Gary Miller here, and I’ve learned that the word ‘easy’ is relative to everything except software implementation, where it apparently means ‘we’ll figure it out as we go.’
Last month I was working with Michael, the CTO at a growing real estate company in Minneapolis. We’d been through their quarterly planning meeting where they’d mapped out this massive digital transformation – we’re talking a $1.5 million investment to overhaul how they handle everything from property management to client relationships. Operations, Procurement, Sales, Finance – everyone was on board.
Michael had done his homework. He’d compared us against that European company with their crazy aggressive pricing, ran all the numbers, got buy-in from every department. Three months of calls, demos, and presentations. When we finally got to the contract signing, he looked me in the eye and said, ‘Gary, this is exactly what we need. How quickly can we get this running?’
‘Implementation is pretty straightforward,’ I told him. ‘Our team will handle the heavy lifting. You’ll be up and running in 90 days.’
Famous last words.
Two weeks later, I get a video call from Michael. He’s got that look – you know the one. Like he’s been staring at spreadsheets for six straight hours.
‘Gary, we need to talk about this implementation timeline,’ he starts. ‘Your technical team just sent us a 47-page document listing everything we need to do before they can even start the setup.’
Turns out ‘straightforward’ meant they needed to clean up fifteen years of data spread across twelve different systems, get approval from their parent company’s IT security team in three different time zones, and somehow coordinate schedules between our implementation team and their people who were already stretched thin from their regular jobs.
‘The Finance team is asking why we need to hire two temporary data analysts,’ Michael continued. ‘And Operations wants to know why they can’t use the system for the first month while we’re migrating everything over.’
I’m sitting there thinking about all those smooth demos where everything worked perfectly with our clean sample data. Reality had other plans.
‘Look, Michael,’ I said, ‘I know this feels overwhelming right now. Every implementation has surprises. The important thing is that we’re committed to making this work.’
He laughed – not the good kind. ‘Gary, my CEO just asked me why we’re spending seven figures on software that won’t actually help us for six months.’
We ended up extending the timeline to five months, bringing in extra consultants, and having weekly calls with all four departments to manage expectations. The project eventually worked – they’re happy with it now – but those first few months taught everyone involved the difference between buying software and actually using it.
Michael and I still laugh about it during our quarterly check-ins. He’s become one of my best references, actually, because he tells prospects the truth: great software is worth the headache, but plan for the headache.
And that’s business software sales for you – the demo is always perfect, but real life has other plans.
Leave a Reply