Stupid Simple Freelancing with Automation

I’ll be honest: I don’t spend much time on keeping my freelance business afloat and organized.

But not in a bad way.

You know how they (but who’s they?) say to spend time on your business, not in it? I never really understood that, but I’m pretty sure it applies here anyway.

All solopreneurs want to streamline biz processes as much as possible, but freelancers don’t really have any other choice. For us, time literally equals money, for the most part. Admin and client management stuff isn’t billable work, whether you’re billing per hour, per project, or per hairs pulled out in frustration over a difficult task.

So you can’t let it take over.

Back-and-forth emails, progress reports, onboarding emails – that’s not what clients are paying you for. So it’s not in their best interest to take up all your time with it, either. They’ll be happy to do their part to let you focus on your work for them.

So from lead generation through to day-to-day client communication, here are a few different ways to add workflow automation into the mix at every step of the sales funnel to save time and frustration for errybody.

Top of the Funnel Freelance Automation Tricks

1. Set up smart contact forms

Do you have one blanket “contact me”/”hire me” form on your website?


You’re making things so much harder for yourself.

The biggest benefit of automation is that while it may take time upfront, it only takes time upfront. Put some work in now to create multiple, specific contact forms on your freelance website. It eliminates a ton of the back-and-forth question asking that comes with learning about a new prospect or client.

Your contact forms should ask all the questions you need to know, instead of going through them via email later on. You’ll get everything you need right away. Another handy thing is that all the good form builders hook up to IFTTT and Zapier, so this first step in getting a new client can kick off a bunch of other automated steps.

My form builder of choice normally Typeform. It’s easy to use, integrates with anything you’ll need it to, and is just ohhhh-s0-pretty!

Google Forms, SurveyMonkey, etc. are also popular and easy options.

Take advantage of contact form and survey form integrations with things like CRM & sales software, email marketing providers, and templates.

For example, this is one of the more specific questions on my own “hire me” form:

Use a hire me form with very specific questions to streamline your freelance client prospecting

It tells me whether or not this is a ghostwriting project, something a lot of freelance writing clients don’t think to mention right away. Better for me!

2. Nurture prospects

So once a new prospect has said, “hey, I wanna work with ya,” there’s still a lot of unavoidable things to hammer out.

Just like with initial outreach, forms can make that first basic communication easier.

For example, do you have a set of questions you ask each prospect or new client? Put ’em in a survey. Guidelines about your “office hours” and other things clients need to know? Create a cheat sheet or YouTube video to send them instead of going through them on yet another Skype call.

Then hook these all together in the order the client should go over them, and sleep in in the mornings, knowing you don’t need to be awake for your clients to get the info they need.

This form mentioned in #1, for example, also kicks of an automated confirmation email which includes information and links based on whether or not it’s a bylined piece. Better for the client!

3. Prospect admin

Besides all the back-and-forth involved in a new client, there’s also a whole lotta other admin to take care of.

It kind of ruins the fun and rush of winning a new deal, doesn’t it?

But things like adding a new client to your CRM and financial softwares, customizing quotes, putting together contracts – soooo much of it can be automated.

With a trigger as simple as adding an email to a certain folder or creating a new entry in your CRM, you can set up a chain reaction of activities in different apps that take care of everything for you.

Boom, instant productivity.

I have my HubSpot CRM, Wave accounting software, and all those other related apps hooked up to IFTTT and Zapier.

Using Automation to Onboard New Clients

4. Finalize deals

Once you and a new client have both said “leggo,” there’s obviously even more “paperwork” (I feel weird calling it that when it’s digital) to put together before you actually start billing them for stuff.

For example, you might have sent them a brief quote or sample contract during the lead nurturing stages earlier. But you likely will have final tweaks to make, contracts to finalize, and stuff like that.

While you obviously can’t create a 100% custom contract from an IFTTT recipe, you can cut down on the amount of customization you have to do yourself. For example, take integrating your contracts and CRM. Your contract software could automatically pull in data and contact information from the CRM deals.

There’s also setting up automations for the future. For example, if your contract calls for resigning or renegotiating every six months, connect the CRM deal to a recurring task in your to-do list or a calendar appointment to remind both you and your client of the expiration date.

5. Take clients through onboarding

So we’ve talked preparing yourself for new work.

We’ve talked about preparing your business systems for new clients.

Now let’s talk about preparing that client.

Onboarding can take work. I’m pretty sure that as a freelance writer, I actually have it pretty easy. I couldn’t imagine doing the amount of briefing I’ve heard and seen happens with more complicated long-term projects like VA work and design or development.

The best tip for managing it all? Processize it all as much as you can (trademarking “processize it,” btw).

Put as much information as you can figure out how to into tools, apps, etc.

Invite clients to project management tools, shared calendars, shared cloud storage folders, and other ways to share information. Anything you find yourself telling more than one client…”put it in writing.” Create official documents for anything you’re repeating over and over.

This makes it easier for both you and your client to go through everything needed to get started. You can spend time on something else instead of going through the same list of procedures for the billionth time. They can familiarize themselves with that same info on their own time by accessing your onboarding tools.

A really great example is the many onboarding Trello boards out there published as examples. In fact, it’s how I was onboarded as a new hire at Mention, as well.

Here’s one example board from the Trello blog:


You could easily adapt this for freelance clients by creating different lists for things like tool access, your contact information and guidelines, processes and timelines, etc.

Ongoing Client Management, Automated

6. Send clients progress updates

Very few clients trust a freelancer enough to have them just go off and do their own thing, incommunicado, right off the bat. Sure, your relationship may build up to that eventually, but you need to earn their trust and prove your worth.

Unfortunately, that can be pretty task-heavy.

With a newer client, you probably need to check in more often, let them know what you’re getting done, and get approval for more stuff instead of making the calls on your own.

But that can quickly turn into sending them either several emails a week, or sending them goddamn novels as your weekly updates.

Reduce time spent sending emails about what’s been done and what hasn’t by using project management software. Something like Trello, Asana, or Basecamp lets you update the client by simply checking off a task or moving a card to the “in progress” or “done” column.

You can also combine these tools with IFTTT or Zapier to create custom email digests – separate from any unhelpful generic notifications the service sends itself – updating your client on the most important changes in the project management tool to let them know what’s going on.

7. Set up recurring emails/invoices

Freelancing is kind of cyclical, right?

Whether you’re doing one-off projects or recurring work or retainers, there’s a bit of a pattern.

  • It might be going through contract renewals once or twice a year
  • Maybe it’s a monthly retainer
  • It could be a bi-weekly invoice

And there’s no need to do all the work for each item each time it pops up with a different client. Processize it! (trademark Brittany Berger, blammo!)

For example, a contract renewal automation can connect to a specific contact type in your CRM. You could automatically send monthly retainer bills and create tasks in your to-do list to follow-up if they’re not paid within the specified timeframe. Hell, you could even automate that follow-up.

You can automate tasks in your to-do list, assigning tasks to your client in your project management tool, sending documents and emails, etc.

Make Clients Happier

Automating things is best for your client. If nothing else can convince you to get on board, that should.

It frees up your time and your focus to spend more of it on them.

It makes their relationship with you more organized, and they always know what to do next because you have systems that make it clear for them.

And it frees up time for them, too.

So start embracing it, y’all, it needs to happen.

7 Stupid Simple Ways to Automate Your Freelancing Business at Every Stage of the Sales Funnel, Plus a Free Trello Board for Onboarding New Freelance Clients