I like to dive in and take stock of what’s happening within an organization when I start a new consulting project/engagement. Over the years, I’ve boiled this down to a consistent set of questions and things I want to research. In honor of prolific sharing and not reinventing the wheel…
I’ll start with whatever I can find on my own through LinkedIn, sites like Crunchbase, and visiting a company’s website and social media channels…Next, I set up Google Alerts including the client’s name and any related industry terms and deliver them to an RSS feed which then sends an automated notification to a private Slack channel.
While I might have a specific title on any particular engagement like Scrum Facilitator, Agile Coach, or Business Analyst, I want a holistic view of the organization, beyond the teams and departments I’ll work with.
Consider this a companion piece to my operating manual on how I build and facilitate authentic, empowered, and resilient remote teams.
My goal is to gain understanding and add value as quickly as possible so I can become a strategic partner and trusted advisor. I get to maintain the objectivity of being an outsider, but I want to have enough information so I can think like an insider.
Company Info
Get the basics down so we can enter any conversation at any level having an understanding of the products and services a client company offers.
- Number of employees
- Public or private?
- Where are offices?
- Values/mission statements
- Percentage of remote folks
- Products/services offered
- In what social channels is the organization most active?
- How many followers?
- What does engagement look like?
- How strong is content?
- What case studies/white papers are available to read?
- Who are the main competitors?
- What is this organization’s competitive advantage/UVP (Unique Value Proposition)?
Organizational Health
- Do employees feel psychologically safe?
- Are people comfortable asking “why?”
- How is morale?
- What does trust look like at leadership levels? Between employees?
- Are titles, roles, and responsibilities clear?
- Has any large-scale change been introduced recently?
- What does learning look like at the organization? Is it valued?
- Does the organization have/support employee resource groups? In what areas?
- Are diversity, equity, and inclusion core values? What does it look like in practice?
- How are teams celebrated?
- How is failure defined and what is the tolerance for it?
- What happens when someone makes a mistake?
- Are soft skills valued? Emotional intelligence?
- Do teams have a sense for how their work rolls up to broader organizational goals?
- Do people understand what’s expected of them?
Team Behaviors
- Do people interrupt each other on calls?
- Do they demean each other?
- Do people gossip behind others’ backs?
- Do a handful of folks tend to dominate all conversation?
- Are people generally resistant to change?
- Who are the influencers? Who are the decision makers? Any challenging personalities or motivations to consider?
- What are working styles/preferences/motivations for the individuals with whom we’ll be working closely?
- When new team members join, how are they introduced, if at all?
- Do teams take time to talk about non-work things?
- Do meetings have goals/agendas?
- Are action items clear at the end of a meeting?
- How are decisions made and by whom?
Measuring Success
- What does performance management look like? Annual reviews? More frequent? How is informal feedback shared along the way?
- Does the organization track KPIs or OKRs or something else? Where do these metrics live and are they accessible to the entire organization?
- Is success for a product, project, service, team, and/or individual clearly defined?
Communications/Tools
- Where do company-wide communications happen?
- Where do team level communications happen?
- If remote, do people use video chat?
- Do people use lots of different terms/acronyms/jargon to describe the same things?
- Do people get confused on what those things mean?
- Are processes clearly documented and shared?
- How are expectations communicated?
Technology 
- Tech stack
- Azure, AWS, GCP? Desktop?
- What problems does the application solve?
- How many users are there?
- What are the different user types?
- See demo or create account myself
- Review existing documentation
- Code review process?
- Release process?
- What does CI/CD look like?
- How often is code released?
- Who owns the release process?
- How well is everything documented? Who does the documenting?
- Where are requirements defined and by whom?
- How much of the testing process is automated?
- How quickly can the org onboard a new developer?
- What happens at the portfolio level across teams/projects? How are things prioritized across the technology organization?
- What is the structure of environments?
- Accessibility needs? Who owns accessibility?
- Which browsers are supported?
- Are there in-house UX capabilities? If not, who owns UX?
- Who owns data privacy/security?
- Is there a data retention policy?
- What are the business drivers for the new functionality or application?
- What are the biggest constraints on this project/engagement? Time, budget, people, something else? Why might it fail?
- When is sign-off needed and why?
- What does support look like? Are individuals working on support and new development simultaneously? If so, how is that structured and how is it going?
- Are they on Macs/PCs/both across the company?
- How will training be conducted? Who owns the training process/documentation?
- Are there any audit/legal considerations to take into account?
- GDPR, HIPAA, etc.
- Legal approvals on language within the application
Agile + Scrum
- How and when was Agile introduced to the company?
- What are the teams’ approaches to estimating? Is that working?
- Who holds the Product Owner role? How hands on are those individuals? How connected to customers are those individuals?
- Does leadership encourage self-managing team behaviors or is that threatening?
- How many development teams are there?
- Is the definition of done clear?
- Is Acceptance Criteria included in user stories? If so, are they sufficient?
- What does the work item structure/hierarchy look like? Ex: tasks, user stories, features/epics, etc.
- What happens when someone on the team hits a blocker?
- What does the feedback loop look like with end clients (or internal clients)?
- Do team members track hours and capacity?
- Do user stories often move to the next sprint b/c they aren’t done?
- How does new work come to the teams?
- When new work comes in during a sprint, is other work de-scoped or do teams try to accommodate the new work on top of existing commitments?
- Do teams have sprint goals?
- How are research tasks documented within a sprint?
- How is each sprint’s progress communicated to executives?
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If Scrum…
- What does successful Scrum look like at this organization?
- How do Scrum teams learn about what other Scrum teams are doing?
- Does the organization have Scrum Masters? If not, who is playing that role?
- What metrics are being tracked? Are team stats compared?
- Why would Scrum fail at the organization?
- Are teams sizing and story pointing work items? Using Fibonacci, t-shirt sizes, something else?
- Are velocities consistent?
- What Scrum ceremonies are held and how often? How long are they?
- For retrospectives, how is team improvement/progress tracked?
- Are sprint demos held?
- What is the functional makeup of teams?
- Is QA truly embedded?
- UX?
- Product manager vs. Product Owner vs. Project Manager?
- Are people managers also serving as Scrum Masters?
Miscellaneous
- What are executive sponsors/stakeholders/team members reading right now?
- In what format and how often do project sponsors/stakeholders like to receive information? Data dashboards, one-page executive summaries, paragraph form, bullets…
- What else haven’t we asked about?
Fellow consultants and intrapreneurs, how do you go about learning what you need to know when you start a new engagement?
Photo by Jessica Ruscello on Unsplash
