Pass the Last Round

You can crush every question in a leadership interview. But what happens when compensation comes up?

Suddenly, the clarity disappears. Answers get vague. Expectations shift. And a candidate who sounded like a confident executive five minutes ago starts sounding unsure of what they want.

Here's the problem: How you handle a compensation conversation says a lot about how you lead.

You don't need an exact number. But you do need to demonstrate clarity, confidence, and the ability to navigate a difficult conversation.

In this episode of Pass the Last Round, Jason and Jeremy break down the compensation mistakes experienced leaders make, how to approach these conversations with recruiters and hiring teams, and why negotiating the right package starts with understanding your value.

The slides matter less than you think. The panel is watching something else entirely.

In this episode of Pass the Last Round, Thrively co-founders Jason Medley and Jeremy Schmidt unpack why the final presentation is one of the best ways to see what it would be like to work with a senior leader.

Jason and Jeremy explore what hiring teams can do to set up a fair, aligned room, and how candidates can show their thinking, state their assumptions and respond to tough questions, because that back and forth often tells a panel more than the content itself.

The takeaway: A great final presentation shouldn't feel like an exam. When both sides leave with a clearer picture of what working together would look like, it has done its job.

Confidence is expected in a leadership interview. But there’s a point where confidence can start to raise a different question: what would it actually be like to work with this person?

In this episode of Pass the Last Round, Thrively co-founders Jason Medley and Jeremy Schmidt unpack a real interview process involving an exceptionally strong senior-level candidate whose confidence in their own value started to create concerns around fit, collaboration, and how they might operate within the leadership team.

Jason and Jeremy explore the difference between confidence and arrogance, why curiosity can be one of the strongest signals of executive maturity, and how the way you talk about your accomplishments can shape how an interviewer sees you.

They also break down how senior leaders can tell stories that make their impact clear without turning every answer into the “I” show, and why asking questions before jumping to solutions can demonstrate stronger leadership than immediately having all the answers.

The takeaway: You don’t need less confidence. You need confidence paired with curiosity, self-awareness, and respect for the people already in the room.

Your experience should show that you know your value, not that you think you’re the only one bringing value to the table.

“Tell me about yourself” sounds like one of the easiest questions in an interview. For experienced leaders, it can be one of the easiest to get wrong.

Too often, candidates respond by walking through their career chronologically—essentially giving the interviewer a spoken version of their resume. But whether you’re asked “Tell me about yourself,” “Walk me through your background,” or simply “Tell me about your current role,” those opening moments are an opportunity to establish something much more important: what you’re about as a leader.

In this episode of Pass the Last Round, Thrively co-founders Jason Medley and Jeremy Schmidt break down how experienced leaders can create a clear, memorable narrative without sounding rehearsed or hijacking the question they were actually asked.

They introduce a simple framework:

What I’m about → What I’ve built → Why I’m here

You’ll hear how to weave that narrative naturally into an interview, why generic leadership language makes it harder to differentiate yourself, and how your first few answers can create momentum for the rest of the conversation.

Because when the interview is over and the hiring team is talking about you without you in the room, you don’t want them simply remembering where you’ve worked.

Your resume tells them where you’ve been. Your narrative tells them what you’re about.

You know you can do the job. But did the interview panel actually see it?

Being qualified for a leadership role and proving you're qualified in an interview are two very different skills.

In the first episode of Pass the Last Round, Thrively co-founders Jason Medley and Jeremy Schmidt unpack one of the most common problems they see with experienced leaders: assuming their experience will speak for itself.

Why do accomplished leaders sometimes struggle to give specific examples? How can talking too much in “we” make your own leadership harder to see? And what does a hiring manager really mean when they say, “I couldn't get enough specifics”?

Jason and Jeremy break down what they're hearing inside real hiring processes and share a practical way to prepare for leadership interviews without memorizing answers or sounding rehearsed.

The takeaway: Your resume got you into the room. Once you're there, don't make the interview panel connect the dots. Make your leadership visible.