How to express your frustration about work without being labelled as being negative?

I used to work as a secretary to a boss in a big company (more than 10,000 staff). Therefore I had opportunities to watch closely this problem.

Each week, my boss had some 15-minute slots to have one-to-one chat with any staff who wanted to register for the session. It was supposed to be a frank session where the boss listened to any problem that the employee cared to share.

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However, as I took notes for the boss later, I usually heard how he referred to people who complained about many problems in the company. Although the boss would promise to look into the problems, later he would labelled those employees as being negative. It looked like those employees would not have promotion chances.

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Then how do you master this skill: frankly telling your boss about work problems while not sounding pessimistic and negative?

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