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Why Leadership Development Fails: 7 Reasons Companies Are Struggling

September 16, 2020

Verity Creedy


Learn the reasons why leadership development fails, and the challenges companies are facing developing leaders in unprecedented times.

7 Reasons Why Leadership Development Fails

The pandemic forced a massive shift in leadership development. Companies had to take their programs all-virtual. That, or hit the pause button. And companies that did nothing made the worst choice. Not Investing in leadership development at all is a reason why leadership development fails. It’s like sending leaders off to run a marathon without a pair of running shoes. Doing nothing at all guarantees instant failure.

It’s clear that companies with leadership development programs are a step ahead in this economy. But there’s always room for improvement. So, what are some of the most common missteps we have seen so far?  

1. Ditching the Classroom

More teams are working remotely, and many companies feel like they can’t bring people together in the classroom. But even if you can’t bring people together in person, it doesn’t mean all classroom training should be stopped.

In fact, people working remotely are looking for more opportunities to connect and learn in the classroom with other leaders. Instead of ditching the classroom, companies can look to virtual classrooms to keep the connection between leaders. And virtual classroom is not a compromise—the return on learning investment is the same as face-to-face engagements.

the old faithful, yellowstone's famous geyser

2. Relying on “Old Faithful”

Rather than investing in new leaders or improving the skills of current ones, companies tend to stick with the usual suspects. And who are we talking about? The people who get things done. The people who have been successful in the past.

Doing this may deliver short-term benefits and results. However, it does little to strengthen the overall leadership pipeline. In addition, it can also burn out those “old faithful” high performers. And that’s why leadership development fails over the long-term for companies using this approach: there is often hidden potential left untapped.

3. Taking a “Build It and They Will Come” Approach

Many companies make online learning and other self-directed resources available to leaders and then think their work is done.

While self-directed learning should be a part of a company’s program, not all development should be this way. Leaving development to individual curiosity and chance is risky—it often doesn’t work.

And it’s not hard to understand why. DDI research confirms that learners are in fact looking for less self-directed learning. Learners are overwhelmed by so much content that is not curated for them.

a leader in a suit working with his body in a pool and his laptop on the pool rim

4. Adopting a “Sink or Swim” Strategy

This is not a new mistake. However, the constant pressure to get things done quicker makes it tempting to follow “natural selection.” But the debate about leaders being born or made is over; leadership is developed over time.

While some people may have qualities that give them a leg up in certain situations, leadership requires focus and practice.

And the evidence is there to support formal development, particularly with key leadership transitions. Companies with transition programs to prepare their leaders to step up are more than two times more likely to be in the top 20 percent of organizations in their financial performance.

5. Compressing Learning to Save Time

Like above, this reason for why leadership development fails comes down to the pressure companies feel to get things done faster.

And companies are legitimately looking for ways to reduce time spent on all activities, including training. However, it’s important to constantly ask, “Are these ‘more efficient’ ways of doing things really getting us the results we need? Or if we must compress time, then how can we be sure we spend time on the most relevant learning?"

6. Employing a One-and-Done Program

Some companies simply invest in a single event or short program for their leaders. But while a one-and-done approach satisfies the need to do something, it ignores a critical fact: leadership behaviors and new habits are developed over time.

Effective leadership development needs to be constructed as a learning journey that unfolds over time. But not only this—it should draw on multiple learning options and modalities. It should also provide opportunities for skill practice and application.

a leader with his phone, looking deflated as he has overvalued technology and this is why leadership development fails for his company

7. Overvaluing the Role of Technology

Despite the attention and investment it attracts, learning technology isn’t having a notable impact on leadership or business outcomes. Nor is technology surpassing high-touch methods such as formal learning and development assignments.

While the appropriate use of technology has the potential to really improve leadership development, it may not always be the best option. The key is understanding the problems technology will solve and the needs it will meet before investing. Both relevance and curation remain critical.

Set up leadership development for success

Especially now, leadership development is even harder to get right. But your leaders need you to get it right because they have more on their shoulders than ever before. And your company’s livelihood depends on it.

But your leadership development program doesn’t have to be a failure. You don’t have to make these mistakes. Prepare your leaders to not just get by, but to thrive in these uncertain times. Ensure they have the essential skills to lead today.

To learn more about why leadership development fails, and to get trends and best practices, download DDI’s Leadership Development Playbook.

Verity Creedy is a Director in DDI’s Product Management team. Usually living in London, Verity has spent time working at five different DDI offices, including our US Headquarters. When she’s not identifying future frontline leader product needs, Verity can be found sweating in spin classes, eating various types of bakery items, and telling people about her adoration for Taylor Swift. If you have any frontline leader product ideas, pastry favorites, or Swifty news, send them to

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