Workflow for Working With Retainer Clients

Over on the Rising Tide Society blog, I talked about how to create retainer offers to diversify and stabilize your income.

I love retainer offers because I get to create long-term, strategic relationships with clients. A retainer offer can be a natural extension of the work that you do in one-off projects like branding, website design, copywriting, or funnel design.

The bonus? Retainer offers are one of the easiest and fastest ways to diversify AND stabilize your income. They’re a source of steady, monthly revenue. Knowing I had reliable income made the jump to full-time entrepreneurship possible. 

And I want to share how you can get that stability too.

Signing a retainer contract feels like you’ve won a gold medal in entrepreneurship. But there’s more that goes into marketing a retainer offer than just creating it. You’ve got to sell it and then KEEP that client on retainer. Feel free to swipe my process!

Introduce the value to your potential retainer client

Many clients can’t see why a retainer would be valuable. Or they know the value but are worried about adding another task to their list – managing a retainer contract. It’s one of the main reasons I suggest working with only past or current clients – they know you, your value, and that you’re here to help them grow – not steal their money.

It’s our job to show them that we can become an asset to their business when kept on retainer. Showing, not just telling – which is why I want you to map your current process.

Converting to Retainer

Below you’ll find an example of what my invitation process loosely looks like when I’m trying to convert a client to become a retainer client. The next section covers the whole process, but this checklist focuses on what I do to convert clients. 

The Invitations:

  • Mention retainer in passing [1]
  • Strategy Call [2
  • Roadmapping [3] – includes a direct invitation
  • Post on social media about retainer clients seeing success.
  • File hand-off – project complete – includes a direct invitation [4]
  • Post engagement congratulatory snail mail
  • Email one-month post engagement: includes things you’ve noticed and how they can DIY fix it (or work with you) – don’t be a jerk.
  • Invite them to book a VIP day as a taste test – includes a direct invitation.
  • Post on social media about retainer clients seeing success.
  • Final offer 45 days post-engagement – includes a direct invitation.
  • Add to past clients list – send monthly emails sharing successes of past and current clients.

Mapping your process

Look over your project workflow; hopefully, you have it mapped out. If not, you can swipe mine below.

By mapping our process, we can showcase how we manage a retainer contract – alleviating concerns or fears from the client AND ensuring that we always know the next step. Sharing your offer is just the beginning of your retainer relationship.

Speaking of the beginning, let’s start there. 

When I first talk with a potential client, I always make sure they understand that my service is part of an ever-evolving ecosystem – it’s not “one and done.” This is critical if we want to ensure clients are prepared for retainer services if we offer them. 

By setting the stage, you’re helping them see that your solution is just the beginning of some amazing results.

Here’s what the process looks like for me workflow-wise – your process may be a bit different, and that’s okay! I’ll explain the phases below.

Phase One: Shadow Hints

When: Sales Process and Project Onboarding {plus in conversations throughout the project}

How: Throughout our discovery, sales, and onboarding conversations, sprinkle in mentions of your retainer offer. Planting the seed that you can continue working together to meet big goals after your initial project is complete. These little shadow hints help raise awareness. That awareness allows the client to be prepared for an offer or invitation in the future.


Mentioning that you just got off a call with a retainer client, you’ve been working on your retainer client’s project this week, mentioning/sharing retainer client wins in your weekly client email.

Phase Two: Building the Case

When: Project Ending – when presenting concepts.

How: Start building the case for a retainer relationship. Remember, your client bought your service as a solution and solutions take maintenance to see long-term and big results. Help your client see the progress you’ve made together so far, and prepare for what’s to come.

Example: When presenting concepts for branding, I’ll remind them of their problem and our design solution. I’ll mention how excited I am to see their branding implemented on their website, social media, or in course materials. Highlighting how versatile the design is and how implementing it will build their brand authority and trust factors.

Phase Three: Provide a Roadmap

When: Project Ending – before final deliverables have been sent. 

How: Hop on a call one last time before you wrap up a project to go over the next steps/strategies. This typically includes conversations about launch plans and ensuring everything is in order (and the client understands how to use their new brand or site). 

At the end of the call, present* a roadmap. This roadmap should include specific next steps for the client for launching (so they have to look at it) and then a few more strategic plans or a checklist for them. The roadmap aims to help them see the value of signing a retainer contract. They could do it themselves, but you’ll be able to show them that it’s better to hire you to help.

*When you schedule this final call, make sure they know you’re presenting a roadmap and next steps. You don’t want to blindside them by turning a celebration call into a sales call. You are NOT making the actual invitation to work with them yet – unless they ask for it.

And yeah. You ARE giving away some strategy for free. But to me, it’s worth it. We want them to be successful, and I’ve never regretted giving an extra 30 minutes to share some ideas.


My roadmap for a branding project typically includes the following:

  • 6-month plan referring back to their goals shared at the beginning of the project (focus on the ones you can actually help move the needle on).
  • List of potential deliverables
  • How we’d measure ROI

Phase Four: The Official Invitation

When: Project Ending – after final deliverables have been sent and invoice paid

How: Send a celebratory email, thanking them for their time together and sharing their excitement. Include a sincere invitation to work with you in a retainer relationship, with a link to a proposal. Be sure to reiterate how you’d implement the roadmap, and the strategy behind working together longer. I like to include the roadmap in the proposal so they remember what we talked about.

Phase Five: Onboarding + Strategy

When: Retainer Begins

How: Onboard your retainer client – this typically means creating a new job in your CRM. Set them up on autopay from the beginning. Schedule a kick-off call that allows you to dive deeper into strategy. Also, ask them to make a list of projects they want to finish while working together. Consider having this as homework before the call. 

This gets added to your roadmap, and you can use it:

  1. To prove ROI – “look at how much we’ve done!”
  2. As a checklist or prompt list, if you don’t hear from them or they don’t know what to work on – “hey, I didn’t hear from you this month – I went ahead and did X because I know you’ve been needing it done!.”
  3. A way to help sell your services for the next engagement.

Always provide a plan. It can be as simple as reiterating their monthly goals and how you can support them. 

Deliver your ROI report from the previous month around the 10th of each month. This helps them to see the value from month to month and prepares them to have a positive response for when the renewal invoice arrives on the 15th. 

This roadmap is also an excellent time to remind your clients of your working relationship. What is urgent or not? What is the scope? How do we work together best? You’re allowing your relationship to get renewed and recentered each month.

If you’re familiar with 80%-20% services, this ROI report is like that. 80% of the “work” is done ahead of time by creating a template, workflows, systems, or whatever you need to do to help automate this. Then you plug in your 20% into the ROI report each month. I usually alotte about 30-45 minutes to this process.

Phase Six: Follow the Roadmap

When: Throughout the engagement

How: Do the work. Work the plan. Stay in communication. Even if they don’t respond, still follow up. Tell the client what you’re working on; many folx hire so that they don’t have to think about the work that’s happening behind the scenes. 

When you deliver your offer, always include your suggested next steps as another way of staying connected and showing value.

Communication here is critical. I like to do a micro-update on Monday mornings. This includes what’s happening this week:

  • What we’re doing;
  • What they need to do; and
  • What’s on the horizon for next week.

Phase Seven: Nurture

When: Throughout the engagement

How: Connect. Connect. Connect. Show up online and connect with them. Whether that’s responding to their newsletters, sharing a post they made, engaging in stories, or commenting on posts. You can write them postcards or send a voice message. If you want, you can also send them a gift (if that makes sense to your business relationship strategy). 

Check in with them and engage. You’re building a long-term business relationship.

Phase Eight: Grow the Strategy

When: Typically 2/3s of the way through {ex month two of a three-month engagement}

How: Start (or continue) conversations about the strategic direction of the business. Is it time to help them bring a course to life (or re-record it with new branding)? Have they been talking about a new project? How can you support them in that? 

Is it time to start planning for the launch of a new offer?

Your client trusts you as a fractional team member to help them grow and move forward. So how can you develop your strategy and help them meet the big goals they discussed when you started working together?


Repeat this process indefinitely! That’s the beauty of retainer relationships. But never forget, this is a relationship. It takes nurturing and care. Support and time. And it pays in referrals, consistent revenue, and lasting business relationships.