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don't get mad, get paid. sounds like IT person on way out. sure she is going to struggle, wouldn't you? try to see things from her point. find out what she want and help her get it. help her succeed with boss! you can't expect her to buy into helping you prove her a failure! you think she is incompetent and without interests of company at heart,i KNOW that is not true. you think she is not doing good job on purpose, would **** me off also. people just want to do good job and contribute. try THAT for an assumption. why should she team with you, Mr Critical Know-it-all? 'horribly designed', 'full-of-garbage'-you are already going down low road. must be some value in that db as they are still using it. one thing you can say on her behalf is she is tight with their money, yes? and she has hung in with them, yes? poor db designer probably had no budget, specs, support. did the best they could at the time. examine why you are mad. can't get PO to make new db? make free strawman db you have working model! see how YOURS turns out. why does she have to be wrong to make you right? why do you have to be hero? allow her be right in front of boss. allow her to know more than you about stuff she knows more than you about! she is bad team player? you don't sound so hot either. what common ground can you find? you both want what's best for nonprofit, yes? you both want to fix it i bet. have you asked her? back off. help her look good to boss. do not worry about whether you look good. you worry about results. people aren't MADE to buy in! that is oxymoron! Users are your concern. users. serve them. do not criticize her in front of them. only praise in public (unless you can't mean it then don't even try) train your contractor to stay focused on job. just get PAID. get money for your time and you will feel better. if you can't get paid for your time and too much bad joss to volunteer say so. offer free phone support. YOU take responsibility for your actions. Golden Rule buster.

No,win if the business manager is providing her with the info to object to a consultant coming in.
What is her motive for not supporting the upgrade,if she only works part-time.
The director has put in in the middle if he did not confer with the present IT person and thus she is feeling threatened of being cut out,which she needs for her own personal reasons.
The no win situation will be if you cannot partake the task that she is currently doing.
Have you gotten input from her on why she is oppose to updating the equipment.

Is there any way that you can include her in process by repairing the damage that is already done.

If the director contacted you then this would give you a direct line to that person unless you have been instructed to work with the current IT person.
Have a heart to heart with the director from a business perspective and detail your concerns about the situation and if you donot feel that you can provide the service for what they are willing to contract for then you have to make the decision to stay or flee.

Ever think of taking in a working model, even an arcaic PII 133 would be an upgrade! With a useable database model, then have her use it for an hour teaching as you go. Winning her over on the idea, rather than fighting every step of the way, would be a sure way to getting them upgraded to 1998 (at least). Besides you are going to have to teach someone how to maintain the systems after you leave.

Saying how bad a system is to the person that (probably) wrote it will never win anybody over, showing them you can optimize it may, showing them a faster/more reliable system and winning them over on the idea would be the best approach.

BTW - Sounds like an issue from circa 1990 or so (DOS 4.5 ?) which means they are using 286 or 386's at best.

To address a couple of the things brought up by Schultz and DMiles, the internal person offers no explanation why she doesn't want to part with the old database. It's not on the network. People walk to a machine and print reports, and re-key data. That ain't right! The internal person claims the users "don't need" Office because Corel WordPerfect is $29 and is fine... That position flies in the face of what the users have told me - they can't communicate with third parties that use Word. They hate the database. They can't use the database. They're tired of re-keying data. Believe me, I want to help this internal person be the star -but she, sad to say, has been neglecting her hardware, her software, and her users' needs. Now SHE has a p.r. problem. They all hate/resent her, and the fact that she works four hours a week (never there), that she doesn't respond in a timely manner to their e-mails. I want to help this person, but I'm afraid she's dug a pretty deep hole for herself.

Yet another comment...I never EVER bad-mouthed the database design in front of the the internal IT person. I called it what it is in my post, but believe me, no one from this organization will ever find their way into this forum. I am already prototyping a new system to demo. Better to ask forgiveness than permission.

Jeff, here are my thoughts. First off, don't " throw in the towel" and give up. From the sounds of it, these people need help, and fast.
I am a believer in that the IT world is not just about computers and packets and bandwidth and patches and exploits. It is about productivity. Making people be more productive while DECREASING the amount of physical labor they must do to be productive.
I work in downtown Chicago, and a block away from where I work, they are building 2 new buildings. Every day I walk past the construction workers as they build these tall buildings (30+ stories each, I think).
These guys were sweating constantly in the humid summer we had this year. They are digging ditches with shovels and pick axes.
Now the weather has suddenly turned cold, and they are still out there, lugging wooden boards around, while wearing sweatshirts and coats and gloves. They will be out there all winter, building these buildings while being in the 20-degree snowing weather that is Chicago.
And here I am, sitting at a desk, writing this answer on a P4 laptop!
It helps me put things in perspective.