Networking is uncomfortable for a lot of people.

As an ambivert with strong introvert tendencies, I get it. 

Talking to people and realizing that moving ahead in your career could depend on you talking to and building relationships with others is daunting.

But it doesn’t have to feel daunting.

Today, I’ll share some insights on how to comfortably initiate career-building conversations.

You can use these insights to network, get informational interviews, and steadily build social capital throughout your career. And not just when you desperately need it.

(If you’ve been around me long enough then you know that I am a fan of the phrase “dig your well before you need to drink from it.” This is me giving you some of those tools to dig the well.)

Before we go on, let me lay 3 crucial foundations upon which all of this will work.

1. Communication and building relationships is a skill anybody can develop. Is it harder for some? I acknowledge that. But it is still possible even if you’re the most introverted of introverts to improve this skill of initiating career-building conversations and relationships.

2. Have a promotion focus. People who have a promotion focus tend to have a positive outlook and will take the outcome of initiating conversations – whatever that might be – in stride. This means that whether people respond to them positively or not, a person with a promotion focus will keep on moving until they reach their goal. 

Don’t create negative outcomes in your head that haven’t happened yet. Keep moving until you reach your goals.

3. Your network is probably bigger than you think. When you start having conversations, you will see just how big.

Now let’s talk about the 4 pointers I want to share today.

4 ways to initiate career-building conversations 

4 ways to initiate career-building conversations

Take initiative.

“You’ll have more friends if you’re friendly too.” My dad used to encourage me with these words as a child. It was his way of encouraging me to take initiative when it came to being social. The same applies to initiating career-building conversations. You see someone working in a position you aspire to? There’s someone on LinkedIn you admire? There’s an alumni from your school working at a particular company? Take the first step to start the conversation.

“But what happens if they don’t want to talk to me?”

There are 8 billion people in the world. Move on and talk to the next person who wants to talk to you.

How do you start such a conversation?

Here’s an example of a message I sent to someone recently:

Hi Kristen! I hope you’re doing well. I have been thinking about my next steps with my role and you came to mind. I would love to learn more about your role in market development and perhaps how I could grow on that path. Do you have time on your calendar in the next few weeks to chat?

The result:

I happened to know Kristen from when we both worked at a previous company. We hadn’t spoken in several months but when I sent this message, she responded kindly and invited me to lunch where we spoke for 30 minutes. She shared her thoughts on how I could move my career ahead in biotech market development. She then (of her own accord) introduced me to two more leaders in our space. One of those two went on to have another enlightening conversation with me about how I could advance.

The lesson:

If I had never initiated the first conversation, I would have learned nothing about what leaders look for when one applies to the type of role Kristen works in. And secondly, I would never have connected with the second leader who provided even more insight.

This is also an example of “you don’t know how big your network could be until you start having conversations.”

Pro tip: In your initial ask, please avoid the temptation to ask “I want to know your story.” Any time someone sends me a message like this, the first response I think of is, “I was born 41 years ago. Which part of my story do you want to hear?” I don’t write that in my response, BUT I do think it.

Be specific with your requests.

Be genuine.

Show genuine interest in the other person’s work. Although it doesn’t happen often, I have been on the receiving end of needless and false flattery. Please don’t falsely flatter people to get on their good side. 

Instead of flattery, talk about something they did that you truly admired, why you admired it, and a practical way it has helped you. When people have approached me this way, I always want to talk to them more. And I have found it true for others as well.

Finding commonalities rarely fails.

Look for things you have in common with the person you want to have a career-building conversation with. Listen when they speak. Look at their LinkedIn profile or website. If you find something you both have in common, you can bring this up early in the conversation. 

These can be great conversation starters.

Open-ended questions win. Every time.

You know what I have found incredibly surprising when it comes to these conversations?

The people who say yes to you ACTUALLY talking about their experiences and insights. 

And you can get them to share even more when you ask open-ended questions instead of yes or no questions.

Here are 3 examples of that:

  1. “What inspired you to choose your career path?”
  2. “How do you see the industry evolving in the next few years?”
  3. “For someone like me, what are some strengths I could leverage, or weaknesses I could work on to work in this type of role?”

Semi pro-tip: after you read this today, use ChatGPT or Gemini to help you come up with some open-ended questions you can ask in your next conversation.)

Starting your conversations with these pointers will lay the groundwork that can help you have smoother career-building conversations with almost anyone.

Did you find this helpful? Comment below and let me know.

Happy Friday.

If you would like to learn how to create a highly optimized LinkedIn profile that attracts opportunities to you, and how to find the right people to start career-building conversations with – in less than 2 hours, and without becoming some kind of “influencer” – join 240+ others who have taken my courses, and get the LinkedIn Profile Clinic Workshop.
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