54 goals conversation starters to spark deep conversations

Gurus: There’s a magic formula to setting and achieving goals! Just buy my book and course nowww.  

Reality: Goal-setting is a discovery process. It’s not linear where A + B + C = D. 

You set your goals through conversations with others and with yourself (reflection). 

You make progress on them by collaborating with others, asking for feedback and help, and even supporting others on their goals too.

In other words, your goals are NOT in a vacuum. 

Given how social the goal-setting process can be, I created these lists of goals conversation starters to help you:

• connect with others and support each other’s goals
• reflect on your goals, so that you get the clarity and confidence you need to achieve them. 

What makes me uniquely qualified to write about this? 

Over the last ten years — across three continents — I’ve started conversations with thousands of strangers. I’ve also interviewed well over 700 people for my projects (namely a street journalism project and a book). 

Speaking about my experience talking with strangers at TEDx! 

In other words, I’ve asked more questions to spark meaningful conversations than most people. 

And, goal-setting happens to be a topic that I’m intimately familiar with. I was an ambitious MOFO for the longest time, and I used to go all-out on my goals. 

While I helped my former business partner generate millions in revenue, I burned myself out many times over and even ended up in ER twice. 

These days, I’m still driven, but I work on my goals with more patience (OK, I try 🙂  

When and how to use these questions 

No hard rules per se, but here are a few suggestions:

• Ask one question at a time. Gauge their response before going deeper. If they seem disinterested in the topic, switch to something else instead.
• Balance between asking and talking. Make sure that you share your answer to the same question, or comment on their answer, so that the conversation doesn’t become an interrogation… I’ve been guilty of that.
• Most importantly, modify the questions and brainstorm new ones based on what sounds/feels most natural to you.
  
  Why is that important? Different people have different ways of saying things: the more you can tailor any conversation starter to your tone of voice, the easier you will find using it.
  
  To make this more usable for you, I’ve tried introducing variations of the same question 🙂

With that said, let’s jump in!

How to make small talk about goals 

1. What’s on your mind these days?
2. What’re you working on/building/creating now? 
3. Anything exciting/interesting/challenging you’re working on?
4. What goals are you trying to achieve these days?
5. How is your goal of <specific goal they want to accomplish> coming along? (if you know what goals they have)

As much as I’m an ambitious MOFO, I also recognize that not everyone is wired the same way. I’d recommend sussing out if they are goal-oriented by asking any of the first three questions first.

Related article: 77 career conversation starters for employees, bosses, networking professionals

Would you rather questions

1. Would you rather set goals or go with the flow? // Would you rather plan for the future or live in the moment?
2. Would you rather set big or realistic goals? 
3. Would you rather go fast or go slow to achieve your goals?
4. Would you rather achieve an impressive goal or a meaningful goal?
5. Would you rather achieve a career goal or a personal goal? 
6. Would you rather achieve your own goals or help others achieve theirs?

Why these questions?

These questions are great for social gatherings and parties: just the right amount of thought-provoking without being too serious. 

Deep questions to help them set goals 

1. What do you want to achieve before the week/month/year ends?
2. What do you want to achieve in the next 3/6/12 months? 
3. What do you want to achieve in the next 1/5/10 years? 
4. What are the biggest opportunities you want to create?
5. What will you say yes to? (credit: Shonda Rhimes – check out her inspiring TED talk) 
6. Who do you need to become?
7. Where do you need to be? // Where do you need to move to?
8. What skills do you need to learn? 
9. What mindsets do you need to have?
10. Who do you need to build/deepen relationships with?

Why these questions?

These are pragmatic questions that help someone plan out their short-term, mid-term, and long-term goals. They are best if the person has some idea of what they want to achieve. 

Questions to discover goals 

1. What’s the theme, word, picture etc. that will define your next year?
2. What will be the best use of your talents?
3. Who do you want to become?
4. How can you align with your purpose and values? 
5. If you had only one year to live, what would you do differently? What would you want to start doing/continue doing/stop doing?
6. If it was the last day of your life, would you want to do what you’re about to do? (Credit: Steve Jobs)
7. How could you accomplish your 10-year goal in 6 months? (This is a variation of Peter Thiel’s question)

Why these questions?

If the person is feeling lost in life, or simply needs to zoom out and look at the big picture, I ask at least a few of these questions to help them realign with who they really are.

Related article: 50 midlife crisis questions to spark deep conversations

Deep questions to help them prioritize their goals

1. What’s the one thing you can do, such that by doing it everything else is easier or unnecessary? (credit: Gary Keller, author of The One Thing)

Why this question: I’ve asked myself this question every day to focus on what I need to get done for the day/week/month, vs. being all over the place. 

2. If you could only work 2 hours per week on your business, what would you do? (Credit: Tim Ferriss)

Why this question: The time constraint might feel too extreme, but it truly forces you to prioritize the things that matter the most for your business/career success.

Questions to prioritize daily/weekly/monthly

To make sure that I’m on track with my goals, I like periodically asking variations of the #1 thing question. For example:

1. What’s your one professional goal today?
2. What’s your one personal goal today?
3. What’s your one professional goal this week?
4. What’s your one personal goal this week?
5. What’s your one professional goal this month?
6. What’s your one personal goal this month? 

Deep questions to help them achieve their goals 

Questions to overcome procrastination (fear of failure)

1. What are you putting off out of fear?
2. What are you waiting for?
3. What is it costing you—financially, emotionally, and physically—to postpone action?
4. If you don’t pursue those things that excite you, where will you be in one year, five years, and ten years?

Why these questions?

These questions came from Tim Ferriss’s fear-setting exercise. In his article, he explained the value of addressing one’s fears: 

“Usually, what we most fear doing is what we most need to do. That phone call, that conversation, whatever the action might be—it is fear of unknown outcomes that prevents us from doing what we need to do. Define the worst case, accept it, and do it. I’ll repeat something you might consider tattooing on your forehead: What we fear doing most is usually what we most need to do.“

Questions to identify obstacles/challenges

1. What might stop you from achieving this goal? What are the most likely challenges?
2. As you pursue your goal, what can go wrong? 
3. What is it in you that holds you back from achieving your goal? (credit: Dr. Gabriele Oettingen)
4. How can you overcome each of these challenges?
   

Why these questions?

While it’s common to do post-mortems and analyze why our efforts fail, it’s less common to do the reverse i.e. pre-mortems. 

A pre-mortem is about thinking through possible reasons why we might fail in the future. While this is less exciting than dreaming up goals, spotting your obstacles upfront helps increase your odds of success, according to motivation research.  

Deep questions to help them reevaluate goals 

1. Have you outgrown your goals?
2. Are your goals still aligned with who you are (your identity)?
3. Are your goals still aligned with your values?
4. If you were to start over again, would you still choose this goal? Why or why not?
5. If you hadn’t invested time/money into this goal, would you still pursue it?
6. What’s the cost of status quo vs. letting go?
7. What’s the opportunity cost of continuing to pursue this goal vs. this other goal?

Why these questions?

Our goals aren’t static: they change as we grow. While it’s important to stay focused, it’s also important to take an honest look at our goals, and see if they are still serving us.

Specifically, sunk cost — the time or money already invested into something — can make it hard to stop pursuing a goal.

Ignoring sunk cost, even if it’s for a moment, can help the other person assess things more objectively.

Deep questions to help them celebrate goals 

1. What’s the most important professional goal that you achieved? 
2. What’s the most important personal goal that you achieved? 
3. What’s the most important goal that you achieved in <specific area of life>?
4. What’s the professional accomplishment that you’re most proud of?
5. What’s the personal accomplishment that you’re most proud of?

To learn from the successes on a deeper level, you could ask them/yourself the following questions: 

1. What did you do to achieve it?
2. Who helped you achieve the goal? How?