Running your own business is awesome. And tough. Just when you’re celebrating that a huge client project is finally finished, you’re also realizing that you’ve got nothing else on the docket and you begin to wonder how you’re going to pay next month’s bills. In your panic, you start emailing friends or old clients hoping that they may have a project to fill up your design schedule and…crickets.  Not only do you feel (and maybe sound) desperate for work, but you get little to no response. Of course, just when you land a huge new project, you’ll get responses to all that searching and you’re wondering how you’re going to do it all. So how do you manage to keep a full project schedule with out sounding like a desperate crazy person?


I know. Upselling is just fancy business speak for those emails I mentioned above that make you feel awkward at best when the recipient responds, and completely desperate when there’s silence from the other side.

But there’s an art to upselling. It’s one thing that can help you round out the number of projects you’re working on so you’re not worried about paying those bills and it’s one of the best ways to make sure you’re growing your business. Follow these suggestions when you upsell to your clients, and you won’t feel awkward or desperate – instead you’ll be spreading the love, and chances are, they’ll be getting in line to work with you.

What to Say & When to Say It

Here are a few ideas on how to approach clients and suggest new projects:

WHAT: just checking in and wanted to see if you had any design needs that I could help out on (make suggestions here)

WHEN:  a few months since you last talked, at the start of the year, when there’s a change in command or a new person has come on board


WHAT: It’s that time of year! Time to get working on those…

WHEN: perfect for when it’s time to ramp up for the holidays, change in season i.e. spring or summer sale, Q4 (or whatever business it currently is – if this is a long standing client, then check your records and see what they were up to  this time last year)


WHAT: I heard of a cool marketing idea…(fill in your project idea here). I think it would really help by (add a numerical list of 3+ ideas that it would help with, i.e., increase sales, build community, launch new product, etc.) Lets see if we can fit this into your marketing plan & budget.

WHEN: around 10-12 weeks after a big project. This is a great secondary project follow up that might drum you up a small project and some extra cash.


WHAT: I’ve got a few open slots on my design schedule this month and wanted to offer the slots to my favorite clients first. (Fill in some project ideas that they may be interested in here)

WHEN: you can only use this one 1-2 times a year with each client. Pick a few at a time, and schedule a note in your calendar to contact them 3-6 weeks before you’re slump times.


WHAT: I loved working with you on (fill in the project here). Please keep me posted on how things go, I’d love to hear about it! If you’ve got colleagues looking for great design I’d appreciate you passing my name on to them. I’d like to do a stellar job for them and a recommendation from you would make my day.

WHEN: As you’re closing out a huge project and you’re awesomeness is fresh on their minds. An extra touch is to mention something that you learned from them and how it has enhanced the project and expanded your skill set or knowledge.

When to Jump In & When to Back Off

Like I mentioned before, upselling is an art. You want to make sure you’re on top of it, but you also don’t want to be that annoying person who just can’t stop looking for their next job. Here’s what I do to make sure I’m there at the right times:

  • when you start a project with a client, schedule a reminder for yourself to write that “loved working with you” email.
  • schedule a reminder to send that “just checking in on project X” about 4-6 weeks after you’d finish. You want to make sure that whatever you worked on is being awesome – and if it’s not, you’ll want to be sure you fix it.
  • look through your client list and calendar at the beginning of each month – make a short list of clients that may have needs and send out the emails that are the “just checking in” and “cool marketing ideas that may help your business”  emails.
  • to save time: write up templates for each of the different upsell emails and then make tweaks as needed for each client.

It may seem like a hassle to keep an extra page on your calendar or notebook of who you’ve talked to and what you said; but believe me – it makes you look like a rockstar to your clients, and it drums up business for you – that’s a win!

How else do you upsell or keep in touch with clients? I’d love to hear your tips.