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In the last few decades, media organizations have experienced an unprecedented period of upheaval in which they have had to hugely adapt their selling practices. Digital media has morphed into multichannel and omnichannel, and in the blink of an eye sales teams- have had to embrace an ‘adapt-or-die’ mentality. The advent of sales tools built to-¯manage customer relationships-¯and-¯orders-¯has enabled managers to more effectively govern the flow of commercial information to the wider business, but challenges remain.-¯-¯

Many businesses seek to address these challenges by adopting new sales tools and practices. Ironically, these same “solutions” cause problems of their own once in the hands of salespeople, but why? Often, a disconnect between decision-makers and end-users can mean that an organization never truly solves its core business problem.-¯-¯

The simplest way to avoid this disconnect? Involve end-users in the decision-making process early on, with questions like:

What do you like about our current system?-¯

Maybe your current system is legacy software near the end of its life, terribly slow, cumbersome, inflexible and-¯costly.-¯Maybe-¯you hate it-¯and are confident that it’s time for a replacement. But those who use the system day-in and day-out have learned to live with it, and there are bound to be-¯some-¯features and functions they appreciate. Make sure you understand what used to work about the system you’re replacing – chances are, you can find a more modern solution that-¯also-¯incorporates these features.-¯-¯

How much do you use our current system?-¯

Not all end-user feedback is created equal. Before you take concerns and recommendations too seriously, make sure you understand how the person you’re speaking with interacts with the current system set up. Are they entering activities daily, using your current CRM to guide their-¯day?-¯Or do they mostly avoid using the system because they find it cumbersome or aren’t sure how? Asking this question will also help you understand who will benefit most from new tools and processes.-¯-¯

What slows you down the most in your day-to-day tasks?-¯

Most legacy systems require complex integrations and ongoing maintenance, making them a nightmare for modern IT teams to maintain. Add to this the challenge of “swivel chair syndrome,” or manually entering the same data in two disparate systems, and you’re looking at an unacceptable list of timewasters. Understanding where inefficiencies sit in your current process will give you helpful clues about where you can improve with a new system.-¯

Can you show me how you XYZ?-¯

Sometimes it’s better to just observe how a system is used. If you’re not sure what your end-users-¯really-¯need, sitting down for a “show and tell” session can be extremely useful.-¯

What day-to-day tasks do you think should be automated?-¯

Chances are, there are several manual tasks that-¯could be automated-¯with the right system in place. Ask your team what manual administrative tasks they would like to have run in the background, and you’ll soon realize both the shortcomings of your current system and gain some great ideas for how to configure your next system.-¯-¯

What alternatives do you think we should consider?-¯-¯

So, you’ve put together a steering committee, understood your organization’s goals, and written a detailed RFP to help you evaluate vendors – who should you send it to? We provide some great ideas in “The Complete Guide to Writing an RFP,” but one great place to start is to ask your team. End users are more likely to hear what their peers at other organizations enjoy using, read industry blogs, and generally be more aware of alternatives. You may find that asking them which vendors you should evaluate adds some interesting ideas to your list.-¯

What do you wish you could do that you can’t do today?-¯

Finish off with a brainstorm about what your end-users believe is possible with the right tools. Chances are, you’ll learn about a critical report they wish they could pull, a tedious process that could be automated, or an integration that’s never quite worked the way they hoped. Ending on this note will also plant the idea that a new, better system is coming, and get your end users excited about the switch.

Bringing it all together

These questions are a great starting point, but there are several more things you can do to future-proof your enterprise software choices. “The Complete Guide to Writing an RFP Based on Your Goals” is a fantastic guide and includes a free RFP template that you can customize and edit based on your needs.


Lineup Systems is the world's leading provider of media sales technology, representing over 6,800 media brands globally, including Gannett/USA Today, New York Times and News Corp. Amplio is Lineup's multi- channel audience monetization solution that helps media companies realize their full reader revenue potential, using data-driven intelligence to engage, nurture and monetize readers with personalized offers that increase reader revenue and reduce churn. Adpoint is Lineup's end-to-end multi-channel media advertising sales solution that helps media companies streamline operations, make better use of data, increase efficiency and boost revenue.