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Exploring the Intersection of Software Development, AI Innovation, and Entrepreneurial Success | 1 on 1 and how to ask deeper questions

1 on 1 and how to ask deeper questions

It can be tough to come up with genuinely open questions on the spot. The best open questions prompt deep introspection and reflection; it can be stressful to hone this skill in real-time. Human learning and growth require four things: new challenges, low ego, space to reflect and brainstorm, and timely and clear feedback. How are these four going for you? Is there one you need more or less of? So much pressure! I recommend creating a handy list of open questions you can ask in your one-on-one meetings. Here are some options to help you start this list.

1 on 1 and how to ask deeper questions

Hey, manager! I’m guessing you already know that when mentoring, coaching, or managing someone, you must bring lots of curiosity when talking with them. This often looks like asking open questions and actively listening as the other person responds. 

Learning agility

They are experimenting with new tactics, approaching new situations with a growth mindset, seeking and learning from feedback, and applying these lessons in real time to new situations. The principle is that leaders need to be learners even in the most challenging circumstances. It is difficult to overestimate how important this is: One meta-analysis of dozens of empirical studies found that adaptability and learning agility were the top predictors of a leader’s performance and potential.

You can build this muscle by, for example, setting your intention each day for how you want to show up for challenging situations. This may sound like: “Instead of trying to have an answer ready for all difficult, unexpected challenges today, I will approach them with curiosity and an open mind, inviting multiple perspectives.” Doing this helps you remain open to feedback, learn, and adjust your response that otherwise may have been an unhelpful default reaction.

If you have a sense that you’ve triggered them, but it’s not clear: 

Get specific and balanced: “What are 1 or 2 things you would change about this?  What 1 or 2 things would you keep just as it is?”    


    1. Make room for optimizing: “If we could improve this by 10% for you/ your team, what would we do first?”
    2. Confirm your concern: “I am concerned that ______ has been hard on you/your team. Am I off on this guess?” 
    3. Address confusion: “What do you wish you had more direction/clarification from me about?” and “What three things can we do this week to create more clarity?”
    4. Confirm your hypothesis: “I wondered if this idea/change/decision pushed up against some key things you/your team cares about. For example, your sense of autonomy [or fill in what you think]  -- but perhaps it was something else that this messed with. What do you think?”  


  • Make room for emotions: “I would have been upset by this. How was this for you?”


  1. Share the wheel: “If you/ your team would have been in charge of this project/decision, what are 1 or 2 things that you would have tried differently.”
  2. Make it safe to critique:  “You’re a person who has a good sense of how folks are taking this -- what do you think people like and dislike about this so far?”
  3. Check your blindspots: “We’re thinking about doing ____________, but I wanted to get your take on it. What do you think could go wrong? What do you think might be good about it?” 
  4. Do a pre-check: “If ____ happens, how would that impact you/ your team?”
  5. Plan: “I’m taking stock of the year/ quarter: What’s one thing I/ my team could do to make things easier for you?”   

If the person shows you they’re upset: 

  1. Make room for context: “It would help me to understand what feels most upsetting about this?”
  2. Clarify:  If they give you a vague phrase, such as “feels wrong” or “seems off-brand”, encourage them with “Say more about that - what makes it feel ___________.”
  3. Look for Bright Spots: “Ok, I hear that it didn’t work well when X, Y, Z happened. When do you feel it worked well?”  or “When does this not happen?”
  4. In your shoes: “If you were me, what would you do next about this?”
  5. Collaborate: “I would like to find a solution together on this -- but I likely need your help -- what could both of our teams do to make it substantially better by Q2?”
  6. Bridge both goals: “What are a few ways we could ______________ while also ___________________?”
  7. Identify two: “What are two things I could do next time to ensure we get it right next time?”  
  8. Identify the following opportunity: “When is the next time when it would matter most that we don’t repeat this situation? What would we do differently next time?”
  9. Prioritize if there are too many issues: “I hear that X, Y, and Z are all going on.  What would it be if we had to pick one of those to address first?”    

Listening Tips To Build Trust and Rapport

  • Ask them if you can take notes so you don’t miss anything - it shows you’re not just passively listening. 
  • Only ask a question with authentic curiosity. People can tell when someone is not genuinely interested in their answers.
  • Avoid machine-gun questioning: Leave 2 seconds of silence after they’re finished talking -- this gives them room to think further, and often they’ll start talking again and share a more profound thought (they usually do - this is awesome) 
  • Look for words, metaphors, and underlying values and passions they repeat, then confirm with them if your inference is correct:  “It sounds like you love ______, is that right?”
  • Thank them for their honesty, even if it slowly trickles in: Relationships take time and intention to shape into long-term trust and rapport – their honest answers are a critical step towards building these things.

Three Levels of Listening

We learned about three listening levels when I trained to become a coach through the Coach Training Institute. I walk through these with my manager training attendees to help them see the difference and begin to practice.

Level 1: Internal Listening

Often, when we’ve asked a question and another person is responding, we are processing in our brain and getting ready to say the next thing: ask a follow-up question, or provide some direction. This isn’t listening. But we do it all the time! Level 1 listening is staying in your head, processing how the information is relevant, how it might impact you, or what your experience tells you about what they’re saying.

Level 2: Focused Listening

In Level 2 listening, you’re genuinely focused on what the person is saying. To the best of your ability, you block out all other thoughts in your brain. Level 2 listening is external to you; your ideas don’t get in the way of hearing this person. You’re focused on the other person’s words and their meaning.

Level 3: Global Listening

In Level 3, you’re still focused on the other person but also aware of more things, like the person’s body language, tone, boredom, frustration, or excitement. You’re aware of how they are reacting to you or how they’re feeling. In group settings, Level 3 is the buzzing in the room when there’s lots of energy and enthusiasm, soft focus when listening closely to a speaker, or when you can sense typing and distraction in the group. If you’re in Level 1 listening all the time, you’ll appear self-absorbed and inflexible, and you will rarely be able to push the team to achieve new and more significant things. Your teammates have a lot to offer—listen to them actively! When speaking with a teammate, aim to stay in Levels 2 and 3; you’ll be more effective at gaining a shared understanding, learning new information, supporting this other person, and making them feel seen and heard.

Get comfortable with awkward silence.

The natural outcome of active listening is silence.

You’ve been listening intently and paying attention to other signals like this person’s body language and tone. So when they’re finished talking, you’ll need to switch your brain into processing mode—which means awkward silence until you’re ready to say the next thing! I’m here to reassure you that silence is usually way more awkward for the person getting ready to talk than everyone else in the room. I promise: even if your brain tells you that this silence you’ve created is BAD or AWKWARD, it’s okay, healthy, and probably necessary, too!

Silence does a lot of work. Silence gives everyone in the room more time to process and formulate thoughts. It creates an opening for others to participate (especially those uncomfortable interrupting or steamrolling others). It can communicate that you’re genuinely interested in hearing what others say. Silence and space are potent tools in your management toolbox, and it’s time to get some practice creating them.

In unfamiliar, high-stakes situations, it can be difficult to remain calm and open-minded. Our instinctive reaction is to stick with what has worked for us. That’s normal, and it can work well in familiar situations. But defaulting to old habits in new situations that call for new solutions is usually a recipe for failure. The challenge is that new, high-pressure situations often create a level of anxiety that triggers the very reactions that tend to limit us, stifling innovation. When we most need to learn, change, and adapt, we are most likely to react with old approaches that aren’t suited to our new situation, leading to poorer decisions and ineffective solutions.

Navigating periods of turbulence successfully requires leaders to adopt a sophisticated form of self-mastery that we call Deliberate Calm. “Deliberate” refers to the awareness that you have a choice in how you experience and respond to a situation. “Calm” refers to rationally considering how best to respond without being governed by old habits.

“Deliberate Calm” is a solution to the adaptability paradox. It enables leaders to act intentionally, creatively, and objectively, even in the most challenging circumstances. It also helps us learn and adapt to novel challenges with high stakes. Deliberate Calm — a practice — that changes our relationship with uncertainty.

1. Establish Trust and Rapport:

  • Start the meeting by creating a comfortable and supportive environment where team members feel valued and respected.
  • Use active listening techniques, such as maintaining eye contact, nodding, and paraphrasing, to demonstrate empathy and understanding.

2. Be Curious and Open-minded:

  • Approach the conversation with genuine curiosity and an open mind. Encourage team members to share their thoughts, ideas, and perspectives freely.
  • Avoid making assumptions or jumping to conclusions. Instead, ask clarifying questions to gain a deeper understanding of their experiences and viewpoints.

3. Ask Open-ended Questions:

  • Pose open-ended questions that encourage reflection and introspection. Avoid yes/no questions, as they may limit the scope of the conversation.
  • Examples:
    • "What aspects of your work do you find most fulfilling?"
    • "Can you tell me about a recent challenge you encountered and how you approached it?"
    • "What are your long-term career goals, and how can I support you in achieving them?"

4. Explore Feelings and Emotions:

  • Encourage team members to share their feelings and emotions about their work, challenges, and accomplishments. Validate their experiences and provide a safe space for expression.
  • Examples:
    • "How do you feel about your progress on [specific project/task]?"
    • "What emotions are you experiencing when faced with [particular challenge]?"

5. Focus on Growth and Development:

  • Inquire about areas for growth and development, both professionally and personally. Help team members identify opportunities for improvement and support them in their growth journey.
  • Examples:
    • "What skills or knowledge do you feel you need to develop further?"
    • "How can we leverage your strengths to overcome your areas of development?"
    • "What opportunities would you like to explore to expand your skillset?"

6. Encourage Reflection and Goal-setting:

  • Prompt team members to reflect on their achievements, setbacks, and lessons learned. Collaboratively set goals and action plans to drive progress and development.
  • Examples:
    • "Looking back on the past quarter, what accomplishments are you most proud of?"
    • "What lessons have you learned from recent challenges, and how can you apply them moving forward?"
    • "What are your priorities and goals for the upcoming weeks/months, and how can I support you in achieving them?"

7. Provide Support and Feedback:

  • Offer support, encouragement, and constructive feedback to help team members overcome obstacles and achieve their goals.
  • Examples:
    • "Is there anything specific you need assistance with or any obstacles you're facing?"
    • "Here's some feedback on [specific area]. How can we work together to address this?"

8. Follow-up and Accountability:

  • Close the conversation by summarizing key points, action items, and next steps. Set clear expectations for follow-up and accountability.
  • Examples:
    • "Let's schedule a follow-up meeting in two weeks to check in on your progress."
    • "I'll send you a summary of our discussion and action items by the end of the day. Please review and let me know if anything needs clarification."

By asking deeper questions during 1:1 meetings, managers can foster trust, promote engagement, and support the growth and development of their team members effectively. These conversations serve as valuable opportunities for building strong relationships, providing personalized support, and driving individual and team success.


Your teammates are guaranteed to have surprising reactions to things that happen in your work environment. How do you recognize, navigate, and best support your teammate?

Tools and tactics are included for each set of skills, so you can experiment and see what will work best for you, your team, and the environment you’re working in. At the end of each chapter, you’ll also find a section called “Coaching Questions”—prompts to help you introspect and begin to hone these skills. Excellent book on the topic:


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