Let's say that your med rare is 130*, and his med is 140*. That's a 10* difference. I would put his on and monitor the temp. When it has risen 10*, I'd put your's on. That should at least get you close.
@sandy_561 I think RonB hit the nail on the head. No one can say a time for how early to put one steak on versus another, as its all based on how fast they get to 130 and 140. Also they will rise some during the reverse sear - not much though if its a fast hot sear, but some.
I have the same situation - my son and I like it medium rare, the women all like it medium well. I sous vide all of them to about 130, then just sear theirs a little longer, checking them with the thermapen after each flip over the SNS or grillgrates.
I let mine rest in between getting them to temp and putting the final sear on them. Lets my bring the grill up to searing temps. Just leave the medium on until it hits the temp you want. Letting the med rare rest a little longer.
Not SV-ing and not reverse-searing, I find in practice that an extra minute to a minute and a half per side handles things nicely. We're talking steaks under 1-1/2" thick for this approach.
I have a Santa Maria Grill with the variables all kind of dialed in. My daughter likes rare, I am medium rare and my wife has finally settled to medium from medium well. I put my wife's on first. Three minutes later I flip hers and mine goes on. Three minutes later, my wife's gets the second flip, mine gets it's first and my daughter's goes on. Then I start monitoring the temps. I lower the grate for the final minute. The three minute rule applies really well but again, it is based on my set-up. jfmorris 's advice, if you have a SV machine, is the fool-proof method.
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