The document summarizes a startup's transformation journey from a "status quo" organization to becoming more agile. It describes initial issues like inconsistent direction, technical debt, and low employee confidence. A transformation coach was then brought in. Over several weeks, they helped shift paradigms, create an agile pilot team, introduce prioritization modeling, generate new ideas through company-wide ideation, and establish structures for execution including product boards and regular sprint demos for executives. The journey resulted in products with traction instead of no traction and a welcoming of surprises and adaptability.

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Leading from the Middle
…a startup‟s transformation journey
Adele Maynes
Latha Swamy

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Inquiry and Sharing

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Intention
Discover something that we did not know
about leadership and transformation…
in moving beyond the “Status Quo”

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Shared Language
Alignment
Visibility

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When we say “status quo”…
…we mean something like…
Organization Culture
• Startup grown to 200 people
• Pockets of home grown agile
• Product organization with a heroic mindset
• Technology organization at the effect of domination
• Low confidence on the Execs ability to steer the organization
• Pulse survey showed accountability and recognition were both missing
Organization Performance
• Constant changes in direction with founders veto power
• Unstable platform, unworkable user experience and piling technical debt
• Stagnated revenue and growth
• Weekly project reports with unactionable metrics
• Unable to react quickly to competitors and market needs

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Our agile transformation journey…
6
pockets of agile
Learning & TransformationStatus Quo
Products with no traction Products people love
new thinking and
new places to think from…
(continual improvement)

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Sharing some of our
on-the-court
experiences…

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Trigger to bring in the transformation coach
Q1 roadmap planning
• Product boycott and domination
• SVP Engg resignation resulting in a leadership void
• Execs not aligned
There was a clear need for a program view that is a common ground between
what the execs want and what the teams are at work on
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Week 1: The Paradigm Shift
Promise made to market were unrealistic
Product and Engineering neither aligned on the scope nor the date
Missing Business agility to innovate and release new products quickly
Proposal to shift paradigms from:
Product and Engineering to Product Development
Adding Capacity to Improving Velocity
Heroic mindset to a Shared Future
Proposed next action:
A 2-day agile workshop to foster collaboration and alignment
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Reality revealed inside of the Created Future
Revelation of what it takes to deliver the new
product by April 1st
No clear MVPs
BOOM
Future created by Execs
At the end of 2 days – execs asked for a
commitment date
Another 2 more days of release planning in a
collaborative way
New ideas discussed to expedite the delivery
of MVP
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Week 3: An agile pilot team was born…
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The Notion of Supply Vs Demand
Finite capacity and Unconstrained
scope was introduced
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The Sizing bonanza
BOOM
2014 Roadmap didn‟t seem feasible
anymore
New thinking was needed
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The Q2 Road mapping
Interest in Pandora
Prioritization Model
BOOM
Crisis
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The opportunity for SAFe and Flow – The
Process…
To have a shared language
and alignment
BOOM
Execs not aligned
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Tagged Roadmapping with company-wide
Ideation
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Product‟s hypothesis…were tested to be untrue
17
Over 450
ideas by
over 100
people
generated in
one day
clustered
into 70

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Ideas were sponsored by various folks…
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52 Ideas were pitched to the entire company!
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Idea Pitching to the Prioritization Committee…
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Every Friday „All Hands‟ …update on the status

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Ideas bought (sold) … using poker chips
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Features to Stories and mapping to sprints by
the teams…
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A Product Development Program Board
emerged…
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Execs to steer the course…
Structures for execution
The Ceremonies and Cadence
to provide big visible actionable
insights to the Execs
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Executing on the plan…
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Sprint
demo
every
Friday

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When we are being a leader and exercising
leadership effectively …
We start…
having a shared language
gaining alignment on priorities
building great products for customers
welcoming surprises and adapt to it
Products with no traction
become…
Products people love

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Some additional places to look
from…

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Where could…
shared language
alignment
visibility
make a difference…in your organization?

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Leading from the Middle
…a startup‟s transformation journey
Questions?
Thank You!
Adele Maynes
Program Manager @ Tagged, adele@tagged.com
Latha Swamy
Transformation Coach, 925.200.7424, linkedin.com/in/lathaswamy

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