How to ask an unknown person for advice

Photo by Evan Dennis on Unsplash

I am signed up as a mentor on LinkedIn. People write to me asking for advice on entrepreneurship as well as career in general. I have learned a few things from the people who ask me for advice. This post is about you can get the most out of asking for advice. I have answered a commonly asked questions as well.

First Principles: Why do we ask for advice?

• To find a better way to do things.
• To learn from others mistakes.

I usually ask for advice when I am faced with an important decision but lack the experience/data to make the call

I would ask my mentor what are the options. Or I would tell them the options, ask them what they would have picked in my situation and why. I still have to make the choice and it could be the opposite of my mentor says. The idea is to get clarity and data points when I have none.

This brings us to the most important thing when you ask for advice or mentorship. Especially when the other person doesn’t know you.

How to structure your query?

A bad example from my career hub:

The guy never got back. I always wondered what he was expecting from me as a response.

These are the important elements in your query:

1. Background
2. Define the problem
3. Ask specific questions
4. Define why the mentor can help
5. Follow up

Background: Always give a background about yourself. Especially if you are reaching out to a complete stranger. This background has to be relevant to the question that follows. If you are asking for a career related question, give an overview of your experience.

Define the problem: Be clear about your problem. The person you are reaching out to doesn’t know you. They are sparing their precious time to help you out.

Ask specific questions: A generic question can at best receive a generic response. Ask specific questions that relate to the expertise of your mentor/advisor.

Let’s say I want to talk to the CEO of a start-up in its growth stage. I am doing this is because he/she has already passed the hurdles of early stages. They would have raised a few rounds of funds as well. I want to understand the challenges he/she faced when they raised their first few rounds of funds. The problem is well defined and the mentor most definitely has an answer. If I asked him a question like, “How can I become an entrepreneur?”, he/she won’t know how to respond.

Follow up: This is an essential part of the whole process. You seek advice & then take action. Your action doesn’t have to be in-line with you have been advised as long as you know why you are doing it. Irrespective of that, it is common courtesy to let your mentor/advisor know what you did and why. This helps both parties. It also makes way for further dialogue. Always check back in and stay in touch.

I have constructed an example to point out good structure to seek advice/mentorship.

An example for good structure

Don’t ask for advice expecting a certain response

A lot of times we ask people question expecting them to reinforce our beliefs. This is a terrible idea. When you ask a question, be open to the response else don’t ask. I have seen people do it in feedback sessions, appraisals, solution reviews etc. It sucks. It hurts when you hear something contrary to your beliefs. But that will help more than someone being agreeable so that you don’t get upset.

In the context of entrepreneurship, people will often ask:

So what do you think about my product?

Don’t use people to inflate your ego or reinforce your perceptions. Ask people because you want to know.

One of the worst things anybody can do to an entrepreneur is, tell them it’s a great idea when they think it’s not. The worst thing they can do is say that you should get back in touch and keep you hanging.

It is ok for me to feel bad because you think my product sucks. I have to pick myself up and do what I have to do the next day. Bear in mind, if a lot of people are telling me the same negative feedback something is definitely wrong.

Should I quit my job and go all out?

Nobody can tell you that, except you. People get excited after reading a few blogs and watching movies. Remember, a lot of people who succeed write about it, people who failed have bigger problems to deal with. They don’t write about it right away. Don’t read a blog and quit. Don’t drink a few pints and quit. Measure your runway, understand the stakes(your family, dependents etc.) and then take the plunge.

I have noticed that people who ask this question want me to say Yes. That doesn’t take away the accountability from them, but in some strange way, they have the notion that it will.

Before I close I want to talk about another common question and how to approach it.

How can I grow in my organisation or advance my career?

When it comes to a career path, usually I can find the answer within my organisation or another. Let’s say I am a business analyst and want to understand my career should look. I look at my boss, his/her boss and follow the chain upwards. Look at how much experience each of them has. This should give me a high-level picture. Next, I pick another organisation where I would like to work and do the same thing. LinkedIn is a great place to look. Next, do the exercise for your dream company.

The next step is to evaluate my skills. I do this by reading the job descriptions in the market for my designation. Then I score myself on the most common points. This will tell me where I stand. Next, I do the same thing for my boss’ position and I know what I need to get there. So on and so forth.

Thanks for reading.