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?
  • 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?
  • 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?
  • 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?   
  • 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?