How Curiosity Can Create Stronger Leaders with Arash Tadayon

Curiosity is at the heart of great leaders because...

If you're always curious, you will always ask a question...

If you always ask a question, you will always get a response...

Which leads to more curiosity and more questions...

Arash Tadayon, VP of Engineering at Trainual, and I had an interesting conversation about this topic in this week's episode of the B2B Leadership Podcast...

Find out how Arash has used curiosity to fuel his entrepreneurial and leadership career.

In this episode...

0:19 - Arash's background - Arash explains his role at Trainual.
1:02 - Approaching the problem differently - How does Trainual differ from Google Docs?
1:56 - Where it all began - How did Arash land his first leadership position?
3:08 - Running first business into the ground - What events led to that outcome?
4:33 - Surviving tough times - What were the circumstances that pulled Arash through growing pains?
6:00 - Next steps of discovery - What happened after Arash's first company ended?
7:41 - New environment, same skills - What was the parallel between skills that Arash brought from his first company to the next?
10:58 - Self-auditing for success - What does Arash's annual self-audit consist of?
13:10 - General entrepreneurship - How does this skill set align with everybody?
14:29 - The entrepreneurial mindset - Arash advises on how anybody can adopt an entrepreneurial mindset.
17:28 - The concept of grit - Is this something you're just born with or can it be developed?
21:09 - Celebrating failures - How is this idea handled inside of an organization?
23:06 - Identifying entrepreneurial mindset - How does Arash identify these traits during a hiring process?
25:48 - Purposefully vague questions - What types of questions does Arash ask?
28:04 - Arash's advice to himself - What advice would Arash give his younger self?

Connect with Arash Tadayon:

Learn more about Trainual at

Learn more about your own leadership style at:

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Great leaders are naturally curious. They always have a way of asking interesting questions.

In this episode, Arash shares how his curiosity brought him to where he is today.

Read on to find out.

Arash's background

Arash Tadayon is the VP of Engineering at Trainual, a SaaS company that works to help business owners and employees document the blueprint for their business.

Approaching the problem differently

How does Trainual differ from Google Docs?

When Arash was consulting, he jumped into a lot of different companies that were using Google Docs for their documentation and they usually spend 15-20 minutes searching for documents in Google Drive.

In Trainual, they created a centralized platform that brings all of the different components of the blueprint into one place which allows people to connect all of these different kinds of disconnected experiences, solving Google Drive's experience problems.

Where it all began

How did Arash land his first leadership position?

Arash was pursuing an undergraduate degree in Computer Science when he got hooked on entrepreneurship. During this time, he started his first company that came out of a project with his roommate which then led to a partnership with Mayo Clinic, one of the most well-known brands in the world in the medical space.

Running first business into the ground

What events led to running his business into the ground?

Arash was very naive and he didn't really understand a lot about running a business. He realized that with the limited resources that they had, they could not figure out the answers to some of the questions that they had.

Surviving tough times

What were the circumstances that pulled Arash and his roommate through growing pains?

The biggest thing that pulled them through tough times was their innate sense of curiosity. They were very passionate about being able to go through the journey of discovery. It was through curiosity that they were able to pull through much of the strife associated with starting a company.

Arash has always been very interested in puzzles and problem solving, so he viewed this as another puzzle to try to go through and solve one piece at a time. Seeing things from this perspective will get you hyper-focused on just the next small problem and then over time, when you look back, you'll see that you've solved a series of small problems, which was a big problem.

It's about those small little steps, not the big gigantic milestones that sometimes people only focus on when they think about progress.

It's a journey of discovery. You're never going to know everything that needs to be done in front of you for the next three months or even one year. Being innately curious is an incredible leadership skill, regardless of your level, position, company, or product.

Next steps of discovery

What happened after Arash's first company ended?

When their first company ended, Arash took the skill sets he learned from it and started his second company when he was pursuing his doctoral work. The second company was in the space of mobile apps.

Arash was interested in learning more about how to create mobile apps during that time. So he and his three other friends who were all computer scientists as well, interested in the mobile apps space, got together to build the second company from scratch.

It was during the time when everyone felt like they needed an app for their business. So the timing lined up really well. They spent some time learning then dove in and started picking up some contract work and slowly scaled that up over the course of the next six years.

New environment, same skills

What was the parallel between the skills that Arash brought from his first company to the next?

What drove Arash to start his second company was the skillset around problem-solving and getting hyper-focused on small problems.

When you create a services company, it's heavily tied to being able to effectively market yourselves. None of them had a background in business. So they took the approach of taking one project at a time.

Being able to market the services effectively as a services company was one of the big problems they were facing at the time but they were able to solve it by attacking very small problems.

There were a lot of non-technical people that were trying to understand the mobile app space. So they took a lot of time upfront to explain even the most basic information to these people. In other words, they met them where they were.

Meeting people where they are is a powerful leadership lesson, regardless of discipline, domain, company, or position. It's critical to read and understand your audience. Nobody will follow you and nobody will even sign up to work with you if they can't understand you. The level of communication is really important to have that awareness to take a step back. How you view and see the world is different than how everybody else sees the world. They don't have the same context as you.

After six years in that business, Arash lost his passion for what he was doing. He realized this when he was going through his annual self-audit where he looks at where he is now versus where he was in the previous year.

His second company was super lucrative and profitable but ultimately, he didn't feel any sense of fulfillment. That's when he made the decision to leave that company and decided to go in a different direction.

Self-auditing for success

What does Arash's annual self-audit consist of?

It consists of sitting down and planning around what his external goals are. It also includes an internal audit of who he is as a person and who he has become over the last year. He makes sure that there is continuous alignment with the changes that he has seen within himself and the person that he ultimately wants to be.

As soon as he identifies misalignment, then it's the same challenge on the entrepreneurial side of going through, doing some problem solving, and trying to identify what were the factors that created this change and how can he alleviate those.

General entrepreneurship

How does the skillset of entrepreneurship align with leadership?

Entrepreneurship is often a misnomer for those that are solely interested in starting companies. The entrepreneurial mindset is something that transcends well beyond starting a company and to every aspect of your life. It's a way of thinking of problem-solving.

There are components of grit and creativity, and if you apply that lens to any challenge that you have, whether it's as an individual contributor, as a leader, there are a lot of different benefits that can be found through that lens that can otherwise become much more difficult.

The entrepreneurial mindset

How can anybody adopt an entrepreneurial mindset?

Oftentimes, as leaders, you're thrown into situations where you don't necessarily have a background or experience to lean on to solve rudimentary issues. It's often a complicated issue where you go through a journey of discovery to identify the root causes and then ultimately have to come up with creative solutions.

In entrepreneurship, you also hit dead ends a lot of times where it's very easy to just give up. But it's the characteristic of grit, an entrepreneurial mindset that pushes you to move forward and not just give up. That is a critical skill for a leader as well.

The concept of grit

How would one go about developing the concept of grit?

The concept of grit is a growth mindset. It's having that positive lens around failure, being able to accept that failure as a component of the process, and being able to grow through it. Regardless of what happens as a result of failing, it is you that controls how you feel about the failure. You can decide if this was a good thing or not.

As a leader, you need to create an environment where you celebrate failures. So not even just address or accept failures, but celebrate them by sitting down and talking through where you failed, and what you learned. Be open about the failure, and have that humility, while still maintaining that positive mindset.

If you set that tone in that culture, it enables autonomy. Arash says, a lot of times when employees and teammates are afraid of failing, they feel like they need to go through a lot of layers of approvals before making a decision. But if you create that culture, where failure is okay, and celebrated, autonomy is the natural result.

As a leader, you want empowered people who work on your teams, whether they're individual contributors, managers, or directors and you want them to empower others. If you create that culture from the top, everything else will fall into place.

Celebrating failures

How is celebrating failure handled inside an organization?

Arash says, in their organization, they create Slack channels where they post their failures and what they learned from them.

The idea of celebrating failures is something that needs to be instilled from the top-down so that the entire leadership team is on board. It should start with you as the leader. If you don't do that as the leader, everybody else won't do that as well.

Identifying entrepreneurial mindset

How does Arash identify the entrepreneurial mindset during a hiring process?

Arash is much more willing to invest in someone that has the entrepreneurial mindset and problem-solving ability, knowing that they're going to be able to ramp up and pick up the underlying tools that they use than someone who has experience in the technical stack and the tools that they use.

So during the interview process, he'll ask a purposefully vague question to see if they can go through the process of asking clarifying questions and trying to better identify and define the problem before jumping in and trying to ideate solutions. And then as they're ideating solutions, Arash will change the components of the problem to see how they adapt to that, whether or not their process changes or if they're able to adapt to the changing environment.

This really helps identify the candidates' ability to be creative and to see whether or not someone gets overly attached to a solution versus being willing to adapt to the changes.

Purposefully vague questions

What types of questions does Arash ask?

Arash focuses on what they call algorithm questions, specifically for software engineers. Before jumping in and even starting to ideate around a potential solution, the candidates need to ask defining questions upfront first. If you just jump right into the solution, you're going to miss it all.

As the interviewer, you can identify the thinking patterns and the potential of somebody to solve problems through this.

Bringing it back to the entrepreneurial mindset, the big problem is solving this vague question. And all the little steps are those tiny little clarifying questions and little pieces that come along the way.

There's no perfect way of identifying whether or not somebody has that characteristic inside them. Because if they do, no matter what problem you throw at them, they're going to be pretty successful in solving them.

Arash's advice to himself

What advice would Arash give his younger self?

Arash had a very big fear of failure during the early years of his career and it caused him a lot of stress and anxiety that was completely unnecessary. It took him years to look back on those failures he had and see them in a positive way.

So if he could talk to his younger self, he would tell himself to not be afraid of failure.

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