The Art of Asking Hard Questions

Achieving your goals comes from hard work. That is a truth and an obvious statement. So why bother mentioning it? It is because so often I see many of my peers who underestimate willpower and dedication. They forget that while sometimes good things come to those who wait, you also only get what you put out. 

Are you feeling underemployed, dissatisfied with your job or internship, or feeling stuck? Sometimes you may blame the job market or your situation. But quite often you need to assess your position and determine how hard are you willing to work to be truly happy? Because at the end of the day, you don’t get what you don’t ask for.

Kevin O’Leary talks about this in his book The Cold Hard Truth. In business you don’t get what you don’t ask for. There may be a great opportunity  waiting for you, but just sit there, dead silent, unmoving, and it will pass on to the person who does speak up. Maybe you feel entitled, but you sit quietly by. Entitlement is not as satisfying as perspiration. Maybe you are scared of failure. But that will only ever hold you back. It could be the risk asks too much. That could also means getting more in return.

Whatever the reason for your lack of success, you are probably thinking it is not for lack of being ambitious. But thinking about success is different than reaching out for it. And success looks different to each person and does not mean you reach the dream job from the start. It just means taking the first step that matters to you in your career.

I learned from a very early age from another great teacher – my mom. I don’t know how many times I would have concerns or questions about things and decisions in my life that I would confront with statements like:

• “I really like x, but I don’t like y. But there is nothing I can do about it.”
• “I wish I could do this. But oh well.”
• “I guess that is just the way things are.”

And without fail my mom would remind me that confronting difficulties, problems or negativity often involves asking something of someone. And that can be a scary thing. For example, you might think asking to work different hours is something you cannot do, because you are afraid of no. But my mom would always say to me “When you ask, the worst that can happen is you get a no.”

I only had to hear this 1000 more times before I internalized it. Now I use it all the time. Every time I want something or need something to change, I am less afraid to ask for what I think is fair. That is because if you do it strategically and be honest, the worst that can happen is they say no.

People can’t read minds. No one goes around giving you what you want. But maybe, if you speak up and ask, you can achieve something and reach that goal you have been reaching for. But you will never know if you don’t ask.

How do you feel about difficult questions? What was the hardest thing you had to ask for?

P.S. I love PR