Meet “Low-Confidence” Jessie and See How She Turned into a Stellar Contributor

3-min. read

I once had a team member whose self-confidence was so low that she hardly could get anything done.

Her name was Jessie, and she eventually turned into one of my top performers.

Low self-confidence can be devastating: It makes things impossible to start and impacts how honest you can be in any relationship and with yourself.

Jessie was the kind of person who’d constantly seek out mentors and advisors. She’d be reading and watching self-improvement content from so-called life coaches, hoping their positive mantras would eventually get her on the right track.

But that didn’t help. Things came to a point where I had to consider putting her on a PIP (Performance Improvement Plan). If you’re unfamiliar with such practice, it is usually the last thing to happen in Corporate America before you get fired.

A PIP usually doesn’t solve much: it looks more like an ultimatum with a set of results to be achieved within a particular milestone. And if you don’t deliver, you’re out.

Instead of hitting those nails in the coffin, I decided to take a more compassionate approach to guide Jessie toward improvement. So, we established working sessions to address her low confidence triggers.

Here’s what I discovered:

1. Jessie stressed over the uncontrollable

When you have to solve a problem, you usually start by deciphering it into root causes to be analyzed. You can control some of these causes, but there are others you can’t.

Jessie was highly capable of doing such analysis. Still, I soon realized that once she had identified the root causes of a problem, she would obsess over what she had no control over. Her mind froze over questions like what would happen if consumer confidence dropped or if the boss wouldn’t like her proposal. Her chronic worry was paralyzing her.

So, we started to work together on her ability to accept feeling helpless. As her manager, it was key for me to state out loud that it was okay not to have an answer on how to address the dependencies that were out of her control.

It helped Jessie move out of her anxiety and free much-needed brainpower.

2. Past mistakes haunted Jessie’s mind

Reflecting on past mistakes is vital. It gives you perspective and makes you smarter.

However, I discovered that Jessie was constantly ruminating on her past mistakes. It was not healthy anymore. She wondered why she had made bad decisions years ago and felt like a failure.

I started to hammer down on a well-suited motto for her: “No shame, no regrets.” What was done was done, and she couldn’t change these past decisions.

It was easier said than done. But with my permission, Jessie’s attention started moving away from past guilt and towards the tasks at hand and what needed to be done now.

3. Jessie was wandering aimlessly

Whenever I met Jessie, I couldn’t help but think about that song on Brainwashed, George Harrison’s last record: “If you don’t know where you’re going, any road will take you there.”

Jessie was not alone. Many of us go with the flow, not thinking much about what we want. If we are not careful, our ambition takes a toll, hurting our self-confidence.

That one was the toughest for me to help Jessie with. After all, who you want to become and where you want to go are deeply personal points.

So, I invited Jessie to systematically map in her mind any of her ideas to an end goal, a desired destination. She didn’t have to share these with anyone else.

Yet, to my surprise, Jessie soon started to speak up at our meetings, articulating how her ideas were feeding her vision of what success looked like. She then extended the practice to team meetings and started to accept different perspectives without being destabilized.

By addressing the root causes of Jessie’s low self-confidence, we saw significant progress within a few months. The need for a Performance Improvement Plan became irrelevant, and Jessie began performing at a high level.

Over time, Jessie’s newfound confidence and clarity propelled her to a director-level position. 

Jessie learned to master her low-confidence evils by focusing on what she could control and clarifying what she wanted to get out of her work.

As her manager, it reinforced to me the importance of fostering an environment that prioritizes personal growth for team members, acknowledging constraints, and helping them envision goals to overcome their self-confidence challenges.

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