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The Leadership Blind Spot: When “They’re Not Ready” Is Really About You

  • December 3, 2025
  • Matt Dickerson
“They just need to build the skills needed to advance. But honestly, I just don’t think they want to put in the hard work.”

It was the fifth or sixth coaching session of a yearlong engagement. As often happens in coaching work, the real problem or disconnect is buried under several rounds of “the real problem is.” It was clear that we had reached the root of the disconnect.

Aaliyah was and is a very successful businessperson. She graduated at the top of her class at a prestigious university and was widely recruited by start-ups throughout the tech industry.

She had gained significant clout in a very short period of time and was widely believed by those at her company to be one of the preeminent experts in their field. She did everything that was asked of her and found other proactive ways to contribute.

“I Never Needed to Be Pushed”—A Common Leadership Trap

“You know, when I was coming up, I never had to be pushed. I worked the long hours, I asked all the questions that needed to be asked, and I took on anything that people put in front of me. I always knew that I needed to advocate for myself and do everything that I was asked to do.”

“Why do you think that is?” I asked.

“Because I knew I was exceptional and I could tackle anything put in my way. I don’t want to sound boastful, but I have the tools and skills to execute at the highest level in this field.” She exuded pride in what she had accomplished and what she was capable of doing. I believed her.

“How does that compare to others?”

She chuckled. “If I am being honest, Matt, I don’t think I have met too many people that I would compare myself to.”

“So, you are a bit of a unicorn, yes?” I asked partly in jest but also to assess my understanding of what she was sharing.

“Yes. Simply yes,” she said as she let out a breath.

“How reasonable is it for you to expect those around you to be… well, you know, you?”

“It’s not, I suppose.”

I continued, sensing we had found something together. “And if you don’t invest time, energy and effort into training them, how much more unreasonable does your expectation become?”

The Leadership Accountability Gap (via Brené Brown)

Brene Brown, in her most recent book “Strong Ground,” sheds some light on this issue in many organizations. She says that when leaders are trapped in this cycle of “they have to prove it” or “they have to find the answers,” they may eventually come to a rude awakening. When they realize that they are to blame for others’ lack of growth, “they can feel shitty because they have not invested in the skills-building that their employees need, and they’ve spent hours, days, months or years attributing the lack of skills to their employees’ attitudes, interests or level of concern.”

In other words, if employees are not meeting the expectations of their professional promise, the blame for underperformance shifts from the individual to those responsible for showing them the way.

A Changing Workforce: Why This Matters Even More Today

Brene Brown goes on to discuss the generational aspect of this that makes this concept more and more important to strong leadership today. As the workforce continues to skew to a younger demographic, it is also true that there is a greater percentage of the workforce who demand this kind of support and upskilling.

Leaders in all industries are going to be able to adapt more quickly than others if they can adapt their thinking.

If they are not getting what they need from members of their teams, it is not because those who are underperforming are lazy or impatient or lacking in self-efficacy, at least not as a default. It is more likely that they are interested in being shown the way.

I worked with Aaliyah to determine a few small steps she could take in between our sessions to move toward the type of support her team members might require.

Our next session was highly productive. She iterated her two small action items and was surprised by the impact.

Small Support, Big Impact

Here is an example that came out in our debrief from the past two weeks.

“I was really surprised,” she said with an unusual bolt of enthusiasm. “I have a guy on my team who I really think just doesn’t have it in him to be successful here. I have routinely been disappointed by his inability to see a few steps ahead on the projects that involve him.”

I was curious where this would go.

She continued, “So, I took to heart the commitment I made leaving our last session. I asked you to hold me accountable to taking one small step toward the one person who I think is experiencing the largest gap in execution. Zach immediately came to mind.”

“So, the next day, I carved out 15 minutes to get on a quick Zoom call. I told him that I wanted to support his work and wondered where he had questions. I invited him to pick the one area or set of tasks about which he felt less confident in his current work. To my surprise, he identified what would have been my answer, too. I asked if I could try to help him there. Ten minutes turned into closer to twenty, but once I started to share some instruction, it was clear that he was taking our time seriously.”

“That sounds like a great discussion,” I affirmed.

“Yes, and the most surprising thing about it is that in the three to four days since, his production has doubled, and we are finding far fewer errors in the work. That 20 minutes will probably save me and my team six to eight hours just this month. And I see a different side of Zach that makes me excited to have him on the team.”

Once Aaliyah made even modest steps in the direction of equipping Zach with follow-up and guidance, Zach had the foundation to show up more effectively for everyone in his sphere of influence.

Reflection for Leaders

What do you do to actively participate in someone else’s professional growth and how do you view your responsibility in this area? How has that been challenged or affirmed by this blog?

Move From Insight to Action

If this message challenged your perspective on leadership, I’d love to continue the conversation:

  • Schedule a Call with Matt via Calendly
  • Email us at  matt@mattdickersonvalued.com
  • Connect on LinkedIn and start a conversation

No obligation—just a chance to explore how clarity can be your foundation for better decisions, confident leadership, and thriving teams.

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