Picking tools you’ll love: don’t make yourself hate it on day one.
Every few years organizations replace a major system or two: the web site, CMS, CRM, financial databases, grant software, HR system, etc. And too often organizations try to make the new tool behave just like the old tool, and as a result hate the new tool until they realize that they misconfigured it and then spend 5-10 years dealing with problems that could have been avoided. If you’re going to spend a lot of money overhauling a mission critical tool you should love it from day one. ...