Questions that make you memorable

You've been following Decrypt Cyber long enough to know finding and staying in touch with mentors is the #1 career hack. But once you get someone on the phone, what do you talk about?

I recently heard a story about someone who Googled "questions to ask during interview" and I immediately felt sorry for them. Good luck standing out, making an impression, and developing an authentic connection with a stranger if your questions came from a generic, SEO-optimized blog post likely written by ChatGPT...

A few guidelines to keep in mind for every networking phone call:

• Always come with questions prepared: You need a pre-written list of questions in front of you before you pick up the phone. This forces you to approach the conversation deliberately and reduces the chances of awkwardness or wasted time.
• Send some of the topics/questions ahead of time in the invite: You're already writing up questions ahead of time, so why not share them? In fact, it's often to your advantage to share them ahead of time because it makes you appear thoughtful and intentional. Everyone hates a meeting invite with no agenda. At the very least, it will make you stand out because almost nobody else does this.
• Keep the questions limited to what you're genuinely interested in learning about: This is why it saddens me to see someone taking questions from whatever happened to be at the top of Google. The best questions are authentic. They don't come from someone else. They come straight from your own curiosity. What are the burning things on your mind? What have you always wondered about? What have you been afraid to ask? Those are starting points for good, genuine questions.
• Never ask questions that are easily Googleable or available on the company's website: It makes you sound naive and is a waste of time for everyone involved. Not a good look. Instead, take a peek at the company's website and ask questions about things you can't find answers to there. Many websites are just surface-level marketing. Use the buzzwords to inspire questions that dig deeper.
• Don't be afraid to ask questions about them as individuals: Most coffee chats cover the same boring topics. "What does your typical day look like?" or "where do you see the industry going in five years?" So boring! Everyone asks these. Instead, construct questions that engage the other person to think critically and creatively about their own lives. These questions can get a bit vulnerable. That's the point. Vulnerability, invoked in a respectful and curious manner, is a source of genuine connection.

Ok, now that I've convinced you to avoid the lazy route of other people's questions, I'll share some that have worked for me. 😉

• Why are you in your position and not others?
• What are some of your favorite parts of your job?
• What would you change about the company if you were queen/king for a day?
• What makes you sigh at the end of the day?
• What are some of the most stressful parts of your job?
• What annoys you?
• What do people get wrong about your role?
• What makes someone successful in your role?
• What gets you super excited about the industry?
• What are some surprising things you've learned between when you started and where you're at now?
• What are some previously held notions or ideas about the job/company/industry you've since changed your mind on?
• What would you go back and tell your younger self?
• What do you regret about your career?
• What do you think you've done really well in your career?

But there's still something missing from the questions above: SPECIFICS. It's worth Googling the person/finding them on LinkedIn and perusing their entire work history.

• Maybe you both went to the same school
• Maybe you both grew up in the same area
• Maybe you just went on a vacation to their home state
• Maybe your favorite sports team is based in the city they work in
• Did they have an interesting first job? Second job? Third job?
• Have they published anything? Go read it.
• Have they spoken at a conference? Go watch the recording.

Noticing the above details helps you construct a conversation that sparks connection. It shows a genuine interest in the other person which is the strongest way to build rapport.

Some of my strongest professional relationships, ones that have lasted years, were born out of a single phone call where the other person felt like I had "done my homework." Like discovering an executive published a book on a super nerdy topic 30 years ago. No one else knew this guy had written a book. He was delighted and impressed that I brought it up. Doing your homework is rare. Those who do it stand out. Effort is salient.

Do your homework.