How to Choose a Personal Trainer in Chicago (5 Questions Nobody Tells You to Ask)
- Darek Kowal
- Jul 13
- 6 min read
Most advice about choosing a personal trainer is written by personal trainers who want you to hire them. Which makes it useless.
The five questions below are ones I’d want to be asked. I’ve never seen a client ask more than one or two of them — usually because they don’t know they should. If you ask a trainer these five questions and their answers are vague, defensive, or scripted, you have your answer about the trainer.
I’ll walk through each one, tell you what a bad answer sounds like, and tell you what a real answer sounds like. Some of this makes me look good. That’s the point. But it also gives you actual criteria — not marketing language — for making a decision that costs you $500–$2,000 a month.
Get the free 8-week strength PDF → Click HERE!
The 5 questions:
“What does your programming look like week 1 to week 8?”
“What happens if I don’t see results?”
“Walk me through a typical first month for a beginner.”
“How do you handle it when my schedule blows up?”
“Have you ever turned someone away as a client? Why?”
Ask all five. If their answers are vague, defensive, or scripted, you have your answer about the trainer. Full breakdown below.
Why These Five (and not the 20 you’ll see in other lists)
The typical trainer-selection article has 15–20 questions: certifications, price, availability, specialties, schedule, etc. All of those are answered on any decent trainer’s website. You don’t need to ask.
The five below are the questions that separate someone with a business from someone with a job. Trainers who’ve been at this a while and take their work seriously have prepared, specific answers. Trainers who are winging it — even if they’ve been “winging it” for 10 years — don’t.
Question 1: “What does your programming look like week 1 to week 8?”
Why this matters: Real programming is progressive. You should do slightly different things in week 6 than you did in week 2 — the whole point is your body adapts, so the stimulus has to evolve. Trainers who don’t program long-term give you the same workout mix indefinitely and call it “keeping it fresh.”
Bad answer sounds like: “Every session is different.” “I mix it up based on how you’re feeling.” “It depends on you.” “I keep things fun.”
Good answer sounds like: “The first 2 weeks are movement quality and getting your baseline. Weeks 3–4 add volume — same moves, more sets. Weeks 5–6 shift to strength — heavier weight, lower reps. Weeks 7–8 are peak and test. Then we adjust for the next 8 weeks based on your data.”
The specifics matter less than whether they can give you specifics at all. If they can’t articulate a structure, they don’t have one.
Question 2: “What happens if I don’t see results?”
Why this matters: You’re paying $120+ a session. Some risk should be on the trainer’s side, not just yours. This question surfaces whether they’ve thought about accountability at all.
Bad answer sounds like: “You’ll see results if you do the work.” “It really comes down to nutrition.” “Consistency is everything.”
Notice the pattern — every one of those puts responsibility fully on you. Which isn’t entirely wrong, but it also isn’t a plan.
Good answer sounds like: “First, we’d talk about it at week 4 — if the numbers aren’t moving, something’s off in the plan. If nutrition is the gap, we address that specifically. If it’s programming, I adjust. If after 8 weeks with adjustments we still aren’t seeing what you wanted, we have an honest conversation about whether this is the right fit — I don’t want to keep taking your money if it isn’t working.”
Real trainers have an accountability structure. Sales-first trainers don’t, because accountability makes it harder to keep charging you.
Want To See What Real Programming Actually Looks Like?
Grab the free 8-week strength program I use with most beginner clients. Printable, progressive, with a training log so you can see the plan on paper before you buy it from anyone.
Question 3: “Walk me through a typical first month for a beginner.”
Why this matters: If they can describe a real client’s typical first month in detail, they’ve been through it dozens of times. If they can’t — or if the answer is generic — they haven’t.
Bad answer sounds like: “It depends on where you’re starting.” “We’d figure that out together.” “Every client is different.”
Good answer sounds like: “Week 1 is usually two sessions — I’m learning how you move, testing what weights are appropriate, and honestly, whether you actually like working out with me. Week 2 we start building the pattern. By week 3 most beginners have their first noticeable strength jump — usually 5–10 lbs added on their squat. Week 4 we take measurements or reassess movement. Nutrition comes up around week 2 or 3, depending on your goals. I don’t hit that on session 1 because you have enough to think about.”
Notice the good answer is a specific narrative, not a script. Specificity is the tell.
Question 4: “How do you handle it when my schedule blows up?”
Why this matters: Your schedule WILL blow up. You’ll travel for work. A kid will get sick. A friend will visit from out of town. Life happens. What separates trainers who last 6 months in your life from trainers who last 3 years is how they handle the chaos, not the calm.
Bad answer sounds like: “I have a strict 24-hour cancellation policy.” “You’ll need to be committed to see results.” Silence, then some version of “we’ll figure it out.”
Good answer sounds like: “I have a cancellation policy — 12 hours’ notice reschedules for free within the same week. Beyond that we talk. If you’re traveling a lot, we build a travel program you can run without me. If it’s temporary chaos, we drop from twice a week to once a week for a month. My goal is you keeping the habit — even reduced — not perfect attendance. Clients who stay 3+ years all had periods where life went sideways and we figured it out.”
You want a trainer who plans for the chaos. Not one who acts surprised by it.
Question 5: “Have you ever turned someone away as a client? Why?”
Why this matters: This is the tell that separates trainers who take their work seriously from trainers running a sales operation. A good trainer has turned people away — for schedule fit, for goal fit, for personality fit. A sales-first trainer has never turned anyone away because every warm body is revenue.
Bad answer sounds like: “Never — I work with anyone who’s committed.” “I try to find a way to work with everyone.” “Only if they can’t afford it.”
Good answer sounds like: “Yeah, probably 1 in 4 prospects I don’t take on. Most common reason is fit — they’re looking for someone who’ll push them too hard and I’m not that person. Sometimes it’s scheduling — they need a 7 AM slot and I’m full at that time. Sometimes it’s expectations — they want to lose 30 lbs in 8 weeks and I’d rather not sell them something impossible. Referrals go out either way. Point is, I’d rather have 15 clients I’m actually helping than 30 I’m taking money from.”
You want a trainer who has criteria. Not one who takes anyone with a credit card.
The Uncomfortable Truth About My Industry
You’re going to have coffee shops full of trainers in every neighborhood who can’t answer any of these five well. That’s not a criticism of them personally — it’s a reflection of how the industry is structured. Most gyms hire trainers, throw them at clients, and don’t teach them anything about programming, accountability, or client-fit criteria. They get better at selling packages, not better at coaching.
The trainers you want are usually independent, have been at it 5+ years, and can tell you specifically why they run their business the way they do. Ask the five questions above. You’ll know within 15 minutes whether you’ve found one.
Want To See How I Answer These Questions Myself?
Book a free 30-minute consult. Phone or Zoom. We’ll go through your goals, your history, and I’ll walk you through exactly how I’d build your program. If it’s not the right fit, I’ll tell you.
Or call/text: 219-484-1992
Serving South Loop, West Loop, Streeterville, Gold Coast, and more neighborhoods. Also offering Online Training.
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