Not For The Faint Of Heart: When Managing An AirBnB Goes Awry

I feel like I’ve had a rough go of it in January and February with our Airbnbs. As with any business, operations ebb and flow from smooth sailing to a complete shitshow. I tend to have months of quiet, where everything seems to be going fine, to 1-2 weeks in a row where things feel like they are falling apart.

Omicron in the beginning of January was no joke. My son Charlie was diagnosed in November with Type 1 Diabetes, and after 2 years in the pandemic we decided to book a trip to Florida to visit Harry Potter World to getaway as a family and let Charlie feel like a normal kid again. The trip was amazing, but the second we stepped off the plane I knew we would not escape Florida unscathed by COVID. Sure enough, after 2 years of avoiding a positive test, Charlie tested positive when we arrived home. 

Not only did it get to us personally, but professionally as well. My cleaner in New Hampshire also tested positive and was out for almost 2 weeks. We had to cancel a booking, and make the 2.5 hour trek up to New Hampshire to turnover our cabins ourselves and make sure that we didn’t lose any more income. 2022 has had a slightly slower start than we expected, and I didn’t want to ruin anyone’s vacation. Luckily, both Charlie and our cleaner came out of Omicron just fine.

Two weeks later, she encountered more bad luck when she slipped and fell at another client’s property and hit her head. (I won’t dwell on the circumstances surrounding her fall, but if you own a property that has a snowy client, please make sure you sand and salt for your guests and cleaners!) Now - I’m over 7 months pregnant at this point and moving pretty slowly, so turning over the properties myself is becoming less of an option. This is where owning an Airbnb and self-managing the property is not for the faint of heart. What transpired next was unfortunate and not my happiest moment in running this business.

I got notice of her condition the night before I had 2 big turnovers - a Friday. The weekend was generating $2K for both cabins, and I was pretty stuck. The labor market right now, especially in North Conway, is extremely tight. Every STR owner is clamoring for good help. Miraculously, North Conway has some great local Facebook groups out there and I saw that a cleaning crew in the area was looking to take on more clients. I reached out immediately, and they were able to save me the next day. 

What transpired the next week is where I feel pretty crappy as a business owner and human being and I’m still reeling from it a bit. The communication on my cleaner’s status was less than desirable. I was getting mixed messages between herself and her partner on her return ETA, and messages would go 24 hours or more unanswered. The ETA I was getting was: “could be 5 days, a week, 2 weeks”. At the same time, the new cleaners I took on had let me know they needed a longer term commitment; cleaning in the short term for me was not sustainable as they were passing up other clients that could be permanent. At this point, feeling like I was stuck, I decided to commit to the new cleaners for the long haul.

I’m totally dejected at this point. I had developed a personal relationship with our former cleaner for 2 years, and cutting her loose when she had a medical problem didn’t feel like my finest hour. That said, I am running a business, and this income impacts my livelihood as well as my family’s. The transient nature of cleaning services, as well as the fact that there is no legalized employment agreement or contracted back-up, makes this extremely difficult. I had asked for clarification at least 2 times, received back pretty inconsistent and mixed messaging, and had to move forward at that point. 

Still, I could have been better prepared for this scenario. Some takeaways and learnings for the future:

  • Impress upon your cleaners that having reliable back-up is extremely important. Understand who it is they can call for help, and have those names and contacts readily available as well.

  • Alternatively, have 2-3 cleaners that you rotate. This is difficult and probably a logistical nightmare, but in the event that 1 can’t show up, you can be covered by the other.

  • If a medical issue or other occurs, be extremely clear on next steps by asking the following questions (ideally having these sketched out in some sort of document):

    • What is the actual date that we should expect you to return? 

    • Can we agree on a regular status update of your condition, whether daily or weekly?

    • In the event that return is delayed, how should we proceed?

  • Better yet, have a protocol for when these sorts of situations arise that you can refer back to.

  • … actually refer back to and update agreements and contracts if you have them, at least every 6 months, so you can refresh yourself on your policies.

  • Have someone else do this entirely. Outsource to a Property Manager and make it their problem. (But let’s be real - it’s still your problem)

  • Always operate with kindness but also firmness. This is a skill that I’m still working on. I used to be anxious, always giving in for fear of someone disliking me, and putting myself at risk. Through the whole exchange in this situation, I do believe that I was kind and understanding in my communication, but in the end had to be firm with what I needed in order to protect myself after I realized that my business was on the line.

What would you have done differently? 


Courtney LevyComment