Master the Art of Following Up

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Constantly following up with clients and prospects can be a bit daunting. It can feel like you’re bugging them and that they don’t want to hear from you. That is rarely the case. I’ve always felt that every time I was sending yet another “hey, have you had a chance to check out the proposal” email, that I was just being annoying. 

That was until several, totally unrelated prospects actually thanked me for checking in.

In small business, people are just always so… freaking… busy. 

Most of the time, you’re not being ignored. It’s just really easy for things to slip through the cracks and for people to forget.

Being diligent with follow-ups and check-ins can seriously improve your business. It can help you land more clients and even reduce your stress. Let’s get into some way you can implement follow ups.


Closing new deals

Too many times I have seen businesses send out a proposal and let the process stop there. They go through all the time of the initial meeting, quoting out the work, personalising the proposal and then… nothing. 

What a waste.

They’re sitting there thinking the client didn’t like the proposal, or went somewhere else. In reality, there’s a pretty good chance they just forgot about it because they were too busy with something else. Depending on the client, you might need to follow up 10 or more times over several months before finally getting their signature. 

Sure, there reaches a point where it becomes too much and you should stop - but that point is probably a lot further along than you think.


Keep projects moving

Have you ever had a project that stopped dead in its tracks because you were waiting on something from the client? If you’re a web designer I know right now you’re going “OMG YES, all my clients take FOREVER to send me content”. If you’re not, then let’s just pretend for a minute.

In our web design business, pretty much every project was held up waiting on content. It was so bad that when a client had their stuff together, it felt like a miracle. But this problem definitely isn’t exclusive to web design. If you need the client to provide you information, files, copy or pretty much anything, you’ll know how hard it can be to keep things moving.

In some cases, you have to put in hard rules for your clients - both contractually and in your process. For example, you might put their project on hold if they don’t get content to you in time, or you might use placeholder text/images. This is venturing outside the scope of this post however.

Outside of that, regular reminders can be enough to push your client to keep things moving along. You might start off nice, but as the due date approaches, you might have to put your foot down and send more regular reminders. Maybe with some stern language...

A system of regular content follow ups was extremely helpful in keeping projects moving for us. But it can feel like you’re being a pest when you’re always on your clients back. We ended up building software to handle the content gathering and follow up process (Content Snare). That way, we could let it be the “bad guy,” save face and do most of the work for us.


Get more referrals

Like I’ve already said, following up a potential client about an unsigned proposal can feel icky. That’s why it came as incredible shock the first time one of those nag emails turned into a referral! This person hadn’t even signed on with us yet, but they were happy to refer us on to someone else. 

That right there is the perfect example of people just getting too busy to sign. But I digress. Following up brings you to the top of mind. If your email hits at the right time, you might just snag another lead. 

That’s why you should also check in with clients after your project is complete. That could be 1, 3 and 6 months after everything has gone live. All you have to do is ask how they are going with their website. Or how their business is doing. Or ask if are they loving their photos from their big day. Whatever is relevant to your industry.

And asking for referrals goes a long way. If they get back to your first email, there’s no harm in simply asking if they know anyone who could do with your help.

Happy clients, better service and testimonials



I’d probably call this final item a “check-in” rather than a follow up, but it still counts. Regularly checking in with existing clients can be one of the best things you’ll ever do in your business.

All you have to do is see ask them how things are going, maybe once every month. Ask them for feedback on your service. Ask them not to hold back if they aren’t over the moon with you. 

There’s a ton of awesome things can come from this.

  1. It shows you care
  2. If you get negative feedback, it’s a great opportunity to improve your service, turn things around and gain an extremely loyal client
  3. If it’s positive, it’s an opportunity to ask for a testimonial. Bonus points if you get on video with them and record it
  4. More referrals

Tools to stay on top of reminders

The benefits are clear. The next challenge is for you to actually remember to do them. You’re busy too right?

Creating a system is key. There’s a few ways to do that.

CRM Tasks

Many CRMs have the ability to schedule ‘tasks’ when you interact with a client in the system. Whenever you send out a proposal or finish a job, pencil in a task for your next follow up. When you do that follow up, set a new task for the next one. Easy!

For check ins, most CRMs will allow you to set recurring tasks. 

In Dubsado, you can set workflows to remind you to send follow ups or even set them to automatically send follow ups for you!

A calendar

If you don’t use a CRM, you can achieve the same thing with a simple calendar. Add recurring events or one-offs to serve as reminders. In most systems (like Google Calendar), you can create a secondary calendar so it doesn’t mix reminders in with your events.

Email plugins

There’s a bunch of tools out there that make email easier to work with. They might add the ability to snooze an email, send later, or remind you to follow up with someone. Boomerang is a popular one. I use FollowUpThen because it’s simple. When I need to schedule a follow up, I simply “bcc” an address like

Specialised Tools

Sometimes you can find tools built specifically for your industry, or that include follow ups as part of a larger range of tools. 

An example of this is Content Snare, our tool built for web designers and online marketers. The difference between this and say FollowUpThen, is that you might want different reminders to go to the client based on how much content they have already provided.

Final thoughts

Following up is one of the most important things you can do in your business. While it can feel like you are pestering your clients, this is something you will soon learn is not the case. 

I’ve been thanked time and time again for following up on proposals (which is essentially asking for money). At first that might sound crazy, but people forget things and are often thankful when someone reminds them.

Obviously this doesn’t mean you should be constantly blasting your clients with emails and coming off needy. Just keep it cool and check in once in awhile.


About The Author

James Rose is the co-founder of Content Snare and Aktura Technology. They’ve built a tool to help web designers get content from their clients and are on a mission to make life easier for web designers through their software, community and blog.