Awkward! Money & biz-awkward situations, handled.

AWKWARD! Handy-dandy steps for handling any awkwardness life throws at you

As you navigate your time in business — and on this planet — you’re naturally going to come up against some awkward-as-shit situations.  People won’t pay on time, or they’ll have complaints you can’t possibly have seen coming, or they’ll demand a full refund for a product they’ve just happily consumed.

Oh, you didn’t like the donuts!?


It’s not easy to handle these things, but here’s a stab at tackling most any awk-a-awk-a-awkwardness you’re currently facing.

Give yourself a minute. As in, say “I’ll get back to you” or “Let me check” or “I’m not sure.” There’s no need to have an answer the minute someone asks a question. If I ask you what the answer to the equation 372 x 485 is, you don’t have an immediate answer. You would need to consult your calculator.  The same goes for, “Can you just rearrange your pricing, add a discount, take away that service, merge it with this one, apply my coupon, and then add a 10% rush fee?” You need a minute.

Talk it out. Trust at least 2 people in the world enough to run scenarios of all kinds past them with complete honesty.  Oh hey, this feels terrible. This is really awkward. I don’t know what to say. I don’t know how to say “no.”

Acknowledge your true feelings and your instincts — yes, sometimes you want to throatpunch people — and then come up with a reasonable solution.

Make a script. Yes, a script.  An exact script of what you’re going to say, not one of those “Oh, I thought about it in my head” scenarios. Write down every word, and rely on e-mail where you might lose your cool or forget to mention an important detail. The more likely you are to freak out while thinking on your feet, the more you want to have a precise, kind script you can tweak for 24 hours or so before sending.

Embrace the awkward. Some parts of business are just plain messy. Saying “This is going to be awkward” at the start of a conversation actually helps.  NO REALLY.  It does.

You’re going to talk about odd situations or field uncomfortable questions or say “yes” when you want to say “fuck no” — or “no” when you really, really want to say “yes” but circumstances don’t allow for it. It will always be awkward to say “no” to people asking for a donation of some kind. It will always be weird to answer the door and then shut it in a salesman’s face. (Kindly, of course.) Embracing the awkward means you set a time limit for handling the situation and you handle it instead of hoping it will go away.

Your honesty does both people in the conversation an immense service.

Now, let’s talk money awkward.  These are often the hardest and most insulting questions to field on the fly without losing your cool.

“What are your deals?”

First, resist the temptation to throatpunch this person.  Have a standing promotion or offer of some kind.  Perhaps it’s your featured package that’s always represents savings, but is in no way time-sensitive.  Maybe it’s a throwaway 10% discount that you give when asked.  If you’re a masseuse, the buy-3-get-1-free package is what you mention at this point.  A photographer?  Mention that your most popular portrait package saves your peeps over $400.

“How much DO you charge?”

When people want a custom service and they’re fixated on price, it’s time to have a conversation. Provide a range of prices and then ask question after question. Tell me more about what you’re looking for. Help me understand what you’d like to walk away owning or having.

Call them out when necessary: you say you want the files, but you REALLY want a bunch of canvases on the wall that you’re “going to print yourself later.” Share your experience of what people say they want and what they actually want, as well as how often they fall down on the followthrough front.  Offer to do the heavy lifting for them.  Then make a suggestion.

“Based on what you’re telling me, I’d recommend picking up _________, which costs ______.”

“That’s too expensive.”

There is no price point below which people won’t balk.  Including free.

Articulate the value of what you do in a clear, non-defensive way.

For example: you don’t have to invest in business knowledge or development, but that will severely limit both your personal and professional growth over the coming years, which could mean you end up with fewer clients, less confidence, and a diminishing sense of direction in your business.  (It could easily cost you thousands of dollars in the next six months.)

If hiring me for $649 an hour helps you map out a 6-month plan, prioritize your to-do list, and move confidently in the direction of your dreams, is it worth it?

“For ___________, you’ll receive ________, ___________, and __________. When you think about how it affects your _____________ for the long term, you’re actually __________.”

“But we’re friends!  Any chance of a discount?”

In your mind, think of your top 3 to 5 friends. Would you be alright working for these people once a year for free? If not, cut the list until you’re like, “Yup, free is okay for you.” Now, charge everyone else full price. That clear line is super helpful. Not clear enough? Consider Brene Brown’s “hide the bodies” friends. If you killed someone, which friends would you call to help you hide the body? THOSE are the people you should work for, for free.

“Because I’m committed to maintaining a sustainable business and not a hobby, I simply can’t work for free. I can offer you a ________________, though!”

“Will you work this event/donate your time for free?”

“Exposure” and “free press” are all well and good, but it’s perfectly okay to turn down offers involving those rewards in the name of keeping both your sanity and your schedule in check. How do you do that? You let people know your calendar is quite full, and your regular rates for doing X service are Y. Simple and straightforward. Not because you’re being a dick, but because you truly are too busy or full or otherwise engaged to take on a freebie at this time, even if it’s the world’s most appealing freebie.

“My free ___________ creation time is all blocked out, but I’m happy to take on this job for _______, a _____% savings from my usual rates.”

“What about this? Do you do trade? Can I pay you in zucchini?  How ’bout Beanie Babies?”

Instead of getting all flustered and giving an answer you know you’ll regret, say the magic words with me: “I’ll get back to you.” Then decide whether you really are okay with being paid in zucchini, or magic markers, or massage sessions, or trips to the spa for free facials. There’s no right or wrong way to barter, but you want to make absolutely certain you truly want what’s being offered and aren’t just accepting the offer out of guilt or obligation.

“Hey I had a great idea!  [insert project you’re in no way interested in] You in!?”

Just like in the land of dating, you can’t send mixed signals. So if you like that guy, you’ve got to consistently like him, right up until the point when you do him. But if you act like you’re interested and then you let him get to third base and THEN you tell him you’re not interested….you’ve only made the situation much more awkward than it had to be.

Tell people upfront, in no uncertain terms, whether a project excites or delights you. Refer other people you trust out liberally and often.

It is much, much, MUCH worse to act as if you care, or feign enthusiasm, than it is to say “No” at the outset.

Think about it: would you rather be friends with someone who sort of likes you, or someone who genuinely looks forward to your company? Would you rather take on a project with someone who’s sort of excited about it, or someone who busts out of bed thinking about new ideas for it at 3:00 in the morning? We both know you’d choose the enthusiasm, so be honest when you’re excited — and honest when you’re not.

“This project isn’t my cup of tea, but I’ll bet ______________ would love to take it on!”

“I work for [insert charity name here] and we’d love to include your donation at our next event!”

Do you already know of — and love — this charity?  Does it inspire respect in your soul?  If  no, be truthful: “I donate X per year, and that’s already been allotted. I would ask __________, though as he/she loves _________!”  If yes, go for it.

Now, get out there and kick the shit out of awkward, warrior business owner peep!

P.S. The sales tool you’ve already got — but probably aren’t using.