Finding the right career coach is a lot like finding the right gym or personal trainer. The fit matters for your unique challenges. You don’t just want someone with credentials…
You want someone who actually:
- Gets where you’re coming from
- Understands where you’re trying to go
- Knows how to help you get there
(without a bunch of fluff is a nice bonus.)
Here in Chicago, there’s no shortage of people calling themselves career coaches.
The trick is figuring out who’s the real deal for you. The person who can help you make confident moves, keep you accountable, and remind you of what you’re capable of when you forget.
Here’s how to find a career coach in Chicago who can help you make it happen.
Understanding the Role of a Career Coach
Before you start looking for one, it helps to know what a career coach actually does.
These coaches aren’t just resume fixers or job search cheerleaders. A great coach is someone who can help you get clear on your goals, build a plan that fits your life, and keep you moving forward when motivation dips.
What is a Career Coach?
Think of a career coach as your personal guide through the messy, confusing, and sometimes frustrating world of work. They’re not there to hand you a magic answer. They’re there to help you figure out the right moves for your career, especially if you are considering a career change. you.
That could mean:
- Figuring out your next career step
- Prepping for big interviews
- Building confidence
- Unsticking your career direction
How a Career Coach Can Help You
A good coach doesn’t just give advice and send you on your way; they help you understand that career coaching is an investment in your future.
They listen.
They ask the right questions to help clarify your career aspirations, which is a key aspect of a traditional career coach.
They help you see patterns and blind spots you didn’t even know you had.
And they’ll give you strategies that actually fit your personality, skills, and goals. Instead of cookie-cutter tips you could’ve found in a quick Google search yourself.
Benefits of Hiring a Certified Career Coach
While not every great coach is certified, hiring someone with a recognized certification can give you peace of mind that they’ve invested in their training and follow a professional code of ethics.
Plus, certified coaches usually have access to tools, resources, and proven frameworks
That makes your sessions more effective, but it’s important to note that the sessions will usually be more expensive.
Identifying Your Needs and Goals
Before you can choose the right career coach, you’ve got to be clear on what you actually need help with.
Career coaching isn’t one-size-fits-all. Someone looking to switch industries is going to need a totally different approach than someone aiming for a leadership role, which is why it’s important to choose someone who is really good at doing one specific type of coaching.
Think about it, you want someone who is okay in everything, or you want a world-class specialist for your needs?
When you take the time to get specific about your needs, you’ll save yourself a lot of trial and error (and probably a lot of money, time, and frustration too).
Assessing Your Skill Set
Start by taking inventory of what you’re already good at. It’s tough but try to be honest.
This isn’t just about hard skills like coding, sales, or design. It’s also about the softer stuff: communication, leadership, problem-solving, creativity. Ask yourself these questions:
- What skills do people often compliment me on?
- Where do I consistently get stuck or feel less confident in my pursuit of career goals?
This self-awareness will help you (and your future coach) figure out whether you need to sharpen certain skills, expand your toolkit, or focus on using what you already have more effectively.
Defining Your Career Path
Not everyone has a crystal-clear vision of their “dream job,” and that’s fine; career coaching helps clarify those aspirations. Really.
But you should have at least a direction.
- Do you want to stay in your current industry and move up?
- Explore a completely different field?
- Or maybe start your own business?
Even a rough outline of your ideal career path will make it easier for a coach to guide you toward the right steps instead of chasing random opportunities that don’t align with your long-term goals.
Determining Your Goals for Career Coaching
This is where you get really specific.
What do you want to walk away with after working with a career coach? It could be:
- Landing a new role within six months
- Building confidence for high-stakes presentations
- Creating a strategic plan to transition into a new industry can be easier with the help of career counselors.
The more measurable and clear your goals are, the easier it will be for your coach to build a game plan that actually works – and the easier it will be for you to track your progress along the way.
(so you don’t get stuck and notice after you spend a lot of money and time.)
You can thank us later!
How to Find a Career Coach
Before you hire anyone, slow down and get methodical.
You’re not shopping for a motivational quote. You’re choosing a partner who’ll shorten your path, cut noise, and keep you accountable. Here’s how to do it right.
Where to Look for a Good Career Coach
Don’t rely on random people who claim to be pro coaches. Go where the signal is stronger:
- Google My Business profile is one of the best ways to find coaches near you. You can see their reviews, they are close to you, you can call them right away, and they gotta be good when they’re #1 in Google.
- Referrals can lead you to the best quality career coaching services available in the job market, especially from senior leaders. Ask 3–5 people you respect (manager, mentor, top-performing peers). Ask them with specifics: “Who helped you land X role / make Y transition?”
- Alumni networks: Your university’s alumni portal or LinkedIn alumni page → filter by “Career Coach,” “Executive Coach,” “Leadership Coach”.
- LinkedIn content search can be a valuable tool for finding potential clients in your industry. Find coaches who publish useful, original frameworks (not platitudes). Save posts; note whose advice you’d actually use.
- Leadership/exec: ICF, EMCC certified coaches can help experienced professionals navigate their career paths.
- Tech/product: Reforge communities, product-led groups
- Early-career/pivots: university career centers, community orgs
Niche directories can help you find the right coach for your career coaching needs.
- Podcasts/newsletters/events: Coaches who teach publicly tend to have clearer methods. Shortlist those whose ideas feel practical, not fluffy.
Not sure how to spot the right one?
We’ll take a look at that in the next section, but for now, you can stick with these red flags:
Red flags when looking for a career coach include not finding someone who offers effective career counseling.
- Only testimonials, no process.
- Guarantees that sound like ads (“6-figure job in 30 days”).
- Vague “mindset” claims with zero structure.
- Endless upsells can deter clients who don’t have clear career goals.
How to Choose a Career Coach Based on Your Needs
Not all career coaches do the same thing. The “right” one for you depends on where you are in your career and what you want to accomplish. Here’s how to narrow it down.
1. Job Search or Career Transition
If you’re actively hunting for your next role, you’ll want a coach who focuses on:
- Resume + LinkedIn revamp that actually gets callbacks
- Portfolio polishing if your work needs to be showcased
- Targeted outreach strategy so you’re not applying blind
- Interview prep + mock interviews until you can answer questions in your sleep
What to ask:
- “What’s your go-to campaign structure for job seekers?”
- “What’s the typical time-to-offer you see for clients like me?”
2. Leadership & Executive Growth
If you’re aiming for senior leadership, director, or C-suite roles, you’ll need a coach who can help with:
- Executive communication & influence so you can lead at a higher level
- Stakeholder mapping to know exactly who matters and how to work with them
- Decision-making frameworks for high-pressure calls
- Team structure & org strategy to manage at scale
What to ask:
- “Do you run a diagnostic in week 1 to identify my biggest growth areas?”
- “How will you measure my behavior change over time?”
3. Career Change or Pivot
Switching industries or roles? Look for a coach who guides you through:
- Skills audit to see what transfers to your new field
- Crafting a transferable story that makes hiring managers buy in
- Market testing so you don’t commit blindly
- Low-risk experiments to validate your new direction
What to ask:
- “Can you map out a 30–60–90 day plan to test a new lane before I commit?”
4. Performance & Confidence Boost
If you’re staying in your current role but want to level up:
- Real-time feedback integration is essential when working with someone in a career coaching relationship.to fix mistakes quickly
- Stress management routines so you perform under pressure
- Presentation & negotiation coaching to stand out in high-stakes moments
What to ask:
- “What’s the cadence for practice sessions?”
- “Do you run mock talks and role plays regularly?”
5. Entrepreneurial Path
If you’re starting or growing your own business, you’ll want help with:
- Offer design & positioning so your services sell themselves
- Building a client pipeline that brings consistent leads
- Pricing strategy to protect margins
- Sales skills to close deals confidently
What to ask:
- “What specific services do you offer for founders?”
- “What metrics do you track, like calls booked, close rate, or revenue growth?”
This way, instead of guessing, you’re matching the coach’s specialty to exactly what you need right now and asking questions that tell you if they can deliver.
Utilizing LinkedIn to Find a Career Coach
Treat LinkedIn like a search engine + portfolio site.
Search & filters (start here):
- Queries: (“career coach” OR “executive coach” OR “leadership coach”) AND (Chicago OR remote)
- Filters: People → Locations (Greater Chicago Area), Industry (your target), Languages (if relevant), Services (Career Coaching).
- Content tab: sort by “Recent.” You want coaches posting original playbooks (mock interview drills, outreach templates, and stakeholder maps) can be found in a career coach directory to assist you.
Profile signals of a strong coach:
- Clear niche (e.g., “Tech PM to PMM pivots,” “IC-to-Manager transitions”).
- Proof: client outcomes (“4 offers in 8 weeks,” “$28k comp lift”), without doxxing.
- Artifacts: Resume/portfolio before → after, case studies, frameworks (e.g., “5-step value map,” “Offer Negotiation Ladder”).
- References: named recommendations that mention processNot just “nice to work with,” but a coach who truly understands your career transition.
Outreach template (you can steal this):
Hey [Name],
I’m in [current role/industry] and aiming for [goal] within [timeline]. I liked your post on [specific]. Could we do a 15-min fit call? I’d love to understand your week-by-week process, typical timelines to results, and what you’d recommend for someone with [X constraints].
Thanks!
No coach will say no to that, literally none.
What to ask on the call (LinkedIn-sourced coaches):
- “Which 3 constraints slow clients like me down, and how do you remove them?”
- “Show me your interview prep cadence (resources + drills).”
- “If we started Monday, what would the first 2 weeks be critical for those seeking career coaching. look like?”
- “What’s your offer negotiation? What is your approach to coaching people in their professional careers? Any recent wins?”
Decision rule (keep it simple):
Here are two rules to follow with all coaches:
- If they can’t outline a clear plan for career advancement, then they might need a coach who specializes in that area. repeatable process, show real artifacts, or define clear checkpoints → keep looking.
- If you hang up with a career coach, you may discover new strategies to enhance your career transition. timeline, milestones, and homework → you’ve likely found the right fit.
Evaluating Potential Career Coaches
Once you’ve got a shortlist, it’s time to separate the “great on paper” from the “actually delivers results.”
This is the vetting stage, the place where you dig into their methods, track record, and client outcomes. Think of it like interviewing someone for a high-stakes role on your team, because that’s exactly what you’re doing.
Questions to Ask a Career Coach
Skip the generic “What’s your style?” and get into specifics that force them to reveal how they actually work. Some high-impact questions:
- “What’s your week-by-week process for someone in my situation?” Forces them to explain structure and milestones in their professional career coaching approach.
- “What deliverables will I have by the end of month one?” You want tangible outputs — not just “insights.”
- “What are the top 2–3 roadblocks you see for someone with my background, and how do we tackle them?”Shows if they’ve really listened to you.
- “What’s the most common reason a client doesn’t get results and how do you prevent that?” Good coaches will be honest about risks.
- “How do you measure success?” Look for concrete metrics (offers, promotions, salary increases, confidence in presenting, etc.).
The right coach will answer without fluff, can give examples from past clients, and will adapt their plan as you talk.
Checking Credentials and Experience
A fancy certification doesn’t guarantee results, but it does show they’ve invested in their craft. Here’s what matters:
- Relevant certifications: ICF (International Coaching Federation), CPCC (Certified Professional Co-Active Coach), PCC/MCC levels for experience depth.
- Industry expertise: Have they worked in or coached within an executive level environment? your industry? Industry fluency means they can shortcut your learning curve.
- Track record: Years coaching is less important than results achieved — e.g., “Helped 40+ mid-level marketers move into director roles within 6–9 months,” showcasing the effectiveness of a professional career coach.
- Background fit: It’s crucial to assess if your background aligns with the career goals you’re pursuing. Ex-recruiters, hiring managers, or execs often bring insider hiring insights.
Pro tip: Don’t just accept “10 years experience”. Ask how many clients they’ve worked with in the last year, and how many had similar goals to yours.
Reading Reviews and Testimonials
Reviews are only useful if you read them critically. Here’s how to vet them:
- Look for specifics: “She helped me land a job in 10 weeks by overhauling my LinkedIn profile and networking strategy” is gold. “She’s amazing!” is meaningless.
- Seek patterns: If 5 different clients mention “clear structure” or “pushed me outside my comfort zone,” you know that’s a core part of their style.
- Check multiple sources: Google reviews, LinkedIn recommendations, industry forums, alumni boards. Consistency across platforms is a good sign when working with one to achieve your career transition.
- Watch for red flags: Lots of praise but no specifics, outdated reviews (nothing in the last year), or reviews that feel copy-pasted.
If possible, ask the coach for 1–2 past clients you can speak to directly. A good coach won’t hesitate and those conversations will tell you more than any testimonial on their site.
Taking the Next Step in Your Career Journey
Once you’ve chosen your career coach, it’s time to hire a career coach and move from research mode into action mode.
This is where you start showing up, doing the work, and building momentum toward the career goals you want. The first few weeks set the tone, so the more prepared and engaged you are, the more you’ll get out of each session.
What to Expect from Career Coaching Sessions
A great coaching program isn’t just “talking about your goals”.
It’s structured, targeted, and progress-driven, especially for those seeking a new career. While every coach has their own process, you can typically expect:
- Goal-setting and clarity work: Defining exactly what success looks like for you.
- Deep dives into your skills and positioning: Identifying strengths, gaps, and unique selling points.
- Action planning: Breaking big objectives into manageable weekly steps.
- Accountability: Regular check-ins so you don’t stall or drift.
Sessions should feel collaborative, not like a lecture. You bring the raw material (your story, your experiences), and your career coach helps shape it into a strategy you can execute.
Setting Milestones for Your Career Development
Milestones are your built-in checkpoints to measure progress. Without them, it’s easy to drift or feel like nothing’s changing. Your coach will help you set:
- Short-term wins: Updating your resume, completing a LinkedIn overhaul, securing your first networking coffee.
- Medium-term goals: Landing interviews, building a personal brand presence, expanding your industry network.
- Long-term outcomes: Job offers, promotions, career pivots, or even launching your own business.
The point isn’t just to tick boxes. It’s to keep building momentum in your mid-career, so each win fuels the next.
Continuing Your Growth Beyond Coaching
A coaching engagement eventually wraps up but the growth shouldn’t stop there. Your coach’s role is to give you tools you can keep using long after the sessions end.
To keep your career moving forward:
- Keep refining your goals to enhance your work-life balance: As your career evolves, so should your strategy.
- Stay visible in your industry: Keep networking, posting, and attending events.
- Track your wins: Document your achievements so you’re always ready for performance reviews or new opportunities.
- Seek feedback regularly: Don’t wait until you’re stuck, small course corrections keep you on track.
Think of coaching as the launchpad. The real flight is everything you do after.
Get the Best Career Coach in Chicago & Dominate Your Career
If you’re ready to stop guessing your next move and actually start building the career you want, working with the right coach changes everything. We help professionals all over Chicago cut through the noise, create a clear game plan, and take confident steps toward their goals, whether that’s:
- A promotion
- A complete career change
- Finally starting that business you’ve been dreaming about
You don’t have to figure it all out alone.
With the right strategy, accountability, and expert guidance, you can fast-track your growth and avoid the trial-and-error that slows most people down. Your career deserves more than “hoping for the best.” It’s time to take control, get clear on what you want, and dominate your next career.
Book your consultation today and let’s build the career you’ve been chasing.