My supervisor doesn’t communicate very well and gives very little positive feedback. He gives directives, without explaining the reasoning behind his decisions. It’s hard to execute what he wants without seeing the whole picture. What can I do to start a conversation with him?

Boss feedback

This is a very common problem with bosses. It’s not because they don’t want to give feedback. But we’re all busy and giving feedback to employees can detract from focusing on the immediate job at hand. Bear this in mind. Ask to see the whole picture to get the job done well.

This was very common on Wall Street. Senior bankers would give only directives. They wouldn’t explain the strategic implications of the work. To overcome this, the best junior bankers would strike a bargain. “You tell me more about what we are trying to do. I can make your life easier by getting more done. And I can give you more time to go hit your tee time. Help me help you.”

I would start with this. See if there are additional elements of the project that you can offer to take on. Nothing pleases a boss more than hearing a subordinate is willing and able to take on more. But obviously, you need to be ready for this. Don’t bite off more than you can chew!

I’ve been at the same company for three years. I really enjoy my co-workers, but the work itself is getting boring. I’m looking at my competition for promotions and I would have to jump over a handful of people with more seniority than me to move up the ladder. How do I know when it’s time to be looking for a new job?

Boring job

First, you need to be honest with yourself about why is your work boring? Is it routine? Have you already become a black belt in it? If so, then seek out new projects and ideas. Every company is always searching for growth. So take the time to come up with new ideas. Present that to your boss.

Or have informal coffees with your boss’s boss. Especially if you are getting stonewalled. I guarantee you any company, unless it’s a non-profit, is always searching for new avenues of growth. Leveraging the people inside the company to make it happen is always better for the company – and for you. If you go elsewhere, you’ll have to start all over again to prove yourself. Remember the adage, “the grass is always greener on the other side.” 

In the rare instance where your immediate boss and no one above them cares about your ideas, and you truly believe they are good, then it’s time to hit the road. Get that resume ready and start making calls!

I work in the technology sector around mostly men. They see me more as cute than an equal. I feel I’m being judged by my appearance. They aren’t overtly sexist, but when I speak up, my comments are often ignored and the conversations quickly shifts away from what I just said to other thoughts. What can I do to be taken more seriously.

No diversity

I encountered a similar situation due to race. This may not be the popular opinion but I’m of the mind that you need to give a little to get a little. To get what you want, you can’t just stand on principle and not compromise somewhat. So pick your battles.

The key thing to remember is every person has biases and preconceived notions about the other gender or other races. Determine what those could be for you and your male colleagues and use them to your advantage to get heard. For example, as an Asian American, there is a preconceived notion that I came out of the womb a math whizz. So I used that to get a seat at the table and became a trusted source for analytical work.

However, I knew that type of work would only get me so far and that to really progress, I’d need to demonstrate my softer skills like salesmanship and leadership. By establishing credibility in the analytics area, I got more leeway to work on other projects. Ones that showcased my other abilities making me more likely to be heard in non analytic areas.  

For women, one potential area is empathy and compassion. Men perceive women to have more of this than themselves and this could be an area to leverage. Areas related to customer journeys, and the subjective view of how products make us feel, are all areas ripe for exploiting this bias. Accomplishing that makes it easier to be heard in other areas. You also try the direct approach but that appears to have not garnered their respect.  Remember success drives opportunity but you need to start with smaller victories first!

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About the Author

Dave is a seasoned executive and entrepreneur who founded several companies in entertainment, investments, and technology, and worked on Wall Street for almost 25 years.

He started his career by joining a fledgling investment bank, Jefferies, when it had less than 200 employees.  Today, Jefferies is a multi-billion dollar diversified public company (NYSE:JEF).  He rose from the entry level position of Analyst to Group Head of Internet and Digital Media and was one of the youngest Managing Directors in firm history.  As one of the only managing directors of color in the firm, he successfully broke through the Bamboo Ceiling. He not only worked hard but also played the corporate game. 

Hundreds of bankers have worked for Dave during his career. He has mentored many of them who have gone on to some of the best business schools and companies in America.  He is eager to share his knowledge with Asian Americans and other disadvantaged groups seeking to maximize their potential and achieve their career goals.

If you want some great career tips and insights check out Dave’s book, The Way of the Wall Street Warrior, at

You can follow Dave at Facebook@Liucrative,Twitter@Liucrative, Instagram@LiucrativeEndeavors, LinkedIn@DaveLiu, or TikTok@Liucrative.

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