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The Harsh and Surprising Reality of Being a Leader

Published on October 2, 2017 12:00 AM EST
Harsh and Surprising Reality of Being a Leader

“This sucks!”

As soon as the door closes and Susan is alone again in her office, she’s filled with a sense of disappointment. Susan has just completed a performance review with one of her direct reports, and the conversation was a tough one. The entire week has been dreadful; Susan had many difficult meetings, and one of her top-performers resigned.

Harsh and Surprising Reality of Being a Leader

In fact this last year, Susan reflects, has been the toughest of her career. It’s surprising because she was recently promoted, and was the perfect fit for this job. Everyone was excited for her to take on a much larger business responsibility. She was qualified, capable, confident, and had managed to steadily help the business grow faster than any of her peers.

Susan still loves the business development part of her job. She continues to give it a significant amount of attention and energy. She thrives when she’s out with clients and prospects, looking for new opportunities.

Admittedly, spending time growing the books out of the office is also an opportunity for her to get away from one aspect that came with her new role: That of a people leader. Despite her previous success and deep knowledge of markets, clients, and the organization, she’s been struggling to find steady ground being a leader.

Frankly, she hates this part of the job. What’s worse, she knows that her team doesn’t think of her as a great leader. They don’t say it – but she can tell.

Harsh and Surprising Reality of Being a Leader

Why Many People Fail at Being a Leader

Susan’s story is not unique. On the contrary, it’s quite common, as Daniel Goleman pointed out in his 1996 article “What Makes a Leader?” The article describes the phenomenon of highly intelligent and highly skilled business people who assume leadership responsibility as part of a career move – and fail at the job.1

Goleman’s article introduced the idea that emotional intelligence was the critical ingredient to being an effective leader. Years later, the phenomenon of people failing at being a leader (even if they’re successful business people) persists today.

I’ve been curious to understand why. Working in a position where I have the privilege to interact with leaders on all levels in many different organizations, I’ve started asking questions. Here are my most interesting findings:

People choose career advancement, not people leadership. They assess their managerial fit, not their leadership fit.

These days, it is widely known that managing is different from leading. However, for many of us, when presented with the next opportunity on the career roadmap, we focus heavily on the management skill-fit while the leadership fit falls to the wayside.

We make sure we are a perfect fit for the position – that we have all of the analytical, strategic, technical, and problem-solving skills necessary – and give ourselves a thorough assessment. Meanwhile, less thought goes into the leadership role and our current capabilities (or lack thereof) in that area.

Harsh and Surprising Reality of Being a Leader

Sometimes, we justify our leadership abilities with: “I’ve led a few people before – that should do it.” Think of your first career move into a broader managerial role that came with people responsibility. Did you ask yourself these questions?

  • Would I be a great fit for providing direction and aligning my team to the organization’s/unit’s strategy?
  • What’s my experience with providing purpose? With inspiring and motivating others?
  • What have I seen work for growing others, and how can I support them in shaping their careers?
  • How easy or difficult is it for me to gain the trust of others?
  • Do I have a practice for staying emotionally balanced, especially under stressful circumstances and during change?

For some of us, leadership comes naturally. For most, however, it’s hard – even under the best of conditions. It takes us by surprise when it really shouldn’t. This is because being a leader is NOT easy.

It is complex. It can be frustrating. It is time-consuming. It’s about emotions and expectations. Leading people is about mobilizing and optimizing the talent and skills of yourself and others in order to achieve results. The good news is: becoming an effective leader can be learned.

Being an effective leader isn’t tough – but becoming one can be.

“If only I knew” or “I wish someone had told me before going into the role” is what I hear most often when talking to people about their journey to becoming a leader. These days, organizations address the need for better leadership training by offering development programs for aspiring leaders.

As a Senior Vice President for Talent Development at a global software firm put it, companies want people to know what they’re getting into BEFORE they get into it. But don’t assume that such programs can replace the need for setting realistic expectations of what it means to succeed at leading people.

I recently facilitated a week long first-level leader development program and invited Alan, a program alumni with whom I had stayed in touch with since he went through it four months earlier. As he shared with the group how his effectiveness as a leader had started to take shape since the program, a strikingly simple, yet powerful message surfaced:

Alan had made the choice to become a more effective leader. As a result, he was willing to give new things a try.

Harsh and Surprising Reality of Being a Leader

He allowed himself to fail, then try again, and trust that it would get easier as he practiced. He focused on a few specific areas where he wanted to improve. He committed to working on these priorities until he mastered them.

One particular trait Alan practiced was leading one-on-one meetings. He asked questions and listened attentively, rather than talking most of the time.

“When I try something new these days, my team asks ‘is this something you learned in the leadership program?’ Then we all laugh about it. They don’t expect me to get it perfectly right the first time. But they notice the difference. They recently came back from a cross-business activity and told me that our team culture is the best.” – Alan B., first-level leader at a global software company

That choice sounds simple, but I’d argue that it is NOT an easy one. It takes courage. Not only because of the vulnerability that it shows, but because there’s typically little organizational tolerance or patience for being a newbie or for trying things out.

But there should be. Alan’s approach is like rapid prototyping for being a leader. At its core, it is Alan’s expectation of himself – that even though he might not be the perfect leader the first time, learning is essential – which ultimately sets him up for success.

If a one-on-one experiment goes just OK, he learns something. If it goes well, he also learns something. In other words, regardless of the outcome, he learns, and pretty fast, too.

Ultimately, the leaders that I spoke with concluded that they would have gone for that job opportunity again, but they would have approached the leadership role that came along with it differently.

Instead of giving their management muscles that extra workout, they would have spent more time earlier in the new role shaping their weaker leadership muscle.

Also, instead of assuming success from the get-go, they would have gone in with a healthy beginner attitude.

“Exemplary leadership is not a thing – the correct genes, an appointment, a technique, or the chance of the draw that favors one individual over another. Exemplary leadership is a way of being, whether you’re leading others or leading your own life. Leadership can be developed; it’s a choice and an option.”- Richard Strozzi-Heckler, ‘The Leadership Dojo: Build Your Foundation as an Exemplary Leader’

2 Powerful Techniques To Help You In Being a Leader

Harsh and Surprising Reality of Being a Leader

There are two powerful techniques for learning to be an effective leader. By allowing yourself to be a rookie again, and learning to fail forward when facing your most pivotal leadership moments, implementing these techniques can help you be the best leader you can be – even without a lot of experience.

The first technique is running a mental stress-test of a pivotal leadership situation before going in. It’s called a Pre-Mortem. It is a powerful method where you prepare yourself for MULTIPLE outcomes, as opposed to fixating on one particular outcome against which you define success or failure.

The second is called an After-Action Review, a technique used by the military to determine the delta between what you expected to happen, and what actually happened. Here’s what the combined approach looks like:

To do a Pre-Mortem of a pivotal leadership moment, ask yourself:

  • What are all the things that can possibly go wrong in this situation? List everything that comes to mind.
  • For each “failure”, what can I do to prevent this from happening? Go back and forth between 1 and 2 to make sure you identify ways for each failure to be resolved.


To do an After-Action Review, reflect on the following:

  • What did I expect to happen?
  • What actually happened?
  • What could explain the delta?
  • What would I do differently next time?

Being effective as a leader can be learned. But it takes the courage to be a rookie again.

For someone like Susan, it might be difficult to feel motivated to give leadership effectiveness another try. The real piece of work would be herself. Alan’s story makes this very clear. His team didn’t change anything.

Their team dynamics and performance changed because of how Alan changed his interaction with them. The team then had the opportunity and space to respond differently to Alan and to each other. Whether or not something similar is worth a try is for each person to decide individually.

Some food for thought, however, comes from Marshall Goldsmith and Mark Reiter’s intriguing finding in their latest book, Triggers: Sparking Positive Change and Making it Last. As part of their research, they asked people the question, “What’s the biggest behavioral change you’ve ever made?”

The most poignant answers came from people recalling the behavior they should have changed – but didn’t. They’re reflecting on their failure to become the person they wanted to be.2

Don’t let the same be said of you. It is okay to be in a learning mode. In fact, have fun with it. It will be rewarded with people wanting to work with you, and be led by you. 


1)“What Makes a Leader” by Daniel Goleman, Harvard Business Review, June 1996

2)Triggers: Sparking positive change and making it Last by Marshall Goldsmith and Mark Reiter, 2016

Harsh and Surprising Reality of Being a Leader
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