3 Leadership Skills Only Learned the Hard Way

leadership, professional development, business coaching, executive coaching, life coaching, failure

Some lessons and skills can only be learned the hard way.

Making sure the projector bulbs work before that big presentation is one. Withholding your wardrobe opinions with your wife is another. Making sure you bring your phone charger on a trip another.

There are also a few serious lessons that effective leaders must learn the hard way. In fact the hard way is the only way these lessons and the ensuing skills are ever learned.

They must be experienced, not explained. Caught not just taught.

Grieving Loss

If you lead a business or an organization of any size there will be losses – be they deals, battles, alliances, partners, businesses, customers or vendors.

Most great leaders have been shaped by their losses as much if not more than their victories. Lincoln lost a child, and a key election. Jefferson lost his wife and only two of his six children made it to adulthood. Steve Jobs lost his job and his company. Nelson Mandela lost his freedom.

It becomes a core leadership skill to suffer and grieve loss, and yet keep moving. But words like tenacious and persistence that adorn the motivational posters are glib and shallow antidotes to the true challenge of loss.

Grief is an unfavored task. The inner struggle of grief is ugly, unpredictable, and emotional. That is why the impulse is to either ignore loss or be totally consumed by it. But leaders who go there find a resupply for their interior world. It profoundly changes their leadership.

But it is a lesson that can only be learned the hard way.

Tolerating Ambiguity

When the conflicting perspectives overtake certainty, directions are vague, the data incomplete yet you must act before the outcome is clear. That is ambiguity, and it demands movement without guarantees. It is where leaders must grapple with an uncomfortable fickleness and unpreparedness.

Here we can note the likes of Kennedy during the Cuban missile crisis, Reagan during the height of the cold war. Google has navigated enormous ambiguity in their business models while the true value of search engines evolved. And Elon Musk (Paypal, Tesla, SpaceX) would likely have a thing or two to say about it.

While you might prefer to hide behind analysis or to power forward blindly on ego, the greatest leaders are able to remain suspended in the middle ground of uncertainty, curiosity and unresolved issues yet keep moving forward.

If loss requires movement amid grieving, ambiguity requires movement without guarantees.

The old maxim “nobody dangles gracefully” is the underlying sentiment. And it is a hard lesson to learn the hard way.

Navigating Unfairness

The third life lesson has to do with the inequities and injustices of life. The partisanship, biases and special interests that favor against your leadership.

They are going to happen in one’s leadership tenure. Guaranteed.

If the first two require leading amid loss and leading without guarantees, this one requires leading with the tide against you.

Maturing as a leader means not letting the inequities lead you, but accepting their reality as merely the context for your decisions and actions.

Leadership examples abound in this category, from Martin Luther King, Jr. in the US to Vaclav Havel of the Czech Republic to the steps Microsoft has taken against technology piracy in China.

Just because things don’t go your way does not mean you are a poor leader. In fact that is when leadership truly begins. Any leader who can relate to these three life and leadership lessons have this in common.

They learned them the hard way.

The lessons may not have been pleasant, but have served well to confirm and establish their leadership capacity in ways a classroom could never have taught.

Please note: I reserve the right to delete comments that are offensive or off-topic.

  • Sandy Rees

    Great stuff Brad. You’re right about great leaders grieving loss. I forget sometimes that in order to reach the good stuff, sometimes you have to go through deep valleys and dark shadows.

  • Thanks Sandy. And you’re right…it is easy to forget the hard parts are part of the journey to the good parts.