My college pal, artist, and teacher Ed asked last week:
I belong to a professional organization of teachers that has been slow to embrace internet technologies. I am interested in proposing improvements to their website but I am unsure how to communicate the ideas. What formatting do you suggest for a written proposal to an organization?
I’m going to broaden the topic a bit, because the answer to your last question is, I don’t know, and I wouldn’t try to convince an organization with a written proposal. In my work, which is primarily done for individuals and not organizations, I only write proposals to make it clear what we’re going to do after we’ve discussed it. I do the convincing before I write word one of a proposal.
In my experience, you’re not going to get very far with a prospective client, or very far with convincing your organization to update their website, if you haven’t sold them on the benefits. The easiest way to do this, in my experience, is to start with having them identify and acknowledge a problem.
For example, “we’re not getting any leads from the website.” Or, “I keep getting email about how hard our website is to navigate.” Management or the client can deal with concrete specifics. They have goals, sometimes ones that they don’t even know about, so your task in early meetings is to identify what those goals are and then explain how an updated technology can solve those problems.
Problems and solutions may be a good format for a written proposal as well, if you’re still determined to go down that route. Provide the problem, and describe the solution. Relate these solutions to the overall goals of the company. We should improve X because it will cause Y, which is good for the bottom line. Or whatever.
Explaining why certain technology is better than others, or why a website shouldn’t look like it was built in 1997 can be more specific and difficult. One thing I try to explain early on is that websites are about projecting an image. Your website should reflect the image that you wish to convey to your clients, customers, whatever. If your website’s image is that of an old man yelling at the kids to get off his lawn, that might not be in line with your organization’s overall strategies.
There’s a lot of resistance to change in the world in general. Change is costly, it’s hard, and it doesn’t always result in improvements. I can understand completely why some people might become resistant to change because of that. How you convince them otherwise is no different a task than convincing a person of anything. Listen to their objections, consider them, and describe how you will overcome them.
Hopefully some of these basic strategies will help you, Ed. If worse comes to worse, find a competing website that does it better, and pull up the two sites side by side, and let them stare at it for five minutes. Then ask, “any questions?” I’ve never tried that before, but I wanted to at my last day job. Let me know how that goes if you try it.
How about the rest of you? How would you approach a skeptical boss or client that a website or other technology needs to be updated? Do you have any success stories or horror stories?
Tags: client management, freelancing, proposals, Web Design


















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That’s excellent advice. I got my first full-time web job by coming to the interview (a panel with six or seven people) with a brief that described how I’d address the issues and future projects they’d mentioned in the job description. I looked at the description, looked at their site, said, “Why yes, you do have problems,” and wrote a paragraph on each of the major points.
Giving them something to read helped me keep my composure, too. Since they kept glancing down, I seldom had everyone’s full attention trained on me.
In that case, it was easy because they’d already identified the problems. If the organization doesn’t understand why the site is broken, you just have to back up one step. (“Comic Sans is a bad choice for a professional organization’s site because.…”) It might help you to start with the problem list and work backward, explaining why it’s broken after you’ve described how your solution is better.
Thanks, Stephanie.
I really like that idea. I’ve done similar, but not to that level of detail. If I ever get another interview, I may do that.