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.

No one can promise you success, but I promise if you take a brand new tool and try to force it to be just like the tool you are replacing you are going to be disappointed (at best).  Salesforce is not CiviCRM, Drupal is not WordPress, Salsa is not Blackbaud. Remember you are replacing the tool for a reason, if everything about your current tool was perfect you wouldn’t be replacing it in the first place. So here are my steps for improving your chances of success:

  1. List the main functions the tool needs to accomplish: This is the most obvious thing to do, but make sure your list only covers the things you need to do, not the ways you currently do it. Try to keep yourself at a relatively high level to avoid describing what you have now as the required system.
  2. List the pros and cons of what you have: Every tool I’ve ever used had pluses and minuses. And most major internal systems have stakeholders who love and hate it – sometimes that’s the same person – make sure you capture both the good and bad to help you with your selection later.
    Develop a list of tools that are well known in the field: Not just tools you know at the start of the project. Make sure you hunt for a few that are new to you. You might think you’ve heard of them all cause you walked around the vendor hall at NTC last year, but I promise you there are more companies that picked a different conference to push their wares, and there are open source tools you might have missed too.
  3. Make sure every tool has a salesperson: Open Source tools can be overlooked because no one sells them to you, and that may mean you miss the perfect tool for your organization. So for open source even the playing field by having a salesperson, or champion, for the tool. This can be an internal person who likes learning new things, or an outside expert (usually paid but sometimes volunteer).
  4. Let the sales teams sell, but don’t trust them: Let sales people run through their presentations, because you will learn something along the way. But at some point you also need to ask them questions that force them off your script. Force a demo of a non-contrived example, or of a feature they don’t show you the first time. Make them improvise and see what happens.
  5. Talk to other users, and make sure you find one who is not happy: Sure your organization is unique but lots of other organizations have similar needs for the basic tools – unless you have a software-based mission you probably do not want an email system that’s totally different from everyone else’s. A good salesperson will have no trouble giving you a list of references of organizations who love the tool, but if you want the complete picture find someone who hates it. They might hate it for totally unfair reasons, but they will shed light on the rough edges you may encounter. Also make sure you ask the people who love it what problems they run into, remember nothing is perfect so everyone should have a complaint of some kind.
  6. Develop a change strategy: In addition to a data migration plan you need to have a plan that covers introducing the new tool to your colleagues, training the users, communicating to leadership the risks and rewards of the new setup, and setting expectations about any disruptions the change over may cause.  I’ve seen an organization spend nearly a half million dollars on customization of a complex toolset only to have the launch fail because they didn’t make sure the staff understood that the new tool would change their day-to-day tasks.
  7. Develop a migration plan: Plan out the migration of all data, features, and functions as soon as you have your new tool selected. This is not the same thing as your change strategy, this is nuts and bolts of how things will work. Do not attempt to do this without an expert. You made yourself an expert in the field, but not of every in-and-out of the new system: hire someone who is.  That could be a setup team from the company that makes it, a 3rd party consultant, or a new internal staff person who has experience with different instances of the tool.
  8. Get staff trained on using the new tool: don’t scrimp on staff training. Make sure they have a chance to learn how to do the things they will actually be doing on a day-to-day basis.  If you can afford to have customized training arranged I highly recommend it, if you cannot have an outside person do it, consider custom building a training for your low-level internal users yourself.
  9. Develop a plan for ongoing improvement: you will not be 100% happy 100% of the time, and over time those problems will get worse as your needs shift. So make sure you are planning to consistently improve your setup. That can take many forms and what makes the most sense will vary from tool to tool and org to org, but it probably will mean a budget so ask for money from the start and build it into your ongoing budget for the project. Plan for constant improvement or you will find a growing list of pain points that push you to redo all this work sooner than expected.You’ll notice I never actually told you to make your choice. Once you’ve completed steps 1-6 you probably will see an obvious choice, of not: guess. You have a list, you listened to 20 boring sales presentations, you’ve read blogs posts, white papers, and ad materials. You now are an expert on the market and the tools. If you can’t make a good pick for your organization, no one else can either so push aside your imposter syndrome and go with your gut. Sure you could be wrong, but do the best you can and move forward. It’s usually better to make a choice than waffle indefinitely.

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