Welcome to IKR (It’s Kash’s Recap!), our new series updating you on thought leadership from Chewse COO Kash Mathur. You can also find thought leadership from Chewse Founder & CEO, Tracy Lawrence, under TL;DR at Chewse! Today’s topic: how leaders can ask the right questions to move themselves and their team forward.

“Think before you speak” – that age-old saying. But how many of us stop to think before we ask a question? After all, it’s the answers we should be spending more time constructing… right? 

Not quite. As a leader and manager, the questions you ask can impact your relationship with your direct reports, how well you can do your job, and the results get from your team. Questions are one of the fundamental elements of how teams work together – so Chewse COO Kash Mathur is here to help make sure yours are as effective as possible.

Why questions matter at early-stage companies

There’s more to asking questions than simply… asking the question. Rather, Kash writes that there are questions you should ask yourself before you get to the business of asking anyone else. In his recent Thrive Global article, he writes: 

“Are you asking questions that help your teams solve problems? Or are you interrogating your teammates and then solving the problem yourself?”

This is a particularly relevant question to ask yourself if you work at a startup or other early-stage company. Startup leaders need to be able to move quickly, respond to new challenges, and think on their feet. But those quick-on-your-feet traits aren’t just present in startup leaders – they’re found at every level of the company. 

If you’re reading this blog, you’re likely well-practiced in on-the-spot thinking. You may frequently come up with creative answers to all sorts of crazy questions. But the speed and flexibility startups need is exactly why you need to prioritize asking the right questions, not just getting the right answers. 

Take the average startup leader, for instance. Maybe you could “interrogate your teammates and solve the problem yourself” – as Kash poses. But the better path – the more productive path – is to do the opposite. Kash says:

“In my experience managing teams at an early-stage venture-backed company, I’ve found that it’s a mistake to assume you know the answers when a problem arises. Asking the right questions — the right kinds of questions — is more productive.”

Asking questions gets you started – the next step is making sure you’re asking the right ones.

Questions & biased thinking

Even if you think you know the answer, and you’re just simply looking for some data points, asking close-ended questions or interrogating your team can lead to negative results. The thing is – startups move fast enough that, even though you may have known everything that was going on a day ago, that may no longer be the case today. 

So instead of asking “leading questions,” practice open-ended questions for best results. Kash, in his Thrive Global article, writes: 

“It’s easy to fall into the trap of asking leading questions and statements disguised as questions. These forms of closed questioning introduce bias and manipulate responses. Research on survey design reveals there’s a 50% disparity in results when questions narrow the options or suggest a desired answer.”

Asking questions isn’t easy – and there’s no “perfect” way to do it. But Kash put together a list of question features. Practice these, and you’ll be on the right track!

How to Ask Questions (& Examples!)

As you practice asking questions, aim for the following elements. Not sure where to start? Check out our examples!

ONE – Open-ended 

An open-ended question is one that can’t be answered with a one-word answer. These questions, by nature of having a more involved response, tend to be conversation starters. You’ve likely heard them referenced in ice-breakers and college improv techniques.

Kash says: 

“Closed questions are OK for digging deeper, but start with open-ended questions to understand what seems important. Then ask more direct questions to get to the root problem.”

As a leader, use open-ended questions when:

  • You’re learning more about a project
  • You’re opening the conversation
  • You want to learn more about your direct report’s analysis/problem solving


  • “Can you tell me more about the sales meeting yesterday?”
  • “What were the results of the tests you ran?”
  • “Do you think we need to adjust course here?”

TWO – Why

“Why” is a question-asking superpower. It gives you even more insight into what was happening, what might happen next, and what’s already been tried. It’s a great way to make people feel heard and push the bar 10x higher. 

Kash writes: 

“Why” questions are a way to get to the root cause and to help someone understand beyond the surface, especially when each question is framed in response to the previous answer… Answering three “why” questions in a row typically revs up a team member’s brain for turn-on-a-dime thinking.”

As a leader, use “why” questions when:

  • You need to dig deeper
  • You want to understand more about the process
  • You want a team member to feel heard & engaged


  • “Why do you think our sales were down last quarter?”
  • “Why have we been struggling with operations?”
  • “Why do you think you were able to finish this project so quickly?”

THREE – Personal

Open-ended and “why” questions are a great start – but the true talent of asking the right questions comes from tailoring your questions to your employees. Not everyone needs such prompting to delivery open-ended questions. Alternatively, some people might feel uncomfortable with repeated “why” questions.

Learning to react and recalibrate based on your team’s needs is perhaps the most important skill a leader can have. On the Chewse blog, we’ve talked about how vulnerability and empathy can help you move faster and unlock your leadership superpowers

At its core, the Chewse dual pillars of Love & Excellence mean we care enough about people to adapt to them, while also holding everyone accountable for their own personal growth and success. Translated to asking questions, Kash writes: 

“Reflect on the point in the conversation when you saw the other person have a light bulb moment, then think about what got him there. The next time you have a conversation, put that knowledge to use and see what happens. As you build the relationship over time through a series of conversations, your interactions will improve.”

As a leader, personalize your questions:

  • Always!


  • For example, I had one team member who didn’t respond as well to a rapid-fire succession of “whys.” To get the detailed picture I needed from this person, I adopted an active listening approach at a slower pace. I got not only the answers I needed, but also a team member who now feels valued, empowered, and energized to solve problems on his own.

FOUR – Process-oriented

Sometimes, your goal in asking questions may be to steer your teammate in a different direction. Maybe the project they’re working on needs a readjustment based on new data, or might need to be refreshed all together. You might think a straightforward conversation is the best approach here – but Kash has a different strategy: 

“People get attached to an idea once they’ve stated it. If you try to dissuade them from it, they may get defensive. However, exploring how they got to the idea instead can get results.”

So how can you explore the idea? Kash continues: 

“Always default to open-ended questions for discovery and process. This will give you and your team newer, more detailed information to improve the hypothesis of a solution. Use questions to invite your team to uncover problems and solutions for themselves.”

Learn more!

This IKR is just the beginning – learn more about how to ask questions and read Kash’s Thrive Global article, 4 Ways to Reframe Questions for More Effective Results, here

“You’ll discover that well-aimed questions can inspire your team to improve processes and find solutions on their own.”