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Deep-Dive Discovery

What We'll Ask

The questions a Deep-Dive Discovery works through, published in full. Read it before the session and the session goes further: most of the value is in what you have already thought about before anyone sits down.

This is not the Strategy Call

A Strategy Call is about 30 minutes and asks about one workflow. This is the Deep-Dive Discovery that can follow it: a working session across a whole department, with pre-work sent ahead. You are not expected to have answers to all of it. It is published so you can see exactly what the engagement involves before you commit to one.

Start with a Strategy Call

Before we start

The goal of the session is to understand how your department operates today and how work actually gets done. Together we identify your business objectives, map the workflows that support them, understand the technology involved, find the process and technology gaps, and define the outcomes you are trying to achieve.

What to send ahead

Five business days before the session, so the time is spent on questions rather than on collecting documents.

  • An org chart for the department, including contractors and shared resources.
  • A list of every system, tool and app the team touches — spreadsheets included, and anything paid for on a personal card.
  • The two or three processes you consider highest-volume or highest-pain.
  • Any existing SOPs, runbooks or process documentation, however stale.
  • Your top three objectives for the year.

How the session runs

Five passes, in order. Each one depends on the one before it.

Objective
Define what the department exists to deliver, and what it is measured on.
Journey
Map how the work actually flows, step by step, system by system.
Gap
Identify where the technology does not support the work.
Outcome
Define the result you want, in terms you can measure.
Living documentation
Write it all into a record that is maintained rather than filed.

The 37 questions

Grouped by what they are trying to establish. Numbering runs straight through, so a question can be referred to by its number in the session.

Department objectives

  1. What does this department exist to deliver? In one sentence.
  2. What is this department measured on today? What number does leadership look at?
  3. What does the business ask of you that you currently cannot deliver, and what is blocking it?
  4. If we sat here 18 months from now and it had gone well, what would be different?
  5. What is your binding constraint right now: people, tooling, data, budget or decision speed?
  6. What is most challenging: volume of work, complexity of task, or expectations from leadership?

Current technology

  1. Walk us through every system this team touches in a normal week.
  2. What is not on the official list? Spreadsheets, shared drives, chat threads, local databases, anything bought on a card.
  3. For each core system: who owns it, who administers it, what does it cost, and when does it renew?
  4. For your key data — customers, orders, employees, assets, cases — what is the system of record, and where else does that same data live?
  5. What connects your systems? A native integration, middleware, a script, or a person moving it by hand?
  6. What reporting exists? Who builds it, and how long does it take?
  7. Where does the same information get entered more than once?
  8. How does someone get system access on their first day, and how do they lose it after they leave?
  9. What are you paying for that nobody uses?

How the work flows

Asked of each of the two or three processes you nominated as highest-volume or most painful.

  1. What triggers this process, and what signals that it is finished?
  2. Walk us through it step by step. Who does each step, and in what system?
  3. What arrives at each step, and what leaves it?
  4. How long does each step take to do, and how long does it sit waiting?
  5. What is copied, pasted, re-keyed or exported to a spreadsheet along the way?
  6. Where is there a judgment call? What is the rule, and is it written down anywhere?
  7. What happens when a step goes wrong? Who finds out, and how?
  8. Where does this process hand off to another team? What gets passed, and how?
  9. How often does this run, and at what volume?

And for each process, the questions that find what the walkthrough misses

  • Can you show us rather than tell us?
  • Walk us through the last time this went sideways.
  • What do you do when the system will not let you do the right thing?
  • Where does the work wait?
  • Who do you have to chase to finish your job?
  • What do you check twice because you do not trust it?
  • What happens if the person who knows this is out for two weeks?

Gaps and friction

  1. Where does work stall, queue or get stuck?
  2. What gets re-done? How often, and how many hours does it cost?
  3. What can only one person here do?
  4. What breaks if volume doubles? What is already breaking?
  5. What is your most common escalation, and what causes it?
  6. What manual check exists only because a system cannot enforce the rule?
  7. What would you struggle to produce evidence for if an auditor asked tomorrow?
  8. What would you fix first if you controlled the budget?
  9. What have you asked for before and not received? What reason were you given?

Constraints

  1. What is off the table? Systems that cannot change.
  2. What is already changing in the next 12 months? Hires, renewals, regulatory shifts, new lines of business.
  3. What is the team’s appetite and capacity for change right now?
  4. Who here would champion a change, and who would resist it, and why?

What you get

A written record of how the department works today, where the technology does not support it, and which workflows are worth changing first — with the reasoning visible, so you can act on it with us or without us.

Take it with you

The same content, nothing withheld and no email required.

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