Welcome to the conversation guide. Let’s talk. This isn’t a massive framework you have to understand. This is just a human conversation.

We’re going to leverage the conversation process that led to a 10-point engagement lift at Google (we designed our approach and then found this article that perfectly aligned with what we found in our 230+ research conversations).

We’re about to talk about career very differently than the way most approach the subject. The cards are fun to use, but this is where we unlock insight. The cards serve the conversation. It’s a pretty straightforward framework:


Past • Future • Present


Two questions for each part of the framework serve as the core of the conversation:


  • Tell me a story about why this motivator is important in your career.
  • What has (or hasn’t) been fulfilling about that?


  • What future career opportunities would help you feel engaged, challenged, and loving life?
  • What details about future options are most appealing to you? (size of company, industry, role, etc.)


  • What action could we take immediately to help you make progress towards your desired future?
  • How could we increase your fulfillment in these motivators today?

After each of these answers to these questions if you believe there’s more depth to explore say “Tell me more …”

A few helpful primers for the conversation partner:

  • Be genuinely curious (especially about the past)
  • Remember that they may not be as far in their career as you
  • You don’t have to have all of the answers 

Advanced Questions

The above is all you need to have a rich conversation. The most common issue in coaching conversations is that the coach is actually giving advice, not coaching. 

When coaching is done well, the coach actually does very little talking most of the time. If you are not confident or experienced as a coach, we invite you to stick with the basic conversation guide above.

But a well-placed question can bring incredible insight. Those more comfortable with coaching may want to go deeper. If you have more experience coaching, use the below question list as a bank of questions to draw from to tailor your conversation. 


    • What does [word] mean to you?
    • When was the last time you felt/experienced [word]?
    • Why is that important to you?
    • What does [word] represent for you?
    • Can you say more about that?
    • What else?
    • What other ideas/thoughts/feelings do you have about [word]?


    • What is an example?
    • Like what?
    • What would it look like?


    • What other angles can you think of?
    • What’s just one more possibility?
    • What are your other options?
    • What part of the situation have you not explored yet?

    Evaluation/Levels of Satisfaction

    • Tell me a story of when you felt/experienced a lot of [word].
    • What about this job encourages/discourages [word]?
    • What does it feel like when you’re in?
    • How can you make the situation have more [word]?
    • What would the ideal situation look like?
    • What do you think that means?
    • What’s the opportunity/challenge here?
    • How might you know when you’ve reached it?


    • What led to [word] being important to you?
    • What have you tried so far?


    • What seems to be the trouble?
    • What seems to be the main obstacle?
    • What is stopping you?
    • What concerns you most about…?

    Finding Your Zone

    • What work do you do that doesn’t seem like work?
    • In your work, what produces the highest ratio of abundance and satisfaction to the amount of time spent?
    • What is your unique ability?


    • What are the possibilities?
    • If you had your choice, what would you do?
    • What are possible solutions?
    • What would happen if you do nothing?
    • What options can you create?


    • What will you think about this five years from now?
    • What would you want others to say about this?


    • What was surprising to you in all of this?
    • What have you learned about yourself?
    • What will you take away from this?
    • How would you pull all this together?

    Taking Action

    • What action will you take? And after that?
    • What will you do? When will you do it?
    • Where do you go from here?
    • What are your next steps? By when will those be completed?


    • What resources would you need?
    • What resources are already available to you?
    • What do you know about it now?
    • How do you suppose you could find out more?
    • What type of person/opportunity could I connect you with to help?


    • What support will you need to accomplish it?
    • How would you like me to follow up with you?
    • How often would you like to revisit this?
    • How should we revisit this?


    Other Tips

    • Please remember to listen more than you talk.
    • Frame the situation to help them feel comfortable.
    • Don’t be afraid to ask questions, but make sure to Listen
    • Try to avoid yes/no questions
    • Ask one question at a time
    • Signal when you’re close to the end
    • Wrap up with a broad question like “Given everything we’ve talked about, is there anything else on your mind?”