I'm afraid I feel my level of sympathy would be 100% correlated with how mandatory the heels are for your friend :-/

On aside, I'm also (genuinely, not snarkily) curious to understand the "Naturally" part in front of "wearing high heels". Don't get me wrong - I personally think they're a fabulously attractive if completely impractical article of clothing, but it feels like in many places in the world they are far from the norm/regular/Natural assumption.

I also wonder if encouraging this form of meetings could be viewed as discriminatory if you have employees who have physical disabilities that might make walking unpleasant or slow.

I think some of us miss that step in growing up where you're supposed to realize you can own lots of shoes for occasions other than fashion. You can have some that are fit for only one activity or used in one location (eg, the gym or exercise class).

Keeping a spare pair of shoes at work would solve this problem.

Sounds like an opportunity to keep a pair of tactical flats in a desk drawer.

"opportunity" here sounds kind of crappy because of the boss/employee power dynamic and the man/woman thing to boot, but if she's not offended by the implication that she should bend to meet the demands of her boss, it could be seen as a plain savvy thing to do.

edit: just noticed I assumed the boss was a dude, maybe that's not the case, but the boss/employee power dynamic is the main bit

Sounds like a personal choice. She has the option to adapt to the circumstances, and has failed to do so.

We aren't allowed to wear flip flops to work. I don't see why heels are tolerated, either.

Work isn't a fashion statement.

Is she forced to wear high heels at work or she simply likes it?

Height differences can also be quite annoying when walking, especially when there are more than two people (eg two taller ones and one shorter).