5 Signs Your Managers Need a Leadership Development Program (Not Just a One-Day Workshop)
If you're an HR or People leader, you've probably been here before: a manager gets promoted because they were great at their job. A few months in, their team is frustrated, engagement is slipping, and you're fielding complaints you didn't expect.
It's not a performance problem. It's a leadership development gap, and it's more common than most organizations want to admit.
Jeremy Jones-Juliá, CultureAlly Director of Learning and Development, and experienced Leadership Coach
Leadership coach Jeremy Jones-Juliá has seen this pattern play out hundreds of times. With over 15 years of experience designing and leading national leadership development initiatives and executive coaching programs, he explains: "The most common shift I see is that new managers still feel personally responsible for being the strongest technical contributor on the team — rather than stepping into the leadership role and achieving results through coaching and delegation. That pull is real, and it's understandable. But it leaves them without the time or headspace to develop strategy, invest in their people, or focus on what the team actually needs from a leader."
These gaps have clear warning signs. And once you know what to look for, you can address them before they cost you top talent, team cohesion, or organizational momentum.
Here are five signs your managers and leaders need structured leadership development and what to do about it.
Sign #1
Feedback Conversations Keep Getting Avoided
You hear things like: “I don’t want to make it awkward.” Or a manager waits until a formal review to raise something that should have been addressed months ago.
From Jeremy’s perspective, “Feedback avoidance usually isn't about not caring — it's about not having a reliable way to deliver it. Most managers default to waiting for a formal review or a scheduled conversation, thinking that's the 'right' time. But delayed feedback almost always lands harder, not softer. What I hear most often when I ask why they held back: they didn't feel confident they could deliver it constructively, or they weren't sure it would go well. The avoidance isn't laziness — it's a skill gap.”
Avoidance is one of the most common and costly leadership gaps. When managers aren't equipped to have direct, honest conversations, small issues become big ones. Performance stalls. High performers disengage. Resentment builds quietly.
Leaders coach more than they direct. Without the skills to do it well, most default to saying nothing at all.
What this looks like in practice:
Performance issues that drag on without a direct conversation
Feedback that only happens during annual reviews
Managers who are liked but not trusted to be honest
A culture where people don't know where they actually stand
What it signals: Your managers need a structured approach to coaching conversations and performance feedback. One they can use repeatedly, not just reference in theory.
Sign #2
Conflict Gets Avoided or Escalated. There's No Middle Ground.
Healthy teams disagree. The difference between a high-functioning team and a dysfunctional one isn't the absence of conflict, it's how conflict gets handled.
Jeremy typically sees two distinct environments. “In one, the leader has tools and practices in place — they work proactively to reduce unnecessary conflict and know how to navigate it when it does show up. In the other, conflict gets avoided until it can't be anymore, and then quick fixes get applied to deeper problems. That second environment tends to cause lasting damage — to team dynamics, to working relationships, and sometimes to behaviors that eventually become unmanageable. The difference isn't personality. It's preparation.”
If your managers either avoid tension entirely (hoping it resolves itself) or let things escalate to HR, that's a signal. Navigating difficult conversations with confidence is a skill. It doesn't come naturally to most people, especially those who were promoted for their technical expertise.
What this looks like in practice:
Interpersonal tension that simmers for weeks before it surfaces
Managers who escalate everything to HR rather than addressing it themselves
Teams where certain topics are simply off limits
Recurring conflict between the same people with no resolution
What it signals: Conflict navigation and courageous conversations need to be core skills in your leadership toolkit, not optional extras.
Sign #3
Change Initiatives Are Landing Poorly at the Team Level
You announce a new direction. Leadership is aligned. But somewhere between the executive team and frontline managers, the message falls apart. Teams are confused, resistant, or disengaged. It’s not because they don't care, but because their managers don't know how to lead through uncertainty.
Jeremy notes the impact of psychological safety. “Psychological safety is what allows people to actually process change — to voice their concerns, ask questions, and admit when they're struggling. When leaders recognize that not everyone adapts at the same pace or in the same way, and create the space for that, teams move through change more cleanly. When that safety isn't there, you tend to see resistance, confusion about the 'why,' rising tension, and sometimes turnover that catches leadership off guard.”
Change is constant right now. Restructures, shifting priorities, new technologies, evolving workforce expectations. Managers who can't communicate clarity during ambiguity become unintentional blockers of organizational progress.
Leadership clarity matters most in uncertainty. If your managers go quiet when things are unclear, your teams feel it.
What this looks like in practice:
Employees saying they "didn't know" about a change their manager was told weeks ago
Managers who visibly disengage during transitions
High turnover during or immediately after organizational changes
Change fatigue becoming a cultural norm
What it signals: Leading through change and ambiguity is a learnable skill set. Managers need more than talking points, they need practical tools to guide their teams through disruption.
Sign #4
Your Teams Are Diverse, but Your Leadership Approach Is Not
Today's workforce spans multiple generations, backgrounds, communication styles, and expectations. A leadership approach that worked a decade ago, or even five years ago, may not be serving your current teams.
Jeremy provides further insight, “At its core, day-to-day inclusive leadership is about creating an environment where every person can show up and do their best work as themselves. The most inclusive leaders I've worked with have made a genuine effort to understand each team member — their strengths, motivators, communication style, how they like to be recognized, and what matters to them personally. They still hold the team to shared goals, but when people feel that their perspective has actually been considered, the level of investment and commitment is noticeably different.”
Inclusive leadership is directly tied to team engagement, psychological safety, and the ability to retain your best people. Managers who haven't built these skills often don't realize the gap they're creating.
What this looks like in practice:
Teams where certain voices are consistently louder than others
Managers who lead the same way regardless of who's in the room
Disengagement or attrition among employees from underrepresented groups
Generational friction that doesn't get addressed directly
What it signals: Inclusive and multi-generational leadership isn't a standalone training topic. It needs to be embedded in how your leaders communicate, give feedback, and build team culture every day.
Sign #5
You've Done Training Before And It Had No Impact
This one is less about a specific behavior and more about a pattern: your organization has invested in leadership training before, but six months later, nothing changed. The workshop was well-received, people said they got value and then life went back to normal.
Jeremy notes a few things that come up consistently. “One is that the program felt like a series of standalone sessions — interesting in the moment, but hard to connect into anything coherent. The other is that people left without knowing what to actually do differently. No clear, actionable takeaway. So the time got spent, the content got consumed, and then nothing changed. That's the gap between a training event and a development program.”
This is the most telling sign of all. It means the issue isn't with the managers themselves. It's with the format of the training.
If you have done a leadership workshop in the last two years and are still reading this, it could be a sign. A one-day workshop, a keynote, or a collection of standalone topics can build awareness. But awareness alone doesn't change behavior. Real leadership development requires repetition, progression, and application over time.
Sustained results require sustained development. You can't change how someone leads in a single session and expecting otherwise sets everyone up to fail.
What this looks like in practice:
Positive feedback from training with no visible behavior change
Managers applying new language but not new practices
HR consistently re-addressing the same leadership gaps year after year
Leaders who complete training but remain stuck in old patterns
What it signals: Your organization needs a structured program, not more one-off events.
So What's the Right Response?
If you recognized your organization in two or more of these signs, a one-day workshop or a collection of disconnected modules isn't going to move the needle. What you need is a leadership development program, one that builds skills progressively, connects learning to real situations, and creates consistency across your leadership team.
Before making a decision, Jeremy asks that you think about this: “I'd want them to know that a program like this is a real investment — in time, in attention, and in the development of each person in it. There's meaningful work that happens between sessions: observing, reflecting, and applying what's been learned. But what they get in return is a cohesive journey — one that moves from self-awareness and trust-building through conflict navigation and change leadership, and ultimately to accountability, influence, and leading with a longer view. It's not a shortcut. It's a throughline.”
-
The most common signs include: avoiding performance conversations, escalating or ignoring conflict, struggling to communicate during change, leading without cultural awareness, and completing training without behavior change. These patterns often signal a systemic gap in leadership development, not individual performance issues.
-
A workshop or one-day training can introduce concepts and build awareness. A leadership development program builds skills progressively over time, with each session reinforcing and building on what came before. Programs are designed to create lasting behavior change — not just short-term inspiration.
-
The CultureAlly Leadership Development Experience is designed for people managers, senior leaders, and executive teams. The core challenges, communication, conflict, change, and team dynamics, are shared across levels. The application and discussion shift based on seniority.
-
The CultureAlly Leadership Development Experience is organized into three phases (Learn, Grow, Lead), each including four sessions. Organizations can begin with one phase and expand over time, allowing for staged implementation and investment.
-
Organizations that invest in structured leadership development typically see improvements in team engagement, communication consistency, retention among high performers, and leadership bench strength. Programs that build skills progressively are more likely to produce sustained behavior change.
