5 Questions to Ask Before Hiring a Career Coach

Making the decision to enlist a career coach is a serious move, and it shouldn’t be taken lightly. Some people might run to Google and conduct a few searches, read through a million coaching websites, and close their eyes hoping they selected the right coach by sheer luck. By the time that Friday afternoon discovery call rolls around, they can’t help but wonder, “Did I make a smart investment or a really expensive mistake?” 

It’s totally common to have second thoughts, but the last thing you want is to make a serious paid misstep that costs you both in time and money. You can, however, prevent both by doing your due diligence and asking the right questions before signing that contract and sending over that paid invoice to see if that coach truly is a good fit for you. In this post, we’ll review the top 5 questions prospective career clients fail to ask when vetting a career coach (and the major one that everyone seems to skip). 

What's your actual process, not just your philosophy?

Understand most coaches are not going to go into extensive detail when discussing their process(es); they will protect their proprietary methods. After all, that is their money-maker. But as a client, there are features about the coaching program you should know about prior to signing on the dotted line such as: program timeline/phases, the full client experience (what will each week be like for you), outcomes, and delivery method (in-person, group coaching, online, etc). Watch for flowery language that doesn’t indicate actionable results. A highly common phrase might sound like “We’re going to help you find clarity.” Uh, that’s a philosophy, not a process. 

You need to hear a coach state: what happens first, what happens in the middle, and what you should have by the end. Notice that this kind of answer highlights what you'll walk away with at each stage, not a breakdown of worksheets, assessments, or exercises. That's actually a good sign, not a red flag. Again, a coach protecting their specific tools and methodology is normal and often means they've invested real time building something proprietary; what matters is whether they can clearly describe the outcome of each phase, even if the how stays private. 

What does success actually look like, and how will we know we've gotten there?

When we think of success, the picture might vary from person to person. Success might mean a psychological (mindset shift), a physical outcome, or even a behavioral change. 

A career coach, for example, might help you “refine your interview skills,” but how are they quantifying your progress? Is it based on specific interview skill benchmarks like handling salary negotiation conversations, or your ability to secure a job with your new skillset? Coaches who lean too heavily on "you'll land the job" language can sometimes be overpromising, since ultimately the hiring decision isn't theirs to make. Just be wary of lofty promises that seem too good to be true. You want a coach who will be upfront about what success truly looks like within their coaching, and not just a blanket statement like, “You’ll feel better.” Will there be milestones you’ll accomplish at each session to indicate success, or will it be an outcome that occurs at the end? What will you be able to do, learn, or experience that will help you improve your current state, and how will you know it? 

What does the actual time commitment look like outside of our sessions?

Depending on your circumstances, you might be juggling a full plate right now. (I mean, who isn’t?) You could be a college student managing a heavy workload, a stay-at-home mom of 3 kids, or you’re managing a million obligations as a working adult. A great coach is upfront and honest about the time commitment required of you to get the most out of the coaching. Will there be homework or assignments that are expected to be completed in a certain timeframe or are you given flexibility? Can you schedule 1:1 meetings with your coach, and will they be willing to accommodate you if they know your schedule is tight? You don’t want to waste money on coaching only to find out you don’t have time to immerse yourself completely in the experience. 

What's the investment, and what is included?

It’s all comes down to the almighty dollar, right? Coaching is a huge investment and you want to make sure you’re not blind-sighted by hidden fees or an unfixed price. Any time you vet a coach, they should be transparent about the cost of the coaching and what it covers such as the number of sessions, materials, etc. If they’re not, it could signal a high-pressure sales process later (i.e. making you watch a million webinars or a long drawn-out “training” video). If you don’t get an actual figure by the time you hop on that discovery call, it might be time to look elsewhere. And once you do find out the cost, you need to figure out what options you have (especially if the price is more than what you anticipated). For example, are payment plans available, and if so, what type of installments? What forms of payment do they take? If the coach acts insulted by your questions, it may be time to move on, as it’s a basic part of any professional vetting process. 

What happens after our engagement ends?

When it’s all said and done and the coaching has commenced, you need to know if any hand-holding will be given after the fact. A coaching engagement has a defined endpoint, but your actual career transition doesn't always wrap up as neatly as the calendar suggests. Listen for whether the coach has a real answer here (not “we’ll see”). Is it a closing session that ties everything together, resources you keep using after the engagement ends, or an open door for questions down the road? If they’re vague or offer no plan at all, it can mean the relationship just abruptly stops right when you might still need a bit of support to carry a decision through. You don’t want to get caught off guard when the coaching is over, especially if you feel you need more time, resources, or guidance. 

Conclusion 

You have every right to ask the questions you need to make an informed buying decision. You want to ensure you’re getting your money’s worth, and fully immerse yourself into the coaching program. If you detect any pushback when asking questions, listen to your gut. You want to work with someone who respects you, and isn’t trying to take advantage of your wallet. 

Ready to Explore Your Options?

Choosing an executive transition advisor is a highly confidential decision especially when you are actively leading an organization. You cannot afford a public footprint, and you certainly don't want to step into a high-pressure sales pitch.

That is why my Free Discovery Call is a private, zero-pressure conversation designed to protect your privacy.

Together, we will evaluate if making a change is the right move for you at this stage, and if it is, we will discuss exactly what Life Design coaching is all about to see if it's a good fit for you.