What Questions Should I Ask a Potential Career Coach? 10 Questions That Separate the Real Deal from the Rest

This is the question almost nobody asks, and it's the most important one.

There's a huge difference between someone who has read a few books and got a coaching certification, and someone who actually spent years deciding who got hired and who didn't. A certificate says you completed a course. Experience inside the hiring process says you've seen how it really works.

But even within "recruiting experience," there's a distinction most buyers don't know to make:

• Talent acquisition (in-house recruiting) means you sat at a single employer and reviewed candidates who came inbound. Comparatively, it's the easier side of the desk. The candidates come to you.

• Agency recruiting means you had to win clients, approach employers, secure roles, and then find the candidates to fill them. You had to do outbound work, navigate gatekeepers, and persuade busy decision-makers to take a call.

That second skill set — the agency side — is the one that maps directly onto what a job seeker actually needs to do. Because if you want to land a role without relying on mass-applying through online portals, you need to approach employers directly. That's exactly what agency recruiters do every day.

A coach who's only been in talent acquisition can still be useful. But a coach who's worked agency-side has done the hardest version of the job, and that's the experience that translates.

The honest answer: any coach whose only qualification is "I decided I liked helping people with their CVs, so I got a coaching certification."

There is a difference between holding a piece of paper that says you can coach and actually having lived experience inside the hiring process. Coaching certifications are largely unregulated. Anyone can buy one. They tell you nothing about whether the person has ever sat in a room and decided whether to extend an offer to a candidate.

Look at the coach's background before the coaching. Were they a hiring manager? A recruiter? Did they run a recruitment business? Have they ever had to make a hiring decision that cost their company real money if they got it wrong?

If the answer is no — and their only credibility is a certification plus a few testimonials — that's where most of your money will go to waste.

Most coaches pitch themselves as doing "a bit of everything." Others go the opposite way and claim one single tactic is the silver bullet — usually whatever they personally lean on. Both are problems.

The truth is, modern job searching needs all of it. A polished CV alone won't get you hired. LinkedIn optimisation alone won't get you hired. Networking alone won't get you hired. Direct outreach alone — without the personal brand to back it up — won't get you hired either. The candidates who land roles fastest are running multiple pillars at once, in a way that compounds.

So the real question isn't "which one tactic do you use?" — it's "do you have a multi-pillar system, and what are the pillars you actually lead with?"

Ask directly:

"What does your full system cover — and within that, what are the things you do differently from other coaches?"

You're listening for two things:

1. Whether they've got a complete system. A coach who only fixes CVs, or only optimises LinkedIn, or only teaches networking is selling you a fraction of what you actually need. The pieces work together. Strip one out and the others underperform.

2. What their actual differentiators are. Every coach can write a CV. Every coach can tweak a LinkedIn profile. The pieces that genuinely separate coaches are the harder, less commoditised ones — direct outreach to decision-makers outside the ATS, and personal branding that builds credibility before you ever apply.

The way I think about it: CV, LinkedIn optimisation, and interview prep are the foundation. They have to be there. But on their own they're table stakes — they don't move the needle in a market this saturated. The real leverage sits in direct outreach (so you're not waiting in a queue of 800 applicants) and personal branding (so when decision-makers look you up, they immediately see someone worth talking to).

A weak coach will either dodge the question with vague language about "holistic support," or they'll oversell one tactic in isolation. A strong coach will tell you exactly what's in their system, what every piece is doing, and which pieces they consider their unique edge.

Don't ask the coach about their results. They'll only tell you the wins. That's not dishonest — it's just selling.

Do your own research instead. Go to LinkedIn. Look at the recommendations on the coach's profile. And don't just read for outcomes. Read for how the coaching was delivered.

Specifically, look for:

• Whether clients mention the coach was hands-on and personally involved

• Whether they describe consistent support, not just a few calls

• Whether the coach actually guided them through the process or handed over templates and left them to it

• Whether the coaching came from the coach themselves — or from a "team" of associates working under the brand

This last one matters more than people realise. A lot of coaches scale by hiring junior associates and putting their own face on the marketing. You sign up expecting the person you saw on YouTube, and you get assigned to someone else entirely. Read the recommendations carefully — if every review mentions a different name, that's your answer.

This is where buyers get burned most often. The pitch sounds great, the pricing sounds reasonable, and then they find out the "12-week programme" is four group calls and a Slack channel.

Ask specifically about:

• 1:1 vs group: Is the coaching genuinely one-to-one, or are you in a group with twenty other people fighting for airtime?

• Between-session support: Can you message the coach directly? Get Loom video feedback on your outreach drafts? Or are you stuck waiting for the next scheduled call?

• Programme length: Is it 4 weeks, 12 weeks, or open-ended?

• What happens if you don't land in the initial window: Do you get cut off, or does support continue?

The strongest structure is one-to-one support delivered through both scheduled calls and asynchronous channels — DMs, Loom videos, written feedback — with programme access of 6 to 12 months or longer.

One honest caveat: open-ended programmes can sometimes work against urgency. If you know you've got unlimited time, it's easier to procrastinate. So while extended access is a green flag, you also need to be honest with yourself about whether you'll do the work without a deadline.

The career coaching market spans £200 CV reviews to £15,000+ premium programmes. Price doesn't automatically signal quality, but it does usually signal what level of attention you're paying for.

Here's the maths that most buyers don't do:

If you earn £100,000+, spending 2–3% of your annual salary on a coach is a small bet relative to the upside. If you earn £150,000–£200,000+, even 2–5% is comfortably worth it if the coaching helps you land a role with a meaningful salary uplift. A coach that helps you negotiate an extra £20,000 has paid for themselves several times over — and that's before you compound that higher base across future roles.

The question isn't "is this coach cheap or expensive?" — it's "what am I actually getting for the price?"

When you compare a low-cost option against a premium 1:1 coach, ask specifically:

• How much actual 1:1 time do I get with you?

• How invested are you outside the calls?

• Do you review my documents and outreach? Send written or video feedback? Help me prep for specific interviews?

In my own programme, the calls are only one slice of what clients get. I'm reviewing CVs and outreach messages between sessions, recording feedback videos, asking questions to help them think through specific situations, and often working around the clock during their active interview stages. That's what justifies premium pricing — not the brand, not the certifications. The actual hours of attention.

If a coach can't articulate where the price comes from, that's a tell.

This one is more nuanced than most buyers assume.

The instinct is: "I'm in tech, so I need a tech career coach." That sounds logical. But it's often the wrong call.

Here's why. Many specialist coaches became specialists because they personally had success in one industry, then started teaching others how to replicate their journey. That works fine if you're in their exact niche — but the moment you sit slightly outside their lane, their advice starts to thin out, because their experience is one person's path.

A generalist coach with a proven system across industries and seniority levels can often be more useful than a specialist whose system is essentially their own career story.

The underlying hiring principles — how decision-makers actually evaluate candidates, what builds credibility, how to bypass ATS dependence, how to position rather than plead — these don't fundamentally change between sectors or countries. I've worked with people across multiple industries and multiple countries, and the structural principles hold.

But you do need to ask the question directly:

• Have you worked with people in my industry and at my level?

• What's your experience across markets, not just one?

• Does your system rely on principles that apply universally, or on specific tactics from your own career?

Geography matters too — make sure the time zones work for live calls, and that the coach understands the market you're operating in.

A coach who's worked across many sectors and levels and has built a system around the underlying principles?

Strong fit. A coach who's only ever hired in one specific industry and assumes their playbook works everywhere? Risky if you're outside their lane.

Pay attention to how the coach behaves during the discovery call. This is the most predictive moment of the whole buying process.

Watch for these patterns:

Won't share pricing without a call. Sometimes this is reasonable for high-touch premium offers. But if there's no public pricing whatsoever and the only way to get any sense of the cost is to get on a call, understand what that call really is — a sales conversation, not a free consult. Some coaches do this well and ethically; others use it to high-pressure people into decisions they wouldn't make if they'd had the numbers in advance.

Guarantees outcomes. Be very cautious of any coach who guarantees "you'll be hired in X days or your money back." Hiring decisions are made by employers — no coach can guarantee what an employer will do. My own tagline is get hired in 60 days or less, because it's what my framework has consistently delivered for thousands of people. But I would never guarantee it, because guaranteeing the actions of third parties is dishonest. If a coach offers a guarantee, read the small print carefully. If it sounds too good to be true, it usually is.

Uses manufactured urgency. "The price goes up tomorrow." "Only two spots left." "You need to decide today." Read the room. Some scarcity is real — coaches who are genuinely fully booked do have waiting lists, and prices do legitimately go up over time as demand increases. But fake urgency designed to push you into deciding before you've thought it through is a warning sign. A coach confident in their offer doesn't need to corner you.

The flip is this: a discovery call should feel like a two-way conversation where you are also assessing them. If you leave feeling pressured rather than informed, that's the signal.

A lot of coaching programmes look amazing in the sales pitch and fall apart the moment money has changed hands. Ask these questions upfront:

• How quickly can I start? Some coaches have weeks-long onboarding queues. If you're actively job searching, that matters.

• What materials and resources come with the programme? Templates, frameworks, scripts, training videos, community access — what's actually included beyond the live calls?

• What happens if you go on holiday or have an emergency? Is there asynchronous support to bridge the gap (DMs, video messages, written feedback), or does everything pause? Communication is the key here — life happens to everyone, but the coach should have a plan for it.

• Do I get to keep the materials? This is bigger than people realise. Some coaches revoke access to everything the moment your programme ends. In my own programme, the CV templates, outreach templates, Notion documents, and frameworks are yours to keep indefinitely. There's no cutoff. The materials are yours.

• Do I get access to call recordings? You're paying for the coaching — being able to revisit it later is reasonable to expect.

The cheapest coaching is the kind where you pay £5k, finish the programme, and lose access to everything you worked through. The most valuable is where the materials and frameworks live on — because you'll still be using them years later in your next role move.

After all of the above, here's the question that, for me, separates serious buyers from tyre-kickers:

"After I land my next role, can I continue using your tactics to keep building my career?"

Most candidates think about a career coach as a tool to solve their immediate problem — get the next job. But the strongest candidates are already thinking about what comes after the next role.

When someone asks me that question, two things become clear:

1. They're already operating from the assumption that the job search will succeed — which means they're going to do the work. Mindset is predictive.

2. They understand that personal branding, positioning, and authority don't stop mattering the moment they sign an offer letter. The same things that make you attractive to your next employer make you attractive to the one after that, to internal promotion panels, to recruiters who reach out unprompted, and eventually to your own clients if you ever go independent.

The job search is the trigger event. The career is what you're actually building.

If you ask a coach that question and they look confused — like the relationship is only meant to last until the offer comes in — that tells you what their coaching is really designed around. Get you hired, hand you off, move on to the next paying client.

If they have an actual answer — frameworks you can keep using, principles that apply long after the job search ends, a way of thinking about your career as an ongoing asset rather than a series of transactions — that's a different kind of coach.

You don't choose a career coach by reading their website or watching their best-performing video. You choose by asking the questions that force them to show you what they're actually made of.

The pattern across all 10 questions is the same: experience over credentials, specificity over vibes, structure over promises, and transparency over polish.

A coach with a genuine recruiting background, a complete multi-pillar system with clear differentiators, real one-to-one delivery, transparent pricing, no manufactured urgency, materials you keep, and a long-term view of your career is rare. But if you ask the right questions, you'll spot one quickly — and you'll spot the wrong fits even faster.

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