I just started a job and don’t make much. My CEO wants me to invite all my coworkers for coffee. Do I have to pay?

Interested in more careers-related content? Check out our new weekly Work Life newsletter. Sent every Monday afternoon.
I just started at a new company and my CEO emailed me to suggest that I reach out and have coffee with everyone in the company to get to know them. There are about 20 people at the startup. I’m in my mid-20s and on the lower end of the pay scale. Because I reached out for coffee, am I supposed to pay or should I assume others will? How should I engage in these coffee chats to get the most out of them?
Jermaine L. Murray, talent recruiter and career coach, JupiterHR, Toronto
Before worrying about breaking the budget I think one important thing to highlight is that coffee chats aren’t always chats that happen over coffee. A lot of professionals use them as a catch-all and easier way to say informational interviews, these could take place over coffee, Zoom or even lunch. If there is some sort of expectation that you go out a few times, double-check with your CEO or even your direct manager to see if you could expense these.
When it comes to the actual conversation themselves, approach them with a genuine interest and curiosity about the person. Be curious about the job they do, their journey and what their opinions are on the company’s product/service. This can give you valuable insight into not only the company dynamics but also the industry you’re in as well at large.
Ask them what they would do if they could do their first 90 days over again and don’t be afraid to ask for advice on what your career goals and plans are as well. One thing I’ll also encourage you to do is focus on getting to know the person behind the job. People are more than their job titles and a good way to build relationships is to find out what your common interests are with them. This allows you to make a genuine connection and build rapport in a relationship. People are more willing to go to bat and mentor those they have a real friendship with.
Jennifer Houle, people and culture director, Raven Indigenous Capital Partners, Victoria
Your CEO’s suggestion to chat with everyone in the company is an excellent one. Taking some time to build the foundation of great working relationships is invaluable and should not be underestimated. To make the most of these chats, come prepared. Think about some questions you could ask that will give you insight into your new colleagues’ roles as well as what you might need to know in order to succeed in your own role, and use these conversations to understand how your roles will interact with each other. This approach will not only help you integrate into the team but also show your colleagues that you are proactive and genuinely interested in creating collaborative relationships.
As for the coffee part, you’re taking that suggestion too literally. Coffee is just a means to the result, which is getting to know your colleagues. Go for a walk, sit outside or hop on a Zoom if you’re remote/hybrid. And if your CEO insists that you actually go for coffee, that’s a business expense you should certainly be reimbursed for. Approaching your CEO about getting reimbursed for coffee expenses might feel awkward, especially as a new hire, but it’s a common and reasonable request. You could frame the conversation by emphasizing your enthusiasm for building relationships and contributing to the company culture. Mention that you want to ensure you’re following the appropriate procedures for business expenses. Most CEOs will appreciate your conscientiousness and commitment to team integration. Remember, it’s all part of establishing open communication and transparency right from the start, making each future “awkward” conversation that much easier.
Have a question for our experts? Send an email to [email protected] with ‘Nine to Five’ in the subject line. Emails without the correct subject line may not be answered.