Ideas and Insights

Resources for technology and digital leaders

The Fallacy of Becoming a “Mature” Product Organization: Secrets From an Operating Model Expert

This article covers the hard truth that “mature” is a bit of a fallacy for product-led organizations. Learn why “sustaining” is actually what you’re after, the three key behaviors that must be prevalent in your organization to maintain success, and the KPIs and green flags that indicate forward momentum. 

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3 Actionable Leadership Insights to Scale Your Organization More Gracefully

Running a team, an IT practice, or an entire organization can sometimes be a lonely job.  As we close out our second year at Tuckpoint Advisory Group, I find myself reflecting on a journey marked by scaling pains and, at times, burnout and overwhelm. In that spirit, I’m sharing three actionable insights you can put into practice to scale more smoothly and navigate the sometimes lonely road of leadership.

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Building a Mature Product-Led Operating Model: The 4 Stages of Digital Transformation

Learn about the four stages of Digital Transformation and identify the common transitions that stump teams and block momentum on the road to building a mature product-led operating model.

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The Roadmap to Product-Led Success: Transforming Your Financial Model

In this article, you’ll learn why transforming your financial model is necessary to become a high-functioning product-led organization, as well as the mindset shifts required to unlock increased efficiency, flexibility, and long-term value creation.

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Why Good Governance is Essential to Digital Transformation

This article sheds light on the concept of governance in Digital Transformation and Operating Model Transformation, why it’s so important to get it right, and the small shifts you can start making today to improve your processes and see better results.

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What the Pandemic Taught Us About the Future of Digital Transformation: A Leadership Lesson

Many companies have started return-to-office initiates, mandated in-person attendance, and are shifting back to pre-pandemic norms. But is it the right play? Today’s article explores this misstep with specific regard to Digital Transformation and sheds light on the significant opportunity leaders have to reimagine the way teams work to build resilient structures that take them into the future.

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Land a Coaching One-Two Punch for a Knockout Transformation

When it comes to digital transformation, many organizations try implementing Agile and Product sequentially, doing one first then following up with the other. In either of these approaches, something is missing from the landing. Today's article shares a proven technique for layering in Product and Agile coaching to make digital transformation efforts significantly more effective.

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Talent Management for Digital Transformation Part III: Addressing Resistance to Change

In the final installment of this series on talent management for digital transformation, we’ll explore the root cause of change resistance, why organizations must address it, and three key elements of successful change-agility frameworks.

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What’s the Difference Between Digital Transformation, Business Model Transformation, and Operating Model Transformation?

The terms Digital Transformation, Business Model Transformation, and Operating Model Transformation are often used interchangeably, but in reality they each represent distinct yet interconnected concepts that are pivotal drivers of change in growing organizations. Here, I define each term and reveal why it's rare – even impossible – to take on any one of these without the others.

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Digital Transformation Problems? 3 Signs a Common Blunder Is Derailing Your Progress

If you’re a leader at the helm of Digital Transformation, you can’t afford to ignore the signs that something is seriously off. Most of these symptoms can be traced back to one root cause, and they need to be addressed so you can get the ROI on your Transformation.

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Operating Model Transformation Is the New Digital Transformation

If you’re driving Digital Transformation in your org, you likely have a handle on WHAT you need to transform, but are you thinking about HOW you transform? Your answer to that question determines if you’re going to get the ROI on your Digital Transformation investments in the long term and achieve the results you’re seeking.

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Transformation Leaders Can Win People Over by Using These Tools to Write Stronger Vision Statements

The best way to get people excited about transformation and encourage them to come along for the ride is to take a storytelling approach. To get internal buy-in, you need to convince people that change is worth their time, focus, attention and precious energy. And guess what: people do not like change. Here’s how you combat change fatigue and resistance with a powerful story.

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Keep the Rest of the C-Suite Committed To Transformation with This 2-Step Guide

Most companies know why they should transform, but fewer understand why they need to keep going even after they roll out a new feature or invest in a new technology. What happens when some C-suite folks start asking, “when are we going to be done?” This two-step guide will help the team recalibrate and recommit to the initiative.

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Digital Transformation for Financial Services

In this article, we explore digital transformation within the financial services sector, examining its key drivers, challenges, and industry-specific overview of digital transformation services that are propelling the sector into a new era of innovation and efficiency.

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Is Culture Blocking Your Transformation? Here Are 3 Evaluation Criteria to Find Out

Company culture is critical to digital transformation. Use these three evaluation criteria to examine the truth of your current company culture, find the existing nuggets that can actually be leveraged to your advantage, and understand the gap between where you are and where you want to be. Only then can you build a bridge between the two.

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3 Progress Markers for Digital Transformation

I always know I’ve got my work cut out for me when a client asks when we’ll be finished with transformation. The truth is, “done” doesn’t exist. Adjusting, evolving and learning occurs over an indefinite amount of time, but that doesn’t mean we can’t look for indicators that progress is happening. Here are the “big 3” signs that I always keep an eye out for to determine if the transformation is headed in the right direction.

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Successful Transformation Begins With the End in Mind

You might think your digital transformation is being guided by your desired outcome, but you’d be surprised how many organizations end up chasing the wrong kind of change because their objectives were too vague. The more specific the vision, the more intentional you can be about making the right decisions along the way.

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The 4 Planning Mindsets Every Transformation Leader Should Know

Summer is in full swing and the last thing anyone wants to think about is fiscal year planning. Who likes fast-forwarding ahead to January when flip flops and beach weather are top of mind? And yet, July is the typical timeframe for organizations to ramp up planning conversations about the coming year.

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