By Gary Bamberger

Introduction

Imagine we want to go on a hike. Without planning or at least having a trail map to guide the journey, we’d be taking a big risk, especially if we’re hiking in an inhospitable environment.  Before I go on a hike, I want to have a plan that accounts for the starting point, how capable the hikers are, how much time the hike should be and what the terrain is like (e.g. elevation changes, washes to cross, etc.).

The same holds true with engaging organizations that are on an agile transformation (or any evolutionary journey). I want to know what’s been done to date, some background on who is going on the journey, what outcomes the organization is seeking and some information about the context.

To gather the necessary intel, I use a library of questions I’ve accumulated based on my experiences and from various other sources.  These questions are organized by the groups of people I will engage to complete my initial assessment.  The assessment enables me to draft a customized roadmap that will be refined and iterated on with the sponsors and key stakeholders.

Below is the target audience and some topics we explore:

1. Executive context

My goals in this area are to understand the current organizational context including the competitive environment.  Here, I explore:

• The purpose and values of the organization and whether these are pervasively driven through the organization

• How socially conscious the organization is

• How does the organization compare to competitors

• How committed leaders are to the change

• What is driving the change and what are the expected outcomes

• What funding is available and how is funding allocated

2. Leadership and organizational alignment

In this area, I am focused on understanding the inner workings of the organization.  These questions examine:

• How are people organized within the organization

• Where is the organization in embracing lean - agile mindset

• What reference materials exist concerning product delivery

• How is product funding allocated

• What governance structure is currently in place

3. Teams and individuals

Questions in this area are to understand the practices currently being used and gain an understanding of team level context.  I’ve also included some of these questions in combination with team-level self-assessments.  Topics I cover include:

• What lean - agile practices are being used (i.e. frameworks, discovery practices, technical practices, established standards, etc.) and how prevalent are these practices

• How are teams are organized and what metrics are being collected

• What level of technical debt exists in the products

• What are teams and individuals experiencing related to culture, organization, practices, impediments, etc.

4. What change management support is available

Here, I focus on the communication and change management capabilities within the organization.  Some organizations have a separate communications and/or change management group.  If not, I blend these questions in as part of the Executive and/or Leader as appropriate.  My focus here is to understand:

• What evolution activities have taken place and what were the results

• What change management support is available within the organization

• How prepared is the organization for the evolution in light of other active change initiatives

How do I use this question library?

When I start the engagement, I will select a customized sub-set (never all) of questions from each area based on my initial discussions with the sponsor.  I use these questions as prompts during initial discussions with people.  These questions are the starting point and may evolve as I learn more about the organization.  You can download a copy of my question library.

You may notice some questions are redundant, which is by design to target different audiences.  In addition, some of these questions are more of a prompt for me to assess where the organization is at so I can build a resonant roadmap.

If you do something similar, how does it compare?