The Short, Slightly Sarcastic Answer to (At Least Eleven) Things You’ve Always Wanted to Know About Selling Yourself. Featuring: A Strong Opinion.

IN: Selling

Q: Should I give away free consults?

A: Are you running a business or a charity? EEEEEEEEEEET. Time’s up. The correct answer is business Ding, ding, ding. And businesses are for profit. Key words: For profit. Respect your own time and prospects will, too. I guarantee the people you look up to aren’t running around giving away free consults.


Q: Why does everyone price things ending in a 9? Do I need to do this? People aren’t stupid. We all know $999 is basically $1,000.

A: People might not be stupid, but one thing they certainly aren’t is rational.  You might feel more “honest” and “authentic” listing your prices as whole numbers, but don’t run off on your high horse just yet. There are two really big reasons why, no matter how annoying, this can be effective: The first is because when people read a price, they anchor to the first number…and round down. If something costs $1.99, their brain processes it as costing one dollar and change. If something is listed at $2.00, however, the brain processes it as being in the two-dollar category…and that category might be one category too high, based on what they were expecting to pay. People’s expectations based on their historical experience plays a BIG part in your pricing. If you violate their expectations, you may be shooting yourself in the foot bone. The second reason pricing things ending in a 9 is effective is because psychologically, the more specific the number, the more people assume it was calculated with care, and therefore valid. When you’ve got big, whole numbers, on the other hand, people sense that it’s a number you just grabbed from the sky, with no rhyme or reason, and that makes them suspicious. Naturally, you can understand. When was the last time you paid exactly $5.00 for a bottle of shampoo? Something about it feels off, doesn’t it?


Q: What do I say when someone just wants to know my prices? I know they’re price shopping me, and I know I shouldn’t be competing on price, because I’ll lose.

A: Get the fucker on the phone. Once they have a chance to make a human connection with you, you’ll stand out in their mind as more trustworthy (and dedicated) than the rest. Not to mention, this is a great opportunity to showcase your personality…and then let the others compete with you on that, instead. At the end of the day, everyone just wants to feel like they’re making the best choice. So help them feel that way. P.S. Stop being so afraid of the phone. Sometimes doing things the traditional, respectable way is the fastest way to stand out in a sea of internet jockstars. P.P.S. Probably don’t refer to them as “the fucker.”


Q: Should I ask for a deposit ahead of time?

A: Is this a real question? In other words: YES, and for two reasons: First, because it’s expected. This is what professionals do. People running around accepting work without sending agreements and taking deposits are amateurs. And second, because in order to work with Mr. Guy #1, you’ve got to decline Mr. Guy #2, #3 and #4. That’s called opportunity cost. And if Mr. Guy #1 decides to randomly cancel on you last minute, you won’t be able to recoup that revenue, because by then, Mr. Guy #2, #3 and #4 have already engaged someone else. Deposits aren’t greedy; they’re necessary.


Q: If they say they’ll get back to me, and then don’t, should I follow up?

A: Better idea: Don’t leave prospects in charge of closing the deal…because they won’t. Most freelancers and business owners assume that if there’s interest, a prospect will follow up with you, leaving you off the hook with a huge sigh of relief. Phew, now my part’s over! Now the ball’s in their court. But leaving the ball in somebody else’s court is the fastest way to lose the game. And this makes sense. If you don’t even have a basketball, you can’t possibly make a basket—which even the world’s worst basketball player knows. (That’s me.) Rather, if you’re wrapping up a call with a prospect and you’re experiencing that fuck awkward moment when you’re both all, “Sooooooooo,” then it’s up to you to call the play. Take control of the conversation and simply say, “Let’s do this: You review the details, and I’ll give you a call on Friday to see what questions you have. Deal?” People are coming to you to be the expert. They’ll respect you when you step up to the plate and take control. (By the way, if they’re hem-hawing about you contacting them again, then you know they’re probably tire kickers, orrrrrrrrrr they hate your guts—neither of which you’ll want to waste your time with, anyway.) Boom, you’re either in or you’re out, prospect. Let’s find out which.


Q: If a prospect asks me to do some work on spec first (AKA for free) “to see if we’re a good fit,” what should I do?

A:  Tell them that your friendly neighborhood stone mason oddly turned down your request to come install a new pool patio for free (you know, so you could see if you liked it first). Since then, you’ve decided he’s probably onto something. In most circles, they call that “getting paid.”


Q: How can I show the prospect that I’m a good fit…without doing spec work?

A: The most important thing you could ever do for your business is know how you’re positioning it. David Ogilvy was great at this: “I could have positioned Dove as a detergent bar for men with dirty hands, but chose instead to position it as a toilet bar for women with dry skin.” Perception has to be created. If you aren’t working to create a specific perception about you + your work, then you aren’t positioning yourself—you’re praying. And this makes success hard, if not impossible. You should be able to align your business with that of your prospects’—and see a clear bridge between the two, based on your positioning. And then, you need to sit down, put that bridge into words, and use those words to tell your prospect, straight up, why exactly you aren’t just a good fit, but THE fit.


Q: Should I list my prices on my website?

A: You know when you walk through the mall, and see a piece of jewelry you would die for in some fancy glass display case, BUT NEVER GO IN AND ASK HOW MUCH? Yes, that. You don’t want prospects to do that to you. By not listing your prices on your website, you’re making an indirect statement about your prices…even if you didn’t mean to. And that statement is this: Shit’s expensive, dawg. Also, I’m probably charging people different fees and I might try to take you for a ride. Meanwhile, even if the prospect isn’t put off by premium pricing, they’re still annoyed by having to contact you to find out, at which point, they automatically assume it’s a sales trap and then they’ll feel obligated to buy and NOBODY WANTS THAT PRESSURE. Get over yourself and list a starting price.


Q: But if I list a starting price, then prospects have a tendency to hold me to that number…and then I look like a jerk when their actual quote comes out being $3,000 higher. Now what?

A: Touché, wise rabbit. This is the same reason why listing price ranges is tricky: Because people will always remember the lower number…and be disappointed when it’s higher. (Sometimes enough to throw off the whole deal.) That said, if your business doesn’t lend itself to a fast and hard price, then why not try listing a few examples of past work you’ve done, what it included, what the timeline was, and what the final price point was? This way, prospects can get a feel for where you stand in the market (and self-select themselves in or out of it, thereby reducing the amount of time you have to spend with people who don’t have the money to buy from you in the first place), and simultaneously, you set realistic expectations that demonstrate a flexible pricing system.


Q: What if I get nervous talking to prospects and “selling myself?”

A: Down some wine, and remember there’s a distinct difference between the you who lays in bed on a Sunday night with sweatpants and snot hanging out of your nose, and the you that’s a product. The you that’s a product is a shiny, branded version of you (and I don’t care what the authenticity brigade says). What would the branded version of you say? How would they act? How would they close the deal? Suck it up and role play.


Q: What if people tell me they like me and my services / offerings / ideas / products…but never actually BUY? What am I doing wrong?

A: Probably everything. But don’t feel bad—this happens all the time, and particularly in coaching, where the benefits are intangible. Selling something like self-realization can be difficult if you don’t know how to do it well. The bottom line: You need to change the thought sequence of the buyer. They’re sitting there thinking, “Yeah, that would be nice to have,” rather than, “Yes, I need this.” And usually, that’s because the way you’re communicating makes your services / offerings / ideas / products something that would be nice to have…but not necessary. How can you use stories to bring seemingly intangible benefits down to earth? If I tell you that by working with me, you’ll become more self-aware, you’re going to nod your head and move along. On the other hand, if I tell you that by working with me, one client who formerly had a difficult time making hard business decisions ended up learning a framework for when to trust herself…and when not to…and went on to make an extra $100,000 that year thanks to her newfound efficiency. Now that’s something you can get excited about. It feels like a smart, targeted investment—not a lofty, self-indulgent one. The motto to remember: Sell ’em what they want. Give ’em what they need.


Q: How can I turn people who ask “to pick my brain” into buyers?

A: You can’t.  Stay away from these selfish, needy buffoons. Your time is money—period. This ain’t Kansas anymore, Toto. <–The first time I’ve ever used the word “ain’t” in a sentence publicly. That said, if you need a polite way to redirect them to the buy button, try saying: “That’s something that I can best explain during a scheduled consulting session. Here’s the link for your convenience.” 🙂  Then stand firm, Dorothy.