Watch the webinar and scroll down for answers to the digital advocacy community’s top hiring questions.
QUESTION 1: What role does AI play in hiring?
Kate and Joe agreed: as exemplified in Shopify CEO Tobi Lütke’s memo to employees, AI is rapidly becoming a “tool of all trades” in the digital world – and it’s a critical tool that can complement (not replace!) human touch in both hiring and at work.
Kate’s take: hiring managers should ask about employees’ experience with AI as a means to streamline their own workflows, but shouldn’t worry about AI replacing jobs quite yet.
“I think leaders should be thinking about… how to make [AI] part of the requirements of a role. When it comes to the hiring piece and recruiting, there’s a lot of talk that recruiting will be replaced by AI. I am not fearful. There’s a lot of nuance that goes into our work… There’s a lot of understanding the message that needs to get across the audience who needs to receive it, and how to make sure those two pieces are connected. So I think that AI is not going to replace the nuance that goes into that.”
In short: AI can help kickstart tasks and streamline an employee’s bandwidth, but can’t drive decisions around talent.
QUESTION 2: How can you tell if someone is a “good hire?” Is there a silver bullet interview question?
It’s tempting to think there is a single way to determine a candidate is “the one,” but Kate recommends leveraging a mix of tools and interview questions to assess a candidate’s fit:
- The Knowledge/Skills/Abilities Rubric: This rubric allows you to dig in and assess candidates on three levels:
- Knowledge, or their understanding of the topic or industry they are working in
- Skills, or the technical skills needed to perform the job (i.e., do they have formal training or need to be trained)
- Abilities, or how someone works (flexibility, adaptability, etc.)
- “Silver Bullet” Interview Questions: The must-have questions Kate recommends to help mine the answers to the above rubric include:
- “Tell me about the best boss you’ve had and the worst boss you’ve had.” This question uncovers how a candidate prefers to be managed, their values and how they relate to authority.
- “Tell me about a time you made a major mistake at work.” This question tests a candidate’s self-awareness, accountability and ability to recover from setbacks.
- Tangential Skills: Are there qualities in the new hire that may not be a 1:1 match for the role, but could lend themselves to it? Kate referenced teachers as particularly strong digital hires: “People want to hire teachers because they can deal with a lot of things coming in, they’re good at learning, they’re good at communicating… we’ve hired a few teachers into digital roles that I know have grown immensely.”
QUESTION 3: What is “hiring trauma” and how do I overcome it?
You think you’ve found the perfect hire. Three weeks later, their desk is empty and you’re back to square one, more stressed and frustrated than before.
“Hiring trauma” is the hesitation and anxiety you get after a hiring decision goes wrong. Thankfully, there are tools to move through it and get back on the hiring horse, according to Kate:
- Rubrics: Relying on gut instinct alone when it comes to hiring can be tempting, but can lead you astray: “You might find someone who’s really charming, but they may be able to charm their way into a job that’s not the right fit.” In lieu of being wooed by a hire’s personality, stick to a clear rubric that multiple interviewers can use that can be cross-referenced later (for example, the Knowledge/Skills/Abilities rubric from Question 2).
- Behavioral Questions: Add questions such as “tell me about a time you had to learn something quickly” to get a temperature check for how a prospective hire would handle high-pressure situations.
- Tests: Include skills tests to evaluate a candidate’s capabilities objectively.
QUESTION 4: Should I hire someone trainable or trained?
The answer to this question depends on your team’s immediate needs and capacity, according to Joe and Kate.
Hire someone trained if:
- You urgently need a skill set your team lacks.
- You don’t have time to train someone deeply.
Hire someone trainable if:
- You have the bandwidth to invest in developing a new hire.
- You want to mold someone to your company’s culture and systems without bad habits from previous environments.
According to Kate, hiring a trainable person can bring long-term loyalty and culture fit, but it requires a realistic investment of time (potentially 25% or more of your schedule for the first 6–12 months of the hire’s tenure as they are onboarded to the team).
QUESTION 5: Is there truth behind generational differences in the workplace (e.g., Millennials vs Gen-Z)?
The consensus was clear: generational differences are real and managers need to adapt.
Gen-Z employees, shaped by the 2008 Recession and the COVID-19 pandemic, tend to be more risk-averse and crave security, financial growth and constant feedback. In contrast, millennials are motivated by mission-driven work, collaboration, and structured career development.
Kate offered key insights on how to motivate Gen-Z versus millennial employees:
Motivating Gen-Z Employees
- Feedback: Offer frequent, positive feedback alongside constructive criticism. Gen-Z employees thrive on “radical candor” and understanding what to do more of – not just what to stop.
- Prioritize Growth and Experiences: Give Gen-Z opportunities to explore different job functions, work on diverse projects and highlight clear paths to career advancement and financial security.
- Balance Independence with In-Person Opportunities: Allow independent work but also create chances for in-person experiences, and respect their preference for quieter, more private workspaces.
Motivating Millennial Employees
- Focus on Career Path: Offer clear growth plans and regular check-ins to help them envision their future within the organization.
- Encourage Collaboration: Create opportunities for teamwork and cross-functional projects, as millennials are energized by working with others.
- Offer Structured Feedback: They appreciate frequent (though not constant) feedback through formal check-ins like six-month or quarterly reviews.
Chart from Empower Strategies.
Understanding these subtle but important generational differences can help you better motivate, retain and grow your team.
Got a burning hiring question of your own? Email [email protected] and we’ll connect you with Kate or help your new hire become a digital advocacy pro.