I have a client whose website was designed more than ten years ago and he refuses to let me upgrade it. He is a lawyer and it is just a small online brochure website so he could well afford it but he just does not see the need!

I have given up asking him.

I must have done a good job on the original because it still works.

Why not target local businesses in your area with a leaflet drop and follow-up with a phone call/face-to-face meeting.

I doubt that an email or even a (cold) phonecall would generate any interest.

Ask your local office supply shop to hand out the leaflets to their customers (they are your target group). Offer a special discount for customers of xyz office supplies. Or go from shop to shop and hand out the leaflets personally (much better than dropping them into the mailbox).

Try some "before and after" photos (screenshots) on leaflets or even emails. Just pick one ugly/plain site and make nice visual improvements, but to still be recognisable as the same site, with a beautiful new design

Well I do have a portfolio section.

I also thought of designing a few websites for free and then contacting them and offering it for a relatively cheap price. If they decide not to purchase it I would then change the Logo and Name since I am targeting similar websites.

I also thought of designing a few websites for free and then contacting them and offering it for a relatively cheap price. If they decide not to purchase it I would then change the Logo and Name since I am targeting similar websites.

This could be a good idea, especially if you couple it with a case study and client's feedback. These few websites could then be loss leaders. If you could then get some kind of feedback what the changed website did for their business, you may have much stronger selling point to your other clients.

I wouldn't waste time with email, anybody vaguely web savvy will instantly assume that its a scam.

I wouldn't waste time with email, anybody vaguely web savvy will instantly assume that its a scam.

Well, maybe not a scam, but certainly not something to take the time to open and read. We all get way too many of them each day.

As jamesMP and onlineleben suggested the local angle might be your best bet. Get yourself out, rub elbows at chamber, church, fraternal and whatever other organizations are around. Face to face relationships when you're not asking for business have a way of becoming very productive.

jimbeetle's suggestion with the church could give you lots of Publicity.
You could for example create a site for the youth organization (Boy Scouts or whatever) of the church for free and than go asking business owners to support this organization in Exchange for free Advertising on this site. This brings you into contact with your prospects (without directly cold calling/selling to them) and it also promotes your fine work.
You could then also put some Advertising on the sides and back of your car like:
dailypress webdesign - we Support your local boyscouts (or whatever).
You can be sure - People will talk about you

I have some luck comparing the website to print advertising in terms of effectiveness and cost. For example, our chamber routinely solicits print ads. Businesses will pay a grand for 1/8 page ad buried in the back for one insertion.... yet you have to play hell to get them to purchase a website for a grand.

Another factor is "Oh web design is easy. My 12 year old nephew just put together a neat justin beeber website"...

I am having a lot of difficulty as of now.

As suggested I think I have to start calling and will have to start with friends and family.

I may also have to design a few more free sites for crowded places and sites with lots of traffic. I will add my own site on the footer although I know most people wont click on it anyway.

Business network international trains members to deliver a 30 sec speech, come with some concise presentation: You have 30 seconds to make your case, what they want to hear is "what's in for me"

It's getting them to listen to something that is not interesting to them that's the problem. ;)

Would you prefer to do business with a posh looking personality or a person with nasty and careless appearance? Website represents the goals and objectives of the professionalism of your business. The main thing is that a website is the representation of the aims and objectives of an organization. It defines the professionalism of your business so it is essential to have an appealing website. It is possible to have a basic website without getting any professional assistance but well-structured website containing informative content, professional images, enhanced features, and functionality attracts more customers and helps in creating massive lead. Try to comfort your customers in a way that they are convinced to do business with you again. A customer can be convinced through various ways, putting your site into search engines, direct contacts, phone calls and one-to-one interaction.

There are probably a lot of ways to make contact with these people, but getting a chance to talk to them is step 1 however you do that. Once you have a meeting I would approach it by asking them questions to show the gap their current web site may have, i.e.

1. Is your web site responsive and mobile friendly?

2. Does the site rank well in the search engines for good keywords?

3. Does it do a good job developing sales leads for them?

4. Could they develop more sales if they had eCommerce?

5. If they are a retail based store do they spend a lot of time talking to prospects and giving them information that could be shared via a web site and free up time to talk to better prospects?

The main thing you have to find out with questions is do they have any sales/marketing pain that you could solve with a web site and possibly corresponding tools like social media, pay to click, etc.

One thing I learned a long time ago in sales is if they have some type of pain you have a good chance of closing a sale, but you must get them to see the pain and then show how you can solve that pain with your proposed solution.

I have used this approach for 10 years and do pretty well uncovering issues and then proposing my version of a solution with this method. I hope it helps.