After 5 years in business, I’ve learned a thing or two. Here are my lessons and how I overcame some hairy situations.

I can’t believe it’s almost been half a decade (!?!?) that South Street & Co. has been around – March is the month! It’s pretty incredible, actually. Looking back there are highs and lows and a s%*t ton of lessons along the way. 

If there are a couple of things that I’ve learned that can help you with your journey, I consider that a win. Anyone who knows me, or who has heard me speak, knows that I surround myself with coaches, mentors and advocates to help me continue to improve myself and my company leading it in the best direction. 

Here are the top 9 things I’ve learned after almost 5 years in business.   

Lesson 1: Over Communicate 

If I had to choose one major thing that bothers me, it’s not communicating. Even with my husband – at the end of the day, I have to ask him what he did today, how his day went and I like catching up to learn what was new.

Clients are no different. They want to communicate with you and they enjoy hearing from you because that’s you telling them that they are top of mind. I make a note to send them “wins” each week showing them how well their marketing is doing. Sometimes I make the subject line something fun like, “Do A Little Dance 💃🏼” so they know we’re watching out for them on a consistent basis. 

Lesson 2: Not All Change Is Bad

This past year, I had a key employee leave. It was hard. I went through being happy for them and then being sad, and then thinking, “What could I have done better?” 

The bottom line: It was the best thing at the time. They got an amazing position, they learned a lot while they were here AND it gave me an opportunity to reevaluate where we were as a company and to implement new programs– which we did. 

I found a program that allows us to streamline our editing process. We’re a very content-heavy marketing agency and so we need a lot of feedback from clients, especially in the beginning, to make sure we’re on the same page with their brand, tone and voice.  

So, instead of us sending emails back and forth with edits, following up, checking in – I found a program that does it for us. 

Now, we’ve cut down the back and forth time by A LOT. (If I had to measure, I would think it was about 5-10 hours per week). That helps me, the clients and the rest of the team because when the client leaves feedback on the document, the team member edits it. Then they upload a new version, the client looks it over one last time and approves it by giving us a “green light.” Then, we post it and we’re home-free! 

This change was hard but it also brought about a new opportunity to invest in programs to help us streamline our business and now with the time we’ve saved, we get to focus on things that help us and our clients more. 

Lesson 3: Cover Your Tracks

As I mentioned this program above, it’s also a way to make sure that we’re following what the client wants and how they want it done (within reason). I had a client who emailed me and let me know that something in a blog post wasn’t approved but had gone out. 

I hate those emails and I immediately get the ‘pit in your stomach’ feeling and start freaking out… internally. I popped up the program, went to their file and found that in fact, it was approved. I then sent the screenshot over to them and asked if this was correct and if not, and what should we change it to. 

They re-looked at it, realized they’d made a mistake and told us to edit it to XYZ. We did and it was no problem. However, I’m so glad that I had that information to go back to because without it we would have been confused and in deep water according to what their edits and thoughts were. 

Pro Tip: After each meeting, I send a recap of what we spoke about from my meeting agenda. This has helped me stay on track with expectations and allows the client to see what we’re working on as well as their action-items. It’s also good to reference in case things get lost in the email shuffle. 

Lesson 4: Say No If The Shoe Doesn’t Fit

We’re friends, right? Because I’m going to get deep here. This was super, super, SUUUUPER hard for me. Whenever anyone sets up an initial call with us, I want to help them; no matter what. 

However, I got myself (and the company) into situations with clients who weren’t exactly the best fit. Maybe we could help them but maybe I knew someone who could do it better. I was telling this to a friend and she said, “Kaitlyn, you’re helping them even more by referring them to someone who you know will do a great job instead of taking them yourself. That’s just another way of helping them.”

I had never considered that before. I was helping them by telling them I couldn’t help BUT I knew someone who could. I’ve recently started doing this – referring potential clients who aren’t a good fit for us to other agencies who are a better fit. The results are amazing. The potential client thanks me for being up-front and honest and is even more excited to speak to the person I’m referring them to because they know it’ll be a better fit. 

Pro Tip: Start small with this and really find who your good fits are. If you’re doubting it or you have that gut feeling, you should probably pass. Also- let’s think about Cinderella here – she ended up pretty well sticking to the shoe that fit, amiright!?

Lesson 5: Carve Out Time To Work 

It’s funny – I did this in the beginning and I stopped… and now I am doing what I did in the beginning again. 

I met with a colleague and was talking about the fact that I didn’t have any time to work when it was only me at the company. He looked at me and asked what I was doing. I said, “I’m meeting with people all over Orlando and hoping to land them as clients.”

He looked me square in the face and asked, “Well, when are you going to do their work?”

I sat back and said, “Well, I don’t know.” 

There are only 24 hours in a day and if you fill-up the 8 working hours with meetings, you’re not going to get any work done. 

The solution is to block your schedule. Here’s what I do: 

Mondays: 9:00-12:00 blocked

Tuesdays: 3:00-5:00 blocked

Wednesdays: 3:00-5:00 blocked

Fridays: 1:00-5:00 blocked

This helps me to focus on answering questions, writing blogs (like this one) and doing any other tasks on my list. Without doing this, I was killing myself. I thought, “Well I don’t have any meetings so that means I’m not working.” WRONG.

Just because I didn’t have meetings didn’t mean I wasn’t working, it meant I was working on work, not client communications. 

Pro Tip: I highly recommend looking at your schedule and finding what times you can block off. Then get an app like Calendly and send people times to schedule directly on your calendar- it’s been a lifesaver for me and there’s no temptation to “squeeze someone in!”

Stay tuned for lessons #6-9 coming Thursday!