You will be able to request and run an informational conversation that the other person finds easy to say yes to.
Arjun found the person he wanted to talk to: a former teacher who had moved into learning and development at a hospital group. He opened LinkedIn, started a message and stopped. What do you say to someone you have not spoken to in years, or have never met, that does not sound like you want something from them, when he did in fact want something?
The answer is to ask for something small, specific and easy to give. An informational conversation is a short chat, usually twenty to thirty minutes, where you ask someone about their work and how they got into it. It is one of the most effective tools in a career move, and most people are surprisingly willing to give one, if you ask well.
The most important rule is to ask for advice and leave any job out of it. Ask for twenty minutes to hear how they got into the field and what the work is like.
There are good reasons for this. A request for a job puts the other person in an awkward position. They may not have one to give, and saying no feels uncomfortable for both of you. A request for advice is something almost anyone can say yes to. Most people enjoy talking about their own path, and being asked for advice is flattering.
It is also more honest about what you need at this stage. You are still testing directions, as lesson 1.3, Test a direction before you bet on it, described. You need to know what the work is like, what skills matter and how people get in. Those are things a conversation can give you, and a job opening is a separate question that comes later, if at all.
Keep the request to twenty minutes and stick to it. A small, bounded ask is easy to accept, and respecting the time limit builds trust.
Why you chose them matters to people. Mention how you came across them, and say in a line or two what about their path caught your attention, because a message that could have gone to anyone usually gets the reply it deserves.
Arjun's message to his former colleague: "Hi Priya, it's been a while since we were both at the school. I saw on LinkedIn that you moved into learning and development at the hospital group a couple of years ago. I'm thinking about making a similar move and would really value hearing how you did it. Would you have twenty minutes for a call or a coffee in the next few weeks? I'm happy to work around your schedule."
For someone he did not know, Arjun used a mutual connection: "Hi Marcus, Priya suggested I get in touch. I'm a secondary school teacher looking into corporate learning and development, and she mentioned you moved from teaching into training at a bank. Would you be open to a twenty-minute call sometime in the next few weeks? I'd love to hear how you approached the switch."
Both messages are short, specific and easy to answer. Neither mentions a job.
If they say yes, prepare three or four good questions. The test of a good question is that you could not answer it yourself with ten minutes online. Asking "What does your company do?" wastes their time and suggests you have not prepared.
Ask about their actual experience. What does a typical week look like? What surprised you most when you started? What skills turned out to matter more than you expected? What do people coming from my background usually find hardest? If you were in my position, what would you do first?
Wei Ling, talking to an analyst at a retailer, asked: "What part of the job do people underestimate?" The answer, that most of the work is cleaning and checking data before any analysis starts, changed how she thought about the role and showed up in her interview answers months later.
Near the end of the conversation, ask one more question: "Is there anyone else you think I should talk to?" This is the question that turns one conversation into three. The person now knows what you are looking for, and they often know someone who could help further. An introduction from them is far more likely to get a reply than a cold message from you.
Make it easy for them. If they suggest a name, ask whether they would be comfortable introducing you, or whether you should mention their name when you reach out, and send that message within a few days.
When you have the conversation, keep to the time you asked for. When twenty minutes are up, say so and offer to let them go. Many people will choose to keep talking, but they will notice that you respected their time.
Listen more than you talk. You are there to learn, and most of the value is in their answers. Take a few notes, but keep your attention on them.
Lesson 7.3, Stay in touch without being a pest, covers what to do afterwards. For now, the hardest part is sending the first message. Write your request to one person on your list in the activity, and send it.
Write an informational conversation request for one person on your list and send it.
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