What To Say Over Coffee with the CEO

There is hardly an easier time to connect with executive leadership than during an internship. The company has a vested interest in its interns, considering they’re essentially spending resources on training you with the hope of a return on investment. As an intern, one is also inherently more interesting than a regular employee — a fresh energy, one foot still in higher education, an unchartered plethora of opportunities, and the Gen Z advantage. It’s often true that simply the Gen Z advantage, and a completely new perspective, can solve some of the hardest problems that the company is dealing with — an innocent question could spark an idea, a cultural misunderstanding could create a solution, and the signature unearned confidence could lead the next big project. Higher leadership is fascinated by us youngins, and rightly so. And therefore, as an intern, it would be a wasted opportunity to not attempt to form a real connection with people that would exponentiate one’s social capital, such as executive leadership.

Now, let’s say, you took the leap, reached out to the CEO to discuss some of your “most interesting findings and ideas over the past three months”, and have been granted a classic 15-minute slot to juice this metaphorical orange. Congratulations, you’ve already done more than the average ‘keep your head down’ intern, and are now up against the overachieving population of students that have also grabbed this opportunity. The challenge now, however, is two-fold. One, anticipating social interaction is not always possible — one might say all the right things, but simply not achieve a deep connection. And two, there’s inherently stiffer competition for this person’s attention than most. In order to maintain your advantage and ensure success, it’s important to prepare suitably, and this includes planning conversation starters, openers and closers, a call-to-action, and most importantly, your mindset.

While the soft skills for an impactful conversation remain the same: allowing the other person to talk, listening intently and noticeably and leading the conversation to where they want to take it naturally, this specific scenario requires a stronger game plan. I, therefore, created a checklist to maximize the outcome from any short yet important conversation.

1. Plan out and practice the moment you meet, and the moment you depart. These are crucial to setting the tone and greatly impact how you the experience will be remembered. Your introduction should be smooth, deliberate and include an informal thesis statement- to allow for a clear context switch. Think of a lecture where your professor doesn’t begin with “Today we will discuss…” — it’s a lot harder to pick up the material without context. When meeting someone from a different world than you, that probably doesn’t have a lot in common with you, it’s necessary to portray the sentiment that this is a natural connection, that you are meant to be there, and that there is nothing awkward about this conversation. Let that shine through your glib introduction and breezy goodbye.

2. Think of a problem you found and a solution you implemented or were part of. This could be really small, in fact, surprisingly, the more miniscule the better. There are a few reasons this is important: it touches upon the common base that is the organization and the shared sentiment of helping it grow. Additionally, although the executive leadership team wants to, and feels a responsibility to know about everything going on in the company, it’s simply not possible. However, this mini catch-up is more valuable to them, because they get to feel involved in some of the inner workings, and get to seem knowledgeable about such intricacies at the next high-level meeting. Any node of information you share with someone that gets them to make a mental note also includes a pointer to you, and portrays you as passionate, well versed in the systems, and a problem-solver.

3. A faux revolutionary idea. This is the bit that will take the most planning, and a couple eureka moments to figure out but don’t waste an opportunity to meet one of the most rewarded high-level thinkers of the organization, and not speak with them on their level. Spend the majority of your preparation time coming up with one solid, revolutionary idea for the company — it requires no actual execution, and you don’t really need to ever follow up, but make it exciting, buzzworthy, and with clear, defined positive outcomes. Successful entrepreneurs, idea machines, and deep thinkers enjoy absurdly ambitious and interesting proposals, and will often look past the immediate hurdles and practicalities and savor the possibility of a revolutionary change. It is this endorphin rush from new ideas and possibilities that brought them there, so give them something to enjoy, mull over, and even if you end up deciding it won’t work — it’s the kind of conversation they’ll find most enjoyable, and will provide most interesting insight on.

4. If you still have a few moments, touch on a recent news story or a finding in a domain of mutual interest — whether that be fitness, apparel, America or even just entrepreneurship. Not only is it an easy and smart conversation to have, but will keep you memorable when that topic is touched upon and serves as a “proof of camaraderie”. Future emails could include more information on “the interesting conversation we had about *insert topic here*”.

5. Always give people a way to support you, especially when they are in the position to do so. Choose a personal project that you think will greatly benefit from their possible association and don’t be afraid to bring it up. Even if they decline your particular request, they may still look up the project later out of curiosity, or mention it to someone else. On the other hand, if this goes well for you, it also provides a great segue into asking for a method of maintaining contact that they will actually pay attention to. Read the vibe, the project and the person — this may range from a Snapchat to a work email or even a mutual contact’s email.

Maintain strong body language, and enjoy your conversation. Your social interaction is already far richer than your average day and has provided you with an incredible learning experience, savor it. Regardless of the outcome, whether you successfully form a memorable connection or not, realize how at this moment, you are interacting with one of the most important and possibly, inspirational people you have recently, and the value of your social capital has increased tremendously. Absorb the energy, feel worthy of that conversation and realize the prospect of a future of many more such intelligent, enriching conversations and connections.