What’s the toughest decision you’ve ever had to make as a Commander (or leader)?

MAJ (Join to see) I commanded two companies, a battalion, and three brigades, so to pull out anyone tough decision is like looking for a needle in a haystack after 37 years. Like you my first command was as a 1LT and there is nothing like hopping into the frying pan right out of the gate in your officer career. One of the many tough decisions I had to make was going head-to-head with General Officer at Mobilization (knowing that if I lost I could get relieved of my command or some type of Administrative discipline), but I knew in my heart I was right and I got my ducks all lined up and went against him head on and in the end I won the tug of war with GO. I was right and my other GO's that knew me came to my side and supported my decision. It was a calculated risk, but I took as every good leader should when they have all of their stuff together in one hand bag (duffle bag). Make sure before you go against your superior you have your stuff together (dress right dress). Good luck my friend and there are many of us you can call on, if you need us Michael! Been there and got the T-Shirt!

Every damn time I had to pick one of my people to go on point during deployments.

In my case it wasn’t a single decision but that nagging worry if I had done enough in my training of AIT trainees on their way to Vietnam as 11Bs-11Cs,I know that my short time with them was not the only thing that would give them a better chance of coming home,but I was a young NCO and hoped my experiences and lessons learned out weighed my immaturity ,hope so.