The Good Hire Starts With Good Questions
October 6, 2026
Welcome to the very first edition of The Good Hire!
I’m Nicole Anderson, and I’ve spent 14+ years on both sides of the hiring table: recruiting and career coaching. I now lead Good Work Recruiting, a boutique recruiting agency focused on tech + SaaS hiring.
I started this newsletter for you: the person building a team. Whether you’re actively hiring for a team right now, a leader always open to learning new best practices, or even an aspiring leader building your toolbelt, you’re in the right place. I will share with you what I’ve learned, and I’d like to understand where hiring gets complicated for you.
In the first edition, you’ll learn three questions that help you confirm that your recruiter understands your business.
Let’s get to good work!
A recruiter can repeat your job description back to you, but still miss the person your team needs. Before you hand over a search, ask these three questions. The answers show you fast if they understand your business, so that you don’t waste weeks meeting candidates who aren’t a fit.
Three questions to ask your recruiter
1. “What would you need to learn about this team that isn’t in the job description?”
As much as we all try, we all know that a job description doesn’t tell a full story. It doesn’t say you’d like a scrappy hire because your product roadmap changes faster than you’d like to admit. It doesn’t describe how you’d really like a candidate to know HubSpot, but you might switch over to HubSpot later this year. The day-to-day of your role matters.
A Good Answer Sounds Like: Your recruiter says specific things they’d like to learn, like why the role is open now and how this person would spend a normal week.
If You Hear This, Keep Digging: If there isn’t anything else your recruiter wants to know about besides what’s in the job description, keep digging. Walk them through a typical week, or what the profiles of successful individuals previously in the role have looked like.
2. “How would you assess a candidate with a non-traditional background?”
Even if you have a specific candidate profile in mind, this question is essential. Many job seekers forget to include important skills on their resumes (as a career coach, I can definitely confirm this!). Their job title might say one thing, but their day-to-day was different. Finding alignment with your recruiter on how to assess candidates with non-traditional backgrounds will ensure that you’re on the same page and not weeding any candidates out too early.
A Good Answer Sounds Like: The recruiter has a plan to test the candidate’s stretch area before presenting them to you. For example, they would ask candidates about a specific past project, or situation similar to what the role faces. They also understand what is a must-have versus a nice-to-have in the role.
If You Hear This, Keep Digging: If the recruiter says they will stay very strict to the parameters of the job description, keep digging. Candidates don’t always fit in neat boxes, and a strong recruiter should be able to explain why an unconventional candidate deserves a conversation, or why they don’t, in plain terms you can respond to. Help the recruiter understand the difference between must-have versus nice-to-have.
3. “Based on our conversation, how would you describe the person we’re looking for, in your own words?”
This question does two jobs: you hear their version of the role while the search can still be corrected, and you find out if they truly listened or just took notes.
A Good Answer Sounds Like: A description that is more specific and narrative-sounding than the job description. In other words, the recruiter can tell you about the ideal hire using their own language. And is the recruiter speaking to both the technical needs of the role as well as the overall team and soft skills? Are they representing the role well? Even better, the recruiter can name a tension, like “you want someone senior, but this sounds hands-on.” That means they’re already thinking about the hire.
If You Hear This, Keep Digging: If the recruiter describes a role that doesn’t match what the person in this seat actually does, keep digging. Find out where the confusion is and confirm the right profile.
These questions help you listen for the right things when you start a search. As a boutique search firm, asking great questions is what I do.
How Good Work Recruiting Can Help
If you’re hiring for a role and ready to partner with a recruiter that asks good questions, I’d be glad to talk it through.
Based on my time recruiting in-house at tech and SaaS companies, I know how much a single hiring decision affects not only the people already doing the work, but the whole foundation of what the business is building.
When you work with Good Work Recruiting, I learn what the job is really like on your team, then share different candidate profiles early, so we sharpen the search together. I also spend time learning why each candidate in the process is motivated by your particular role, to ensure long-term fit.
What are you hiring for? What’s been hard to pin down? If anything comes to mind, we can talk through what you need and whether Good Work Recruiting is the right fit to help.