First, you should eliminate the notion of "someone to talk to on a long, boring flight." That's the reason my buddy transitioned from F/A-18D WSO to Financial Management. Most of the pilots that were accustomed to single seat flying sometimes wouldn't even talk to him in air.
If you're flying an aircraft with more than one crewmember, make sure that your entire crew is involved from the get go. Hence the reason for the term "crew." I personally love flying a multi-piloted platform, and I have crewchiefs and aerial observers on my crew as well. While I may have signed for the bird, and am ultimately responsible - every single member brings something to the table. When I was going through the syllabus for Division Lead, I had a crew chief that had already gone through WTI. As I started to slowly get overwhelmed with the flight, I brought him up in the tunnel and asked his advice from a tactics perspective, and additionally had him help take the load off (since my copilot was evaluating me). Guess what, I got an above on crew coordination and was proposed for WTI. Flying is not what makes you a pilot, it's everything else.
That same crewchief was aboard my dash two when I was returning to Al Asad Air Base in Iraq from Al Taqqadum, in less than optimal weather. Visibility was so bad that dash two had to turn on his IR searchlight and train it on me to see my aircraft. When the crewchief couldn't see anything to the side or behind him, he crawled up in the tunnel and sat on the map case. When the non-flying pilot asked what's up, his reply was "I can't see sh!t in back, and it sounds like you guys are working hard up front. So, I figure I'll be most useful backing you guys up watching the gauges. Don't worry about the engines, transmissions, hydraulics, or the master caution panel, I'll watch those. Just focus on flying and get me home safe." I only wish that he wasn't getting out, it'll be tough to replace a crewchief with that much SA.
Additionally, regardless of rank - you need to foster a relationship with your crew that allows them to challenge/question what you're doing. Remember, you're not responsible for just your life, but the life of everyone else on board. So if they're not comfortable, maybe it's time to knock it off.