7 Leadership Detractors to Digital Transformation and Advice on What to do

I recently moderated a Driving Digital Clubhouse on winning over detractors in digital transformation. A detractor is someone or a group in the organization that is slow to adapt to changes. Some detractors just need more help and attention in understanding and working through process changes. Others may be deliberately trying to slow transformations down or even instigate their failure.

I already have a top post on how to handle detractors in digital transformation where I reference several articles on who to partner with, what to communicate, and how to handle conflicts in digital transformation.

Digital Transformation Leader Detractors - Isaac Sacolick

So when I introduced the concept in the Clubhouse,  I wanted to get new perspectives. Here are some of the challenges we reviewed that I group into two challenges: leaderships issues and issues with teams or individuals. I will cover up detractor issues with teams and individuals in a follow-up post.

1. Misaligned leadership incentives

Let's face it, there will be some winners in transformation and others on the sidelines. If you're changing the business model, setting transformation priorities, or debating what parts of the business receive investment, then some leaders will get the nod while others are going to see reduced emphasis and clout in their business and operations. For some who are not getting the priorities set their way, their knee-jerk reaction is often to double down efforts on their business and around their expertise, which can be detrimental to the strategic and transformational goals.

What to do about it - This depends on your role in the organization and your relationship with this detractor. If the detractor is an executive in the organization, then it falls on the CEO to recognize the issue and realign incentives. But you may have to inform the CEO of the challenges and offer recommendations. 

Regarding the detractor, your best course of action is to find ways to partner with this executive by finding transformational benefits that may align with their goals. But if the executive isn't ready to listen, then you just might have to work around them strategically and manage tactical conflicts when they arise.

2. Leaders seeking transformational certainty 

This group wants a prescribed business and project plan before they are on board with any transformation program. Some want ROI and fully-committed KPIs before teams start planning, experimenting, releasing MVPs, and capturing feedback. Readers of my blog will recognize these as non-agile leaders and a detriment to the culture and process required to iteratively improve products, customer experiences, workflows, hyperautomations, machine learning capabilities, and emerging technologies. 

What to do about it - If you're the CIO and in a position to do so, call out these behaviors as detrimental to transformation. If you're not, then make sure your leaders aligned to agile transformation take on this challenge. Business plans, roadmaps, P/Ls are all achievable in due time, but transformation initiatives must start with simple one-page vision statements followed by ongoing experimentation. Enabling a leader to throw roadblocks before agile teams plan and experiment is a good way to slow progress and demoralize innovation leaders.   

3. Leaders who delay decisions and flip direction

Sometimes it's good to play a "wait and see" game when faced with few good options. Other times, you'll learn something new or recognize a significant opportunity and want to pivot your digital transformation program.  

Neither of these practices is detractor behaviors, but, on the other hand, when leaders consistently fail to make tactical decisions, set directions, or reveal priorities, they hurt teams from driving transformation at optimal velocities. The other side of this coin - when leaders repetitively flip their decisions - that too is a detracting behavior because it demoralizes teams to constantly rework their plans and implementations. 

What to do about it - I have two recommendations. 

First, I find that teams, departments, and organizations struggling with decision-making may not have decision-making authorities and responsibilities defined. If you don't know it's your call, then chances are you're not going to make the decision. Identifying principles and responsibilities is one way to address gaps on who decides what, when, and how. But IMHO, avoid doing this with complicated RACIs - I'll have to cover that in another post.

The second is to put some formality into decision-making by requiring that decisions are documented and published at the end of every meeting. It establishes a cultural norm that you're not just in a meeting to discuss; you're there to make decisions. And when decisions are documented, leaders are less likely to flip on a dime.

4. Leaders that permit loudest-voice exceptions

You finally get buy-in from the CEO, leadership group, or program sponsors on priorities, governance, policies, or priorities - only to find out that a leader has already provided an exception to the rules. You dig deeper, and there's no rationale to the exception - this was just a case of a loud voice just getting what they want and circumventing the rules.

What to do about it - This can be frustrating, but what you do about it depends on the greater context. What's the impact of the exception? Is this a battle worth fighting? Are the loud voices onto something that you should pay greater attention to, or is this a repeat behavior by them or the leader granting the exception? 

If you decide to take on this battle, my suggestion is to bring the leader and the person granted the exception together to talk through any objections, why the exception was granted, and if there are alternative options. 

5. Leaders who shoot from the hip

Many leaders have bought into becoming more data-driven organizations, and using analytics, citizen data science programs, and proactive data governance to help people across the company make better decisions. But there are laggards, often those with the most experience and subject matter expertise, who continue to rely on their intuition and don't review and seek out data that backs their hypotheses. It's hard to promote data-driven behaviors and cultures when some leaders evade the best practices.

What to do about it - Sometimes, you have to drive change from within. Recruit an insider from the leader's department or organization to become part of a citizen data science center of excellence. More than just access to data and technology, provide this person or people with mentorship and guidance on influencing change in their department. 

6. Leaders who prioritize everything

Leaders who make ten things the number one priority, or force rank fifty goals but expect teams to follow through on all of them, are undermining digital transformation. In one of my five-minute videos, I call it the fairy tale roadmap because some leaders are just too good at telling this story that everyone will get what they want. It's not realistic, and it demoralizes teams. These leaders are detractors because, without priorities, the team is left on its own to sort out all the stakeholder expectations that come with a wide and deep portfolio backlog.

What to do about it - CIOs, CDOs, or whoever is leading the digital transformation effort must step in and provide clarity on the short-term priorities versus the longer-term roadmap. This won't be a popular role or happy message, but it is necessary. Business leaders must understand what is above and below the line - and then the CIO/CDO can speak to how to grow organizational capacity through partnerships, hiring, technology, and other strategies. 

7. Leaders who are never satisfied with team performance

This might be the most harmful and detracting behavior. 

Digital transformation is a multi-year journey in most organizations, and sustaining the velocity, intensity, and commitment is challenging. You don't want burned-out teams after six months, and one way of avoiding this fate is to celebrate the small wins and accomplishments. 

Maybe you're releasing a new digital product and just completed the second MVP release? That's time for a small-win celebration, but the product manager who wanted five more features may not see it that way. Or maybe it's the CFO who sees progress but wants faster and greater financial returns? Or maybe it's the CEO who wanted more progress on priority number five on the roadmap. 

All of these are detracting behaviors that can be very upsetting to teams that put in their hearts, minds, and energy into their work, only to see that it wasn't good enough.

What to do about it - First, digital transformation leaders must celebrate with their teams and promote longer-term happiness when good work is done. Then, handle the leadership issue one on one - ideally by getting the person to get more directly involved in the process. Have them join sprint reviews, brainstorming sessions, or any collaborations between the team and customers. 

When leaders are more involved in the planning and delivery processes, they are less likely to be critical and more likely to become supporters.


Digital transformation isn't easy! I hope you found some answers in this post but please reach out to me with your questions, comments, or suggestions. In an upcoming post, I'll cover team and individual (non-leader) detractors and advice on what to do.

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld, CIO.com, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.