If you are refering to training and rolling at your gym with your friends, IMHO you should not be thinking about "winning" or losing. Winner in every roll is the one who learns the most..
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"The Spice must flow..."
A lot of it depends on the particular training partner. If its a training partner that I know my skill level is much higher I will generally focus on executing newly learned techniques by the book whether it be a submission, sweep or escape. This allows me to become more proficient while the less experienced indiviual also gets a variety of reps in because I'm not trying to destroy him.
At the different gyms I have trained at across the country there has always been at least one individual that is close to the same weight class and skill level. These training partners are who I spar with more often as the fight date approaches because not only does it push cardio but it normally tests all aspects of my game. This is where I go hard because my training partner expects it and vice-versa, yet, obviously not so hard as to injure my partner.
Then you have the bigs guys. I fight at 135 lbs so almost everyone is bigger. However, against the bigger guys whose skill set is still developing the above still applies but I will have to use a lot more energy, obviously, due to the weight difference. Against larger opponents with more experience, it's survival mode. Work to the best of your ability. Generally the bigger, more experienced training partners are looking to work technique against smaller opponents.
Bottom line, I respect my training partners and roll with as many as possible. Hopefully, something is learned by both on each roll!!
This... there is no winning and losing in training, it's just learning... there is a massive difference between training hard and training like its a real fight.
if you are not willing to try no techniques and positions when rolling in class, how will you progress? technique is far more important than the ability to go hard... i really hope some of these posts help?