5 Ways To Recover When Your Boss Ruins Your Perfect Plan

Hmm… I’m thinking of something that will make this day POP. But what would that be? Do I take the easy road and create a fun Casino theme? Do I look into creating a ’70s disco theme and have our team disco their way through the day? Or Do I create a 007 (James Bond) theme and make it a mysterious day? The choices are endless. 

For those who don’t know, I have a task to plan our company retreat every quarter. I look forward to this assignment because, besides doing a lot of strategic planning and hard work, I get to surprise the team with several unique activities to spice up the day and create deeper bonds between the team members.

Planning a retreat takes time and patience. Not only do I have to match up everyone’s schedule to pick our retreat day, but I also need to make sure that all the sections of the retreat perfectly line up throughout the day.

And as much as I prepare and plan ahead of time, life happens, and plans need to change.

A week before our retreat, Tom reached out to me and said, “Hey Sami, I have some bad news. We have a program happening on our retreat day that needs to happen.” I tell him no worries and that I’ll figure it out. But inside, I’m scrambling to think about how I will re-adjust an entire schedule that was planned down to the minute.

I decided to take one team-bonding activity out of the retreat so we could be done by 3 pm instead of 5 pm. This would allow enough time for Tom to breathe after our retreat and make his program on time. Simple, right?


Right after I made the changes, we booked another program on the same day as our retreat, and Tom had some personal events come up. These two things caused the whole agenda to blow up. At this point, I concluded that we either…

A.) Have the retreat but realize it will be cut extremely short and every team-bonding activity taken out. (Not a good option).

B.) Move the retreat to a new day that will work better with our schedules. 

I decided to move the retreat to the following week. Little did I know that this was a day where again, at 3 pm, another program was recently booked. At this point, I had already re-arranged the schedule and had to re-book a few of our paid activities. I’m not sure how many of you lovely readers plan retreats for your organizations; however, when you book someone and change the date, nine times out of ten, they will charge you a fee for changing the date or cancel altogether without a refund. Luckily, we were able to make a date change with another small change fee. 

I crossed my fingers and hoped that we wouldn’t have to change anything else!

A week after we were supposed to have our original retreat, it was finally retreat day, and we were starting in one hour. Finally, it was happening, and I was so excited.

Every retreat day, I wake up early to ensure everything is ready to go. This retreat was no different. I logged in around 7:30 am, did a few emails, got a few projects done, and then messaged the team around 8:45 am, “WHO’S READY FOR THE RETREAT!” I am sure they could feel my excitement through the chat. Jay sent a “Woot Woot!” and Tom sent a “So slight problem with today…” 

My heart sank. We were going to have to re-schedule our retreat…again. 

Challenges Come Up, Make A Backup Plan

It can be challenging to make plans around others’ schedules. Even if you have full access to their calendar, sometimes thing’s come up or aren’t on the calendar, and we have to change plans. That’s why it’s crucial to have a backup plan…and even a backup plan to the backup plan. 

I keep five tips close to me when things don’t go as planned.

Always have a “rain-check” day

Even if you are planning something completely virtual, it’s wise to have a backup plan / a backup day for personal reasons, hiccups in schedules, or illness.

Make sure all activities are moveable

This is important. Before you book an event, speak with the host. Let them know you are planning for a team, and if something goes wrong, they can move their schedule with you. This should also be spelled out in the event contract.

Breathe, sh*t happens

People get worked up when something goes wrong. A retreat (or any event for that matter) never goes perfectly. It’s on you as the planner to keep calm and make adjustments. You’re the one in charge, and you’re the one looking for solutions. Getting overworked or stressed out usually leads to bad decision-making.

Have backup activities

In the event that part of your retreat runs short or your main event backs out on you, always have a backup activity (or two). For example, I had six activities ready to go with this past retreat just in case we needed them. Sadly, we didn’t do a single one because the day got away from us; however, I can use these for other retreats, or I can use these throughout the quarter as a fun activity to share with the team. 

Make sure the team is in good health

This is important for us. We do not want to host a retreat if someone is ill or will not be present. Our strategy retreats are vital for our team, and, as said before, it’s the time when we plan out our whole quarter. If anyone on the team is sick and unable to pay attention or attend fully, that would be a challenge for the next three months as we’d be planning things for them without their direct input. As a team, we would rather move our retreat day than have a member missing or ill during our time together. 

The most crucial takeaway today would be to make it happen. No matter what. Re-schedule, make some phone calls, adjust the schedule if needed, but make it happen.

To wrap up the epic whack-a-mole story of our retreat planning, we decided to keep the retreat that day and work around the scheduling conflicts for the day. We got through all our work planning for the next three months and still had time for one group activity. While I was the official retreat planner, it took a team effort to make the day happen.

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