Recently, I worked up the courage to cold-invite a senior person out for coffee on LinkedIn. He’s an investor and was formerly C-suite at a Fortune 500 company. He had liked one of my posts, which logically meant he found something useful in what I wrote. But I still felt he was out of my league.
And that showed in my message:
“This is a long shot and might come across as being presumptuous, but if you are ever back in Singapore, let’s catch up over a meal or coffee. My treat.”
He replied. He said the invitation was welcome and that he was honoured by it. Then he added something I still think about:
“Eliminate this inferior, self-effacing language from your communications, even if the person is more senior than you.”
We all have these moments. Students feel it at career fairs. Mid-career professionals who’ve been retrenched feel it because the job title they used to lean on is gone. One student told me he becomes wallpaper in group conversations at networking events — when the other two people are more senior, he freezes up and stands there until the conversation moves on without him.
So how do we find within ourselves something valuable to offer? Here are three things that have worked for me.
1. Intellectual: Bring something you have thought about more deeply than most people
Most people throw up their hands in defeat. “I don’t have anything to say that a senior person hasn’t already thought about.”
Fair enough, if you’re trying to teach them about their own field. But can you teach them something outside their day job that they’re curious about?
I was having coffee with a senior director at a government agency recently and the conversation turned to AI. Instead of talking about it the way most people do, broad strokes, “AI will take all our jobs”, I did two things. First, I gave him intelligence from the working level. I listed the five things I actually do as an intelligence analyst and described specifically which parts AI can already do better than me. By doing so, I gave him insights, i.e. a framework. A structured way to think about AI’s impact on any job by breaking it into five functions. Frameworks are what senior people take away from conversations, because frameworks help them think about their own problems long after the coffee is over.
You don’t need to be an expert. You need to have thought about something more carefully than the average person at the table and be able to lay it out simply.
2. Emotional: Be genuinely curious instead of trying to impress them
Most people who approach senior professionals want something, a referral, advice, a job lead. Someone who shows up with genuine curiosity about what they’ve built, with no agenda beyond wanting to understand it, stands out precisely because it almost never happens.
There’s science behind why this works. Harvard psychologists Diana Tamir and Jason Mitchell ran a study in 2012. They put participants in a brain scanner and gave them a choice: answer questions about yourself, or answer questions about someone else. Talking about yourself lit up the brain’s reward system. Then the researchers upped the stakes. They offered participants more money to talk about other people. The participants turned it down. They gave up 17 to 25 percent of their potential earnings just to keep talking about their own thoughts and experiences. We spend 30 to 40 percent of everything we say telling people about ourselves.
So when you’re standing next to someone senior at a networking event and your brain is telling you “I have nothing to offer this person,” the research says otherwise. You have something almost nobody else in the room is offering: a genuine question and the willingness to listen to the answer.
I once met a former banking executive at a networking event. He’d left the bank and was now investing in biomedical research ventures. He was funding something I’d never heard of before: a model where anyone could commission scientific research on a specific question. Imagine you have cancer and you want someone to test the effect of a specific drug on your specific type of tumour. That’s what his portfolio company was building. I had a hundred questions. He had answers he clearly didn’t get to share often enough. He stayed to talk with me for an hour, even though people at these events usually bounce to another conversation after ten minutes. That’s because I wasn’t trying to impress him or get anything from him. I was genuinely curious.
Don’t overthink this. Be genuinely interested in the other person instead of using scripts like “what advice would you give your younger self?” That kind of question makes people perform wisdom and the answers are always superficial and forgettable.
3. Practical: Look for something practical you can help with after the conversation
The first two are about what happens in the conversation. This one is about what happens next.
My friend leads the innovation arm of a semiconductor manufacturer and reports directly to her CEO in the US. For months, she’d wanted to automate how her team coordinates projects. She had the idea. She knew roughly what the output should look like. But between running a department and reporting to the CEO, she didn’t have time to figure out prompt engineering herself.
Then a young engineer from another department sent her a message asking for an internship. He wrote something to the effect of: “I’m just an engineer but I know a bit of AI from compulsory modules in school. If there’s any project that needs someone to do the hands-on work, let me know and I’ll be happy to work on them.”
She took him on. The company called it “reverse mentoring,” which sounds like a corporate rebrand of “junior person does tech support for boss.” But what actually happened was more interesting.
Once a week, she’d sit down with him and walk through the problem she was trying to solve. She’d explain the policy constraint, the C-suite deadline, the political friction between departments. He’d go away and either build a master prompt that solved it or just do the work. What did he get out of this? Not just a line on his CV. He was learning how a company actually runs, by sitting three levels above where a fresh graduate would normally sit. That access is something no internship programme would have given him.
The same principle works even if you’re not inside someone’s company. You just have to discover what they need help with outside their day job. A senior director I know runs a podcast about career transitions on the side. He didn’t need my help with his actual work. He needed interesting guests for his show, and I could help with that. Another former corporate leader now runs a non-profit that takes people with disabilities on outdoor expeditions. He’s always looking for energetic volunteers who’ll show up on a Saturday morning.
You only discover these side projects if you carry the conversation past the LinkedIn headline. Most people at a networking event only tell you their job title. The person who runs a podcast after hours, who mentors kids on weekends, who’s quietly building something that has nothing to do with their day job, that person only appears if you go deeper. (I wrote about how to do that.)
So what now?
The next time you’re standing at a networking event, or staring at a blank LinkedIn message, or sitting across from someone in an informational interview, and the voice in your head says “I have nothing to offer this person”, remember what that investor told me. Eliminate that thinking from your philosophy.
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