I’ve spent the better part of my life in writing workshops, from which I am thoroughly certain of the following fact: everything is in how you phrase it.

It might very well have been that someone’s poem was the biggest pile of actual trash and horseradish sauce you’d ever read, but if you lead with, “I think this is actual trash and likely the dummest thing I’ve read this side of the Millennium, seriously why haven’t you given up the craft and taken a job wherever they’ll give you one?” not only are you likely to offend the writer, more notably, you also wouldn’t help them. They’d be too busy stopping up the blood your word-arrows spewed to absorb any constructive criticism you might have had to offer.

And so it goes with helping people Live Simply.

Countless clients have told me stories of times they enlisted the help of their friends and loved ones during the editing process [For the purposes of this article, we’ll stick with closet editing as our example].

Expect in pretty much all cases, said friend or sister or cousin carried out their duties with a frankness that can only be euphemistic for “so mean about it I kicked them out and spent the rest of the day hiding under my covers, weeping ever so slightly while questioning if I’ve ever made one sound sartorial decision in my clothes-wearing life.”

Statements like:

“That is the most hideous thing I’ve ever seen, please find a wire hanger and take my eyes now.”

“Have you gone blind without me realizing? Ray??”

“What in the hell were you thinking when you bought that?!”

“When are you going to wear that. WHEN. NEVER. You don’t ever get dressed anymore. Your whole life is about being covered in baby throw up. Give it up.”

“HAHAHHAHAHHAHAH. EW.”

I’ve been witness to plenty of these scenarios; friends or family members will happen to stop by while a client and I are editing her closet, and want nothing so much as to get involved.

Whether it’s a chance to feel better about their closet situation by picking on someone else’s, or seen as an opportunity to unleash year’s worth of accumulated opinions, (“Here’s my chance to finally get her to get rid of that wretched, slutty, sequin dress.”) people seem to forget the basic principles of human interaction when they enter the editing arena.

Well–pause–it’s either the scenario described above, or the friend or family member is so faint of heart she can’t bring herself to make any decisive contributions at all. Rather, the “helper” is content to sit there like milk toast, chewing her gum, and occasionally looking up from her phone to mumble a “yeah, maybe…” or my personal favorite, the, “Oh my god, I don’t know how you’re doing this.–GAWK–My closet is such a nightmare. I have so many—” She goes on and on about herself.

Rare is it, indeed, for a non-professional to actually be of assistance in such circumstances. Conveniently, hi, I do this professionally, nice to meet you! Allow me to humbly give you some pointers, oh well-intentioned one.

See, the thing about it is: your friend or sister or spouse wants and needs you to be honest, and so your inclination to keep it real is spot on. But no one wants to feel dumb, unstylish, demented, delusional, et al, least of all when that person is likely already feeling overwhelmed and vulnerable.

Tactless stating of personal opinion not only can hurt your friend or family member’s feelings, and thereby put a damper on the relationship, it also won’t help them Live Simply. They will be far too wrapped up in reactionary feelings to be able to continue making clear-headed decisions.

It doesn’t matter, by the way, how close you are with a person. Not even your Siamese twin is going to find malicious truth helpful and enlivening.

So, the next time you offer to help your Person edit their closet or their garage or their parent’s storage unit, realize first and foremost that you are potentially being granted access to one of a person’s more vulnerable, flustering moments in life. With that in mind, temper your honesty with kindness, remembering that delivery is everything. You don’t have to put on a show or recite some soliloquy, and you certainly shouldn’t lie, but you can deliver the truth with care.

“I think you have other pieces that are more flattering,” you can say.

Or: “I prefer the one you tried on before to this one.”

Or: “Those are similar, but I think this one is more the look you’re going for.”

Or: “That pattern isn’t worthy of being on your body.”

And, whenever you aren’t sure, “What do you think??”

Because in the end, what people really need is less an honorary panel member of the fashion police and more a sounding board for their own thoughts, opinions and beliefs.

Image credits: Home of Iris Apfel; Photography by Roger Davies for Architectural Digest, J Crew Ad Campaign 2010, scanned by A Lovely Being, Home of Katie Kime, photographed by Genevieve Garruppo via Lonny