You already know Sigma's feelings about cool female leaders so let's do cool female leaders: the sequel.
Sigma bases a lot of his opinions on people on his gut feelings about them and Shepard is just a person that he has a good feeling about. He saw her rally the troops during the Xenomorph attack, he knows she's a good leader with a good head on her shoulders. When Tabris showed up at the bar he was like "Uuuuuuhhhhh" and when she got all lap dancy with him he was like "UHHHHH WHAT IS THIS ABOUT, 'CAUSE IT'S NOT ABOUT ME!" Tabris seemed like a nice lady, if mischievous, but he hadn't seen her in the heat the way he had seen Shepard and he didn't know enough about her to form an opinion of her. So when he saw that Shepard was with her, he instantly trusted Tabris. If it had been anyone else, he probably would have burned the note without reading it for fear of being anthraxed or something. And thank god he didn't, because he now wears that feather around his neck. He's eternally grateful to Shepard, especially. He owes her big time and knows it. She could leak the fact that he's a spy at any time she wanted and she doesn't, even though he's going to go on to do increasingly shitty things, and that takes some real strength and he probably wouldn't do the same in her shoes. So cheers to you, Shep. Let's hope they do a cool thing sometime together in the future.
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Sigma bases a lot of his opinions on people on his gut feelings about them and Shepard is just a person that he has a good feeling about. He saw her rally the troops during the Xenomorph attack, he knows she's a good leader with a good head on her shoulders. When Tabris showed up at the bar he was like "Uuuuuuhhhhh" and when she got all lap dancy with him he was like "UHHHHH WHAT IS THIS ABOUT, 'CAUSE IT'S NOT ABOUT ME!" Tabris seemed like a nice lady, if mischievous, but he hadn't seen her in the heat the way he had seen Shepard and he didn't know enough about her to form an opinion of her. So when he saw that Shepard was with her, he instantly trusted Tabris. If it had been anyone else, he probably would have burned the note without reading it for fear of being anthraxed or something. And thank god he didn't, because he now wears that feather around his neck. He's eternally grateful to Shepard, especially. He owes her big time and knows it. She could leak the fact that he's a spy at any time she wanted and she doesn't, even though he's going to go on to do increasingly shitty things, and that takes some real strength and he probably wouldn't do the same in her shoes. So cheers to you, Shep. Let's hope they do a cool thing sometime together in the future.