Growth is rarely neat. Teams expand, roles blur, workflows evolve—and communication systems are often the last thing anyone wants to touch while everything else is moving. I’ve worked with companies that doubled their headcount in a year but kept the same phone setup they’d had since the early days. Others tried to overhaul everything at once and accidentally created weeks of...

I’ve spent years advising companies on digital transformation, and there’s a pattern I see over and over again. A business migrates to the cloud, streamlines its software stack, adopts remote work tools — and then, quietly, it keeps parts of its traditional infrastructure alive. Not because leadership is resistant to change.Not because they “don’t get” the...