In Working With Others, How Do You Challenge Them To Make Them Better?

Leadership Lesson: Although leadership is about working to eliminate and minimize environmental, developmental, and mission-related obstacles, making someone or something better in the course of that work, it can’t be fully effective without challenging those who are led.

The leadership of yesteryear – coordinating people to carry out cookie-cutter, repetitive tasks that benefit a mission or organization – is long gone.

Even though most workplaces have evolved past that type of work and mentality, as time goes on, there is even more to leadership than just getting the best results. It’s not only about the task at hand but also about what is built for the future, in both the organization or group and the people carrying out the work.

Leadership is about getting the best out of resources, whether that’s in the form of capital assets, the tools of the trade, or the people that make it all possible.

And the very best leaders are those who elevate the performance and/or results of everything touching her or his business or mission.

And that’s especially true when it comes to the people being led.

When measuring a leader’s effectiveness and legacy, it is not only the mission’s results, which should be measured, but also how well those being lead would be able to maintain, utilize, and evolve the mindset which allowed that environment and culture to be created and to thrive in the first place.

Related: The Leader’s Legacy: How Do You Determine How History Will Remember Your Name?

And a leader’s ability to elevate performance can occur in many ways, whether it’s through passive or proactive exchanges.

One example of a passive tool people use to learn, whether they realize it or not, is the process of watching their leaders. They scrutinize and analyze the value of the example their leaders provide. Everything they’ve witnessed, if absorbed and harnessed, leads to a trickle-ripple effect — the impact trickles down to those being lead and subsequently ripples out in the actions of everything they do.

But that ripple effect of influence should go beyond passive witnessing in the environment. It can have an impact through a more proactive effort.  

So how can we proactively get the most out of those around us, whether we’re a leader or not? How do we get the best out of those around us?  

How do we challenge others to be the best they can be and deliver the best they’re capable of? 

Going beyond merely training or teaching, here are some of the ways we can challenge others, no matter what our leadership position may be. 

Refining What They Do 

Part of making someone better is not only providing them with new tools and knowledge but also refining what it is they already bring to the table. Impacting someone should not stop at providing them with the new but should also go one step further to refine what they can currently do.

This refinement comes in the form of questioning current mindsets and ideas, leading someone to defend what it is they believe and what they can do. What they bring to the table is their foundation, so it makes sense to ensure what is built upon is sound and reinforced.

Asking For More 

Beyond refining what someone is currently capable of, it’s important to support someone beyond what they’re currently providing. That’s where the growth and development exist – recognizing what someone can bring to the table and asking them to share it in the environment for the mission. 

These may be skills which aren’t necessarily called for by the current responsibilities but which should be harnessed anyway due to their likely positive impact. We need to make sure someone brings everything they can to a position. This process enhances who the person is and brings improvement to the mission through a diversity of skill sets.

Pointing Out What They Don’t See 

Beyond refining someone’s approach and asking them for what they haven’t necessarily put forth, there’s also pointing out skills they’re not even aware they have.

This identification comes in the form of getting to know people, watching them, and taking stock of how they work. Too often, people have skills they’re not necessarily aware of or for which they don’t give themselves credit.

Following Up 

The last, general piece of challenging someone to make them better is following up. Working closely with someone means regularly and frequently touching base to make sure things remain on course, whether that be a project, a responsibility or duty, or their own development.

This comes in the form of accountability. We need to make sure people are keeping to what they say they are going to do. Lack of accountability is part of what leads to the breakdown of progress. We can’t say we want something at one point in time, without following up to make sure we’re working in the right direction thereafter.


Supporting someone doesn’t mean taking it easy on them as they make their way. We need to challenge others in a developmental way.  

Challenging is a form of respect. It is a form of commitment, investment, and honesty.

It is a form of transparency. It demonstrates completely what goes into developing someone. The person being challenged understands exactly where they stand, both in the eyes of those around them and in their own career and development. 

Nothing is left on the table. Every skill, ability, and idea can be taken into account. Most everything that is applicable to the environment can be provided. (I say “most” because you can’t capture absolutely everything, no matter how hard you try. One also has to be reasonable in the expectations for those being challenged.)

We need to get better. We need to make others better. We can — and should — do that for each other.

Related: What Kind Of Environment Does Your Leadership Leave In Its Wake?

It’s there for the taking, if we want to step up and make others — and ourselves — better. 

Go out. Challenge and be challenged.



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