Capitalizing on the Offseason


You’ve been in hustle mode for months… just trying to keep your head above water while you try to take care of your clients, field new inquiries, keep your blog + social media up to date, and juggle literally #allthethings.

But the offseason is near! And while your weekends will be a lot less white dress and a lot more white wine, you know that booking season is right around the corner.

Every year you say it’ll be better. You’ll be more organized. You’ll keep the chaos less chaotic. And every year you end up overwhelmed in your sweatpants by 10 AM on Tuesday because – let’s face it – the offseason doesn’t really mean “off.”

Psh. No sweat. This master list of five action items will ensure you make it to yoga AND coffee with the girls without missing a beat for your biz. (I know you totally just said, “Yeah, right.” But for real – I got you.)

1: Invest in systems for your business.

Priority One: a Client Relationship Management (CRM) tool

What is a CRM? It’s basically your sanity. The right CRM will help you organize your leads (and resulting clients), it will keep track of detailed info on each client, it will centralize the essential docs that are the cornerstone to the relationships you build, and it will automate key parts of your client experience.

#allthethings. Seriously...

  • Send automatic response emails to new leads

  • Create a follow-up process so that no client slips through the cracks

  • Schedule communications to set expectations and next steps after booking a client

  • Automate touch points with clients throughout your time together (i.e. planning tips, crucial considerations, pre-wedding check-ins, etc.)

  • Develop a post-wedding offboarding process

I highly recommend checking out Dubsado (my personal fave, and that’s an affiliate link), 17hats, or Honeybook if you’re serious about a baller system to keep you organized. And beyond that, once you choose your system, take the time (or hire someone!) to get it set up and running for you! A system without a strategy is just an off-the-shelf system. These tools are incredibly powerful, but you need to USE them to the fullest extent to reap the most benefits.

2: Streamline your workflow.


Start by documenting every step in your workflow… each tiny, granular internal task that you complete, every button you click or setting you choose as you do each task, every communication, document, and touchpoint you have with your clients. What do you do when someone sends you an inquiry through your website? How fast will you respond? What email template will you use? How about your action items when a bride decides to book you? When do you send your first invoice? And at what point should you be reaching out for that first follow up? This “lead stage” is just a small part of your overall client experience, but it’s a good place to start documenting.

Rule of thumb – if you don’t write it down, it doesn’t exist.

When you’re done documenting one stage, organize your list into an online system that unclutters your desk (and your brain). I personally use and love Asana to track and manage my workflows. I took my documentation and transferred it into their system, added myself (or my assistant) as the responsible party for each task, and then assigned due dates for each item on the list. I copy the master template each time I bring a new client on board, adjust the due dates as needed, and then we get to work. This system has been a great quality assurance tool to ensure that everyone internally is on the same page, and each client is receiving the same very high level of service (regardless of how busy we are at the time!). It’s a productivity game-changer.

3: Create content strategically, in advance.

While time-consuming (and daunting if you’re not a fan of writing), blogging regularly throughout the year is important to the vitality of your google presence, and done strategically, it can do a lot to enrich the experience your clients have with you.

The first thing I recommend is creating a questionnaire (or a few!) that you can send to clients throughout the planning process. A “getting to know you” questionnaire during onboarding is a great way to collect personal stories and details about the couple - like how they met, the proposal story, what they’re most excited about, what they’re most nervous about, their wedding inspiration, etc. Additionally, a vendor questionnaire is great to help keep all vendor info in one place. And a style questionnaire can help you understand where your couple is drawing inspiration for their wedding details, sentimental touches they’re incorporating, etc. Gathering this information up front will make the content creation process easier later on.

Beyond that, there are undoubtedly questions that new inquiries always have, or thing you regularly address with your clients. Instead of writing the same email over and over, use those topics in your content strategy, and then find ways to use that content in your workflow to SERVE your clients better.

Whether for a blog post, short social media caption, or even a submission to a publication, developing a content strategy, doing the prep work, and planning ahead can help shape the dialogue around your brand. By consciously deciding the image you want to portray and taking steps now to refine your content process, you’ll speak directly to your ideal client.

4: Add to your team.

Every CEO needs a squad. So in the offseason, consider finding a go-getter who matches your drive and vibe to help handle the aspects of your business that you a.) don’t have time for or b.) just plain don’t like. Because at the end of the day, wouldn’t you rather NOT have to deal with maintaining your books? Or your flooded inbox? Or all those blogs we just talked about?

The best thing about hiring in your offseason is that you’ll have time and energy to mold and train someone to be and know exactly what you need them to be and know. Not to mention, if you’re following along with the action items we already talked about, your workflow will already be intricately documented, making the transition to your new team member seamless. If you can invest solid time into developing a sidekick, you’ll be ready to hit the ground running when things pick up.

5: Set goals for the next month, season, year.

Summer time chaos is not the best time to look at long-term goals (let’s face it – we can barely see to next week). The offseason offers you a time to check in, evaluate the position of your business, and determine how you want to see it grow over the next months/years/decades.

It is so important to note the difference between working IN your business and working ON your business. While all the IN stuff has to happen (client follow up and editing and communication and blog posting and so-on) the ON stuff can’t get pushed to the back burner forever. Eventually you’ll burn out because you won’t see the point in why you’re going through all this insanity day in and day out. You need to have one eye on where you’re headed to stay motivated to keep going.

During the offseason, step back a bit. Evaluate how your business runs. Identify where you really rock it, and where you need to make improvements. Plan for how, by this time next year, you’ll be better than you are right now.

Pick two or three big goals. Identify manageable milestones you’d like to achieve. Break those milestones down into tasks you have to finish to keep moving towards your goals. And then set everything to a timeline you can actually see sticking to. When the small steps are identified, it will seem easier to accomplish the leap. Write it all down and spend time making your plan look and feel legit. It will be so rewarding to come back this time next year and see the progress you’ve made!

Use this season to really slow down. Implement new strategies and processes, spend time on yourself, and decide how you want to see your business change in the next season.

Ultimately, you’re working to create the business you want to work for. Don’t lose sight of what drove you to pursue this crazy, exciting, chaotic, empowering dream of entrepreneurship.

*Post contains affiliate links.

SystemsAnnie McCartyComment