I have been wanting to do this in our own company, and in fact, we had decided to do this with a number of roles, assigning them as virtual roles, but a legal adviser told me that if i ever fell into a dispute with a client, where they made their purchasing decision based on the (apparent) size of my company, they could take me to court for mis-representation and i could be done for fraud.

So i think legally, you need to be very careful.

Thats a perfect storm of several very unlikely events.

I think when lawyers are involved, theres always a danger of optimising for the worst possible situation, which takes up a lot of time and effort, and often doesn't leave you, your customers or your business in a better situation.

In any case, no matter your final decisions, it's always prudent to be aware of the worst case scenario.

This is the reason that we send all invoices out in my girlfriends name because I'm a freelancer and a very small company most of the work I get is from people who know me directly and there is a massive personal relationship there.

It's really easy for money to get in the way of a friendship / client relationship but having a separate third party makes that so much easier to deal with.

It makes it very easy to bring up billing in the middle of of an email.

"It would be great to get together to discuss x next week, I'm across your way on Tuesday if your free (by the way, x mentioned that your invoice is still outstanding, any chance you could take a look at that so she stops moaning at me! :) )"

Makes the whole thing much simpler and gives them an easy way of responding with some humor.

(I will mention that x actually does exist and it is her email, she also looks after the accounts.. my main point was that the separation of the billing parts from the 'doing the work' parts has been a good thing for us)

I think this identifies a real problem, but I agree with those who are suspicious of the proposed solution. All that goodwill I would gain from playing good-cop-bad-cop with a sockpuppet as my partner will vanish, threefold, if and when my customers begin to suspect that I'm making stuff up. They will commence to wonder how many other aspects of my company are completely fictional, like my portfolio, or my qualifications.

What I wonder is how much it would cost to outsource Tony. The job of being Tony is, in the simplest form, really simple: You have to physically exist, and send out stock emails that I compose for you, and forward the responses to me. Obviously if your Tony candidate can write and speak well and has great customer-service skills they can do more, like actually respond to calls and emails without checking back with you.

sounds like a neat business idea. You could get a bunch of polisci majors who can't find jobs in this economy (http://news.ycombinator.com/item?id=1545019) and hire them out to be "fictional tony's". Sort of like a more specific version of the Amazon Mechanical Turk.

Amazon Mechanical Jerk. I like it.

Nothing about the article says that Tony is a jerk or a thug. Tony's requests for payment will be exactly the same as any other company trying to get paid for their hard work from a customer that is a jackass who won't pay. You start out with polite reminders, and gradually increase the sternness of the letters. At some point you start sending physical letters in the mail, via certified mail, you start printing headers in red, then you switch to the phone calls, and finally, Tony shows up in their front office and sits there every single day and asks to see the president, for as long as it takes. Then you'll get paid. And after the first time this happens, no more products on credit for that customer, payment in advance only.

Also, no products on credit for new customers either. Credit is only for ESTABLISHED customers.

Your first goal in setting up this business is to resist the terrible, perhaps irresistable temptation to use this name.

This is terrible advice.

If a client isn't holding up their end of a contract with you it doesn't suddenly make it okay to start lying to them to get what you want.

What happens when the client finds out that you invented a fake person to pressure them into paying you? What happens when word gets out in your industry that you are a liar who will stoop to deceiving your customers if you're not getting what you want?

There are few, if any, things more important in business than your name and your reputation. I would much rather take the loss on the contract and move on than risk being seen as untrustworthy.

The fake person is not to pressure them into paying you. It is to separate financial and customer service concerns.

If you want to talk about dishonest no good lowlifes, let's talk about the client who doesn't pay for the product.

Dang it, meant to down-vote you, but the voting arrows are broken here forever.

There is no excuse for lying.

Establishing a fictional name in order to separate concerns is not lying unless you are prepared to assert that Marion Morrison, Samuel Clemens and Brian Hugh Warner are lying when they do the same.

You make some very good points on the cost/benefit issues of this kind of strategy, and I'd be interested to explore them.

Although the incendiary language makes it hard to discuss substance.

Is everyone in accounts departments pressuring others to pay? Are you not 'getting what you want' if you're not paid on time?

Or are you entirely justified to follow up a late payment in both of these circumstances?

Terrible. Liar. Deceiving. Untrustworthy.

These are indeed incendiary words, and they were used to make a point, but certainly not to make a personal attack, so I apologize if it came off that way.

My point in using language like this was to illustrate how others may perceive you and your business if word of the "Virtual Tony" gambit got out. It's not fun to see things like this written about you, and it can kill your business.

In my experience there are two kinds of clients that don't pay on time: clients that genuinely want to pay but can't for a legit reason, and clients that have no intention of paying you and will do anything to weasel out of it.

It's the latter that could really use the "Virtual Tony" against you if it ever came to light. These are bad people anyway, and by doing something dishonest in return you are just giving them more ammunition to get away with it.

Did you happen to catch the case of Carl Herold on Reddit a month or so ago? He had a deal go south with a client and the guy smeared him all over the internet and almost ruined his business. [1]

In that case, Carl was in the right and still had all kinds of harm done to him because of a disgruntled client. Imagine if Carl had pulled the "Virtual Tony" on this guy. I'm guessing Reddit wouldn't have jumped to his aid to help him out because they would've seen him as dishonest.

To your point, you are certainly justified in following up with a client if you're not getting paid. And I certainly think there's validity to the idea that a third party, good cop/bad cop relationship could help things turn out better for everyone in the end.

What I totally disagree with is making that person up and impersonating him or her to your client. It's a bad road to go down and not worth the potentially devastating hit your reputation would take if it got out.

1- http://www.reddit.com/r/AskReddit/comments/ckcjc/reddit_can_...

Once again, plenty of valid and well thought out points, and I agree with all of them.

It was your response that made me re-think the way I phrased the original article. While I know some people who have been successful using this kind of strategy for years, it's certainly not something I'd generally advocate for all of the reasons you've pointed out.

Carl certainly would have looked more dishonest in that scenario. However as I understand it, his scenario was a partnership with another company. So it may not be directly applicable to my article, which is in regards to service companies acting as vendors to other companies.

One last footnote: in my experience, there is a third kind of client that doesn't pay on time. The apathetic client. This client is often large and deals primarily with much larger companies, or has a billing department in a different country, or is unfamiliar with your company's contract.

In this situation, as others have suggested, a gentle reminder email from accounts@your-compay.com may be a good way to get attention drawn to your pending invoice without personally stepping into the middle of the transaction.

This was the main point I was trying to communicate anyway - the importance of separation between accounts and the day-to-days.

Just make an automated system that reminds clients that their bills are overdue. Then it makes sense for it to come from accounts@yourcompany.com - it's just a bot.

Really, there's nothing dishonest about sending email from accounts@yourcompany.com when you're dealing with accounts. Just happening not to mention that you're using a different email address for that isn't a big deal.

What if one feels uncomfortable with inventing a fictional person? Is signing emails 'Company X Accounts Dept' a reasonable compromise?

Opinions?

You'd be shocked how easy it is to make The Computer into a bad cop.

This is your automatic notice: our accounting system has classified your account as delinquent because $YOU_FAIL_AT_TIMELY_BILL_PAYMENT. If you do not bring your account into positive status, the system will mark your account for escalation of collection activities. To make a payment, $PAY_AS_AGREED_YOU_MAMOO. If you believe you are seeing this message in error, $FEEL_FREE_TO_ASK_ME_TO_MARK_YOU_CURRENT_BEFORE_YOU_PAY because $THAT_WILL_BE_A_FUN_CONVERSATION.

You can automate paper nastygrams -- not that anyone will notice if they're actually sent by hand, mind you...

The best thing about an apparently automated system is that when they call you to complain you're not undermining any relationships by saying "yeah... our system does that. So have you paid yet? Why not?"

Good point, you've probably just summarized Paypal's Antifraud department.

I like it! That reminds me of the "Dear $CandidateName$," PFO letter I got after a job interview...

I'm sorry I gave you the wrong impression with that article. My aim was to outline how important this kind of separation is, and I then provided an example of a strategy that I don't employ myself, but other people do. Unfortunately, instead of a discussion based around separation of accounts people and the service providing people, the discussion turned to the ethics of creating fictional employees.

I've edited the article in order to keep the focus on the point I was trying to make. In any case, thanks for taking the time to comment.

i dealt with a company that did this: after a short time it became obvious what was going on.

as customer i no longer trusted the company: they were lying to me, trying to make their business look bigger than it actually was.

if they were dishonest about this, what else were they being dishonest about?

at the first opportunity, i took my business elsewhere.

This opens up an interesting discussion.

To what degree is it alright to 'peacock' your business and appear bigger than you are, if (a) you're absolutely certain you can cover the client requirements, and (b) the client is choosing between you, and a few other solutions/providers?

Out of interest, did this company do something bad to you? Was the service unacceptable, and did you previously have a good working relationship with them?

Don't "peacock" your business. Most of the business you're going after cares less about this than you think. That's especially true during economic downturns, where big is synonymous with overpriced.

In the long run, you aren't fooling anyone with that (they're going to figure it out), it's a terrible, unnecessary mental burden, and your customers will probably find out that you've been deceiving them.

In my first company, my partner and I fell prey to that need to exaggerate our stature. It was almost entirely fueled by our own insecurities, not actual client expectations. In retrospect, we both believe that a large part of our inability to weather the dotcom bust was tied to things we did out of an imagined need to "peacock".

after some time, they delivered me a faulty product: i wanted to return it. it turned out they were 'peacocking' their customer service team as well as their accounts team.

i don't think it's ok to 'peacock'; it's tantamount to fraud.

if your clients are concerned that you cannot cover their requirements, you should address these concerns, not lie to them as this impedes their due diligence. if you get caught, your reputation is destroyed, and i would be surprised if there were no legal recourse.

Interesting - so there was only an issue when they caused you a problem through their negligence. It didn't actually have anything to do with the accounts team or customer service itself.

I certainly agree with your sentiment though - misrepresentation is bad, and to be avoided.

For a sole proprietor who is trying to win business, but has no resources, funds, or choice, I view this kind of 'peacocking' as a functional but temporary solution; especially if the sole proprietor is certain they can fulfill the clients requirements.

It's amazing you took your business elsewhere because they were "peacocking" and not because their products were faulty, as you said. Most people would take their business elsewhere when they find the quality is unacceptable. But you were OK with the unacceptable quality and planned to continue to be a customer, it was only because of the peacocking that you left.

Sounds to me like dododo was initially willing to give them a chance to rectify their mistakes, but not after discovering "they" was a lying weasel.

you're right---consistently faulty products would certainly make a bigger (negative) impression than peacocking.

but in this instance, for some time, the products were just fine.

a customer's trust is most tested when things are going wrong, not when they are going well.

So dododo, why were you refusing to pay that company for the product you received?

Really, I am not surprised that you took your business elsewhere. Probably did them a favor - most companies prefer paying customers.

unfortunately for them, i was a paying customer. sorry if my comment gave you a different impression.

Thanks for the clarification. I thought when you said that the "same thing" happened to you you meant you were contacted by a fictional Accounts Payable department after not paying a bill. But I see in a later comment, by "same thing" you just meant the part where the owner pretended to be an employee.

When I went back to read the article, I realised that I wasn't portraying my point very well.

My main focus was the importance of separation between accounts and day-to-day client relationships, and I've made changes in the original article to reflect that.

As always, thanks very much to everyone who took the time to post their thoughts, it helped me focus the article on the main issue I was attempting to discuss.

Does anyone else think this sounds weirdly passive-aggressive?

I've thought of this before, but dismissed it as being completely dishonest. What happens when your client decides he/she likes Tony and decides he wants to take you and Tony out to celebrate some business milestone that your service was key to achieving? Do you get a buddy to play Tony? How far down the rabbit hole will you go? Even worse, what if the clients decides to sue based on some bad advice "Tony" gave? Then you're in all kinds of trouble.

I appreciate the advantages of psychological separation between founder/pal and money chaser, but why not just send an email from 'Accounts?'

This is unethical. What happens when a client discovers that you've been deceiving them?

It's unethical if you're doing it purely for personal gain.

If you're unable to hire a person to do this for you, having some distance from clients about sensitive financial matters can be beneficial for both you and the client.

It's a decision you need to make though - are you comfortable with this level of 'deception' if it's conducive to better relationships with your clients?

If so, go ahead.

If not, ideally hire someone else, or do it all yourself.

I was fortunate in that I could support an accounts person very soon after I started my business, but I think this strategy is akin to "No, you look great in those jeans", a statement that also benefits both parties. :)

If you really believe this, put your money where your mouth is: Tell all of your clients that you do this.

Then, report back to us what they think. Somehow I don't think they'll buy the "I was lying to you for your own good" line.

Can you outline a scenario where you would be doing this for gain other than personal?

Sure - my point was that it's beneficial to you and the client to have one insulating layer in regards to accounts.

Ideally, you'd want this to be your accounts person.

Yes, but in the non-ideal case, the client is still being deceived.

The general question is: do we have the right to deceive people "for their own good"? I say no.

They are not being deceived. They are being told to pay for the product they received in accordance with the contract terms they agreed to. There is nothing deceptive about a company wanting to be paid for services rendered or products delivered.

A client who pays past the due date, or who doesn't pay at all, is much more "unethical" than that.

Sometimes there can be legitimate reasons for slipping past the due date.

Even if there aren't any legit reasons, countering an unethical move with another unethical move is definitely still unethical in my book.

I wish I could up-vote this more than once.

There's nothing unethical about this. The unethical part is the client who doesn't want to pay for the product they received according to the previously agreed terms. Now THAT is unethical, and those people should be shot, and their dog should be shot as well. Sending them a friendly repayment notice instead of doing what really needs to be done is a great act of kindness.

You don't have to lie to your clients in order to decouple the billing role from individual people. In my company we have a "billing@company.com" alias. Invoices go into a database and are mailed out to customers from that alias. Our billing system logs when the invoice was sent (and re-sent, if necessary). Incoming mail to that alias gets routed to the people responsible for dealing with invoices. Notices of overdue payment can come from the same alias (however we prefer to handle such matters personally and more directly).

If you are a one-man shop, go ahead and create the role alias and then delegate when you grow.

Even better but not explicitly mentioned in the article, a fictional Tony gives you some much-needed emotional distance in any money-related dispute. I see countless sole-proprietor businesses suffering damage because the owner, perhaps understandably, takes customer disputes personally. With a fictional bad cop, you are left free to 'play' the good cop, which might even help you to see the customer's side of the situation. Yes, you should do this anyway, but it's clearly harder than it sounds.

Are you saying it's easier not to take abuse directed at Tony personally even when you know you are Tony?

It's easier not to feel obliged to vigorously defend "Tony" or your "automated email system" when the client claims the money has been transferred over and complains about being harassed. It's amazing how complex and restrictive your impersonal internal systems can become when it comes to preventing you from switching client's access to a service back on whilst you're waiting for payment too.

On the other hand, it's harder to use a glib "it's just procedure, I'm sure you always were going to pay" to smooth things over when the passive-aggressive payment demand that's got the client riled is signed with your name, CEO.

When you don't sign your own name, it is easier to think your are really playing a role, so it isn't you they are criticizing, it is that guy.

Personally it doesn't work that way for me.

On top of it, I'd feel bad constantly for pretending to be a Tony when I'm not one.

Nah, that's unethical, but...

It could be useful to do this internally. I'm just starting up a business by myself, and I was thinking of making a list of all the roles I need to fill, as a reminder to not just code.

It's easy to put on different hats when reacting to external crises, or events, but I don't want to forget about internal initiatives. E.g. proactive sys-adminning, creating marketing plans, etc.

It seems like the best-case scenario here is to just rely on software to do the chasing. Everyone already knows that software is a jerk.

FreeAgent does a great job of telling me when invoices are overdue. If I could configure it to send an obviously-automated email whenever that happens, it'd solve most of my invoice-chasing problems.

How would this idea fit in with a web startup? Should the founders be directly handling money issues with users?

If you have more than one founder, can't you have one founder be the one dealing with money issues and another founder be the one handling other interactions? Like a good cop/bad cop thing?