Ask your self or any stranger passing by if you/he/she require some guidance towards a prudent future action in life. Almost always you will find your mind looking for validation of your plans through expert advice. I do too, nothing wrong with it.

Although we seek it, only a handful feel comfortable explicitly expressing their need for it. The ones that do, momentarily overcome their ego and extend themselves in the hope to learn from those whom they deem as experts. This choice is critically important. Whom we make ourselves intellectually vulnerable to defines how we allow them to mould our opinions and sometimes decisions.

In perpetuity, I find myself playing roles on both sides of this fence. My curiosity and obsessions with human experiences fuels my need to speak with people that I respect about problems that I care about. And from time to time, readers of such essays, aspiring entrepreneurs, and friends of friends reach out to me for advice, putting me in a position of responsibility as their guide.

One such person scheduled a call with me today. He had a flamboyant background working with a successful tech startup before their success took an unfortunate turn for the worse. He is currently employed with a large insurance firm where he acts an insignificant small gear in a slow moving massive machine. I don't mean to undermine his position but simply express what I heard as I heard it.

He asked me, "Akhil, I'm in this slow paced job that I despise. I wish to quit and get back into something more exciting. I would love to leave the country and maybe work for a company abroad. I know you've done all of this before. Can you please give me some advice?"

I replied, "Is your highest priority getting a fast paced job or leaving the country?"

Him: "I want an exciting job. I don't mind working in India, but my top priority is to leave the country."

Me: "That doesn't answer my question. What is your highest priority?"

A not so convincing answer from him, led to a digression in conversation. I shared with him an out of context yet unimaginably important piece of advise. Something I wish I had learned earlier in my career.

Whether asking someone for advice or trying to win a legal battle in court,

The quality of answers you get will depend upon the quality of questions you ask.

I continued to explain the importance of preparing for a conversation instead of going all commando. Having an objective in mind and a notepad in hand can help steer conversations towards constructive action items instead of simply an exchange of opinions.

I suggested that Instead of asking me for generic advice, it would serve him better to ask for help/guidance towards a specific goal. With this I laid down a few options in front of him:

  1. Do you simply want to quit the existing job and look for a fast paced, challenging role in another startup?
  2. Is money your focus for the next 2-3yrs? If so, would you take up the next opportunity that paid you 3x your current salary?
  3. Is your highest priority looking for a way to leave the country and move to a certain part of the world?
  4. Or would you want to take time off, learn a new skill and put yourself on a steep learning curve that makes you valuable for industries of the future?
  5. If nothing else, are you reaching out to me hoping to explore the opportunity of contributing to a project that I'm working on?

With these options, he immediately realized that he seeks advice not because he needs my help with something, but because he is confused. He thanked me for giving him perspective on how to approach his next steps and asked for sometime to think about these options.

Most people seek advice when they are confused, not when they require actionable guidance towards a specific goal. These both are very different conversations and you should know that going in.

My simple rule in life: Whenever in doubt, make a list.

Knowing and sharing your options are a great place to start conversations. It gives structure to thoughts, help avoid digression and act as agenda items for deliberation. I highly recommend knowing 3 things before you enter any conversation:

  1. A higher level priority in life/career/business that you are hoping to optimize for (eg: Find an exciting job, Get an introduction to someone etc..)
  2. The options that lay in front of you (Eg: Work for a startup/corporate, Start a business venture, etc..)
  3. A list of questions that would get you answer that point towards one or more of your options. (Eg: In what kind of environments do you think I can best use my (x,y,z) skills?)

Sit with a notepad to list down learnings and write about the learnings you've had either on a blog like this or a journal (I use Evernote for the ones that I don't publish) .

Without this asking for advice can be an infinite exchange of random opinions that may sound amusing but don't lead to constructive outcomes.

Next time you find yourself reaching out to someone for help, try this approach.

If it helps, please tell me about it. Write me to on or simply leave a comment below.