Evaluating Leadership: Beyond the Basics

In the high-speed tech world, hiring senior talent often feels like trying to assemble a puzzle while riding a horse-drawn carriage on cobblestones. We tend to focus on the familiar pieces – experience, technical acumen, and perhaps even charisma. Yet, as our industry continually reshapes itself in response to new trends, regulations, and societal shifts, are these conventional elements enough? How can we identify those uniquely malleable and adaptable leaders who not only keep up with the pace but also chart new courses? Let’s delve into some less-trodden paths of the interviewing process, designed to reveal the truly dynamic individuals who can effectively lead in our ever-evolving tech landscape. Buckle up as we explore a fresh approach to assessing seniority.


The first thing that you should make sure to include in your interviewing process is an assessment of agility. Especially given how things always seem to be progressing faster, any leader has to be adaptable and malleable. You don’t need a battalion of cheese sentinels (that is, people who ensure no one’s moving any cheese).

For example, you can ask them about a recent change in the industry, such as a new regulation or a technological advancement. How have they reacted to it? Or, how have they reacted to a radical change of scope in a project that was already underway in the past? And, of course, there’s always the possibility of asking people to describe how their leadership has been affected by COVID-19, from when it started till today.

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Industry Awareness

In fact, each leader has to be aware of several industries. The bare minimum is the leadership profession and the company’s market. So, assess both.

The former is about being cognizant of what leadership means and different approaches. So many leaders were simply promoted one day and never bothered to actively learn what the role entails. There’s no reason to be a trend chaser, but they should at least know what’s “the talk,” just as I would expect an engineer to be interested in new libraries.

For a connection with the company’s market, that’s not always as easy to check because their previous industry might be different than yours. However, for high-profile positions, I think spending some extra time to be ready for this is worth your while. My habit is to leverage my different newspaper subscriptions to search for news about their industry and draw a question or two about it. Has there been a big merger? Maybe a public company has had to back off from its strategy. If they’re not aware of any of this, they just might be disconnected from the value of what they’re doing.

Risk Aversion and Innovation

One cannot maintain an edge while being afraid of making any changes. To be at the leading edge (the name of my free community), changes, experiments, and risks must be managed. Thus, I like asking for examples of risk management in the past. Leaders should be calculated, but if that is translated to extreme buffering of any deadline, it will create a culture of low expectations.

Similarly, when considering innovation, I’d like to hear about cases where they’ve placed a bet and how it turned out. If it failed, how did they react? Do they learn from failures or just learn to give up to avoid failures?


Lastly, given that leaders ought to provide positivity in an organization and help people believe the impossible is possible, they should have an optimistic viewpoint most of the time. In my books, I’ve called this the Executive Mindset, which means that leaders should act as energy sources. The person sitting in the back of every meeting and telling everyone that the project’s doomed? That’s not a leader.

So, talk a bit about the future and get a sense of the person’s viewpoint. For example, do they feel society is doomed because of TikTok and Twitter? Will we all lose our jobs to AI, or is it genuinely an opportunity? Is the fact that it’s more challenging right now for startups to raise funding a daily obstacle, or can they see the cup half full (“we can create real businesses again”)?

My personal experience shows that leaders who possess these skills are often more likely to succeed than others who are more knowledgeable in a specific technical vertical or have more experience. There are things that are not easily taught. By the way, the same applies to a good sense of humor, or speaking several languages. Don’t just look to check the obvious boxes when interviewing. Look for those things that will matter when push comes to shove.