How to connect with executives

It’s 9:03 am on Monday morning and I’m sitting outside a meeting room twiddling my thumbs. My hands are sweaty. It had been three minutes past the hour, I was now wondering if she forgot about me — how long before I just leave, would that be rude?

These other thoughts were also buzzing around in my head:

She’d finished her previous meeting and was heading out of the room to come meet me.

“Hi, are you Jay?”

“Hey Catherine, that’s me. How are you?”

“Doing well, come in, let’s chat”

Over the course of the next hour, I learned a lot about Catherine. She was a former director at a startup, she had two kids, and loved biking. We connected over her role as a VP and how she got there. I shared my own career ambitions. We were able to connect over her philosophy on raising children, and how that’s changed her working style. To this day, I have a wonderful friendship with her and have relied on her for perspective-shifting career and life advice.

Many of us will have encounters with execs that could change our lives. This can happen in interviews, coffee chats or an introduction from a colleague. This meeting, and subsequent relationship, turned out to be one of those encounters.

It can be stressful to “network” and to reach out to folks that are more advanced in their career. They’ve had more experience than you, have more of a reputation, and are quite busy.

The process of building relationships with those in “power” should not be thought of as that. Remove the titles, remove the status, and connect with these people just as they are — people. Seek to develop an authentic and genuine relationship, ask personal questions, and share vulnerable aspects about your own life. These connections will provide you with personal joy, learning, and opportunities in the future.

Using the tips below, you can create these same genuine relationships — especially for those early in their careers looking to connect with more senior people.

  1. Approach the conversation with respect and be specific
  2. Do not be self-deprecating nor overconfidence
  3. Bring an intense amount of curiosity
  4. Stay in touch

Let’s begin.

1.) Approach the conversation with respect and be specific.

These people are busy, so respect their time.

A great way to do this is to be specific in your request for time. Why are you looking to meet with them? Is there a set of experiences they’ve had in their career that you’d like to hear about? Maybe you have a similar background (school, hometown, etc) that you’d like to connect about? State this in the initial email or LinkedIn outreach.

Here’s an example of a recent LinkedIn InMail I sent to an executive at a fast-growing company in the Bay Area.

— — — — –


Hi Mary,

I hope you’re doing well. Looking to connect for 3 reasons:

1.) To learn more about your journey and lessons in Business Development.

2.) Dig a level deeper on the content in your articles you’ve posted on LinkedIn.

3.) Connect with a fellow Canadian in the Bay.

Would you happen to have 15 minutes either Thursday or Friday the week of January 6th?

Thank you, Mary, hope to connect!


Sure. Contact me at and we can set up some time.

— — — — –

This is a real exchange with someone with more than 20 years of experience in her field at one of the most exciting startups in the Bay Area. Be specific with your request, add context on what you’re looking to learn and input a common connection you have with them (for me it was being Canadian). You’d be surprised by how many people reach back out.

The caveat with this is that volume matters. I’ve had friends tell me that no one replies to their outreach, and reaching out does not work. My next question to them is how many people did they reach out to, and the answer is usually between 1–2.

Use quantity when reaching out, knowing only 20%-30% of people will have the interest and the time to follow up with you. When you’re in front of these people, then it’s time to focus on the quality of the discussion. Remember, quantity first then quality and focus once you’re with them.

2.) Do not be self-deprecating nor overconfident.

It took years of awkward interactions to internalize this one. Have you thought or said the following when reaching out to execs?

“There’s no way I can reach out to them, they’re way too (busy, senior, experienced, etc), why would they want to meet with me?”

“They must have better things to do than to meet with someone who just started their career!”

This self-deprecating energy you bring into the conversation will put them on a pedestal. View these senior individuals with respect, but remember they are just people. People like you who have difficulties in their lives. People like you who are trying their best to do well in this world.

Empathize with their struggles — maybe share some of your own. Seek to connect with them as friends, rather than a professional mentor. It is a waste of their energy if they’re using the conversation trying to build up your own confidence. That is not their job.

The frame of mind I use going into these conversations is to find ways to help them. Their children may be applying for college, and I can provide some perspective on that. Maybe they’re mentioning and area you have more personal experience with that you can share. There could be an article or a book that you could share with them based on the interests they highlighted in your chat. Despite being the younger, less experienced person in the meeting, you can still help. You just have to be more creative in finding ways to do so.

Not being overconfident is a no brainer. Thinking that you’re hot shit does not work. Have humility, be curious, and present yourself with confidence. Those will always be your competitive advantages.

3.) Bring an intense amount of curiosity.

I prepare for meetings by researching them beforehand. You can do this by looking at their LinkedIn profile, Googling them, and asking people in your network who know them for advice on what to bring up in conversation.

With the preparation completed, you should now have a list of questions to go through and ask them about their careers or some of their hobbies/interests. But here is an important distinction with these questions.

Have questions ready, but do not force them into the conversation. Be curious, ask thoughtful follow-up questions and see where the conversations go.

Here’s an example of the beginning of a recent conversation with that same executive, Mary.

— — — — –

Jay: Hi Mary, how are you? How was your holiday break?

Mary: Great Jay, thanks for asking Have spent a lot of time with friends and family.

Jay: Awesome, what did you all do? How many family members do you have? Any kids?

Mary: Yes we have two kids, one 5 and one who’s 6 months old. It was the first time we had some time off after the newborn, so we took them all to visit my parents over in Toronto. It was quite a needed trip.

Jay: Wow, congrats on the newborn. I’m pretty naive, but is having the second child a lot easier than the first? Or is it still tough? Also, how do newborns travel, any issues or did they sleep through the flight? Also, how often do your parents get to see their grandchildren?

Mary: Honestly, each time my partner and I have had a child, it’s been tough, as with any new parents. I find it hard to manage my work, and ambition for the firm by spending quality time with the kids. Thankfully, my partner and I have flexible work schedules that allow us to tag-team quite well for us to spend quality time with the family, but also continue to do well with our careers.

In terms of spending time with our parents, that has been a recent issue for sure. We come from a cultural background that prioritizes a lot of time with family. Both my partner and I have a lot of siblings, all that live on the east coast, it’s just us out here in San Francisco. After this holiday in Toronto, we’ve seriously considered moving back but just love it here so it will be a hard decision to make.

— — –

Cutting off this fictitious conversation here.

At first, ask general questions but then LISTEN and ask thoughtful questions to follow up. If you engage with people on a personal level and do not get to your prepared questions, you’ve still won.

People struggle to develop a personal relationship by asking personal questions in a professional context.

It may feel awkward at first, but try it out. You’ll make yourself stand out from those who focus only on career questions. Once you develop that personal connection, the professional advice will come.

Is the person you’re meeting with not engaging as well to your general/personal questions? Perfect, that’s why you’ve come prepared with questions you can turn to. Likewise, if time runs out and you need to ask a question, save it for email or as you’re wrapping up.

4.) Stay in touch

When interacting with soon to be mentors, at the end of the conversation, state the following.

— — 

Jay: Hey Mary, have had a great time getting to know you over the past 15–20 minutes. I have learned the following lessons from your own life (state lessons learned), and am going to look to apply them in the following ways (state ways to apply lessons learned).

I was curious, if you found this as enjoyable and fun as I did, would you be open to setting up a recurring conversation for us to reconnect and for me to learn even more about you and your journey?

Happy to even send over an invite for once every few (weeks/months), and we can keep it as tentative because I know things come up.


Mary: Sure Jay, let me get you in touch with my executive assistant Brad and he can set some time up for us.

— — 

With this request, you’ve expressed your interest and intention to continue the relationship. When asking this question myself, I’ve had most say yes, and I have also had a few say no. Either response is great because you have expressed your intentions and shared how much this relationship would mean for you.

Regardless of if you have a recurring meeting established, stay in touch through email and LinkedIn. If you see an article that reminds you of the conversation you’ve had, send it over to them with no expectation for them to reply. Know someone else in your network that you think would be valuable to them? Introduce them.

Final Points

The process of building relationships with those in “power” should not be thought of as that. Remove the titles, remove the status, and connect with these people as they just are — people. Seek to develop an authentic and genuine relationship, ask the questions, and share about the more personal aspects of your own lives. These connections will provide you with personal joy, learning, and opportunities in the future.

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