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Dave Wilkin is the CEO of Ten Thousand Coffees, a global enterprise talent development technology company.


When you only have a few minutes of someone’s time, especially when it’s someone you admire, there’s a lot of pressure to steer the conversation in the right direction.

Getting the most out of that brief interaction, however, only requires a small amount of homework, planning and consideration. By researching a few facts and jotting down a few notes, students, recent grads and early-career job seekers can be better prepared to ask the right questions, tactfully request a favour, and leave a lasting impression that sets the foundation for mentoring.

Networking coffee chats and mentoring have gone virtual with COVID-19, and there are a number of ways mentees can get the most out of their time with an established professional.

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I connected with Jad Shimaly, CEO of EY Canada to ask him to contribute to this step-by-step support guide for mentoring career conversations - what to say, ask and how to make the most of your time.

Step One: Think about what you want to get out of the interaction

When reaching out to a new connection or prospective mentor, it should be for a specific reason, such as learning more about that person’s industry or profession, asking them about job opportunities, initiating a formal mentoring relationship, asking for introductions to others in their field, or some combination thereof.

Once you’ve noted what you want to get out of the conversation, plan ahead for questions and background research that can help you get it. Before meeting any individual for a virtual coffee or phone conversation, take a few minutes to pause and think through how you can make this interaction most valuable for you. Identify your conversation goals and the specific areas of focus you want to use to guide the discussion. Also think about some of the potential next steps and any asks that you have early on, especially if you’re hoping to establish a long-term mentorship.

Step Two: Come prepared

Once you’ve determined what you want to get out of the conversation, be mindful of the time you have with that individual and do some light research to home in on relevant questions to guide the discussion. Jad Shimaly, chairman and CEO of EY Canada, says doing some quick Google and LinkedIn research to gain an overview of the individual’s background and experiences is a critical step in preparing for any new meeting.

“Once you know what you want to learn, and you know something about the person you’re talking to, ideally you can come up with questions that apply to both,” he says. “Have a few questions that can start up the conversation, then go with the flow, and keep pushing your questions so you can get into different areas you might not have expected.”

Step Three: Make a personal connection

The most memorable conversations are often the ones that establish a personal connection. For example, with some light research a young person recognized that Mr. Shimaly had been involved in a number of initiatives dedicated to literacy and education, and asked if education was a big part of his upbringing.

“All it took was a little light research about me online and she was able to connect with me on a topic that’s a big part of who I am as an individual,” he says. “Suddenly, she had made a connection with me at a very different level.”

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Find areas of the individual’s education, career or work history that can spark a similar personal connection that can lead to a longer-lasting relationship.

Step Four: Don’t be afraid to make an ask

At the start, you set a goal for what to get out of the interaction – including next steps. When individuals offer their time and energy to supporting you, they will be open for you making an ask for how they can help. Mr. Shimaly emphasizes that requesting a favour is not only acceptable, but encouraged, so long as it’s approached the right way.

“Mentors want to help – that’s why they’re investing their time with you,” he says. “Make sure to raise your ask at an appropriate time in your conversation, with the right context and acknowledge that you’re not taking it for granted. Chances are you’ll get the support you’re looking for.”

Dave Wilkin is a serial entrepreneur and founder of – an award winning virtual mentoring and career development technology.

This article supports Ten Thousand Coffees as part of national career month. In partnership with Canada’s major colleges and universities, Ten Thousand Coffees’ leading technology smart matches industry professionals to provide career mentoring and networking to students and recent grads. Ten Thousand Coffees is making virtual career conversations easy, find your school and sign-up for free today at

Stay ahead in your career. We have a weekly Careers newsletter to give you guidance and tips on career management, leadership, business education and more. Sign up today.

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