Stephen Chillura on the Questions Worth Asking Before Taking a Leadership Role
CHICAGO, IL / ACCESS Newswire / September 29, 2026 /Stephen Chillura has spent time in physically demanding work, including tree logging, before moving into roles that ask him to manage people instead of chainsaws. He says the shift from doing the work yourself to being responsible for how others do it is bigger than most people expect.
"People take the promotion because it looks like the next step, " he says. "They don 't always stop to ask if it 's the right step for them, or if they 're ready for what it actually asks of them. "
Chillura, based in Chicago, says he built his approach to leadership out of hands-on work, not out of a classroom. He treats the decision to lead the same way he treats any other decision that carries risk: with a short list of questions, asked honestly, before committing.
Question One: Do You Want the Responsibility or Just the Title
Chillura says the first question is the one people skip. A title can look like proof of progress. Responsibility is different. It means answering for other people 's mistakes, not just your own.
"If you want the title more than you want the job, that 's worth noticing now, " he says. "It gets a lot harder to notice once you 're three months in and the team is looking at you for answers. "
Question Two: Can You Say Hard Things to Someone 's Face
Chillura says leadership runs into trouble the moment someone avoids a hard conversation. He learned this doing physical work, where a mistake has an immediate, visible cost and there 's no room to soften it later.
"In a job like logging, you tell someone their technique is wrong because it 's dangerous if you don 't, " he says. "Office work doesn 't have that same immediate danger, so people let bad habits slide. A good leader still says something. "
He says anyone weighing a management role should ask themselves honestly whether they can deliver hard feedback without dressing it up so much it loses its point.
Question Three: Are You Willing to Do the Job Before You Ask Others To
Chillura says he distrusts leadership that starts with instructions instead of example. He says his own early experience, working alongside people rather than above them, shaped this view.
"I don 't think you get to ask someone to work hard if you 've never shown them what that looks like from you, " he says. "That 's not about doing their job for them. It 's about knowing what you 're asking. "
He tells people considering a leadership role to ask whether they 're prepared to put in visible effort, not just direct other people 's effort.
Question Four: What Happens to Your Standards When No One Is Watching
Chillura says this question separates people who are consistent from people who perform for an audience. He points to fishing and weightlifting, two things he does on his own time, as places where nobody is grading the outcome except him.
"There 's no one keeping score when you 're out fishing at five in the morning, " he says. "But the habits you keep when no one 's watching are the habits your team gets on a bad day. "
He says a leader whose standards drop without an audience will eventually let that show at work, even if it takes a while to surface.
Question Five: Are You Ready to Be Judged by the Team 's Results, Not Your Own
Chillura says the hardest adjustment in moving into management is accepting that your own output stops being the measure. The team 's output is.
"You can work harder than everyone on your team and still fail as a leader if the team doesn 't perform, " he says. "That 's a hard thing to sit with if you 've spent your career being judged on your own work. "
He says people who aren 't ready to accept that shift should think twice before stepping into the role, not because they can 't grow into it, but because going in without that awareness makes the adjustment harder than it needs to be.
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About Stephen Chillura
Stephen Chillura is based in Chicago, Illinois. He has experience in tree logging and agriculture, and has worked in leadership and management roles built on that hands-on foundation. Outside of work, he spends time weightlifting and fishing.
Contact:
Info@stephenchillurachicago.com
SOURCE: Stephen Chillura
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