Photo by Markus Spiske on Unsplash

Why We Pick The Wrong Leaders

Brendan Sapience
6 min readFeb 24, 2021

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One of the most common misconceptions about management is that years of experience correlate to quality: This is why at least 90% of job posts for managerial positions have explicit requirements on the minimum number of years in leadership.

Why is this a persistent belief? Simply because like in any other field, it is generally assumed that practice makes perfect... It is obviously not true for leadership otherwise there wouldn’t be as many tenured leaders out there that happen to be absolutely terrible at it.

It is especially weird since finding a new leader is generally considered a high stake & high impact decision for organizations: Get the wrong one in and attrition will go up, morale will go down and productivity will tank; get the right one in and wait for issues to sort themselves out.

What we get wrong

It starts with how we pick leaders: Hiring teams usually dip into one of 2 pools: the outdoor pool of external candidates coming from other organizations and the indoor pool of internal talents ready to take on new responsibilities.

The outdoor pool

This is where the years of managerial experience and the size of the former teams is considered a critical requirement:

“He’s managed at least 40 people for 10 years in a successful organization, he must be good at it!”

The problem is that neither of those metrics is a proper measure of how good a leader actually is.

Equating past experience to quality of leadership means trusting an unknown organization (with other priorities and a different hiring team) to have made the right decision in promoting the candidate to management in the past.

It is certainly the easiest thing to do since it doesn’t require a ton of extra vetting but it makes no logical sense to delegate such an important vetting process to an unknown organization.

The indoor pool

With internal promotions, it isn’t much better: It too often boils down to a combination of an individual contributor being considered successful and good timing (like sudden growth, an unexpected departure, being in the right place at right time, etc.).

“She’s exceeded her quota consistently by 200%, there is now an opening so let’s give her a chance to drive the same success in others!”

This type of thinking is appealing (after all, such a solid performer should be rewarded!) but quite flawed because the measure of success for an Individual Contributor has nothing to do with important leadership traits like humility, charisma or empathy.

For instance, in organizations where obedience through hierarchy is expected, a “Yes Man” can appear very successful... however, if promoted, he will typically make for a poor leader because his priority will be to conform instead of fighting & working for his own team. Not the leadership anyone needs.

What we don’t do well

A secondary issue is that most organizations don’t seem to invest in upskilling their existing leaders. So how exactly are they expected to become good at it?

For most companies, leadership enablement isn't a priority at all precisely because they assume their leaders to already be good at it (“they all have years of experience!”): if the organization is growing fast, why spend time & money teaching a skill people already own?

There is also seemingly very little done around accurately & systematically measuring leadership effectiveness by establishing targets on attrition rate and normalized employee satisfaction scores.

Photo by Thirdman from Pexels

So what should we do?

Instead of focusing on Past Experience & Team Size we should consider more actively measuring Attitude & Potential by looking at some of the traits that make a manager a good leader:

  • a balance of confidence & humility
  • a balance of toughness & kindness
  • adequate personal motivators

Ask them how they learned to lead

Leadership isn’t an innate skill: no one is born with an outstanding ability to ignite and fuel an internal commitment from others to rally around a common vision.

People who become really good at it only get there by knowing they can improve and actively seeking to learn, they usually have interesting stories of introspection and reflection that propelled them forward.

“How have you grown as a leader since you started your journey?”

If the answer is enthusiastic & detailed, chances are that the candidate routinely goes above and beyond to own & refine their managerial skill set. If the answer is short & rudimentary, perhaps they are unlikely to have spent any significant time asking themselves the right questions.

Ask them for past employee references

It is common to ask for a reference from a past employer or a former manager but very rare to see a hiring manager ask for former employee references.

“Please provide us with a couple of references of people you have directly managed before.”

This would only apply to people with past managerial experiences but when vetting out a candidate’s potential to manage, why not ask people having experienced it before?

Ask them what past mistakes they made

It takes some humility and honesty to recount past mistakes in front of a stranger during an interview. The only thing that makes failures of the past easy to admit and explore is having consciously learned from them.

Since there is no innate leadership skill, it is important to understand if the candidate is capable of introspection and self-propelled growth.

“What leadership mistakes have you made and how did you realize them?”

Good leaders typically consciously convert mistakes into learning experiences and their journey is always worth exploring in detail.

Ask them what they read

People who actively seek to improve on their leadership qualities do so by going down every available learning avenue they see and more often than not, it means finding & reading books.

“What books on leadership & management would you recommend someone?”

Ask them what they have read and what they recommend (and why), you will often get an enthusiastic and detailed answer… and additional titles to add to your own reading list.

Ask them about the most satisfying part of their job

When vetting out a potential leader, it is important to understand what their motivators are. It could be money, power, influence, the respect of peers, feeling like the smartest person in the room, winning on numbers, teaching others, the approval of management, etc.

“Tell me a few aspects of your past job that made you proud.”

Someone’s drive is always a mix of several motivators therefore understanding its finer composition is difficult in the relatively superficial context of a job interview... but one way to indirectly peek is to ask the candidate what aspects of their previous job make them particularly proud: it almost always reveals what is important to them and therefore what their actual motivators are.

Photo by Miguel Á. Padriñán from Pexels

Leadership is NOT the only career path

People management is often seen as the only way to climb up the ladder and is therefore seen as a reward for the best & most productive team members, but this is a mistake: everyone can become a boss but not everyone can become a good leader.

Focusing on measuring the right leadership attributes when hiring or promoting along with building alternate career paths that do not require people management is a necessary key ingredient to scaling organizations well and preventing both general discontent and attrition.

I started my own leadership journey in 2010 because of good timing and a vacancy. The vetting process I went through then consisted of a 15-minute phone conversation with a single person and none of the questions I was asked had to do with my potential to lead others. Of course, I will always be thankful for the opportunity I was given; however I gladly recognize that the team I led then deserved a more thorough examination of my potential: every team deserves a good leader and every organization needs them to grow well.

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Brendan Sapience

NY based technology executive with an passion for coaching & growing people, building bridges across cultures & playing with fluffy dogs