This document discusses ways for CEOs and software leaders to better partner for digital transformation. It recommends that CEOs embrace shared ownership of business goals, measure value beyond just quality and progress, and support cross-functional teams. Software leaders should commit to delivering innovations that execute on business priorities and make adjustments based on learning. Both should be willing to rapidly evaluate initiatives and cancel those that are not providing value. The goal is for organizations to break down silos and adopt an agile approach like Amazon, with regular product releases and data-driven decision making.

1. Getting Fancy:
Creating A Partnership
With Your CEO For
The Digital Era
10/7/19
Jeffrey Hammond

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2© 2018 Forrester Research, Inc. Reproduction Prohibited
1 Forrester Data Global Business Technographics Business And Technology Services Survey, 2017
2 McKinsey & Company, February 2017 (https://www.mckinsey.com/business-functions/organization/our-insights/the-people-power-of-transformations?cid=other-eml-alt-mip-mck-oth-1702)
…but only 34% of CEOs reported a
successful transformation2
72% of firms are undergoing digital
transformation or investigating one1…

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Former CEO – national restaurant chain
"We struggled to understand the
importance of technology strategy to
our brand."

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CEO of a professional services firm
"Getting my software leader to
understand how to set priorities and
flow for the business is pretty darn
hard.”

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CEOs control half the barriers to software progress
1. New trends to speed app delivery with
quality?
2. How measure progress and
improvement?
3. How prepare for AI/Cognitive and IoT?
4. How build the right software faster and
meet customer expectations?
5. What is my career path from AD&D
leader?
1. How best collaborate/partner with
business stakeholders?
2. How overcome cultural barriers to Agile
within enterprise?
3. Which new skills should we acquire?
Develop?
4. Are we measuring the right things to drive
the right actions?
5. How communicate value of projects with
nonobvious business benefits?
Controlled by CIO, AD&D Controlled by CEO (and C-suite)
Source: “CEOs: Foster The Software Teams And Talents Your Firm Needs” Forrester report.

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Expand Your Transformation Efforts Outside IT
Software
Product
ManagerEngineering
Manager
CTO
Architect Developer

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Engaging W/ The C-Suite – Let’s Boil It Down
Source: “CEOs: Foster The Software Teams And Talents Your Firm Needs” Forrester report.

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What Do We Measure?
http://gravasco.blogspot.com/2017/01/3rd-sunday-ordinary-the-streetlight.html

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Shared ownership of business goals & priorities
• Set clear, concrete goals for the
business
• Communicate how the business
must change
• Declare what operational
improvements are needed
• Accept shared ownership of
business priorities
• Deliver software that executes on
business priorities
• Make adjustments as teams
learn how to work together
Push Executives To: Software Leadership Commits To:

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Embrace Measuring Value As Well As Quality/Progress/Efficiency

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Embrace the “Leap of Faith”
• Embrace “learning” as a
consequence of “innovation”
• Drive innovation out of the lab
• Take the “leap of faith”
• Keep the lights on
• Maintain the technology
landscape
• Deliver new apps as promised
(Justify the “leap of faith”)
• Reduce the span of the leap
executives must take
Push Executives To: Software Leadership Commits To:

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https://thenewstack.io/spotify-learned-flop-app-store/

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Organizations which design systems ... are
constrained to produce designs which are
copies of the communication structures of these
organizations.
Melvin Conway, 1967
Conway’s Law

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Put Another Way
http://bonkersworld.net/organizational-charts

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Embrace the spirit of “Agile” and “Dev-ops”
• Create, and support cross-
functional teams
• Prioritize collaboration around
products and customer
experiences
• Engage in “Silo-busting”
• Embracing product/service
centric teams
• Internalizing the Agile manifesto
• Allowing enough “slack time” to
support schedule flex
Push Executives To: Software Leadership Commits To:

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CEO Silo Busting – Amazon Style
Source: Rip Rowan on Google Plus
[Jeff Bezos] issued a mandate that was so out there, so huge and
eye-bulgingly ponderous, that it made all of his other mandates look
like unsolicited peer bonuses. … “1) All teams will henceforth
expose their data and functionality through service interfaces.” …
Like anything else big and important in life, Accessibility has an evil
twin who, jilted by the unbalanced affection displayed by their parents
in their youth, has grown into an equally powerful Arch-Nemesis (yes,
there's more than one nemesis to accessibility) named Security. And
boy howdy are the two ever at odds.
But I'll argue that Accessibility is actually more important than Security
because dialing Accessibility to zero means you have no product at
all, whereas dialing Security to zero can still get you a reasonably
successful product such as the Playstation Network.

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How Amazon Got To Two Releases A Second
https://www.youtube.com/watch?v=esEFaY0FDKc

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Make rapid, data-driven save/kill decisions
• Embrace Agile funding (CFO)
• Team-based budgeting
• Regular re-evaluation of progress
and learning
• Adopt business value metrics
• Be willing to advocate “killing the
job”
• Embrace a portfolio investing
model
Push Executives To: Software Leadership Commits To:

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How To Adopt An Agile Financial Approach
https://www.forrester.com/report/Digital+Business+Requires+Agile+Financial+Planning/-/E-RES111121

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Agile Budgeting Processes: Plan, Budget, Deliver
https://www.forrester.com/report/Digital+Business+Requires+Agile+Financial+Planning/-/E-RES111121

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Adopt Intra-Year Planning For Road-maps, Portfolios and
Budgets
https://www.forrester.com/report/Digital+Business+Requires+Agile+Financial+Planning/-/E-RES111121

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Bringing It All Together
› Understand the ”Leap of faith” – justify and reduce its span
› Be ready to educate and scale beyond IT and development
› Embrace business value and work hard to measure it
› Embrace technically astute executives, even board members
› Understand software industry models and borrow from them as
needed

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Thank You.
Jeffrey Hammond
Vice President & Principal Analyst
@jhammond
jhammond@forrester.com