I say this a lot, but it’s worth repeating:
The goal of an interview is not to get an offer.
And if you’re the one hiring: the goal isn’t just to fill a role.
The goal is fit. Alignment. Mutual clarity.
Sure, you need skills. But what really makes or breaks a hire is everything that happens outside the job description. Things like grit, resilience, comfort with ambiguity, and the ability to thrive under pressure. The willingness to ask hard questions. The courage to step into chaos and still bring clarity.
Which is why the best interview questions are the ones that surface those qualities. The ones that don’t just tick a box but help you figure out whether someone is going to be able to scale with the company. Whether they’re going to be an anchor or an accelerant.
So, this week’s newsletter is all about that. Better questions. Deeper signals. Clearer alignment.
For both sides of the table.
For Hiring Managers: Don’t Just Screen for Skills
Anyone can look great on paper. But a resume doesn’t tell you how someone will show up when priorities shift, when teams are lean, or when they’re owning a function for the first time without a ton of hand-holding.
At a high-growth company, that stuff matters more than a polished LinkedIn summary.
So how do you interview for that?
You start by getting curious. Ask questions that uncover mindset, resilience, and problem-solving. Here are some we like:
What’s a time you stepped into something totally new and figured it out as you went? What did that look like?
What you’re looking for: adaptability, initiative, and comfort with ambiguity.Talk to me about a time you failed or dropped the ball. What did you learn? How did you recover?
What you’re looking for: accountability, self-awareness, and growth mindset.When things get chaotic or priorities change rapidly, what anchors you? How do you stay focused?
What you’re looking for: self-regulation, focus, and ability to prioritize under pressure.What kind of management style helps you do your best work? What derails you?
What you’re looking for: alignment with your team’s leadership approach.If you're managing others, how do you balance clarity and autonomy? What do you expect from your own manager?
What you’re looking for: leadership maturity and expectations alignment.
If you're hiring for a role that’s still evolving (and let’s be real, most are), you need to know how someone reacts when the plan isn’t clear and the path forward requires initiative.
You also need to be honest about what it’s like to work at your company. Don’t just sell the dream. Talk about what’s messy. What’s hard. What kind of person struggles on your team, and what kind of person thrives.
Those conversations are what build trust. And trust is what sets the tone for the rest of the relationship. It’s where retention starts.
For Candidates: The Offer Isn’t the Goal. Clarity Is.
It’s easy to walk into an interview thinking, “I just need to impress.” That makes sense. The job market is rough, and rejection is personal. You want to feel chosen.
But here’s the real win. Walking away from an interview with a clear, honest picture of what you’d actually be stepping into. And whether or not that’s a fit for you.
Startups are messy. Roles evolve. Structure is often a work in progress. That doesn’t mean it’s a bad place to be. But it does mean you need to do your due diligence.
The interview isn’t just about being chosen. It’s about making an informed choice.
Ask better questions. Go beyond the surface-level stuff. Look for signals of how they operate under pressure, how they support their team, and how they’re thinking about growth.
Here are some questions to help you dig deeper:
How is the team handling growth right now, and what support will I have in place to be successful from day one?
What you’re looking for: realistic expectations, onboarding clarity, and how resourced the team is right now.If we’re having this conversation a year from now and it’s gone really well, what would you be thanking me for?
What you’re looking for: clarity on expectations, goals, and how success will be defined.Tell me about someone who thrived here…and someone who didn’t. What made the difference?
What you’re looking for: traits that align (or clash) with the company culture and pace.What’s still messy or evolving in this part of the business?
What you’re looking for: honesty, transparency, and your comfort level with those realities.What’s your leadership style, especially during high-stress times or when priorities change fast?
What you’re looking for: self-awareness, consistency, and compatibility with how you’re best managed.
And one of my favorite closing questions to ask at the end of an interview:
While we’re talking, do you have any concerns that I can address?
What you’re looking for: real-time feedback and how aligned their impression is with what you want to bring to the table.
Their answer (and their body language) will tell you a lot. And if they fumble or dodge? That’s a signal too.
The Bottom Line
The interview is the beginning of the working relationship. It sets the tone. It builds trust. Or it doesn’t.
Ask better questions. Be more honest. Think beyond just “can they do the job” and get curious about “will they thrive here.”
Because when you find someone who matches your stage of growth, your pace, your vision, and your values?
That’s when things take off.
See you next Monday,
Robin
#gorogue