Three Steps to Stop the Game of “When” at Work

When I’m helping a group of employees optimize their work+life fitness someone will always say, “Yeah, my work is done for the day and I want to leave the office, but I don’t want to be the first one to get up and I don’t want to leave before my boss.” In other words, they are waiting for someone else to say, “When!”


When I was little, my friends and I played variations of the game “When!” We held our breath until someone yelled, “When!” Kept our eyes wide open until someone shouted, “When!”

Exit Sign

I’m reminded of this game when I’m helping a group of employees optimize their work+life fit and someone will say, “Yeah, my work is done for the day and I want to leave the office, but I don’t want to be the first one to get up and I don’t want to leave before my boss.” In other words, they are waiting for someone else to say, “When!”

But two things happen. First, everyone else is waiting and watching not wanting to make the first move. And, further complicating matters, are those few people in the office who can and want to stay later, therefore, unintentionally raising the bar for everyone else. So, how do you leave, assuming you are at a good stopping point with your work, whether or not anyone else is?

Challenge the “Yeah, But … “

This “yeah, but … ” fear of leaving before your peers and/or boss is one of the primary work+life fit roadblocks that I address in chapter 10 of my book. To move past it, here’s a three step process that I use in my workshops.

Step 1) Determine if the “yeah but, I can’t leave before my peers/boss leaves” fear is based on fact.

Ask yourself, “Has my boss actually ever said, ‘you can’t leave before me?'” Or, maybe your boss never said anything directly to you, but have you heard him or her say something to anyone else? Have you seen anyone else suffer negative ramifications from leaving before the boss?


Answer: From my experience, nine times out of ten, the answer to all of these questions is “no.” Then you need to seriously challenge the wisdom of staying, waiting and watching. Get to the gym, see your kids, eat a healthy meal, or whatever else it was that you want to accomplish.

When faced with the fact that there’s no real evidence supporting the fear of leaving before their peers or their boss, employees in my workshops will admit, “This makes no sense,” and commit to experiment with leaving when they feel they can.

In fact, in a recent workshop, for the first time I had a senior leader start the “yeah, but … ” conversation by confessing, “Yeah, but I feel bad leaving before the people who work for me leave.” Immediately, a couple of his direct reports in the group laughed and said, “Yeah, but … I can’t leave until my manager logs off or leaves for the day.” They were waiting for him … he was waiting for them! Soon everyone was chuckling about ridiculousness of this wait-and-see game of “who’s going to go first.”

Periodically, however, someone will say, “Yes, I did leave before my boss and she was looking for me to help her with a project.” Or “Yes, my colleague often left before his boss and he was let go in the last round of layoffs.” Go to Step 2.

Step 2) Take the facts supporting your belief that if you leave before your boss, bad things will happen to the next level.

Ask yourself, “Was there something unique about the time your boss couldn’t find you or when your colleague was laid off that makes it irrelevant to your day-to-day reality?”


Usually people will reflect on these experiences for a minute and say something like, “Yes, it was a unique situation. It involved a last minute request from her boss. She ended up emailing me and I offered to work on it that night or come in early. She said, ‘fine,’ so I guess in the end it didn’t matter.” Or, “The entire group in which my colleague worked was let go, so the fact he left before his boss really didn’t make a difference.”

In rare circumstances, this exercise will conclude with the difficult recognition that, “My boss does always come out of her office at the 11th hour with fire drills and if you aren’t physically there to respond then it’s a major problem. So we all just sit there until 8:00 pm when she leaves.” Or, “Steve was the only person let go in his group and the only reason seems to be that he often was the first person out the door every night.” In these instances, go to Step 3.

Step 3) Carefully consider how you want to respond, because even in this case you do still have choices.

You could choose to pick one day of the week as a test. Leave when you’re at a good stopping point with your work, even if it means risking wrath should a fire drill happen. If it does, regroup and revisit whether or not you can comfortably leave even one day a week. If you can’t, this may be a signal that you need to find another job.

But for 99% of the people who challenge the fear, the reality sets in at Step 1 that they no longer need to sit, wait, and stew until another brave soul gets up and says, “When!”

All of us at every level are working hard enough without wasting any precious time and energy participating in this mindless game with no basis in reality. But the only way we are going to break the cycle is to challenge this common fear roadblock when it pops up and find the courage to stand up and say, “Hey guys, I can’t play today. Here’s how you can reach me if I’m needed, otherwise, I’m going home.” Say, “When!”


Have you found yourself, either consciously or unconsciously, participating in the game of “When!” and not leaving work because you are waiting for someone else to go first? Did you ever challenge this roadblock? If you didn’t, why not? If you did, what happened?

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