VACATION PLANNING

Planning for Vacations 

Ahh, vacation. Such a magical word, right? Just thinking about it conjures up thoughts of white sand, turquoise waters, and enjoying a nice spritz while basking in the tropical sun.🏖️ But for all our entrepreneurs, small business owners, workaholics, & company leaders out there, does it also bring a feeling of anxiety? Of wondering who is going to answer your emails? Who is going to support your team? How behind will you be when you return? And worst of all, how much time will you spend actually working on your vacation?🤢 

Well, if you identify more with the latter half of that vision, then this blog is for you. I’m going to share my story and the strategies I utilized to be able to leave work for almost 4 weeks in a row with no stress and no anxiety. (This last part sounds like an infomercial, but I promise it’s not!) 

The Situation 

So, I too used to be a member of the vacation stress club which required me to “check” two overweight bags to accommodate all the guilt and anxiety I’d feel for leaving work – talk about extra luggage fees! I always felt like I was letting someone down or being selfish by not working, felt like I needed to check in, stay on top of emails, answer the occasional Teams message – all the things that showed my team that I was still supporting them, even though I was technically gone. And then, 2022 came along and I got engaged. We nailed down a date for the wedding & then started talking about a honeymoon… to Thailand… for 2 ½ weeks. Cue. The. Anxiety. I knew then, I had to create a plan. There was no way I was packing that suitcase full of anxiety, or guilt, or work for that matter this time around. I had to create a plan!.  

A Sidenote… 

An additional, unspoken victim of this “working on my guilt-ridden vacation” habit was my team. By working on vacation, my actions were telling my team this was the standard, the expectation even. In my head, I was trying to exemplify how dedicated I was to the business by answering a question while I was 2,000 miles away that really was not urgent to begin with. But in reality, these habits were setting a precedent, telling the team that they also needed to be available in similar situations when on vacation – and this could not be farther from the truth. When you’re on vacation, we want you to be on vacation! Leaders included! So, for that reason also, I knew a change was needed. I had to create a plan, I had to set a new precedent.  

So, what’s the plan, Stan?! Let’s dig in!  

Step One: The List 

First thing you need to do is create a list. What things are you responsible for? What things do you hold the keys to? In what processes are you the bottleneck? Who relies on you for direction, information, a pass through of work? If this seems like a daunting task for you, an easy way to start this is by tracking your time. If you already track your time, great – start there! If you don’t, you can easily start by using an app like MemTime that tracks where you spend your time on your computer. If you are in more of a hands-on industry, then this may take a little more thought & manual effort.  

Step Two: Organize the List 

Now that you have a comprehensive list of allllllllll the things you are responsible for and all the processes you hold the keys to, we need to categorize them.  

1. Things that only you can do. Get stern with yourself on this one. Are you really the only one that can do it? You may be, but you also may just be a control freak (like me🙋🏼‍♀️) and afraid to let it go. If this is the case, what is the absolute worst thing that could happen if you handed it off for a week, a month, a [fill in with the length of your vacation here]? And, if you did hand it off and sh*t hit the fan… what would damage control look like? Or is there another “human” resource you could engage in your absence to ensure that the sh*t did not hit the fan? 
    
   For me, this wasn’t much. I had one client that I was still hanging onto that needed a solution, but other than that, most of the things could be delegated. So, I came up with a plan for that client – I was going to off-board them.😨 Now, in my mind, this was a big undertaking, and while it did take time and preparation, it actually went super smoothly – I started three months early (one month of observing, one month of hands on training, and one month just to be a resource for the new point person as questions arose). 
    
   Now, I know the solution to the items on this list will look different for everyone. Your main options are 1) you’re going to need to get the work done ahead of time, 2) you’re going to need to communicate to the end-recipient that it will be delayed, or 3) you’re going to need to find someone to fill in.  Whatever the answer is here, put a plan & a timeline together and get it on your calendar. Now. 
   P.S. And an added benefit if you go with option #3, upon your return, you may even be able to leave this work with this person & free up more of your sacred, finite time.  
    
2. Things that you can delegate. Now, this list should be lengthy because newsflash: you are most likely not a rocket scientist (and if you are, chances are you have some other rocket scientists working in your business that can help you). This list should be most of the things you do in your day, and while it will take planning to give others the tools, resources, and keys to the kingdom of your brain to handle, it can be done. Group these activities together as best you can. For example, you may have a “communications” category that includes email, messaging apps, texts, etc. and you may have a “tech” category that includes passwords that you hold, tech that you are the owner of, etc. Get these into groups however you can because it will help in the next step.  

Step Three: The Game Plan 

Once I had a good understanding and a few running lists of all the things I needed to off-board, delegate, or give directions on before I could leave, I put it all into a process and made it available to my team. I even met with them about it so that they understood how to utilize it as a resource when I was gone and give feedback if there was anything missing.  

So, here’s my process! 
Keep in mind: this will vary by business type, but hopefully it gives you a good starting place! 

• Section 1: Out of Office Prep 
  Your check list to be completed at least 2 weeks prior to departure. 
  The Checklist:
  

• Email Signature Updates + Out-Of-Office (OOO) Responder (Pre-Leave & During Leave) 
• Add a memo to your current email signature immediately that you will be out of office for an extended period of time in order to make your contacts aware well in advance. 
• Create an out of office responder anywhere from 1-2 weeks prior to your departure so that your contacts receive a response notification that you have upcoming extended travel plans. 
• Update your out of office responder 1-2 business days prior to your departure with contact information of key team members in your absence and the date you are scheduled to return. 
  
• Pro Tip #1: Create reminders or calendar appointments for yourself to update the above items on specific days based on your departure date!  
• Pro Tip #2: I usually add 1-2-days to this so that I give myself time to get back & get organized. 

• Designate a Key Lead Team Member or Colleague 
  This will be someone who understands your business and whose judgement you trust implicitly if sh*t does hit the fan. This person will be the primary resource for your team if bottlenecks arise, be able to think on your behalf, and as a last resort, be able to contact you in case of emergencies. Preferably, this is someone in your organization, but if that resource isn’t available, turn to a trusted advisor that knows your business.

• Schedule Pre-Departure Meetings 
  Meetings should be scheduled at a minimum of one week prior to departure to give time for the info to sink in and to address any follow-up questions that arise. Here’s a list of people to think about meeting with:  
• Meeting with Key Lead 
• Meeting with Team Members you Manage (group meeting) 
• Meeting with members of Leadership Team 
• Meeting with Admin Team

• Schedule Return Recap Meetings 
  This is where the 1–2-day buffer upon return comes in handy. The morning of your return, you’re going to want to block for you. But afterwards, schedule meetings with your team so that you can get filled in on what transpired while you were gone. 
• Meeting with Key Lead 
• Meeting with Team Members you Manage (individual meetings) 
• Meeting with members of Leadership 
• Meeting with Admin Team
  

• Section 2: While I’m Gone 
  After you complete this section, it will be utilized as a resource for your team while you are gone. Make sure this is available to them. 
  The Checklist:  
• Work Reassignments 
  This will house a list of any work that you are responsible for that will be reassigned while you are away. Below is an example of how I utilized this in my role at the time of my honeymoon; keep in mind that I also prepped, trained, and handed off the work ahead of time so that each person knew what they were required to do.  
• Client A: assigned to Team Member 1 
• Client B: assigned to Team Member 2 

• Chain of Command 
  Designate who is responsible for different situations and who they should turn to if they are unable to resolve or need additional support. The final “go-to” in each list should be your Key Lead.  
• Bookkeeping Team: Team Member 1 → Team Member 2 → Key Lead 
• Client Issues: Team Member 1 → Key Lead 
• Client Billing Issues: Key Lead 
• Urgent Payroll Issues: Key Lead 

• Tech Stack Access 
  Often times in a team, only certain people hold the admin keys to your tech, if you are that person, that requires designating a point person that either has your login information or their own admin access as an alternative should a situation arise. Also keep in mind 2-factor authentication when working through this section. Here is an example of my designations:  
• App 1: Team Member 1 
• App 2: Team Member 1 
• Secured Folders: Key Lead 
• Bank Info: Key Lead 
• Your Email Server: Admin Assistant 
• Etc…  

• Approval Requests 
  In our organization, we use approval requests for things like changes to passwords or time-off requests, designate someone to be point person on this (probably your Key Lead) in case the request/change required is urgent. 
• Password Changes: Key Lead 
• Time Off / Sick Pay Approvals: Key Lead 

• Meetings 
  In this section list any recurring meetings that you lead or have responsibilities in and designate who will be responsible in your absence.

• Emails 
  I know for some this can be a scary one to hand off! But it must be done! Ideally you want someone managing your inbox while you are gone so that you don’t return to a bajillion emails. At least have someone who can delete any spammy solicitations, flag things that need a response, or delegate things out to another team member who can resolve the request in your absence. I had my admin assistant use a folder system to keep things organized: 
• Email Manager & Access: [name of person here]
• Inbox Folders for Organization:
  
• FYI but Handled: Emails will go in this folder for conversations that have been addressed but that I should be made aware of. 
• Needs Attention: Emails that need my response, input, or action will live in this folder. 

• New Clients/Work 
  In this section, specify who is in charge of new clients and/or new work when you are away. If there is no solution for this, pro-tip is to designate an initial contact person who communicates that you have a “waiting list” and sets up an appointment for when you return.

• Voicemail 
  In this section, specify who is responsible for managing your voicemail and returning or delegating any messages, even if to communicate that you will follow-up upon your return. Alternatively, change your voicemail to alert people that you will be unavailable during X period of time.  
   
• Section 3: Re-Entry!  
  Your (surprisingly!) short check list upon your return.  
• Remove your Out of Office response if not automatic

• Remove Any Tech Access 
  You may have provided administrative access to team members based on who you designated as point people above. Review your designations and make sure to remove access as needed.
  

• Update Template Process to Account Problems Identified 
  This is your reminder to review this process and update based on feedback from your team provided during your re-entry meetings. There are bound to be some changes your first time around!  

Make sure to review your lists created in Step 2. Ensure that the above covers all delegation of work and/or access required for your team to work smoothly while you’re away. Add and adjust as needed.  

That’s a Wrap! 

Okay, hopefully you stuck with me through that lengthy Step 3 – I know it was along one, but there was a lot of info we needed to pack in so that you can leave your guilt, anxiety, and work at… well, work(!) while you’re on vacation!  

But, as a special treat this month, Alexis & I (Taylor) will be talking about this topic in our mini-webinar series that we do every 3 months... for now! So, tune in for a quick 30-minute sesh on Tuesday, April 30th at 12:30pm PST, you can reserve your spot using this LINK! We’ll be doing a live Q&A so you can ask all your questions on how to put this into practice in your business. As much as we love numbers, we also love helping you achieve a better work/life balance! 

And last but not least, don’t be afraid to utilize this process with other team members when they take vacation! It’s not just for the owner or the team leaders!  

Until the webinar or until next time we can dream about sandy beaches…😊