Great Questions, Great Leaders

What's up, everyone. This is Alex Lieberman, co-founder and Executive Chairman of Morning Brew. Today, I am talking about how the greatest leaders ask the best questions. Let's hop into it. 

The importance of asking really good questions

So I was listening to a podcast interview last night, and it was with Keith Rabois, who is the co-founder of Opendoor. He's the co-founder of OpenStore, and he's a general partner at Founders Fund. And Keith was talking on this show about how one of his co-founders, I believe for Opendoor, was an incredible judge of talent in the interview process. Like he made a point of saying how this co-founder would walk into interviews with candidates, and he would just have a spidey sense of if the person was good or not. And I just thought that was so incredibly cool to have basically this secret weapon in your company, where you have someone who walks into an interview, not knowing really anything about a candidate, and then they walk out of one knowing if they are the person for the job or not. And so that led me down a rabbit hole around the art of questioning. And I wonder to myself, what did this co-founder of Keith ask in the interview process that gave him such high-quality information or signs to be such a good judge of talent? And more than that, I asked myself, how can we all learn to ask the right questions since some of the best leaders that I have worked with in my life, they are incredible at asking really good questions? But first I want you to understand why asking great questions is so incredibly important. Richard Thalheimer, who is the founder of Sharper Image, has this amazingly ironic quote that sums up the power of questions. He said, it's better to look uninformed than be uninformed. It's ironic because Sharper Image went the way of Toys R Us, FAO Schwartz, and so many other bankrupt retailers, but his point stands. The best leaders never let their ego get in the way of asking questions that take them from being uninformed to being informed.

And the reason that asking great questions is so important is because they are the conduit to making great decisions. And Tim Ferriss has an amazing analogy for how questions act as an amazing tool for people. 

Tim Ferris sound bite: Questions are critically important because first and foremost thinking goes on here is largely asking yourself questions and answering them. Secondly, if you want to get anything in life, chances are it's inside someone else's head, the knowledge, the skills, the blueprint, and the pickaxe for getting that gold is in the form of questions. 

Alex Lieberman: The pickaxe for getting that gold is in the form of questions. I think that is such a powerful point. And it makes me think of just an incredibly simple formula that shows why questions are so powerful: Great Questions lead to great information, and great information leads to great decisions. Our decision-making is only as good as the inputs that we put into our brain and questions are the most effective tool to fill your brain with great inputs.

John Wooden’s seven questions

 John Wooden, who is the legendary UCLA basketball coach, he had seven questions, the same seven questions that he would ask himself, and that he believed every leader should ask themselves to effectively lead their organizations.

He asked, am I investing in myself? Am I genuinely interested in others? Am I grounded as a leader? Am I adding value to my team? Am I staying in my straight zone? Am I taking care of today? And am I investing my time with the right people? Now this is just one man's line of questioning. And while there aren’t right questions or wrong questions, there are things that make these questions by Coach Wooden so great. All great questions reveal blind spots. They surface biases and beliefs. Great questions act as an engine for new ideas. Great Questions make people feel more connected to one another And Great Questions give people direction while empowering them to act autonomously. And Great Questions literally sit at the heart of doing a great job in so many areas of business. Yet, I feel like we don't talk about them nearly enough as an entrepreneur myself, I ask questions when I don't understand a topic and I want to better understand it. I ask questions when I don't align with someone's perspective, and I'm trying to understand what assumptions they are making. I ask questions when I'm being asked for my opinion, but I want to better understand the context in order to try and provide a more informed perspective of my own. And I ask questions when I want to help someone answer their own question without me offering my opinion, more so being a guide to them.

Examples from Morning Brew

So let's make this tangible with a few examples. What does it look like to ask great questions and why are they so powerful? Every single time I start a new project or set a new long-term goal within a business, I ask a set of questions. And by asking these questions, I create a roadmap of all of the steps I need to complete if I want to get from point A, which is not having accomplished my goal to point B, which is accomplishing my goal. So let's use the example of hiring someone. Say I want to hire someone. The questions I'll ask myself to know every single step in the process will include, why do we need to make this hire? Does this hire push forward our biggest priorities? Do I know enough to know what I need to look for in this hire? What are the superpowers this hire needs to be successful? When do we want to have this person start at the company? Who is writing the job description? Who is doing recruiting? How many steps in the process are there? Who do I want to include in the interview process? What is the budget we have for this role? The list goes on. There are way more questions than the 10 that I just said, but you get the point. By asking the most important questions, I know that I've effectively created a to-do list of all of the things that I need to complete to complete the project and complete it well.

Great questions from Twitter

So staying on the topic of hiring for a second. Another example of the power of questions is in the actual interview process. I mentioned this at the top of the episode how Keith Rabois had so much respect for his co-founder’s ability to identify great talent in an interview. And all I thought to myself was, what questions is this person asking? Now, I don't know what his co-founder is asking that was the secret sauce for finding great talent versus not great talent. But I did take this question to Twitter and I got a ton of responses. I asked people, what is the most powerful interview question you ask, the question that provides the best gauge if someone will be an all-star or not? And so I wanted to share with you two of my favorites and why they are specifically such great questions in my eyes. The first question is from Ankur. Ankur is an entrepreneur in India. He's the former CEO of Groupon India. And he said his favorite question is, explain something that you know, really well, assuming I know nothing about it. I love this question because it allows you to go deeper on three questions with a single question. Ankur’s question tells me what it looks like for a candidate to be passionate about something. It tells me if the candidate is actually curious, and if they know what it means to go deep down the rabbit hole. And it tells me if the candidate is foundational enough in terms of their learning, to be able to explain a complex topic really well. Now, to move to the second question, it is from Andrew, who is the founder of an e-commerce community. And his favorite question to ask candidates is, what did you do to prepare for this interview? I love this question for a very different reason from Ankur’s. I love it because it is the most tangible way to understand how motivated someone is to work for you and how hard they work when they are truly motivated. 

Recap

Okay. So there is so much we have talked about in today's episode about asking great questions, so let's do a quick recap. Questions are a wildly powerful tool that we all have in our careers. And I know over the last six years of building Morning Brew, asking great questions has enabled us to continue building this business even bigger. It's the way that when we had really aspirational goals, we built them into these small, intermediate steps to know where we were going. And it's how we found great talent in everything from our creatives and our writers to our sales org. Great Questions help us reveal blind spots, connect with others, and get below the surface. If done well, they give us great inputs that allow us to make great decisions as leaders of all different sorts of organizations.

I want to hear from you

Now it's time to hear from you. What is your favorite question to ask in an interview process? Shoot me an email to alex@morningbrew.com and I'll take the few best questions that I get from Founder’s Journal listeners and include them in an upcoming episode. And while you do that, please subscribe to Founder’s Journal and leave a review on the podcast player of your choice, whether it's Apple, Spotify, or any other player. It is the number one way that we grow this show. It's how we get to the top of the charts. And it's how new people find out about Founder’s Journal when they've never heard of it before As always, thank you so much for listening and I'll catch you next episode.