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Enterprise Agile Planning, Transformation

6 Agile Transformation Challenges Facing Post-Pandemic Leaders

Get ahead of these common transformation stumbling blocks.

Published By Brook Appelbaum
agile transformation challenges

In some ways, the past few years have felt like an eternity – in others, it seems like we were just ringing in 2020 full of anticipation and hope. One thing has become clear for organizations in this pandemic era – change is hard, and if you don’t have a transformation plan, you’re more likely to fall victim to one of these common Agile transformation challenges.

At the start of 2020, the need for Agile transformation was already knocking on the door of most major organizations.

The pressure for adaptability, innovation, and speed in an ever-changing, ever-smaller world was mounting. And then a pandemic swept across the planet, accelerating the ideal timeline for transformation from “someday soon” to “yesterday.”

Quite literally overnight, organizations had to learn how to embrace hybrid working environments, support their employees as whole people, and somehow keep the figurative lights on during a truly unprecedented time in our collective history.

Somehow, individuals, teams, entire organizations learned to adapt to this new normal. But not without some missteps along the way – a phrase often heard in the early days of the pandemic was that organizations were, “building the plane while flying it.” Changing to an Agile way of working was both nearly impossible and desperately necessary for survival.

If you’re embarking on an Agile transformation in your organization, be sure to avoid the following 6 Agile transformation challenges.

Read Next: 9 Agile Transformation Metrics for Executives to Watch

Not Enough Buy-in

Newton’s first law of motion, also known as the law of inertia, states: An object in motion, stays in motion. An object at rest, stays at rest. It is quite literally against the laws of physics for things to change – so we cannot expect people to do so with one impassioned call to action from an executive and a well-designed slide deck.

Real Agile transformation requires buy-in at every level of the organization, consistently, over a long period of time – but specifically leadership.

Agile transformation requires executives who embrace, champion, and demonstrate Agile values. It demands managers who are willing to navigate conflict in healthy ways as teams adjust to new ways of working. And it requires all of leadership to manage this change within the organization as they are learning themselves.

Without sufficient, consistent buy-in, especially from leadership, your Agile transformation is unlikely to have lasting power.

Read Next: Enterprise Agile Transformation

Not Communicating Vision and Strategy

Change is inevitable, but Agile transformation is not – it’s the result of a clearly communicated, clearly defined vision and strategy. One of the most common Agile transformation challenges arises when Agile leaders fail to communicate that vision and strategy – not just at the beginning of the Agile transformation, but throughout each phase of the transformation.

There are several ways for Agile leaders to not only communicate once, but continuously communicate about the vision and strategy behind the transformation. As the organization grows in Agile maturity, this vision and strategy will likely shift.

Developing clear, open channels of communication upwards and outwards early in the transformation process will help to ensure that the entire organization stays aligned throughout the process of becoming more Agile.

Neglecting the Process

Agile transformation is, at its core, a transformation of culture above anything else. And transforming organizational culture, of course, takes time – and patience. Embracing Agile requires individuals and teams to unlearn old habits and learn new ways of working and thinking about work.

One of the biggest mistakes organizations make is failing to allow space for the transformation process to take place.

Many organizations, eager to experience the benefits of Agile, try to rush through the critical, formative process of transformation – and thus stunt their own growth.

Read Next: Are These Agile Transformation Blind Spots Holding You Back?

Not Putting Culture First

The next two Agile transformation challenges are related to each other – both speak to the failure to put people and culture at the center of the Agile transformation. This is often referred to as doing ‘Agile theater’; organizations will claim to ‘be Agile’ or that they are ‘going Agile’ but demonstrate a limited understanding of key Agile principles.

Often, this is seen in businesses where the push to become more Agile comes from the top: Teams receive the message that they are supposed to ‘be Agile’ now, without a deep understanding of what this means or should mean for the way they do work.

As a result, teams tend to overemphasize certain elements of Agile – such as increasing efficiency or cutting waste – without a complete understanding of the why behind these concepts, which are essential to making them sustainable (or effective).

Read Next: The Pandemic Created a Renewed Urgency for Agile Transformation

Failing to Invest in People

Agile is fundamentally about people: About creating organizations where people (employees) can do their best work and, in turn, create more value for other people (customers). Agile organizations know that their most valuable assets are their people – and especially during times of turbulence and change, it is the experience and wisdom of people that will carry the organization through.

This is why investing in people is a key component of creating a healthy organizational culture. This means:

  • Promoting from within when possible
  • Offering ample opportunities for professional development
  • Encouraging employees (and ideally, paying for employees) to pursue advanced certifications, training, and skills… even if that means they might require higher pay or leave their current role
  • Offering competitive salaries and benefits packages
  • Providing opportunities for advancement

Investing in people is certainly an investment – but it’s one that Agile organizations simply cannot afford not to make – because it pays off: A low employee turnover rate is one of the most rewarding long-term effects of a successful Agile transformation.

Read Next: The Agile Manager’s Handbook

Failing to Embrace Failure

Perhaps one of the hardest cultural shifts involved in Agile transformation is learning to embrace failure. Agile culture is rooted in experimentation, iteration, and learning – because without these, there is no innovation.

If we cannot try and fail, then we will not try – and once we stop trying, we stop innovating.

We are all desperate to innovate – but many of us have been raised in the traditional, Western “success at all costs” corporate culture that discourages failure. It’s a difficult, but essential, collective cognitive shift that is required for organizations to truly embrace failure as a part of learning. But failure to do so is a failure to innovate – which is why this Agile transformation challenge is one that simply has to be overcome.

Read Next: NatWest Finds Their Key to Agile Transformation


Although no two Agile transformations are the same, examining the missteps of others (and how to overcome them) can help you take a few shortcuts on the road to Agile maturity. Take a deeper look at the most common Agile transformation challenges (and how to overcome them) by downloading the eBook, “Why Agile Transformations Fail.”

You’ll learn:

  • Why organizational psychology is critical to Agile transformation momentum
  • How a lack of executive sponsorship prevents transformation success
  • Why traditional planning and budgeting practices cripple transformation efforts
  • How the inability to align around shared objectives impedes change

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Written by Brook Appelbaum Director, Product Marketing

Brook Appelbaum is the Director of Product Marketing for Planview’s Lean and Agile Delivery Solution. With nearly 20 years of marketing experience, Brook has led many different product and digital marketing teams. However, her favorite leadership role is that of a Product Owner. As part of an Agile marketing team inside Planview, Brook drives the campaign and product marketing strategy for the Lean and Agile Delivery Solution. And she thinks LeanKit is the coolest.