The Technology Leader’s Gambit: Mastering the Endgame With a New Value Stream Management Playbook

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When The Queen’s Gambit debuted on Netflix in October 2020, it was an instant sensation that single-handedly revived interest in a game as old as time. The titular gambit (a calculated move, according to Merriam-Webster) is a cunning chess opening characterized by its attacking prowess, where the player sacrifices a pawn to gain control of the center of the board

One of the most arresting visuals from the series is Beth Harmon’s drug-induced visualizations of entire chess games being played out on the ceiling above her bed. The series creators gave form to what many chess masters do in their heads: they can see several moves ahead and anticipate how each move will play out.  

If you’re an IT leader at one of the world’s largest enterprises, you’re responsible for the cumulative output of tens of thousands of practitioners, and hundreds (if not thousands) of apps and services. What could be better than an executive plane from which you can visualize your digital portfolios and calculate the moves to help the company achieve its objectives and financial projections? 

Winning the Game in Three Moves 

In chess, your goal is clear: isolate the king. What’s the equivalent for an IT leader overseeing nine-figure budgets in a global economy altered by a pandemic? 

It boils down to three key outcomes: 

  1. Build a strong partnership with the executive management team: Turn IT into a partner to the executive team, so you’re no longer playing on opposite sides of the board. Rewrite the relationship and transition from order-taker to innovator. 
  2. Have direct impact on business success: Align IT initiatives with enterprise goals and help the company achieve its endgame. Make decisions and recommendations that deliver quantifiable and tangible business value.
  3. Lead an efficient and optimized IT organization: Win the game in fewer moves. Constantly find new ways to minimize waste and reduce costs that shorten time-to-market, increase throughput and improve product quality.

Just like in chess, you have to play to win. You have to learn not just the rules of the game, but lots of strategies and maneuvers. Many organizations are just playing the game at a rudimentary level because they can’t overcome the forces working against them.

Four Forces Counter-Attacking Your Strategy

Even the most talented and business-savvy CIOs, IT executives and product leaders face their fair share of challenges advancing these goals. Generally, there are four significant forces at play and they are deploying their pieces — intentionally or unintentionally — against you. Warning: They are much weightier and consequential than they may appear. 

1 Habit 

Just because you learned the rules of the game doesn’t mean you know how to play well. 

More than ever, organizations operate in ever-changing markets that require immediate decisions in order to outpace and outsmart the competition. But despite heavy investment in enterprise Agile frameworks (such as the Scaled Agile Framework® (SAFe®), DevOps and Cloud, for most the ROI is weak. Portfolios still struggle to tangibly deliver faster

At the core of the problem is the fact that Lean and Agile talk about organizing around value and improving the flow of value, but few organizations are equipped with tools to apply those principles. So, they slide back into the old habits and ways of work, in ways that you don’t see. But make no mistake, doing the ceremonies of Agile without really being Agile is killing digital transformations far and wide. 

2 Opacity

Strategic awareness separates the expert tactician from the grandmaster. 

Visibility and insights into what’s impeding value delivery and efficiency are hampered by siloed data. IT organizations are siloed from the business, functionally specialized, and disconnected from each other. As a result, leaders experience difficulty making fact-based, evidence-based decisions, investments, changes to the status quo, and resource allocations

Business decisions made without full, impartial end-to-end visibility — particularly at the executive level — can have grave implications. Incumbent companies that form the backbone of the world economy are at an inherent and significant disadvantage in this regard. Over-reliance on proxy metrics that track detailed activities, not business value and results, lead to local optimizations and do not facilitate feedback and learning.

3 Perception

An opponent’s rating can be highly effective in psychologically weakening your own position.  

When IT is still perceived as a cost center as opposed to a profit center, digital transformations take on the same mentality. When the focus is on cost reduction, it follows that the outcomes that get measured have nothing to do with faster time-to-market, more competitive product offerings, or the ability to pivot rapidly. 

A cost-centric framework does not deliver increased velocity, productivity or efficiency, and ultimately the business gets a lot less for less, instead of more for less. For IT transformations to succeed, this perception has to change. 

4 Mistrust

Your army grows stronger with better cooperation between all the pieces.

IT and the business have not always been aligned, neither in structure nor in purpose. The absence of a common set of value-oriented metrics, compounded by the existence of two very different vocabularies — technical and business — served to create an “us versus them” mentality. Interestingly, this has somewhat improved during the pandemic, which forced the two sides to work together to support customers and business continuity. 

The fact that IT is now trying to shift to a product-oriented model won’t dispel that lingering distrust overnight. The lack of shared fact-based data results in frequent finger-pointing between IT and the business. The result is that the software delivery efficiency of these companies is abysmal when compared to that of digital startups or the tech giants.

The Executive Value Stream Management Playbook 

So what’s your playbook? How are you going to play to win, while fending off the counter-attacks? How do you go from reacting to control? 

The Queen’s Gambit heroine Beth Harmon (a character inspired by famous male chess prodigy, Bobby Fischer), boosted her phenomenal intuition by poring over chess strategy books. And in the climactic match, she phoned her fellow grandmasters to strategize her endgame. 

IT executives — you have Value Stream Management (VSM). 

VSM Portfolio Insights go beyond static views, one-dimensional reports, or one-off value stream maps. This new real-time visibility reveals the dynamics that are impacting business value delivery, enterprise initiatives and digital transformations across your value streams. 

From concept to cash, defect to resolution, risk to mitigation and debt to pay-off, there’s now a playbook for shepherding your organization towards business goals and continuous improvement. 

Don’t flip the board or crumble under the pressure: Download the IT Executive’s playbook now to learn the 12 plays to building a high–performing tech company within a traditional business using VSM.

Learn More About VSM Portfolio Insights

Tasktop Viz’s VSM Portfolio Insights is a first-of-its-kind, portfolio-wide dashboard breaks down value stream silos to provide real-time visibility and actionable insights into IT’s impact on business value. Read on.


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