The Top 10 Biggest Mistakes of Delivery Transformation to Agile – And How to Avoid Them

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Hey there!

My name is John and I‘ve been helping companies through agile transformations for over 10 years as a coach and program manager. In that time, I‘ve seen organizations make all kinds of mistakes trying to adopt agile.

Some of these blunders have minor consequences, but many can completely derail transformation efforts. The journey to agile is filled with pitfalls!

In this guide, I want to share the top 10 biggest mistakes I see companies make when trying to achieve agile delivery. I‘ll break down why each causes problems, with real-world examples.

More importantly, I‘ll provide tips to help you avoid these missteps and set your transformation up for success.

Let‘s get started!

Mistake #1: Lack of Leadership Commitment

The number one reason agile transformations fail is lack of committed leadership.

Without executive champions investing real time and political capital, a transformation is hollow. Leaders must walk the talk.

At one company I worked with, the CIO proudly announced they were "going agile" and made a big show of giving teams new hats with the Scrum Master title.

But his attendance at retrospectives quickly tapered off. When engineering teams raised obstacles, he brushed them off rather than removing impediments.

Within a year, the entire effort collapsed as teams drifted back to the status quo. They accurately sensed the CIO‘s apathy and followed suit.

Tips for Success

  • Educate executives on agile values in depth before kicking anything off. They need fluency beyond buzzwords.

  • Make leadership involvement tangible. Define specific ways leaders will participate and hold them accountable.

  • Connect agile metrics to executive incentives. Reward outcomes like customer satisfaction, quality, and flow – not utilization, velocity or deadlines met.

  • Ask leaders to publicly share agile growth experiences at town halls. Vulnerability and modeling go a long way.

Mistake #2: Lack of Clarity on "Why"

I once interviewed an executive leading a major agile transformation effort at her company. When I asked her about the goals, she said:

"To be honest, I‘m not entirely sure why we‘re doing this. But it seems like what innovative companies are doing these days."

Needless to say, her initiative dissolved into chaos.

Without a compelling rationale grounded in business outcomes, people won‘t make real changes. "Agile for agile‘s sake" goes nowhere.

Tips for Success

  • Link the transformation to strategic goals like improving customer satisfaction, accelerating innovation, or reducing risk.

  • Make those connections explicit whenever you communicate about the effort.

  • Involve teams in defining transformation goals tailored to their contexts. Local relevance drives engagement.

  • Celebrate wins that advance strategic goals, even if they don‘t perfectly fit an agile model. Outcomes matter most.

Mistake #3: Viewing It As a Project

Here‘s a common scenario:

A CEO attends a conference and hears agile is all the rage. She comes back determined to make the company "agile" within 9 months.

An extensive project plan is created encompassing process changes, reorgs, training, new roles, tools, etc. After a big kickoff, changes start rolling out across divisions.

But once the scale and disruptiveness becomes clear, executives balk. They ask to pause the project until headwinds subside…and it quietly fades away.

Agile transformation is not a project with a start date, launch, and completion. It‘s a journey of continuous improvement and growth.

When framed as a time-bound project, leaders underestimate the effort required. They fail to establish sustaining habits and behaviors. Initiatives stall once the initial energy fades.

Tips for Success

  • Adopt a growth mindset. Focus on incremental progress through experiments and feedback rather than big bang launches.

  • Plan for the long-haul. Communicate that meaningful change will take years of persistence. Celebrate small wins along the way.

  • Build internal coaching capability. Project teams leave once their work is "done." Coaches guide continuous evolution.

  • Establish rhythms like working groups, training programs, and leadership forums that sustain focus.

Mistake #4: Over-Reliance on Consultants

Consultants can provide valuable perspective and experience launching agile transformations. But organizations often become overly reliant on external experts.

When consultants leave, internal leaders are unprepared to drive real transformation. They know the textbook terms and moves but lack the deep experience to enact meaningful change.

At one company, consultants guided a 12 month transformation effort. As soon as the engagement ended, agile practices eroded. Teams reverted to old habits and tools within months.

Tips for Success

  • Transfer knowledge through mentorship and job shadowing. Don‘t just hand work to consultants; learn from them.

  • Customize approaches to fit your culture. Don‘t let consultants push ill-fitting models.

  • Build resilient internal capabilities, like agile coaching and change management skills. Don‘t outsource key ingredients.

  • Taper support over time rather than cutting cold turkey. Take a gradual release approach.

Mistake #5: Lack of Middle Management Engagement

While executive leadership is crucial, companies often neglect to engage middle managers in agile transformations.

This is a huge oversight. Individual contributors take cues from their immediate supervisors, who must role model agile values.

Without middle management buy-in, agile changes will be blocked by the layer closest to staff. Leaders issue high-level decrees that never manifest at team levels.

One company realized this painfully late. After a year of struggling transformation efforts, the CEO discovered mid-level leaders were still directing people via old command-and-control practices.

Tips for Success

  • Provide tailored agile training for managers focused on mindset, leadership, and coaching skills. Don‘t lump them in with individual contributors.

  • Clarify agile roles for middle managers. Help them transition from controlling work to supporting team autonomy.

  • Forums for middle managers to discuss challenges and share practices help alignment. Avoid leaving them out of key conversations.

  • Make managers partners, not obstacles. Engage them early and often in shaping transformation initiatives.

Mistake #6: Thinking It‘s All About Delivery

When I ask why companies want to become agile, they often cite goals like:

  • Accelerating software release cycles
  • Improving project predictability
  • Reducing defects

These delivery-focused aims are important. But agile transformation cannot stop at IT and product development teams.

The entire value chain must align – from finance to marketing to sales. Otherwise, delays and mismatches outside development teams will persist.

Focusing narrowly on delivery without addressing the broader organization is like pouring more water into a leaky bucket. Improvements are limited and temporary.

Tips for Success

  • Conduct end-to-end value stream mapping. Identify all constraints on flow – not just development teams.

  • Realign supporting processes like budgeting, HR, PMO practices, and KPIs to support agility.

  • Prioritize improving outcomes over adopting practices. If rigid planning cycles still dictate release dates, agile practices won‘t fix that.

  • Build initial support beyond delivery teams. Marketing, finance and other groups can benefit from agile too.

Mistake #7: Forcing Change With an Iron Fist

I occasionally encounter leaders who take a very aggressive approach to agile transformation.

They declare swift unilateral changes and mandate 100% conformance. Those viewed as resistors are pushed out.

This "my way or the highway" approach seems strong on the surface. But it‘s ultimately fragile and limited.

Real change comes from genuinely persuading people, not beating them into compliance. Forced marching to agile breeds anger and resentment. The forms remain, but the mindsets stay stuck.

Tips for Success

  • Assume the best in people. Opposition is often grounded in real risks and losses people face from change. Listen with empathy.

  • Customize the approach to appeal to different perspectives and needs across the org. Meet people where they are.

  • Give space for people to air doubts and participate in shaping solutions tailored to their work.

  • Proceed with patience and care. People need psychological safety to unfreeze old habits and try new practices.

Mistake #8: Lack of Skills Training and Coaching

Many agile transformations consist of some basic introductory workshops, then pressure to make big changes fast.

But real skill-building takes time and practice. It happens through rigorous hands-on training AND ongoing expert coaching.

Classroom courses give exposure to concepts. Coaches make change stick through individual feedback and habit formation.

I was recently invited to observe a newly formed "agile team." It was painful. They clearly sat through some lectures on Scrum, but had little grasp of core skills like breaking down stories or collaborative planning.

No coaching meant bad habits went uncorrected until they solidified. It was like watching someone try to learn tennis by reading a book.

Tips for Success

  • Make training experiential, with simulations and group exercises. Conferences and passive lectures have limited impact.

  • Develop expert internal coaches or leverage experienced external coaches. They are force multipliers.

  • Focus training on behaviors over concepts. What tangible actions make an effective product owner, for example?

  • Define competency models and provide hyper personalized development plans. Measure progress empirically.

Mistake #9: Poor Pilot Selection

Before scaling agile changes, it‘s wise to run limited pilots and demonstrate benefits. But organizations often sabotage these proofs of concept by picking the wrong pilots.

Rather than choosing small, receptive teams with a high chance of success, leaders go after the biggest, toughest parts of the business.

When these complex pilots (predictably) run into problems, it drains momentum and triggers concerns agile just won‘t work here.

A CIO at a major bank told me how their first agile pilot was in the company‘s largest division in Asia – involving over 200 people spread across 5 countries.

It was doomed from the start. The team was too fragmented, work too interdependent, and change resistance too high.

A simpler pilot could have built enthusiasm and case studies to enable bigger initiatives.

Tips for Success

  • Target small, cohesive teams doing relatively contained work. Think 1-2 pizza team size.

  • Seek out respected local leaders excited to experiment. Their credibility can sway skeptics.

  • Avoid high-stakes initiatives at first. Start with low-risk pilots focused on learning.

  • Define clear success criteria upfront and measure them transparently. But expect a bumpy start.

Mistake #10: Declaring Victory Too Soon

After finally powering through initial agile changes and getting a pilot or two off the ground, leaders often declare victory and lose focus.

But meaningful transformation takes years of persistent effort to stick. Early wins are exciting – and fragile.

When urgency and attention fade, people revert to old habits. Coaching and practices erode. Progress stalls.

That‘s what happened at a tech company I worked with. After two successful agile releases, executives figured the job was done and priorities shifted.

Within 6 months, teams abandoned retrospectives and planning sessions. Code quality and collaboration declined. We were back at square one.

Tips for Success

  • Celebrate wins but communicate transformation is an long journey requiring ongoing vigilance.

  • Collect data on agile metrics and have leaders review them regularly. Transparency maintains focus.

  • Establish regular rituals like working groups, training programs, and community events to sustain momentum.

  • Formalize agile roles and competencies so that expertise persists despite turnover.

Wrapping Up

Well, we covered a lot of ground here!

As you can see, agile transformation is filled with potential pitfalls. But by understanding the most common mistakes and taking proactive steps to avoid them, you can set your organization up for success.

If you keep focus on the long-term goal of achieving a true agile culture, remain flexible in your approach, and prioritize enablement of people, you‘ll avoid the most painful blunders.

And remember, transformation is a journey! It requires persistence through inevitable bumps and missteps along the way.

If you take the time to build understanding across all levels of the org, equip people with new skills, and continually adapt based on feedback, you‘ll get there.

I know it‘s not easy. But staying aware of the biggest mistakes companies make can help you craft an approach that sticks.

If you have any other questions as you embark on your agile transformation, don‘t hesitate to reach out! I‘m always happy to help.

All the best,


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