A "Start with Why" Approach to Coaching Career Exploration

"So what brings you in today?"

"Well, my advisor said you could help me figure out what I want to do with my life."

Does this sound familiar? If your mental response is anything like mine, it probably includes a bit of pressure, a pinch of stress, and a hearty dose of panic. For a long time, I struggled to come up with a way to really dive into this conversation. When I first started as a coach, I tried to give them what they were asking for. We'd look at a couple majors, browse some occupations on O*Net or a similar resource and make a couple recommendations. This approach wasn't terrible, but it was a little shallow. I really didn't do anything for the client that a google search couldn't. The student saw value in having some tools to use, but should those have been how we spent the coaching time? I don't think so. They could have easily been resources I sent them later to use, if they were relevant,.

With a little more experience under my belt, I started making a different mistake. I'd push back too hard against the students' desire to leave a 30-60 minute chat with their whole life figured out, spitting statistics at them about now often people change careers on average, how often people can functionally answer "what's your passion" or similar questions, and how many people even stay in a career field directly related to their major. While these points can take some of the pressure off, I may have inadvertently been sending the message that their problem didn't matter and that I couldn’t' help with it anyway.

So what's the balance? Well, I believe it starts with strategically setting expectations. Help the student to reframe the problem they're coming in with, how that problem might be solved, and what the role of a coach is in that process. This is pretty standard professional coaching protocol, but especially when working with college students in volume, it warrants regular reminders.

Many have seen Simon Sinek's first TED talk, "Start with Why" in which he discusses the concept of the "Golden Circle." He claims that most people think from the outside in: what do I do, how do I do it, and why do I do it? He even claims that not everyone can even get to the why. I believe this concept can be adapted to be an excellent way to frame expectations of career exploration, while adding one additional important question of "who."

When students come to you and want you to help them figure out "what they want to do with their lives," they are jumping directly to "What." However, they are rarely ready to go there. If they were, they would already have more clarity on the potential answers; they may still need some coaching, but the starting point would feel less like 'totally lost' and more like 'almost there'.

I suggest simply writing this visual (below) out, maybe on a white board or just on a sticky note. Explain that before you can know "what" you have to be comfortable with 'who, why, and how'. Who are you? Why do you work? How do you work? Ask the student how much of those 3 questions they feel they have really figured out. Avoid prescribing a starting place, let them decide what they should work on first. Odds are, they'll admit it's not the "what" yet, and they'll have just pivoted your coaching session to something way less nebulous and more actionable for both you and the client.

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Who

This question may not seem as powerful as "why" but it is more foundational. The first step for a student (or anyone) is becoming comfortable with 'self.' This means being able to identify preferences, personality traits, psychological thought patterns, and other features that are similar or different from the individual's peers. Self-awareness is where emotional intelligence begins and, by extension, meaningful self-efficacy and decision making.

Ideas

• Personality, Preference, or Interests Assessments (with the purpose of self-awareness, not a list of job recommendations)
• Have the client come up with examples of projects or work that has made them either frustrated or fulfilled, try to get to why that was the case
• Discuss what makes the individual different than their peers, including their background and experience up to this point

Why

"Why" is a profoundly deep question. It will continue to change and adapt over a person's life, but it is an important consideration in choosing a career rather than something you figure out after already starting that career. This might seem counterintuitive; the client may say "how can I know why I do something, if I don't even know what I do?" But the "why" doesn't serve the "what." This "why" can start more broad. Often a student will say "I don't know what I want to do, but I know I want to help people." They're starting to hit at the why, which is great. The hard thing about that statement is that practically all work helps people in some way, which means that "why" concept needs to be fleshed out more. A person's "why" should be something closer to a personal mission statement. Why do they want to make a difference in the first place? Why do they want to work at all; is work an ends or a means?

Ideas

• Ideate on what problems in the world drive the individual crazy
• Discuss what makes them feel especially proud or accomplished
• Workshop a personal mission statement

How

I tend to address this question as an expansion to "who". At this point, the student has an idea of who they are, but here is where we can start to pinpoint how they work well. How do they function in a team, and how do they leverage their unique talents and thought patterns to excel? Their high potential areas are how they're going to tackle their personal mission and how they're going to apply themselves in whatever roles they take on in the future. Focus on strengths (be it CliftonStrengths or just a regular idea of personal strengths) and role in a team. If you find that this overlaps with your strategy in the "who" question, then adapt it to work for you; you don't necessarily need to stick to this strict order. Just remember the Who>Why>How>What structure progresses from most abstract to most concrete.

Ideas

• Strengths or Skill inventories
• Teamwork or Leadership assessments or studies
• Discuss previous work they've done; what has made them successful or unsuccessful?

What

And, we've arrived. The big scary question for career coaches, "what should I do with my life?" Remember, your job is not to spit out the answer for anyone, not because it's bad pedagogy but because you actually can't do that well, no matter how much you've talked to the person. The client has to be the one to figure this out, but if you've had robust conversation around the above questions and the client is comfortable with them, they are naturally getting close to a "what" already, even if it's still fuzzy. From here, encourage them to try things: talk to people in various fields, volunteer, shadow, show up to events. This could finally be a good point to discuss a bit of chaos theory in careers: the idea that their first job or even career cluster might not be the one they retire from and that each opportunity leads to and reveals more opportunities.

Ideas

• Encourage informational interviews
• Try stuff, try stuff, try stuff
• Study actual job postings and descriptions for what seems exciting or "sounds like you"

Conclusion

Whether you're working with college students or clients already in their career, this structure should work for you in setting expectations on coaching career exploration. Your meetings may not start with a well-meaning advisor referral if you're not in higher ed, but plenty of them still likely begin with a high-pressure, possibly unrealistic expectation. Reframing that expectation well takes practice, and I'm still improving myself. However, it is worth the effort with every new student or client; it will establish trust and allow you to really get some good work done, rather than forced conversations that the client will perceive as not leading to much.

I make no claim that coaching around this structure is a totally novel idea. Great coaches and professionals have thought about all of these questions (not least of all Sinek, whose talk I have linked below). However, this is my personal perspective on it and how I apply it, primarily to setting expectations. I hope you find all or some of it helpful in your own practice, mentorship, or coaching, and, by all means, please share what you do differently or any other advice you have found helpful on setting expectations or navigating career exploration!

Start With Why Ted Talk - Simon Sinek

https://www.youtube.com/watch?v=u4ZoJKF_VuA&t=599s