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Offsite In Hell

Last Updated On: 2025-09-01 04:31:53 -0400

Once upon a time, a long, long time ago, I went on a team offsite and, well, it was not my favorite experience. Here are the litany of things that went wrong.

Day 1

  1. Racing thru the airport, after snow delays, to a connecting flight to arrive at my connection seconds before boarding.
  2. Realize at the Airport, just before boarding, that you’ve never gotten a response from your Team Lead about the latest spec you submitted 4 days ago – in response to their request for it. Slack them and get told ‘I will go through it and send you comments’.
  3. Showing up, at 11 pm, to discover the door locked and my team at dinner. A call to the team lead and I was told “The door code is in Slack; back soon; bye”. No. The door code is not in Slack. Nor was the door code in the Team Offsite Google Doc. There was a subtle mention “the door code has been emailed out”.
  4. Discovering that Thunderbird is no longer, suddenly, pulling in emails from the Outlook pop server.
  5. Sitting on the front porch of the offsite location like a digital homeless person until I can get access to the misbegotten, excuse for a “email” system, that is Outlook Web Access and find the email with the door code.
  6. Sleep as well as you ever do (which is to say not well).
  7. Get up at the crack of down to create a presentation based on this belated approval.
  8. Realizing that your one IT responsibility was “bring an HDMI cable” and that you failed at that (my bad; I changed laptop bags at the last minute).
  9. Discovering, the first morning, that even though the IT failure at the last offsite was connecting laptops to the site’s big screen TV, the offsite facilitator didn’t bother to try this until the morning of the offsite, 1.5 hours before go time.
  10. Skipping the team breakfast to walk just under a mile to the local Walmart to get an HDMI cable and a ChromeCast so all bases for laptop to TV connectivity are taken care of.
  11. Discovering that the flat screen TV is bolted to the wall in such a way that you can only find the HDMI port by braille.
  12. Find out that the Internet access for the flat screen TV doesn’t work but, thankfully, the Verizon Hot Spot you pay for personally can save the day.
  13. Finding out that the Flat Screen TV’s mirroring options don’t work because the owner of the facility has deliberately disabled the installation of custom Roku channels (which are required for software only screen mirroring). No worries, you anticipated this - so onto the ChromeCast – Google will save us, right???
  14. Painstakingly you battle your way through the cluster fsck of configuration options that is the Google Home ChromeCast setup wizard (really Google – I just want to present my screen; I don’t need to configure Google Voice Assistant but no – its all integrated together). Contemplate taking the ChromeCast and throwing it onto the roof of the offsite location but, no, you decide to be an adult.
  15. Finish the configuration and walk back to the kitchen to discover that the offsite has started without you. No one bothered to walk the 25 feed across the way to tell you this.
  16. Deep breath, deep breath and realize that you actually have grown up over the past decade – 40 year old Scott would have quit on the spot and simply gone to the airport.
  17. In case you haven’t kept track, it is only 8:57 on the first day.
  18. Calm down and begin to engage with the team.
  19. Never get the opportunity to give your presentation it but, instead, have your Team Lead call you out on the things left out (no; they weren’t left out; they were in there but you disagreed with the order; they were there). This is somewhat similar to the last offsite when your presentation got highjacked partway through and you never got to finish.
  20. I’m sorry but not submitting a specification for a system that is literally man years of effort to build when you have a team that is maybe 1.7 engineers in size isn’t missing anything – it is called being realistic based on understood constraints – particularly when the MVP date is less than a quarter away and you know that time to hire people is between 2 and 4 months (assuming that you have the person in hand and ready to go).
  21. Watch the Team Lead make his representation for what you’re building with all kinds of “Hand Wavy” motions over every single hard technical problem – all of which are enormous.
  22. Fume in silence and put on your team happy face.
  23. It isn’t even lunch time yet.
  24. Have lunch and it is simply outstanding. This is the one good moment of the day and I did bask in the glory that was that sandwich.
  25. Go back to the flat screen TV and discover that the Team Facilitator can’t manage to use ChromeCast to put together the Zoom call. Revert to the HDMI cable and find out that his laptop only had “mini HDMI” (and, yet, he’s the one who asked you to bring the HDMI cable). Make a few more configuration changes to make this work and be told, just on the cusp of making it work, “Nope; sorry we have to start this now” and, somehow, be made to feel like this was all your fault.
  26. Move onto the group anti bias and diversity training and discover that no one’s laptop will work with this 65” TCL / Insignia TV, not your MacBook, not her Windows machine, etc. At least that makes you feel mildly better (tv, bad hdmi cable, unclear – I NEED TO KNOW).
  27. Your Verizon HotSpot again saves the day so in the next session you can use YouTube for some mandatory videos. Show that session’s facilitator Tea and Consent and have a nice moment enjoying it together.
  28. Sit through 3 hours of group anti bias and diversity training. And I’m not saying that this isn’t important but on a virtual team that has ever had 2 opportunities to work together ever, is it really worth spending 3/16 of our total time on this?
  29. 20 minutes of downtime until the team “bonding” exercise.
  30. Finally complete the bonding exercise and head for dinner. The passage of time is not apparent here but it is now 9:30 pm before appetizers arrive.
  31. Finish dinner and get home to a bed – at 11:30 pm. Yep. That’s roughly a 17 hour day.
  32. Finding out from your wife that your latest consulting bills STILL have not been paid. 51 days since the invoices were sent. “Mailed the Wednesday before from New York City” is just plain bullshit; this isn’t the era of the Pony Express.
  33. Sleep poorly and vent this spleen. What fresh and different hell awaits me for Day 2 ?