Your First Job: The Questions You Need To Ask During On-The-Job Training


Whether you’re starting a summer internship, a full-time job, or switching to a new role – chances are you’ll be job shadowing for your first few weeks.

This can be intimidating. You’re expected to adjust to a new set of expectations and absorb information within a short span of time. To add to this, the person training you may be moving onto another role, making this learning period especially crucial.

However, there’s no need to worry. To help you get the most out of your training and get a head start in your new role, here are some key questions to ask:

The practical questions

As you begin your training, asking these questions will help you master the day-to-day tasks and duties involved in the job.

“What is the best way to communicate with my manager, client contact, etc.? If email is preferred, does this person typically prefer detailed messages or high-level points?”

“After you’re gone, who is the best person to reach out to with questions? Are there specific folders, binders, or resources that you can point me to?”

“Are there any skills that you’ve found to be particularly important in this role?”

Getting their perspective

As you develop a more personal relationship with your trainer, you can ask these questions to gain valuable insight into their personal experience with the role or company.

“Was there anything that surprised you when you first started in this role?”

“What do you see as the most challenging aspect of this role? How would you define success in this role?”

“Do you see any opportunities for improvement in the way this organization conducts its business?”

As you start to acquire the foundational skills associated with the role, it’s time to understand the company’s expectations of you. This will help you set goals and identify areas of focus within your first few months.

“How will I be evaluated? Is it formal or informal, frequently or infrequently? Is it based on soft skills, specific metrics, or a combination of the two?”

“What do you view as the priority project in my first few months? Is there anything that can be pushed off until later?”

“How does this role fit within the goals of the immediate team, the department, and the company overall?”

As you train, make sure to keep these things in mind:

Regularly check in with your trainer to ensure that you’ve understood everything correctly, i.e. “I’d like to summarize what you just taught me, to make sure I captured all the details.” This demonstrates that you’re engaged and proactive.

Don’t ask questions for the sake of sounding intelligent – your trainer will quickly take notice of this. Ask questions when you’re genuinely curious or confused about something, and listen carefully to the response.

Be observant. If your trainer repeats something often, it’s probably important. Take quick notes at the end of the day to summarize the key points for that day. This will allow you to quickly jog your memory the next morning.

If the relationship allows for it, you can ask about the person who was previously in your role (if it was not the trainer themselves). Did this person get promoted or move to another part of the organization? This will give you a sense of the opportunities available for you.

Most importantly, thank the person for their help. Training requires preparation and patience, and consumes valuable time out of the person’s day. After training is complete, it’s a great idea to send an email or a handwritten note to thank your trainer for their time. This will leave them with a positive impression of you and a sense of accomplishment.

Do you have experience with on-the-job training, as either a trainer or a trainee? Do you have any additional tips that you’ve used? Tell us here!

About the author

Allison Tse is a marketing professional with three years of experience in the credit card industry. She currently works at CIBC, but started her career at American Express after graduating from the Queen’s Commerce program. Outside of work, Allison loves to cook and is currently pursuing a Culinary Arts Certificate at George Brown College in Toronto. Check out her profile on LinkedIn