In many ways, talent management systems optimize not for the best talent, but for those who have made the safest choices. Legacy company leaders are essentially politicians. If you overlook the last decade or so, the typical path to political success was not necessarily in driving any inspiring agenda, but by avoiding land mines. 

There are substantial land mines that should be avoided (moral, ethical), but we often fail to separate those from simple innocuous gaffes or butt fumble moments that make for viral memes. The best leaders, true visionaries, aren’t afraid of the ladder. Kunal Shah often talks about how being shameless is a core ingredient to being impactful, because being shameless allows us to ask “what if?” without any fear of judgment. Baseball Hall-of-Famer Lou Brock captured this best:

Show me a guy who’s afraid to look bad, and I’ll show you a guy you can beat every time.

But recruiting processes are hellbent on identifying the butt fumble moments where someone looks bad to eliminate candidates rather than identifying high-potential traits and adapting to accommodate them. I’ve written before about job descriptions with split personality disorder and job postings that are essentially looking for individual parts to be a whole. But we’d be much better off if we settled on a few key traits we are seeking and find the best candidates at those, rather than simply eliminating people because of some context-dependent red flag. Far too often we fail to consider that someone’s red flag–a failure, a firing, or otherwise–is not due to any character flaw, but could simply be due to their willingness to stretch themselves, take on an uncomfortable challenge, or stand on principle.

Yet, most companies value perceived safety, and if you look at most C-Suite executives, you won’t see any failure. You know what you also won’t see? Any real risk. It is important to balance internal talent progression with external recruiting, and this topic alone is worth a future deep dive. But when many CEOs, for example, have been in their same company for much, if not all, of their careers, what does it say about their tolerance for outside-the-box thinking and risk? They’ve never been uncomfortable, and despite words like fail fast and other cliches adorning posters around the office, they’ve spent their entire careers in the safety of a big company. They learned how to play the game in a particular corporate culture, and winning is all they’ve ever known. Is this because they are truly superior talents, or simply that they’ve never really tried to push themselves beyond their comfort zone?

I have met some of the former and plenty more of the ladder. 

As a huge design thinking advocate, I’ve become familiar with the closely-linked concept of Integrative Thinking, and recently read The Design of Business. One of the underlying implications is that every decision we make in business has a range of consequences, both intended and unintended. 

When it comes to talent progression, for all of the benefits a company gets from “lifetime” employees as leaders, there are two very-real challenges that emerge:

  • Lack of empathy 

When all you’ve ever really done is win, it can be really hard to empathize with people who struggle (no matter how valid the reasons for their struggles are). I’ve found that executive leadership teams often have an extreme external locus of control when it comes to evaluating team members, and fail to see how someone struggling with onboarding, for example, is more of a reflection on their leadership than it is an indictment of the newcomer. 

In one company I worked for, nearly 20% of new joiners to a particular organization failed probation, without the team’s head ever being questioned. To me, it goes without saying that this accountability goes squarely to the head, who is either failing to give clear instructions and set expectations, failing to give effective real-time feedback, or failing in the recruitment and interview process.

  • Perceived threat

When you’ve spent decades in an organization, through cycles of ups and downs, it is natural to feel a sense of entitlement when it comes to advancement. You’ve paid your dues. But this also means that, while you’ve become very well-versed in the way one company does things, you undoubtedly have blind spots to other strategies.

This is where outside recruitment comes into play, and it’s an eternal challenge to integrate talent at intermediate and senior levels with lifetime talent. I’ve often seen, somewhat understandably, incumbents take a hostile, competitive approach with incoming talent at similar levels of the org, based on the zero-sum mindset outlined above, wanting to protect their empire.

This is not to say that a leader can’t be effective without having experienced a significant failure in his or her past. But to truly be effective, and to be able to balance learned company experience with outside knowledge, it’s important for the leader to build an environment in which both paths can co-exist and thrive. And rather than recruiting the perfect resume, past failures should be lauded as signals that someone is humble (nothing humbles you quite like significant failure), comfortable with uncertainty (almost every job description talks about “dealing with ambiguity”) and open-minded to trying new things.