Diego von Sohsten of Teamworki: “Choosing an idea can be hard”

I had a tendency to give up too early. People around me told me that, leading to one of my favorite mantras: only finish what you started after trying all reasonable ways to make it work. It takes a lot of reflection and self-awareness to identify such patterns in your behavior and correct them, but […]

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I had a tendency to give up too early. People around me told me that, leading to one of my favorite mantras: only finish what you started after trying all reasonable ways to make it work. It takes a lot of reflection and self-awareness to identify such patterns in your behavior and correct them, but being surrounded by the right people, who genuinely want to see you grow, can also be a trigger for positive change.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Diego von Sohsten.

Diego von Sohsten is the Co-Founder and CEO of Teamworki, an AI-powered employee engagement tool for agile companies. Diego is on a mission to help managers build alignment and a culture of feedback at work. He has managed teams and strategic projects in large tech companies for about a decade.

Diego believes in the power of bringing people together and rallying around shared goals to achieve powerful outcomes. Born in Brazil, since 2017 he lives in the Canadian city of Saskatoon, or “the coldest place on Earth” as he claims.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I always wanted to work in tech, more specifically in SaaS (Software as a Service), but it wasn’t clear to me — as a young adult — what role would make me fulfilled. In Brazil, having a day job while pursuing a university degree is a matter of financial survival, unless you come from a wealthy family. Due to that reason, I kicked off my career at 18 as a Software Developer after passing a competitive interview process in a consulting company.

It wasn’t long until I realized that while I enjoyed working with Developers to solve problems, I didn’t want to be one of them. I could play to my strengths and provide more meaningful contributions from a business standpoint. I took the plunge and wore Project Manager and Product Manager hats since then.

Having managed many people and initiatives for about a decade, I visualized common traits in the highest-performing workplaces, where people rally around common goals while fostering a culture of feedback. As I heard from one prospect last week, planting that seed isn’t an HR-only responsibility anymore. Managers can and should lead that process with their teams.

After feeling inspired by former managers and coworkers who adopted that mindset, I took the entrepreneurial path: my startup is building a product that equips managers with a structured toolkit to unleash employee engagement and performance.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

The HR department is a powerful ally when it comes to building high-performing teams. However, in modern organizations, managers are also stepping up and implementing tools such as One on Ones, collaborative Team Meetings, and their own Check-ins. Managers now understand that building trust and fostering more engagement lead to better results.

With Teamworki, I believe we are slowly disrupting the “employee engagement” category by not relying only on HR-driven surveys, but also equipping Managers with a structured framework for building high-performing teams. We analyze the feedback that employees provide via the tools previously mentioned and, by leveraging machine learning, we can suggest how engaged employees are and where potential issues may exist, requiring immediate action.

Our product is part of a movement: the same that advocates for adopting lean management and agile practices at work. We aren’t disrupting the industry alone, our product is part of it. With that said, we have seen tremendous growth in adoption, especially from functional managers in Sales, Marketing, Customer Success, and R&D stepping up.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Having started a career so young, oftentimes I wasn’t taken seriously by our customers. I tried to make up for my inexperience by sacrificing my social life and reading as many books as I could. I even grew a beard to look older!

In retrospect, while learning new skills is crucial (can’t say the same about trying to look older), that goal could have taken a healthy direction rather than becoming an obsession. Making my career the only thing that mattered backfired, impacting my mental health and pushing my life goals a bit farther. I was only able to find a better balance years later.

In a nutshell, don’t be ashamed of your inexperience and learn to enjoy the journey. Negative self-talk feeds impostor syndrome and leads you to bad decisions in life.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

I had the privilege of reporting to two amazing female executives in my career. The first was working very hard to grow the regional branch of a well-known consulting business in Brazil. She gave me the chance to formally work as a Project Manager, leaving my Software Developer days behind, which was a hard transition given the scarcity of opportunities in the area I wanted to pursue. She also disrupted many stereotypes at the time: first of all, by being a woman in a C-level position, in a misogynist country. In addition to that, she genuinely cared about her staff, hearing me on my worst days, cheering me up and challenging me to face my fears.

The second was also a C-suite leader, this time in Canada. She represented a unique mix of people skills and servant leadership. Being the only female in the boardroom must have been tough, but her leadership inspired people and made her division the number 1 in revenue in the company. She had a brilliant ability to understand where her direct reports were coming from, empathize, and find solutions together without telling anyone what to do.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I believe that disruption brings new tactics for solving a challenge exponentially better than before. By “better”, I mean at a fraction of the time or the cost, generally speaking. The tricky part is when you end up causing a more severe problem as a result. To top it off, it takes time — I would say years — for the impact to be properly assessed as positive or not.

Uber’s growth led to riots on the streets. In my home country, for a while, you wouldn’t feel safe at all using their services, given that some cab drivers would chase the car you are in, block the road, and damage the vehicle. As the dust settled, the industry changed and Uber became the default option for private transportation. Was it worth the hassle? When I think of customer satisfaction and job opportunities, the numbers indicate that was a change for the better.

More regulated industries, such as legal services and healthcare, deal more with data privacy concerns and that’s why there is more bureaucracy when it comes to improving the status quo. Having said that, there are many players in those spaces removing unnecessary friction and time will tell if they effectively solved a problem.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

I had a tendency to give up too early. People around me told me that, leading to one of my favorite mantras: only finish what you started after trying all reasonable ways to make it work. It takes a lot of reflection and self-awareness to identify such patterns in your behavior and correct them, but being surrounded by the right people, who genuinely want to see you grow, can also be a trigger for positive change.

The second one is around imposter syndrome and feedback. It’s so tempting, especially when taking part in a new project (and in a new environment), to believe the negative narratives your mind tells you. You may feel you aren’t making an impact or you aren’t the high-performing coworker people believed before hiring you. I learned from people who went through the same situation that asking for feedback is the best way to overcome those fears. Oftentimes, that narrative is completely inaccurate and you just need to hear that from someone else to reframe your attitude.

Finally, something that I learned from writers and leaders I tremendously admire: aligning your passion with professional goals is something everybody should try at some point. If you are a high-achiever, there’s a “what now?” moment in your 30s and there couldn’t be a better time to give a shot at something new, that solves a problem for someone, while bringing you fulfillment.

We are sure you aren’t done. How are you going to shake things up next?

We just started. We chose, as our initial and primary audience, managers our message resonated with. Educating people on modern and agile management practices, consequently expanding our audience, seems the next step for us, so we will soon spend some time in that area.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

Choosing an idea can be hard. You can use whatever prioritization framework is out there, but it can take time until you’re confident enough to start. The lightbulb moment, for me, came after reading “Zero to One” by Peter Thiel. He advocates for creating new markets and differentiating yourself, as a new business, rather than improving on others’ models. Those words, along with a lot of research, were the factors that made me double down on Teamworki’s idea, taking the plunge and leaving a successful career as an employee behind.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Mark Manson claims that “everybody is wrong about everything”. Nurturing a learning mindset, trying to be “less wrong” rather than “right” can lead you to a place of curiosity. You will ask the right questions because the overarching goal is to learn. That attitude helped me get situated in new environments and build trust with people.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

What if you could select causes that you are passionate about and could bring a positive impact to the world, and somehow you would be matched with inspiring people that are leading change in those areas, or even organizations that are taking concrete actions on making the world a better place? I’d be interested. Sign me up!

How can our readers follow you online?


Email: [email protected]

This was very inspiring. Thank you so much for joining us!

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