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Management Journey: Technical Superstar to High-Impact Leader

January 10, 2022

How to move from relying on technical career strategies to adopting a leadership perspective in a management role

It’s not uncommon for people at the top of their fields to move into management. Oftentimes, though, they find their skillset ill-suited to leadership roles. There’s a whole organisational theory rationalising this experience called the Peter Principle. In a nutshell: ‘people are promoted to the level of their incompetence’.1 Alarmingly, there’s a spillover effect on teams - one study marked a 6.1% decline in individual performance after a colleague receives a performance-based promotion to management.

The outcomes don’t need to fall in line with the statistics. Ryan Pestano has a roadmap for the transition into management. He sees the risks of relying excessively on the technical career strategies that had previously worked, but lose their effectiveness at the level of management. Ryan helps us navigate past these pitfalls and beyond by adopting a leadership perspective in the management role.

Ryan overcame that very hurdle himself after almost a decade as a hypercompetent engineer. After a brief period in middle management, his career progressed rapidly through various executive roles. At IPONWEB, he now leads his team and partners as they apply closed-loop machine learning to the most lucrative industry on the internet: Advertising. He tells us how he crossed the bridge from technical specialist to regional leader. 

Leadership vs Supervision; Trading Toolkits

Earlier in Ryan’s career, he used to believe that his skill, talent, and ability were the reasons he was the manager. These qualities had definitely propelled his career as a hotshot engineer and opened up opportunities for advancement but his mind would change after he came to see management as a leadership role and not a supervisory one. To be effective, he’d have to go ‘beyond checking code’ and resist the temptation to try and replicate success by imposing what worked for him on everyone else.  

With a mind on the leadership aspect of management, Ryan tells us about how he began to think about fostering creativity and bringing the best out of his team. A cornerstone of his journey has been self-directed learning. Leaders are readers, the saying goes and Ryan explains: “It’s fifteen dollars between you and a leadership book that’s sure to offer something of value. The real key to maximising what we learn is application. It takes effort to isolate actionable lessons, but what we learn only makes an impact when we apply it, and start measuring its effects.”

As a recent example, Ryan shared how he synthesised a strategy from several books to improve communication and collaboration across his team. With members based in different countries and from very different cultural backgrounds, he mediates team meetings to bridge gaps. In practical terms, he referees discussions with his teams in Moscow and Tokyo to balance their assertive and agreeable attitudes. This helps ensure that issues are raised, there’s healthy pushback and matters are resolved so action can be taken. Ryan admits that this solution’s not perfect but that’s hardly the point. Find little applications for the things you learn and that’s where the magic is. As the team sees your efforts to understand their perspective and accommodate it where possible, they will help you along. That cooperation and motivation build up your effectiveness as a leader. 

Surround Yourself with Talent

Ryan recalls a specific instance that really triggered the mental switch from supervisor to manager: it was the moment he realised he was no longer the smartest person in the room. Thing is, as a leader, that’s exactly what you want. The expertise they bring to the table unlocks new dimensions and brings new perspectives to your team. He observes that many first time managers may feel threatened by this but the sooner they reframe this talent in the context of the team, the sooner they begin to see their team holistically. Each person, managers included, is not competing individually against another. They are a unit whose sum is greater than its parts. 

Progression into leadership wasn’t a goal that Ryan had set. Experience taught him that the people who do the most for the company, those who are impactful, gain the highest respect and financial rewards. This put him on a path to pursuing impact. Over the course of his career, he meet superstars whose technical genius he would never match. He felt real limits to his development in this arena so he decided to connect their expertise with another area of business he understood better than those colleagues - customers. That is how Ryan created value for the company. The more he got into it, he realised that it was a matter of figuring out how to improve the way the business’ systems interacted. This process of piecing together these puzzles piqued his interest in management and leadership. 

Ryan has made a career of being an architect of innovation. He isn’t a one-man idea machine though. He believes in recruiting the right people, giving them the resources they need and finding opportunities for their brilliance to shine. That is where his strength as a leader lies. 

The Mentorship Mindset

Ryan approaches leadership as a skill set to be grown. He tries to learn from whomever he can. It helps tremendously to have a mentor to brainstorm with. We can ask questions, and hopefully that mentor can filter the enquiries through their experience and reflect a more meaningful question back at us. 

There will be times when we make ourselves available as mentors. Coaching individuals toward a particular perspective can be a challenge. For Ryan, effective mentorship is rooted in listening first. They might be speaking outside of their expertise, but how they approach a subject will reveal much about how they think. There’s always a benefit from listening. Asking good questions comes next. Listening will help us formulate good questions. We should all feel free to let the people we coach dwell on questions, even ones they bring to us for answers. They'll learn to figure out things for themselves and develop autonomy. Answering questions off the cuff often yields inadequate answers, and we’d only end up teaching our people to come to us with every problem. When we enable our people to ask the right questions, we’ll find they have a lot of the answers themselves.

Final Thoughts

Leadership is about creating value, making the most of our team, our partners, and our stakeholders. The job requires a new skillset, especially if we’re switching over from a technical background. As we hone these skills through our journey, we’ll find ourselves achieving more than anyone else would have expected.

  • Actively try to learn new things and find ways to apply them to the benefit of your team
  • Collaborate with technical talent instead of competing with it
  • Listen intently, ask the right questions and empower mentees to think critically


The Peter Principle: A Theory of Decline.

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