How to Ask Insightful Questions of a Mentor

When I was a leader, there was a time that I thought that improving my coaching skills meant giving better advice and moving quickly to solutions 😅. I was wrong. The first thing they teach in coaching certification is this: Coaches don't give advice. Instead, we believe that the coachee is the best person to solve their own problems as it helps them take ownership, builds creativity and fosters resilience. When I see leaders made this coaching mindset transformation, too, they get better growth, creativity and results in their teams. Here are three shifts you can make to improve your coaching skills as a leader: ➡️ SHIFT 1: Transform from hearing to intuitive listening. Intuitive listening is hearing a person fully beyond their words at face value. It is that little jolt, nudge or zinger you feel inside when you sense something is off, not lining up or maybe information is being withheld. You can ask questions like: ❔"I have a hunch there might be a deeper worry here, but tell me otherwise?" ❔“How long has this been a concern for you? Why is that?" ➡️ SHIFT 2: Move from problem solving to problem identifying. So much “coaching” is fruitless because leaders are too quick with advice or getting into action that we solve the wrong problem. Here are questions to help you get to the root of the issue so you solve the RIGHT problem. You can ask questions like: ❔“Why would it be so bad if XYZ happened?” (Points you towards the worry or belief holding them back) ❔“If you could make XYZ happen, what are you hoping that helps you avoid?” ➡️ SHIFT 3: Shift from telling to asking. Once the problem has been identified, it can be so tempting to unleash all of the brilliant advice that you've been holding back ;) However, great coaches know that asking the client/coachee how THEY'D solve the problem leads to better creativity, results and ownership. You can ask questions like: ❔What's been your current approach to solving this? ❔What else could you try? ❔What worked when solving another similar challenge? ❔How could this be happening FOR you? TRY THIS NEXT: In your next coaching conversation, ask one more question that you normally would before jumping into action. What coaching strategies have you tried to help you ask better questions and refrain from jumping in to solve the problem?

Here’s something I’ve never shied away from: Asking tough questions. I’m in talks with executives all the time, but I’ve never let their stature intimidate me. My selection process goes beyond the resume resumes and references. It's about understanding the deeper layers of a candidate, and learning about their motivations, values, and the experiences that shaped them. I grew up with the Oprah show on daily. I’ve admired how she masterfully uncovers the true face of her guests through tough, yet thoughtful questions. I aspire to use similar techniques to get to the heart of a candidate’s story during interviews. Here’s the thing, asking tough questions isn't about grilling someone, it's about creating a space where honesty, authenticity, and vulnerability can come through. Now, no two interviews are the same. Which is why it’s important to dive deeper into the story to uncover various aspects. Here’s how you can frame these tough questions as per each candidate: 1/ Ask About Their Vulnerabilities Asking questions that allows candidates to reflect on their struggles, resilience, and growth is an integral part of the process. An example: What’s the biggest failure that you’ve experienced, and how did it shape your approach moving forward? 2/ Discover Their ‘Why’ Understanding why someone does what they do helps reveal the candidate’s core values and motivations, and gives insights that can help in determining if their personal goals align with your company’s mission. An example: Can you mention a transformative personal story, and how it influenced your professional decisions in the past? 3/ Encourage Honest Self-Reflection There must be questions that allow the candidate to introspect about their career, as the answers highlight how they handle self-reflection, growth, and change—key traits in today’s rapidly evolving business environment. An example: How do you assess your own growth and progress in your career? 4/ Get Personal Within Reason Without crossing professional boundaries, asking personal questions can give you a window into how candidates think and prioritise in life. This approach can shed light on the values they bring into the workplace and how they lead others. An example: Are there any life experiences that you believe have prepared you for this leadership role? Can you elaborate on one? Trust me, these questions will save you a lot of headache in the future. Thank me later! #Interview #Hiring #HeadHunting

Why Mentoring is Helpful? Finding a mentor was one of the best decisions I ever made during my 30+ years of leading real estate companies and working with churches. For over 20 years, I was mentored by the same person, whether I was a CEO in the United States or the Middle East. This person, who was 20 years my senior, had succeeded in the business world that I aspired to enter. This mentor was someone I admired, both from a family perspective and regarding work-life balance. I thought, “Yeah, I can learn a lot from him.” When selecting a mentor, the key is to ask them about their mistakes. The most valuable insight for you as a mentee is learning from the errors they made throughout their career. Your goal in a mentee-mentor relationship is to avoid some of those pitfalls. If you are interviewing a potential mentor and all they discuss is their accomplishments, they are not a suitable mentor. So, before you hire a mentor candidate, ask them these questions: · What was one of the biggest disappointments in your career? · When you were building your organization, what setback can I learn from? · Regarding your decisions, what are some things you would do differently now that you have learned from your experience? · What is the most significant mistake you made in your career, and how did you grow from it? As a mentee, you want to acquire knowledge from your mentor. Let’s say you're trying to set up and grow a real estate company. You're speaking with someone who has experience accomplishing what you want to achieve. This person has likely made decisions and mistakes they would approach differently now. You can learn from their experiences or perhaps from those who have navigated challenging business relationships. This can help you identify what to look for in your current situation based on what they went through. A mentor relationship can be incredibly positive and beneficial for you as a leader. If you've been a mentee or a mentor and had a positive experience, please share it in the comments below; I'd love to hear about it. 20/20 Foresight Executive Talent Solutions #mentoring #coaching

🤔 One of the skills I've worked hardest to improve is asking better questions. Here are 7 tips I've learned to ask powerful questions: 1️⃣ Ask one question at a time Don't spray questions like shotgun pellets. If you ask 3-4 questions in a row, people will forget them. Ask one -> Get an answer -> Ask the next. 2️⃣ Opt for shorter questions Asking long questions is often as bad as asking multiple questions. Long questions confuse people. It takes a surprising amount of confidence to ask short, simple questions. 3️⃣ Become comfortable with silence If you ask a good question, you should expect some silence. Silence is the noise thinking makes. Leave space for it. 4️⃣ Ask open-ended questions You'll get way better information if you avoid simple yes/no questions. They're often too limiting. For example, asking your boss “How do you think I’ve been performing lately?” is fundamentally different than “Do you think I’ve been performing well?” 5️⃣ Avoid “Why” questions Questions that begin with “why” tend to make presumptions or assume the worst (e.g., “Why did you…”). They put people on the defensive. You want to invite someone into a discussion with you — not shut down the conversation with a question that prompts defensiveness. 6️⃣ Ask “What” and “How” questions Questions that start with “What” or “How” invite the other person to share their ideas (without any presumptions). The biggest difference you can make in your questions is to substitute "What" and "How" questions for "Why" or yes/no questions. 7️⃣ Don’t hide answers in your questions Questions like “Why wouldn’t we just [take this course of action]?” are what author Michael Bungay Stanier calls “offering advice with a question mark attached,” and it’s a subtle form of manipulation. Ask legitimate questions — not contrived ones. Thanks to friends and mentors like James Pratt, Harry Gefre, Brittany Blumenthal, and Bobby Moran for teaching me how to ask better questions!

Last week, my son, a college freshman, had his first meeting with his mentor. Imagine my surprise when he sought my advice ;) — I guess parents are worth something after all 😁 It's a significant milestone, and it got me thinking about the essence of effective mentoring given my own experience as a mentor and mentee. While there's an abundance of literature on this topic, including a recent piece by Harvard Business Review, many tend to skim the surface, offering broad, somewhat simplistic advice. Reflecting on this, I penned down some tailored guidance, which I believe might be valuable to others embarking on this journey. Here's what I shared: 1. Embrace the art of listening: Your first meeting is more about tuning in than speaking out. Show a genuine interest in your mentor's narrative. Inquire about their professional voyage - how it began, the decisions they navigated, and the turning points. 2. Seek wisdom, not just facts: Ask about the lessons they've learned along the way. What would they do differently if they could rewind the clock? Their hindsight can become your foresight. 3. Prepare, Prepare and then Prepare more: Before seeking advice on specific decisions like program selection, job opportunities, or electives, make sure you've done your homework. Understanding your own choices deeply enriches the conversation and the guidance you receive. 4. Explore beyond academics: Ask about the activities they engaged in outside their formal education or job that propelled their career - be it internships, part-time roles, additional courses, or club memberships. Understanding their strategies and how these choices shaped their path can offer practical steps for your own journey. In my own experience, a long term relationship with your mentor can be rewarding for both and has the potential to be truly transformative. What are some other non-obvious tips for speaking to your mentor/mentee? I’d love to hear your thoughts. #mentorship #relationships #student #learning #mentors

It's surprising how many people have never had meaningful career conversations with their managers (or their direct reports). I don't mean conversations that are solely backward-looking about recent performance or forward-looking about the next promotion. I mean holistically taking stock of the journey: where you've come from, where you are now, where you're headed, where you'd like to go, the tools you need in your toolbox to get there, and the people you need in your support crew. Several years ago, I created a framework to guide career conversations with my direct reports. It's a somewhat cheesy framework, but it leads to rich conversations and strategic, as well as tactical, action plans. It's not meant to be prescriptive, but rather a guide for meaningful reflection and action. I offer it in case it's helpful to anyone here. (I'd also love to know how others approach leading or engaging in career conversations. Do you have your own framework that you'd be comfortable sharing?) Here’s mine: GROWTH G is for Goals. Personal and professional aspirations: How do you think about these today, and how have they evolved over the past 2, 5 years? What matters to you when you reflect on your career adventure thus far? What do you want to build on and carry forward, or leave behind? R is for Reflection. Self-awareness and feedback: What significant milestones or achievements have you accomplished in your career so far? When have you felt strongest and most fulfilled? Least? Where are you currently stretching and reaching the most? Where do you feel most uncomfortable – both positively and negatively? O is for Opportunities. Skill development and growth path: Together, we’ll identify the skills needed to develop further on the current path, or to strike out on a new path. W is for Wellbeing. Personal and professional balance: How are you balancing your work and personal life? What strategies do you use to maintain your wellbeing? Are there any areas where you feel you need more support or resources to ensure a healthy balance? T is for Team: Collaboration and mentorship: Who are the key people in your professional network? How are you leveraging relationships for growth? How are you contributing to others' growth? Who can and should we expand your network to include? H is for Holistic Action Plan. Actionable steps and accountability: What specific actions will you take to move toward your goals? How will we track your progress? What milestones will we set to ensure accountability and continuous growth?

I tend to get nervous when I’m in big groups. In casual conversations, when I don’t have a defined role - I’m not there as a coach or an advisor - I get nervous and my natural tendency is to fill the silence with words. Over the years, I’ve learned that conversations are about much more than creating opportunities to express yourself. I’ve also learned that my default approach - filling the space - doesn’t allow me to learn a lot about others, or build real connections. The best addition to my toolkit has become the “open question” - basically, any question that can’t be answered with a simple “yes” or “no”.  I’ve come to love open questions because, in their very nature, they ensure more balanced conversations. They allow whomever I’m speaking with to set the conversation’s parameters. Instead of making the conversation about me, open questions shift the focus to the other person.  I get to listen and to learn.  I keep a note on my phone with a list of great open questions that I hear others ask, or open questions that I’ve asked that led to high-quality, beautifully balanced, and meandering conversations. Right now, three of my favorites are: 👉🏼 How do you spend your time (replacing “what do you do for work?”)? 👉🏼 What is one suggestion you’ve recently shared in multiple settings? 👉🏼 What is missing from the current dialogue about [topic the other person knows a lot about]? What question have you asked recently that led to a fascinating conversation, or that caused the conversation to go in unexpected and insightful directions?

You can ask better, more beautiful questions. Lazy Questions Don’t Work. Here’s Why. Yesterday, in a high stakes meeting, and the leader opened with: "What do you want to get out of this meeting?" Meh. Not the worst question—but certainly not the best. It felt like a filler. No spark. No clarity. No direction. Weak questions lead to weak results. When I was earning my professional coaching certification (PCC), I came across a book that completely reshaped my thinking around SMART questions: A More Beautiful Question by Warren Berger. This book didn’t just help me and my team ask better questions—it taught us to ask transformational ones. The kind that unlock new thinking, challenge assumptions, and create momentum. 💡 Back to that boardroom moment—imagine instead, the leader asked: 🎯 1. "What needs to be different by the end of this meeting—for you, your team, or the business?" → Anchors expectations. Cuts through the fluff. 🎯 2. "If we succeed here, what changes tomorrow?" → Pushes beyond the task to long-term impact. 🎯 3. "What’s the most important decision we’re not making?" → Surfaces tension. Sparks bold thinking. 🧭 Your Quick Coaching Challenge Ask your leaders to write down 3 questions they plan to ask this week. Then—ask them to revise and share before and after. Make the questions sharper, braver, and more strategic....and more beautiful. Because lazy questions lead to lazy answers. Beautiful questions? They lead to transformation. At L4 Learning Solutions, we help executives and senior leaders become more intentional, more strategic, and more impactful. Asking better questions is just the beginning. We’re offering a Strategic Analysis of Team Effectiveness for organizations ready to elevate performance, engagement, and culture and build better leader pipelines. 📩 Let’s dialogue around how to better support your team. Reach out to schedule a call. 💬 What’s the most beautiful question you’ve heard recently? #LegendaryLeadership #LeadershipDevelopment #ExecutiveCoaching #StrategicQuestions #WarrenBerger #AMoreBeautifulQuestion #BetterQuestions #Transformation #L4LearningSolutions