Pickering, who represented Team GB in the 4x100m relay at the Beijing Olympics, quit athletics after back surgery derailed his London 2012 ambitions.
And he's now looking towards next year's Winter Games in Sochi as part of the British bobsleigh team.
However, he'll be keeping a close eye on Dasaolu - who clocked the second fastest time ever by a British sprinter when he ran 9.91 seconds last month - while attending a three-day conference for Winter Olympic hopefuls in Bath.
"I trained with James for three years and he's a good friend, so it's really nice to see him performing well because we've always known what a talent he could be if he stayed free from injuries," said Pickering.
"I was delighted to see that run in Birmingham and if he can show that sort of form in Moscow then he should be in real contention. The key thing is not to put too much pressure on him."
Britain's four man bobsleigh team finished fifth at last year's World Championships in St Moritz while driver John Jackson - currently on crutches with an Achilles injury - showed similar promise on the technical Sochi track, ranking fifth in the test event.
Pickering's outings last year were restricted to the two-man bob but breaking into the crack first choice four-man team is his top target - though dislodging the settled crew of Jackson, Stuart Benson, Bruce Tasker and Joel Fearon will not be easy.
"I'm still really trying to learn the technique of bobsleigh, last year I didn't really know what was going on but I feel I'm really getting to grips with the sport now," added Pickering.
"I feel much more comfortable in and around the team than I was last year. It's quite easy to be good at bobsleigh but to get to be very good is really difficult and quite complicated but I'm learning fast and getting there.
"We've got great strength in depth but I want to be the best. I think I'm in a great place with my training and I'm where I want to be as we look towards the World Cup season and, hopefully, the Olympics in Sochi.
"I went through a period of not enjoying athletics and I needed a new challenge and this has been a great decision for me.
"There is a much more team oriented approach to bobsleigh, which is something I really enjoy. We had some great results last year, which should really give us confidence as we look towards the Olympics."
© Sportsbeat 2013