Imagine joining a startup team where everyone is rowing in the same direction—except one person. They’re technically skilled but disengaged. They only do the bare minimum, avoid ambiguity, and rarely take initiative. Over time, that lack of drive slows down progress and pulls the entire team back.
This is a familiar scenario for many founders. As one of them once put it: “We simply can’t afford someone on the team who lacks the will to do the work.”
Why “Will” matters
In startups, competence and motivation are not interchangeable. A skilled hire without the will to push through uncertainty, take ownership, and go beyond the job description won’t last long. That’s why the “Skill vs. Will” matrix isn’t just useful for delegation—it’s equally powerful when applied to hiring. The challenge is spotting motivation early, before a new hire walks through the door.
Below, we’ll explore how to assess drive during interviews and how to use the first 90 days to confirm whether it’s genuine.
Interviewing for will
Early-stage startup interviews often focus on technical skills. That’s logical—but insufficient. Here’s how to go beyond skills and test for motivation:
- Look Beyond the Role Itself
– Consider how the role might evolve in 6–12 months (or even 18).
– Will it be independent or cross-functional?
– How much ambiguity or pressure will they face?
This helps you shape interview questions around real expectations, not just today’s job description. - Ask for Stories, Not Opinions
Generic questions bring generic answers. Instead, ask:
– “Tell me about a project you truly cared about. What did it take?”
– “Share an example of a cross-team project. What made it hard, and how did you handle it?”
– “Have you ever worked late to meet a deadline on a project you were passionate about? What kept you motivated?”
Look for patterns of ownership, adaptability, and initiative—not “hero” stories. - Watch for Authenticity
When candidates tell stories, dig deeper:
– What did they learn?
– How did they feel during the process?
– Would they approach it differently now?
Pay attention to their energy, body language, and sense of purpose. True motivation isn’t about charisma—it’s about genuine connection to their work.
Testing “Will” in the First 90 Days
Even a strong interview can be misleading. That’s why the probation period is not just for onboarding—it’s a testing ground for motivation.
- Give Autonomy Early
Assign tasks with minimal structure. The goal isn’t perfection—it’s to observe how they handle ambiguity and responsibility.
– Do they clarify expectations or wait passively?
– Do they bring forward ideas?
– When faced with obstacles, do they find a way forward? - Look for Follow-Through and Collaboration
Motivation shows in everyday behaviors:
– Do they keep commitments?
– Do they communicate proactively when timelines shift?
– Do they close loops without reminders?
Watch how they interact with teammates: Are they generous with knowledge? Dependable? Enjoyable to work with? - Prioritize Early, Honest Conversations
Don’t wait until the end of probation. Use 30- and 60-day check-ins to ask:
– What’s going well?
– What’s challenging?
– Where do they feel energized—or stuck?
Share your feedback early. If initiative seems low, raise it directly and set clear expectations.
Final thoughts
In a startup, every hire is a bet. You’re not just filling a position—you’re shaping the company’s trajectory. Skills may get the job done, but willpower fuels momentum.
By designing your hiring process and probation period to uncover initiative, ownership, and motivation, you minimize the risk of hiring someone who looks great on paper but stalls in practice.
