The Best Time and Place to Say 'I Told You So'

Over at Ask a Manager, Alison Green fields a question from a reader who wonders if there is a professional way to tell her boss I told you so.

Said boss had the writer and her coworkers go through training on signs that a client's proposed project should be turned down -- only soon after to ignore various "red flags" en route to assigning her to a project that turned out as badly as she expected, based on the training.

Green provides a good way to do this, and notes that some bosses might be receptive to learning that their employees are indeed actively thinking on the job.

The following parts of her advice particularly resonated with me:

Image by Kelly Sikkema, via Unsplash, license.

[R]ather than wait for your boss to bring it up herself, another option is for you to bring it up proactively. You could say, "I'm concerned about issues XYZ with this project. Since you've stressed that we should flag potential problems early so we don't greenlight projects that end up being problems, I'm curious about whether you'd put this one in that category or whether you think it's worth continuing with. I'm wondering about whether I should have pushed harder a few months ago when I raised these worries or whether you're looking at it in a different way than I am."

...

Also, if you're not already putting your concerns in writing before an ill-advised project begins, start doing that. Then if those concerns come to fruition, you can forward that to your boss with a note like, "I'm seeing a lot of the concerns we had in the beginning playing out now, like XYZ. Can we talk about the best way to navigate this at our current stage?" Your tone needs to be collaborative problem-solving, not "I told you so" -- but it might drive home the point that you are anticipating these things. [bold added]

Several readers chimed in to similar effect in the comments, indicating that perhaps with certain absent-minded, blame-shifting, or incompetent types, careful note-taking of this type might be a good policy generally.

I myself once did a similar thing after getting wind that someone I needed to collaborate with might cause me trouble. When the potential problem arose -- disagreement over how to split a payment -- I enjoyed instantly shutting it down with a forwarded email.

Perhaps the best way to say I told you so is tactfully and ahead of time, preferably with the aid of the person you'll need to say it to or about.

-- CAV