaCry (via security weaknesses or gaps in  Windows XP / Vista / 7 and Windows Server 2003 and 2008 systems. ) The exploit that does this is called EternalRomance, and if this is all sounding familiar , it should be , because WannaCry spread by using an exploit called EternalBlue . Both the Eternals are from the NSA and were leaked out into the wild with devastating consequences.

Where does BadRabbit come from

Current general consensus is most likely it comes from Russia - it appears to be targeting corporates and government installations in the Ukraine and surrounding countries.

Why should you worry ?

Yes, it’s not spreading as fast WannaCry - however because the internet is global and open if you do any kind of shopping online, or global website browsing , you could be at risk of getting infected. 

Risk Points 

Windows software that is not patched or updated regularly - any computer running Windows Vista or XP, and staff that are "too busy" to critically evaluate the messages and popups that they see when browsing the web , especially if their job involves doing any form of online research or searches.

Tips for your staff :

  • Don’t download Flash from any website except Adobe - ignore pop up messages that looks confusing
  • Don’t buy  or order goods and services on a website that does not have a green padlocked SSL
  • Don’t work in older versions of Windows Operating Systems - and specifically move away from Vista, XP and Windows 7
  • Always keep up to date with your Windows security Patches.

What can you do on your website to prevent or mitigate this ?

  • install a business grade Organisational Validation, or Extended Validation SSL certificate
  • Ask your developer to mitigate  that Javascript  injection is prevented on your website.
  • If you have a wordpress website, ensure that comments can only be loaded by verified user accounts and have to be moderated or approved so you can delete the spam and suspect ones.  


Password Managers are not a laughing matter.

What is a Password Manager ?

It’s a tool that you use to Store, Create and Manage Passwords across your accounts and multiple devices.

How do they Work ?

On a browser , you will install a plugin to the browser that will prefill the passwords for you , when you are logged into the Password Manager.

They are also available as apps across most smartphones and tablets, where you will be able to copy the password from your Password App and use in a mobile browser or app. There is usually a time limit on the app version , which will delete the password from your clipboard after a minute or so.

Why do you need one ?

  • It’s hard to keep track of all your passwords
  • Re-using passwords is not a good idea ( but we do it because of the aforementioned point re how hard it is to keep track)
  • They can randomise passwords ( ie you only need to remember 1 password and all the others are random anyway)
  • You will never need to reset a forgotten password again ( provided you haven’t lost the login or saved the wrong password to start with)


My top 2 recommendations :

Mac  users - 1Password , which has a much slicker UI and works better on Mac than LastPass.

Windows users : LastPass works well across windows environments, also has a decent app for the iPhone and iPad - the Mac experience is a bit clunky