Role playing with "Skip" (a difficult seller)

Services for Real Estate Pros with Owner of FlyersToYou, Inc. and former Top Realtor

How do you sell to an old codger who smokes cigars and cusses like a sailor?

Well...Greg Nino posed that exact question in a recent blog called "Meet Skeptical Skip". It was a great exercise in role-playing.

That blog can be found here.

A Little Background

Seems Skip has a home to sell and is interviewing a bunch of agents. He wants $500,000 (even though the home is only worth $485,000 tops). He also wants to close in 30 days or so.


He tried selling it FSBO for the last 8 months, but failed. And now he's wondering how YOU intend to market his home!?!

The Role Play

I love role playing. Well, wait... actually, I hate it! LOL! Way back in my mortgage days, it seems I was always chosen (in front of the entire company) to play the role of loan officer...while someone else got to play the role of "Feisty Realtor" (yes, mortgage companies DO actually use those kinds of role playing situations!! LOL!! really had to be on your toes...because whoever was playing the Realtor would inevitably try to trip you up every 30 seconds or so along the way. Sometimes it got to the point of being ridiculous, which is why I never liked them in that kind of setting.

BUT, role playing is a vital part of becoming a successful you HAVE to do it!! Whether you practice in front of 1,000 fellow loan officers, or one-on-one with a close associate, or even by yourself with a pad of paper and some expected responses is up to you. But it's absolutely necessary in order to hone and fine-tune your selling skills!

Back to the "Skip" Blog

Skip owned a Ford Dually because,'s "American". He loves eating Spaghetti 'O's out of the can and he hunts squirrels. He claims to be a war veteran (there's even a mannequin with a uniform on it) and he's a retired machinist.

The blog was very entertaining and I think it's up to over 100 comments now.

It was fun to watch as fellow Rainers posed questions to Skip. Some gave up on Skip completely, some closed a little too soon...and some hung in there the entire way.

The "Piece of String" Close

Yesterday, I blogged about an old boss who taught me a very valuable lesson using a simple piece of string. How it can be much more effective to ask questions rather than shifting immediately into sales mode. So I posted a response on Greg's blog. It was slightly different than many of the others...and no, I didn't win the listing. :(

But I DID receive three emails this morning from fellow Rainers who said they enjoyed reading my little sales strategy. They mentioned that, because comments have a tendency to get lost in the shuffle on busy blogs, that perhaps I should post my own blog so others might see if there's something they can use.

So that's what I'm doing. Below is my "Piece Of String" tactic with Skip in its entirety. My hope is that someone will bring something away from it that might be useful in their own selling situations. Have fun!

Here's my Comment posted in its entirety

Interesting post (I LOVE these kinds of roleplays!)


Shelve the marketing answers for right now. Skip doesn't really care about that stuff (yet). He WILL, of course...but he's testing you first. He's a tough old coot (which should be painfully obvious by now.) I wouldn't go anywhere near his questions just yet....and I certainly wouldn't espouse the virtues of the internet and/or call capture systems, etc. PLEASE don't be offended by that. It's just an observation.

When a client asks a question...he's controlling the situation...NOT YOU! You need to get control back before anything you say has any bearing on this "meeting".

Let's see what we can already gather about Skip.

From his age, we can be pretty sure he actually WAS in the service (no one under the age of 60 wears suspenders anymore). And 60 is Vietnam era. It's also a pretty fair bet he's a blue-collar guy...based on...well, EVERYTHING about him!!! So if you think your white collar selling tactics are gonna go ANYWHERE, I have news for ya! They're not.

(So let's try a different approach).

"Skip, your questions are great, but let's come back to those in a moment, ok? the time I leave here this afternoon, you and I need to decide whether we're a good fit in working together to sell your house. I'm pretty sure we are, but we'll have to team up on this in order to get it done. Because of that, I'd kinda like to get to know you a little better...things like how long you were in the military and what you did when you got out?"

Skip: ::: Slightly caught off guard and a little suspicious about the military question :::

What makes you think I was in the military boy?

"Well...I couldn't help but notice the uniform over there on the mannequin, and you sorta remind me of a favorite uncle of mine named Bob. His real name was Robert. (Skip's real name is something else too) Uncle Bob was in the Army and he smoked cigars too. He was also a bit feisty when it came to business, but he always wound up making the right decisions. Probably similar to you! long were you in??"

Skip: I did almost 20 years and three tours in the army. But that's before your time.

"Yep...I'm glad of that too. My whole generation is pretty lucky to have had you guys over there to help us live the lives we do. What did'ja do when you got out?"

Skip: I became a machinist, same thing I did in the army. Did that for pretty near 25 years before retiring.

"Well, I'm glad to hear about both of those experiences. Wanna know why?"

Skip: Sure. Why?

"Because to sell your house. it's gonna take what you learned from BOTH of those experiences in order to get the job done. When you were in the and your fellow soldiers probably never backed down from a fight, did you?

Skip: Hell no! NEVER!

"Good...cuz I don't either. If things get a little tough...I'm not running, and it's good to know you won't either. I also need to count on you having my back...just like your old army buddies did. And you can always count on me having yours too. I also need a good machinist on this team. Wanna know why?

Skip: Yep.

"Because a machinist understands that without the right tools...the job can't get done."

You all can take it from here because you can already see where I'm going with it. If I immediately start stating what I can do...without him on my side...I've lost the battle. And I'm not going to let him control THIS conversation at all. I'll ask the questions, thank you...and guide him wherever I need him to be.

And I'll walk out with the listing (probably at $490,000 but I'm okay with that.) He'll also know I'm every bit as good a Realtor as HE was a machinist. And if he ever had a boss who didn't appreciate his skills (he did, by the way....we ALL have)...then he'll know exactly why I need him to appreciate mine.

Someone else can take it from here....I just wanted to point out that I hadn't seen anyone guiding the conversation yet. And it's so easy to do!

Here's a hint: Skip is a laydown. He'll do whatever you want. Let him fuss a little. No big deal. He's a puppy dog at heart.

Just my four cents or so.



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Mary Pope-Handy
Sereno Group Real Estate - Los Gatos, CA
CRS, CIPS, ABR, SRES, Silicon Valley

You know, if Skip can't get along with his own kids, I'm not so sure he'd be easy to work with on something as challenging and emotional as a home sale in a buyer's market. My sense is that one Skip would be as much work as four more realistic and reasonable sellers. I would not be fighting to get this listing.

Aug 14, 2008 02:49 AM #1
Carole Lhuillier
Keller Williams Realty SunCoast - Saint Pete Beach, FL
Our Home Team SunCoast

Dave, this was so great and very entertaining.  Of course, the points you made were of a more straight to the point and serious nature and certainly worth reminding others of.

Good luck to you in growing your business as I am sure you will continue to do very well judging from the personality that shows through inthis blog.

Carole Lhuillier


Aug 14, 2008 02:54 AM #2
Hurst Real Estate & Auction - Morristown, TN

I think your role playing brought out some good points but I don't think Skip wouldve played along with your role.  Skips want and need control and when you try to take it from them, they will sense it and you will lose the struggle. (and the listing)

Aug 14, 2008 02:59 AM #3
Tricia Jumonville
Bradfield Properties - Georgetown, TX
Texas REALTOR , Agent With Horse Sense

I loved this!  Very entertaining, and a great way to get the point across (to the "seller", and to us). 


Aug 14, 2008 03:10 AM #4
Mark Wilson
We Make Houses Home - Cedar Park, TX

Great point Dave.  My mentor once told me that you have to put yourself in the prospect's shoes; I try to do that in all aspects of the business and it is very effective. 

Aug 14, 2008 03:12 AM #5
JoEllen Stranger-Thorsen
Eustis, FL
Lake County, FL

There are many "Skips" out there and it surprises me how many agents weren't even willing to try to win the listing or wrote him off as too difficult to work with. I bet your approach would have won the listing and a valued client.

Aug 14, 2008 03:16 AM #6
David Daniels
Owner of FlyersToYou, Inc. and former Top Realtor - Hemet, CA


Those are all great points. I'm not actually sure how long I would've dealt with his "attitude" either, BUT...I HAVE had sellers who were very difficult (at first). They'd been through the mill with other agents, and were sourpusses when it came to even the mere THOUGHT of having to repeat those same experiences with someone new.

I wish I could say the following happened every single time...but it didn't. However, more often than not, those sellers became pussycats and some of the easiest and best clients in the world to work with. They only wanted to know that someone was actually on THEIR side for a change. Once you established THAT relationship...they'd do anything you asked (including sending you referrals!)

Skip's own kids may have abandoned him...but I wouldn't be too quick to judge. He could have been in the midwest....his ex and the kids moving to getting caught up in drugs, bad grades, whatever. He's a military guy...a blue-collar guy....and maybe the kids didn't like the way he handled his "fatherly advice". We don't really know what the circumstances are around that. But I'll bet my last dollar, he's got pictures of them in his wallet...and he looks at them every night before he goes to sleep. And he regrets not having been there for his kids more. I'll bet he even drinks a bit to handle the feelings of guilt. In THAT circumstance, it's a sadder situation isn't it? Nonetheless...if I ever decided not to do business with some of my sellers based on their personal lives...I'm not sure I'd have had as much business as I did.  

In fact...even with my current real estate marketing firm...(with Realtors as my customers)...I have some who drink too much, some who are gay, some whose kids are also not to be found, some who are swingers, some who don't pay their bills, and some who cheat on their taxes. The only ones I won't do business with are the ones who won't pay their bills. LOL!!

Thank you for commenting!!


Thank you so much for those kind words. We've been very fortunate already! FlyersToYou has been around for 7 years now...and even in today's "strange" economy, we continue to grow at a pace that's sometimes hard to keep up with! As agents begin to understand the concept of personal branding more....or who want to provide their sellers with the absolute best marketing materials...we're one of the only marketing companies that actually COME FROM a real estate background. It's easy to find graphic designers. They're everywhere. But to find one who has actually done what YOU do for a us a unique advantage over our competition!

Thanks again for the compliment!!


You're absolutely right. I obviously wrote the I made Skip play into my approach. But he COULD have said "Hey Buddy, while I appreciate what you're trying to do, I ain't interested in becoming your friend. Either answer my question about how you're gonna market my home, or I'm calling someone else."

My answer?

", I'm curious as to what gave you the impression I was trying to become your friend? If we become friends during this transaction...great. But what I'm ACTUALLY trying to do is determine whether we make a good enough TEAM to get you the highest net profit on the sale of your home. That IS something you want to accomplish, isn't it?" He almost can't answer with anything but "yes" in one form or another.

(That would probably get us back on track.)

Great points though. Thanks for commenting!! :)


Thank you for taking the time to read this whole thing! I know it's long...and takes a while to develop. But hopefully it DOES help others in realizing that it's the QUESTIONS we ask that are more important than the ANSWERS we provide. If THEY ask the questions...we have no control over the answers...but if WE ask the questions...we can guide them wherever we want.


Clothing store salesperson: "Can I help you?"
Our answer? (In unison) "No thanks, I'm just looking." (end of rapport)

Clothing store salesperson: "Hi, is this your first time in our store?"
Our answer? No.
Salesperson: "Oh, well then welcome back! We've rearranged things a bit recently. So, if you're looking for something in particular...I can probably point you in the right direction."
Answer: I'm just here to look at shirts.
Salesperson: Well...we just got our newest shipment in...they're over here :::walking toward rack:::

(just getting the rapport started)

A similar approach could have been used if the customer answered "Yes, it's my first time in your store."

One's a successful salesperson...and one's not.

Tricia, thank you for taking the time to comment. I appreciate that!


You had a great mentor. "Putting ourselves in their shoes" works not just in business....but in "regular" life as well. Heck, just yesterday, my dog Kane had a "piddling accident". I thought..."Oh man!!! I HATE cleaning up after this kind of thing!" It was happened. Nothing I could do now would change THAT. So, I took a breath...kind of thought to myself how HE must be feeling (he knew he made a mistake)...and handled it much better than had I simply REACTED! We have to try not to REACT...but rather take a breath, think first and RESPOND in a great many aspects of our lives!

Thanks for the comment!


I couldn't believe that either!! A lot of people were simply ready to totally write Skip off before even trying. Does that mean we're obligated to work with EVERY SINGLE CUSTOMER no matter how difficult they are?? Of course not. Makes me feel sorry for all the waitresses in the world!! But it never hurts to try and ascertain whether there's a way to make it work in a real estate transaction where we stand to make a decent amount of money in exchange for a little more effort and/or understanding.

I'm not sure whether my approach would have worked or not...but I DID take a lot of listings where it seemd like a LOT of sellers started out in "Skip-mode"!!!

Thanks for commenting!!!


Aug 14, 2008 04:35 AM #7
Michelle Chamberlain
Above All Financial Services -Pennsylvania Mortgage Broker - Secane, PA
Suburban Philadelphia Mortgage Broker

I'm going to disagree with the comment that this approach wouldn't have worked with Skip because Skip needed to take control of the situation.  Skip may have wanted some control, but Skip also wanted his house sold  and that trumps his need for control. Remembet this wasn't a cold call so this sale is there, if you approach it correctly.   In fact, I think Greg's punchline to the exercise (which may have been lost in the humor of it all) was that the guy was actually going to buy  multi-million dollar property and wanted the agent to represent him as a buyer, if she'd be willing to work with him and give him what he wanted on the seller side.  Again, none of the potential agents learned this because they didn't ask the right questions.

I am not trained in sales, but I am trained in Customer  Service and I have trained people in it as well.   The end result is the same.  Meeting the customer's needs.   When you fail to ask probing questions and take control of situation you are either going to forget something relevant, lose the sale, or get flustered so that you come across as not knowing what you are talking about. 

Great post Dave.

Aug 14, 2008 10:58 AM #8
John Doe
San Diego, CA

Dave, great post once again!  I have dealt with clients like this before and I know how difficult they can be.  However, whenever I run into someone like this, I make it a goal to befriend them and show them that I am the person they should be working with.  My father was a successful salesperson and taught me a lot tricks of the trade.  One of the things he taught me is that every client (or potential client) is like a Master combination lock.  The goal is to find the right "combination" to unlock them.  It can be fun if you make it a game.  It has help me MANY times to look at it as a game rather than get frustrated and down because I am "working with that guy".  And if it doesn't work out, then it wasn't meant to be.  As nice of a person as I am, there have been times with the chemistry with a client just wasn't there.  It happens.  This is sales - move on and don't take it personally!

Aug 15, 2008 02:48 AM #9
Nannette Turner
Keller Williams Lynchburg - Lynchburg, VA
Online Marketing Home Ownership Advocate Specialis

I was a part of the role play and read your comments in that post.  My question is if you would have had to continue to reiterate your role in the sale of Skip's house.  I think you would have through out the entire listing/sale.  No doubt Mr. Skip would have been a taxing client.  Depending on how much I had on the table, I'm not sure I'd have the time to deal with a high maintenance client even if I could "win" the listing.  Call me lazy, or whatever, but I can't help but want to go after easy money and pick my battles.  Explaining to Skip every week for 10-12 weeks why his house did not sell could be taxing on ones brain.  I'm afraid Skip would "forget" and take advantage of opportunities to attempt to turn the tables.  Just MHO.

Aug 15, 2008 10:47 PM #10
David Daniels
Owner of FlyersToYou, Inc. and former Top Realtor - Hemet, CA

Michelle (Above All Financial Services),

Your last paragraph intrigues me!! You and I have had some GREAT "conversations" via email...and I would have bet my bottom dollar that you had TAUGHT sales training!!! And now, I come to find out that you're not even "trained in sales"???? I almost fainted when I read that!! LOL!!

One of the most astute, insightful, realistic and convincing people I've met here on the Rain....and no sales training?? Just goes to show that "Howdy folks, what can I do ya for?" doesn't necessarily represent itself as a sales skill I guess. On the other hand, your Customer Service training has served you very well, my dear!

And you're so right in your last paragraph!! If I allowed my client to get me was hard to find my way back. So, in those circumstance, no matter what they said....I often responded by saying something like "John, I'm really glad you brought that up. Let's come back to that in a moment." And then, simply go back to my question asking. By the way, that NEVER meant I wouldn't allow them to ask questions. It just meant that they couldn't control what I needed to accomplish first.

HINT: Have a pad of paper handy in your sales presentation. When the client asks questions, answer the simple ones if you can stay on track. For those that might veer off-course, tell your customer this: "Cindy, I want to make sure we get all of your questions answered, so I'm going to write each of them down. That way....when we're finished doing what we're doing now, we can go back and put your mind at ease by providing the answers you need, ok?"

Worked every time.

Thanks for visiting Michelle. I appreciate you!


I love your analogy about customers being like Master combination locks....and us needing to find the right combination!!! I always did well with the "Skips" of the world because they at least let me know where they stood!!! The ones I had trouble figuring out the combination to are the ones who sat there without saying a word.

I, too...consider sales a bit of a game. That can sound harsh if taken the wrong way. It's not that I didn't care. It's just that it often felt like a chess game. They'd make a move...I'd make a move. They'd think they had a Checkmate...and I simply moved my King over one square to avoid the loss.

My goal??? ALWAYS to walk away from the game with everyone winning.

I never achieved a 100% closing ratio either. But if I LEARNED something from the experience, I considered it a success...and moved on. Great points!


Great question and comments! But scroll back up to my response to Mary. She had mentioned that if Skip can't even get along with his own kids...he might just be too tough a customer to work with. I often found just the opposite to be true. In my real estate days, MY most difficult clients were the ones who never came across as difficult, but proved to be almost more than I could handle.

I read several of your blogs (I love your writing style by the way). There was one about a Mr. Buyer who flew up to see property after several months of corresponding. He and his wife were supposed to come up together, but they didn't. So he flew showed him property. Two weeks later, SHE flew up. They'd been searching for properties for three years.

THOSE are my toughest customers, NOT the Skips of the world. Skip simply tests you a little because he wants to make sure you're the right one for him and he's afraid of being taken advantage of. Once he knows you're okay...he'll become a pussycat (in my experience anyway).

But the ones who can't make a decision if their lives depended on it are the ones who frustrate me the most. Skip would have been tough for about an hour. The rest of the transaction would have been easy. Your clients may not have been as "gruff" as Skip, but they would have tested my patience completely!! Not because they were taxing or belligerent, but because they are the types who are simply incapable of making a decision and are afraid to act. The ones who can view the nicest property in town. The one being offered for $30,000 below market...the one that is in pristine condition, perfect neighborhood, great schools...has everything they're looking for...and they want to think about it for a few days. Of course, the property is sold to someone else...and your buyers are somehow upset at YOU??? And they want to start the 6-month process all over again???? No thanks!

Those are the people who you could show two color swatches to. One's burgundy...and one's bright red. Ask them to choose the one that they (as a couple) like best. Explain that you're going to go refill your coffee cup and return in two minutes....and they need to have an answer by then. After all, they're just color swatches for crying out loud, right???

You go get more coffee (it should probably have a splash of something ELSE in it because of what you're about to face!!)...LOL....but you sit back down and ask "So, which color did you choose?"

They didn't.

Mr. liked the bright red one. He likes fast cars, and they're always red. He likes cute women in red dresses...and he owns a truck that's red and is probably wearing a red shirt. SHE hates red. She likes the richness of burgundy. The feeling of luxury it evokes. She has auburn colored hair (dyed)....and her Lexus has burgundy interior.

They argued while you were gone...and they're both sitting there with their arms folded when you press for an answer to your simple question about a color swatch. THOSE are my most difficult customers!! Skip, on the other hand, in his not-so-delicate fashion...would have said "Burgundy is a sissy color, and anyone who chooses THAT color probably had to keep his mouth shut while in the army."

He chose red. Whew! A decision maker!! How refreshing!

Note: Decision makers ALWAYS trust their decisions (even when they're wrong). But people who CAN'T make decisions will FOREVER wonder whether they made the right one. I'll take the decision maker any day!

P.S. Thank you for adding me as an associate! I can't wait to see what your next post is about!


Aug 16, 2008 01:48 AM #11
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