Not many people would actually "like" cold calling but it is something that has to be done if you want to be successfull. You have posted things are getting desperate well it is time to change what you are doing because it either a) doesn't work or b) no longer works. Sorry not trying to be harsh here but you have asked for help and unfortunately your best bet is to move out of your comfort zone and do something different.
The main thing with cold calling is to find what works for you. You obviously aren't the "hard" sell kind of person, neither am I but working in the car industry and attending plenty of training sessions with different trainers I was taught how to do this. The thing is to find "your" way of doing it.
First break it down to the basics.
Meet & Greet - You need to make the initial contact, This is where you can really stand out or just be "another" sales rep.
Qualify - Do they need/have they considered uniforms? (This is where your ears need to do lots more work than your mouth, remember the golden rule 1 Mouth, 2 Ears use them that way. (listen twice as much as you talk) Are you talking to the person who could make or influence a decision? During this part it is a good chance, especially if your waiting for "the manager/owner" to find out how many staff they have, do they have multiple sites, etc. This gives you the background information.
Presentation - This is where you speak with whoever is responsible (Ask if now is a good time, if not when would be a good time for you to call back). Don't assume I'm busy at the moment is a no, They may very well be busy and the last thing you want is for them to not give you their full attention. This is where you can use the information you haver already gathered to discuss needs and wants with them. (Hopefully you will already know how many staff (probably allow about 3 tops per staff member, unless there are a lot of casuals) This means you can avoid "assuming" things... very dangerous thing to do that! (ASSUME is to make an
*** out of
U and
ME) You should also now have an idea of why they don't have uniforms. (could be lack of funds/perceived cost of uniforms, Not sure if there is really any benefit of uniforms, time constraints, especially in a new business, not sure where to go or who to speak to to get them?
Use your presentation to answer there questions - remember this is presentation of how you can benefit them. This means you need to have a think about there "objections" and find them solutions. (Eg cost, you have a
DTG machine so it makes no real difference if the order is staggered over a couple of weeks so they can pay for it in smaller amounts. (You don't have to discount but 2 payments of $300 sounds a lot better than $600)
Trial Closing - This is where you start asking questions and phrasing statements towards getting the order, it is also an informal way to find out any other objections you may have missed. You want to lead in to a commitment from them. Phrase your questions so that you know by the response if they are ready to order. WOuld you like the Polo's or Shirts? This is where styles and colours can be used to your advantage. Get them "ordering" what they want. Will it be all the staff? How many would you like per staff member? All these leed to little "ticks" that they want to order. If they have any objections handle them and move on to another closing question. If it is something you need to get back to them on don't let that be the deal breaker. If you keep getting "crooses" against your closing questions you have either not covered something, they aren't happy about something or the answer is no. Don't be afraid to ask if they have questions or concerns. YOU WANT to know the problems, otherwise how can you deal with them?
My advise is if after your trial closes all you got was no's and they aren't ready to order DO not ask them too. This is the point where you can leave the door open or next time you call past the door is shut. THANK them for their time, leave order forms with them. Let them know how to contact you if they have any questions, Let them know you will be in touch and make sure you call them in a couple of days and thank them again for their time. This is a good chance to ask if they werent going ahead if they would mind sharing with you why for your own benefit with dealing with customers in the future (this can lead in to a situation where you may be able to solve the issue for them and get the order, If not you at least will get some feedback for next time)
Closing - THERE SHOULD BE NO SURPRISES for either of you at this stage. Something a lot of salespeople skip too quickly too. If you have set it up well then you have already been given the "green light" to pull out your order book (or sheets) and write out an order. (Don't use "I'll write up the order and send it through when I get back to the office" DO IT NOW while they are ready, you don't know who they will talk to or who will walk in the door after you leave. They probably wont have sizes on hand that doesn't matter just ask them to let you know by such and such a date. (Are you able to supply blanks sizes for the staff to try on, this can save you hassles with wrong sizes ordered) You can still do up a fancy one when you get back and email/fax/post or ideally drop it off to them (A good chance to take a sample back or ideally a size range for staff to try on for sizing)
Follow up - One of the best salesman I ever worked with still calls me every year on my birthday, as he does EVERY customer he has ever sold a car too (and he is now at retirement but still working part time)
and says Happy birthday, how's the wife, kids etc. Takes about 2 minutes at most. (In his case he spends about 2 hours every day doing this!) And you would be amazed how many people come and find which yard he is working at to buy from him. A small thing, there is no selling at the time just a courtesy call.
If you have sold uniforms to a retail store I would be calling every couple of months, staff turnover could lead to more orders or clothes that are getting worn, have been wrecked in the wash or just want some more to save washing all the time. STAY IN TOUCH!
Hope this helps, I'm sure others will have stuff to add
Sure-fire shirt selling methods? 
