3 Ways to Reform Detractors that Really Undermine Agile and Digital Transformation

Last week I covered seven leadership detractors in digital transformation and what to do about them. The list included leaders seeking transformation certainty, decision delayers and flippers, and ones that prioritized everything. If you are a CIO, CTO, CDO, or another transformation leader, I am certain you've encountered these detracting behaviors and that you'll value my advice.

Then later last week, I recorded a Five Minutes with @NYIke video on three types of anti-agilists and what to do about them. That list includes detractors pushing waterfall planning practices and mindsets and two other behaviors that can undermine agile cultures. I include five recommendations that you can also use to address all three anti-agile detractors and promote an agile culture. You can find the video at the end of this post.

Reform Detractors to Agile and Digital Transformation - Isaac Sacolick


Finding ways to sway detractors into supporters, or at least prevent them from raising their voices to drown out the visions and plans of transformation leaders is critical. It prevents leaders from creating the force multipliers that accelerate digital transformation.

Behaviors that Detract Agile Cultures and Transformation Mindsets

So in this post, I will share seven more detracting behaviors that you can find on agile teams, DevOps organizations, product management, IT operations, and business teams that are part of the transformation program. These are anti-behaviors and can be detracting multipliers if leaders don't call it wrong and undesirable conduct.

1. Publicly says yes, privately undermines leadership

This behavior is not only detracting, it can be insubordinate. If a detractor repeatively tells people to do things against management's policies, priorities, and standards, then the issue needs to be handled with human resource leadership.

But sometimes, it's not a black and white case of disobedience, especially if leadership isn't specific about their directions and when to voice opposition or concerns. 

What to do about it - Create inclusive opportunities to share opinions, but also ensure people understand leadership's decisions. Employees should know when are the appropriate times to ask questions, challenge assumptions, and voice concerns. Equally, decisions and directions should be documented, shared, and have a time and place to be reviewed and challenged.  

2. Repeats raising the same questions and concerns

We want people to ask questions. We want a culture that enables everyone to challenge the status quo and present new opportunities.

We don't want people wasting everyone's time asking the same question week after week. And once we give voice to concerns and address them, we don't want the same objection raised to the judge and jury unless there's new evidence.

What to do about it - If you're noticing a theme here, I am a strong proponent of document decisions and meeting outcomes. If you are sensing that one or more people are repeating themselves, add documenting questions and concerns to the list and share all these lists publically. Then, you can politely address repeat questions with a simple response of when you discussed it last and ask if there's anything new to review.

3. Hoards information or over-complicates knowledge sharing

When you are transforming, there are always subject matter experts that understand existing workflows, customer interactions, business rules, legacy technologies, and data definitions. Are they openly sharing their knowledge with everyone and partnering on its evolution, or are they hoarding information or making existing practices sound more complicated? 

What to do about it - It's important to understand what's driving and motivating these behaviors. In many cases, it's a form of self-preservation as the person doesn't know where they will fit into the transformed world. This often happens when management oversells automation's impacts or doesn't clarify how people's roles and responsibilities evolve as the company transforms. 

Secondly, leaders should promote knowledge sharing, documenting, and simplifying core transformation practices and ensuring that new investments meet these objectives. This is leading by example, and once illustrated, it creates a path to address subject matter experts that are slow to share information or create roadblocks. 

Four more detracting behaviors and what to do

Now, I have four more detracting behaviors and what to do about them! 

Please sign up for the Driving Digital Newsletter, and I'll be sharing more about detracting behaviors and what to do about them - plus these four more.

In the meantime, please subscribe to Five Minutes with @NYIke and watch my 31st episode that focuses on anti-agile detracting behaviors and five recommendations on what to do about them.


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