3 Magic Questions: How to Avoid Being Salesy as a Career Professional

3 Magic Questions: How to Avoid Being Salesy as a Career Professional

How do you sell career services without being salesy, pushy or sleazy?

You’re in the middle of a great initial career conversation or discovery call. You’ve built rapport, the potential client feels heard and valued, and you know you have the expertise to support them.

Man conducting career consultation on phone

So many career counsellors, coaches and helping professionals transition from non-profit models into for-profit business. If you never talked about money with clients before, it can be challenging to talk about your fees. 

At our sister company, CareerCycles, each new client starts by having a free 15 to 30 minute career consultation. Over hundreds of conversations, 3 magic questions have emerged that help explain our narrative career counselling model in simple terms and work to convert potential clients into paid programs.

Magic Question #1

Multiple hot air balloons scattered across a blue sky

What possibilities are you considering?

This is an amplified version of “What led you to connect with us?”. Most people typically start with common questions like “Do you fix my resume? Do you get me a job? What tests do you use? How much does it cost? ”.

Our advice: don’t answer these right away. A phrase like “I will get to all your questions about process and fees in a moment, but first let me hear from you…” followed by our first Magic Question is key.

This allows the client to start with why they are calling, in a positive way. It’s not "what's wrong?”. Instead, it’s "what are you hoping for?”. They tell you a short story, and in return, they feel heard and know that you actually care.

Career Services Manager Jennifer Mackey conducts most of the discovery calls at CareerCycles. By beginning with this question first, instead of answering the logistics & process inquiries that most people start with, she begins building a relationship, and trust, in the first few minutes. “I’m telling the client: what matters most is you”, she explains.    

Pro tip: Be careful in asking additional questions like "What would you like about that possibility?" That’s too deep and detailed for a quick consultation. This also addresses common pitfalls, like giving away too much of your expertise for free, and spending too long in these fit meetings, overwhelming the client and your daily schedule.

Magic Question #2

Woman touching a lightbulb and surrounded by many other lightbulbs

What have you done so far?

Instead of “how did you find out about us” or “what’s your experience with career services to date”, this broader question takes into account that over half of Canadians don’t turn to career professionals for career help.

Here, this open-ended question leaves lots of room for stories about the steps they have taken, both formal and informal. This provides a sense of where they’ve been and where their mindset is. They may have talked to a friend or family member. Maybe they’ve decided they are fed up with job boards. They might have no possibilities in mind and feel stuck. It can also let you know - did they see a social media post, your website or did another client refer them?

Pro tip: The answer to this question is usually a goldmine for clues about what worked and what fell short, which lays the groundwork for our last magic question.

Magic Question #3

Two women seated in office One with hand raised to ask a question

What questions do you have about our process?

This last question gently changes the conversation to focus on your narrative approach, and, you guessed it, on the money. Here, you get to explain why your services are unique. You can insert your well-crafted value proposition here, or read on for two approaches that work.

At CareerCycles, they explain it this way: they help people make well-informed, proactive and empowered career and life choices. Using an innovative, consistent and inspiring framework that moves away from traditional tests and towards a more holistic approach, you gain clarity and explore with intention.

In my private practice as a Millennials Career Coach, I tell clients about our definition of career as a reflection of you are and how you want to show up in the world. I explain that holistic means that the context is you and your whole life, not just your job history and skill set. From the influence of others in your life to what might be on your Instagram feed, who you are right now matters. 

I advise that a narrative approach means that you tell stories and share your experiences with me. From that very personal lens, I help you get clear about what you want, then about how and when you can actually go after it. I also briefly explain how I use the Online Storyteller software to help deliver my services.

Jennifer typically then provides info about booking a first ‘roll-up-your-sleeves’ session at $87. If a client picks a package after this first session, CareerCycles credits the $87 back to the total package price. If this seems confusing to you, they frame it really well on their website. This package presentation works because they reassure new clients that even if they do only one meeting, the first session is super valuable and juicy. Then they make sure that first session is awesome for the client.

My process takes more time, but it works for me. I start asking about non-monetary resources like the time and effort someone has to devote to the process right now. I ask questions like “what room to do you have in your schedule for sessions and take home activities? You mentioned that you have x, y and z on the go. Do you have room in your life for a deep dive career development program?” Then I segway into asking what financial resources they have, and suggest a program that fits within their budget.

Pro Tip: This question is great because you get to learn what they have gleaned from your marketing, while also introducing your services as an answer to their question. This makes it feel natural and not like a sales pitch.

Your Magic Questions

Here at OneLifeTools, we write often about how to explain narrative career counselling and assessment in simple terms. We invite you to try these questions and let us know how it goes.

Woman blowing sparkling question marks into the air from her cupped hands

We’d love to add more approaches that work for you to this article, so that others in our Community of Practice feel more empowered to conduct excellent, timely and impactful career consultations that convert. Please reach out to us with your story by commenting below, or by emailing and we’ll call you to get details about your own magic questions.

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