I'm considering a position with a company that has faced significant IT challenges, particularly with their on-premise Microsoft environment. Last year, I conducted a health check for them and identified numerous issues, especially since their current managed service provider seems to be more focused on upselling rather than fixing problems. They've recently let go of their IT manager, and while they want to modernize their setup, most of their systems are still managed on-premise with very little implemented in Microsoft 365. It's been over 15 years since I've been in a full on-prem environment, and I'd like to know if there are any good resources to help me get back up to speed. My ultimate goal is to help them transition to the cloud, but I may need to manage this current chaotic situation first.
3 Answers
Honestly, if I were you, I would focus on getting everything squared away in 365 first, skip the hybrid joining, and not worry too much about fixing the old on-prem setup immediately. Once you get their cloud services working, you can tackle integrating Entra and leave the cumbersome on-prem stuff behind. Just keep in mind that if they do have a large server infrastructure, you might have to address some on-prem issues first.
It's a bit risky to criticize the MSP when you’re not fully acquainted with the setup yourself. Just keep that in mind—it might not look great.
Considering their licensing issues, you might want to prepare for a significant license purchase. It's best to gauge their reaction—sometimes, knowing you could spend around $50k on licenses can change their perspective on how to fix things.
Actually, it might turn out that they could save money on licensing. The MSP has them on Office E3 licenses with extras, but if you switch to Business Premium, that could cover their needs with fewer costs, especially if you add Defender.
Yeah, I see where you're coming from. It’s a touchy situation.