pretend to loose to them...they dont like losing much
They like the other pretending (warning sign) to lose even less than they like losing. You will lose their respect and they will become more suspicious of you.
thats what someone meant when they said 'challenge in a supportive way'
Supportive way = opening them up to new ways of looking at things, thinking about things, i.e., towards a greater insight, understanding. Towards positive growth - be it mental, physical, emotional, etc.
Do it through challenge means don't hand-hold them through it, but, allow them to come to the conclusions by the way you steer it, present the argument. I.e., challenge them to THINK.
At work:
Being recognised with increased responsibility, pay and promotion. Being told I've done a good job isn't enough (I already know that). If that's all I get, I will feel like I'm being used and will most likely move some where else where I DO get increased responsibility, pay and promotion.

@ bolded. So true, my INxJ got his evaluation and scored perfect on everything. When his boss handed the evaluation over to him and congratulated him, he looked at him irked, and asked, "What do I do with this? How is this helpful?" (I.e., if he was already perfect, there was no challenge, or point to his work, for the future). So, the boss finally relented and gave him back 'helpful evaluation' - it was, not suprisingly, in the arena of social etiquette. Telling my INxJ that sometimes, when he (boss) talks to him, he can see the INxJ's eyes gloss over (i.e., he's tuned you out), or hunched eyebrows (he's irked), and the boss knows that he's been rambling and not getting to the point causing that response in INxJ...hence, the helpful criticism - that the INxJ has to learn to be patient and more accomodating to how others may interact, or, speak, express their point. I laughed out loud when I heard that....
(to add: he won't say it, but, there is that little part of him, the little boy, that is quite proud at the achievement of a perfect score - as me going,
NO WAY? Perfect? I don't believe it, show me! made him run to get the evaluation, handing it over going, "See how stupid it is...what do I do with such evaluation?"

rolleyes

. I did it more to show I'm proud of him, encourage him, without calling it out, outright, and he won't admit it, but he did appreciate that gesture

)
However, he also could care less about promotion, in terms of the title, the promotion is only relevant insofar as it gives him a pay raise and more responsibility (challenging work).