The 5 Questions Top Biz Leaders Are Asking Themselves and Each Other

Jenna Kutcher 

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February 1, 2023


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 Do you ever have those events in your life where it kind of forms a chasm, almost like this before and after? You can trace changes in your life or a change in your trajectory or a change in your direction just from one decision or one person or one event. 

I feel like I have a lot of those, and a lot of times when I think about my career or where it’s taken me, I often take the time to trace the origins of a lot of those big things that unfolded before me. It’s funny because I can viscerally remember four years ago getting a text message with an invitation that really did change my life. I accepted (even though it was challenging to do so with a little baby) and I know saying yes changed my life and career forever.

I now say yes to that invitation every year and every single time I go, I feel like it creates this chasm in my life, this before and after. I create new friendships, I get new ideas, I unlock different strategies. 

One of the things that I love about this group is just this level of trust and confidentiality, and so I’m not coming on the podcast to share everybody’s secrets, but one thing that I wanted to share with you are the five questions that we all had to answer, and I actually think you’re gonna be super surprised at what questions we were asking and answering as a collective group.

I also want to share this as a way to encourage you to create a similar sort of practice, whether it is just with yourself in solitude or with other peers in your industry, or other leaders in your area. These five questions are what we talked about the entire weekend, and so I’m gonna walk you through the questions and what some of my takeaways were in answering them so that you can steal this framework for yourself and know that you are using the framework that some of the top leaders in the world are using to help guide them to better conversations and better answers.

Question 1: What are you thankful for? 

Sounds simple because it is. This was a really beautiful way for everyone to start their shares – and there’s a lot of science behind the practice of gratitude and how it can change your life. One thing I realized being in the room was that people were really specific with their gratitude and that it almost felt like a lot of people had been holding their gratitude in. 

I don’t think a single person brought up any business accomplishments in their gratitude which really just made me think about how it’s not about WHAT you do but HOW you do it and WHO you do it with or for. So much of the gratitude was focused on family and relationships. 

How you can apply this: How can you make gratitude a staple in your daily life or with your team whether you make a list or have a slack channel or start each call with sharing something you’re thankful for. 

Question 2: What is exciting you right now? 

I love this question because humans are innately excitable and curious! You know when you’re talking to someone and their eyes just light up and they could talk a mile a minute – that passion is just contagious. 

Like right now I am obsessed with health stuff and biohacking and if someone asks me a question I could go on an hour long tangent about all of it and my experience with it. 

I also think as leaders it was so cool to hear what people are excited about and what they are trying/experimenting/learning about/researching. A lot of times we don’t pause enough to inspect where our excitement is or what that’s telling us and how it might be guiding us in a new direction. 

Question 3: What is working for you right now? 

You’ve likely heard Pareto’s Principle that 80% of your results likely come from 20% of your efforts. When you know what’s actually working or driving results, doubling down or optimizing those efforts can explode your results. 

This was a chance for us to share what is going great, where our expertise lies, or any strategies that others in the group could adopt. I loved this question and hearing the various answers just because it can spark an idea or a focus for others. 

When’s the last time that you really looked at what is working for you, what’s driving the results, what’s your needle mover, what’s that top offer or product, etc. 

Question 4: What are you struggling with right now? 

Again, not a mind blowing question but when is the last time you actually paused and answered it honestly? It was interesting because we ran a gamut of topics with this one from struggling with depth in friendships to struggling with team or hires – I also loved that we were publicly sharing this area of our lives/businesses because it gives people the opportunity to pull you aside and say, “I heard you and I’m here” or “Here’s something that’s helped me.” etc. 

It’s also awesome to hear people you look up to or perceive in a certain way to say, “Hey, I’m struggling with this right now.” This was also a HUGE eye opener in terms of just checking in on our friends more. We all get busy and no one wants to be a burden but there was a theme that people want to connect and be checked in on more. 

One thing that I found was that my strengths lie in places where others weaknesses lie and vice versa. When you take the time to not only acknowledge but express where you’re struggling, relationships naturally deepen and it also invites people to step in and share their strengths with you. 

Question 5: What do you need help with right now? 

It’s humbling to stand in a room of brilliant minds and say: I need help. And yet, that was where the actual magic lived. The way that we did this is that every person had 15 minutes and it was up to them how they spent that time. They could talk the entire time or be concise and leave time at the end for people to chime in and offer insight/advice into what they needed help with. 

When was the last time you actually asked for help? And what did that ask look like? 

A few things I noticed: 

The more specific you can be in your ask, the better support you can get. Do you have clarity in what you ACTUALLY need help with and are you asking the right questions? There’s that quote from Einstein: “If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask… for once I know the proper question, I could solve the problem in less than five minutes.”

It’s so important to have a level of discernment when you ask for help. A lot of times people can have incredible ideas but you have to be in touch with yourself if their ideas/solutions are aligned with your vision or goal. Bring your discernment to the table and really be honest about what is and isn’t aligned with you. 

Don’t be afraid to circle back! A lot of times we ask for help and then just wait for people to show up but sometimes we have to be more assertive in the exchange. There are a few things in my notebook that I wrote down as things I needed to follow up on and it’s up to me to remain poised in that position of asking for help but not putting all the responsibility on the helper. 

The Big Picture

Alright, so there you have it! What would it look like for you if you brought these 5 questions into your life and business? Maybe you put a recurring calendar event so that once a month you’re assessing and answering these questions – better yet, run these 5 questions with people you love or peers in your industry. These are the basis of the powerful life-changing conversations we had at the mastermind and a way that we can not just support one another in real time but show up for each other throughout the year. 

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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