The Hardest Job
- Heather Tenuto
- Jan 20
- 2 min read

My favorite interview question:
“What’s the hardest job you've ever had? “
If you are looking for resilience, this is the question.
Cahal Grennan, a great sales leader, asked me this years ago, and I’ve never stopped using it.
The question usually gets met with a question, “What do you mean by “hard?”
“I will leave it to your interpretation. So, what is the hardest job you ever had?”
Everyone is resilient in some way. How someone answers this question can tell you so much about their resilience.
Some people will tell you about working for a difficult boss; “She micromanaged me.”
Some people tell you about being bored out of their minds, “I just had to sit there all day.”
Others will detail hard labor. I told Cahal that my hardest job was washing pots at a camp. He told me about digging ditches.
The key is the follow-up questions. Ask for details. Were the scenarios really challenging? Might they encounter similar obstacles in the job they are vying for? And most importantly, how did they handle it? Did they power through because the experience was important? Did they find a way to make it easier? Did they quit? What did they learn about themselves as they navigated the role?
As a hiring manager, it’s essential to understand what will be challenging about the job you are trying to fill because you need to find someone who can dig in and push through when it gets tough. Will the job be physically taxing? Will it be tedious at times? Will they need to work with managers who prefer more oversight?
You want evidence that your candidate has been through this type of difficulty and found a way to prosper because you might need them to do it again.
In my experience, grit is very valuable and difficult to find, especially if you don’t ask the right questions.




Comments