Preliminary Landscape Assessment

The Foundation That Makes or Breaks Everything

The Real Purpose (What They Don’t Tell You)

The Preliminary Landscape Assessment isn’t really about gathering information. It’s about building the political capital and contextual intelligence you need to successfully facilitate Phase 2.

Here’s what you’re actually doing beneath the surface:

Building Trust Networks

Every interview is a relationship-building opportunity. When someone spends 90 minutes honestly discussing their frustrations with you, they’re investing in the process. They become stakeholders before Phase 2 even starts.

Mapping Power Structures

The org chart tells you reporting lines. Interviews tell you who actually gets things done, who blocks change, who influences decisions, and where the bodies are buried.

Identifying Language & Culture

Every organization has its own vocabulary, sacred cows, inside jokes, and taboo topics. You need to learn this language to facilitate effectively.

Testing Readiness

Are people ready for honest conversation? Or is this a blame culture where everyone’s in CYA mode? This assessment tells you how to structure Phase 2 for psychological safety.

Surfacing Hidden Agendas

Who requested this initiative and why? What political outcomes are people hoping for? What are the real (vs. stated) success criteria?

Pre-Interview Preparation: Do Your Homework

Before You Talk to Anyone (4-6 hours of research)

Company Intelligence:

  • Read the last 2 years of press releases, blog posts, or annual reports
  • Understand their market position, competitive pressures, recent wins/losses
  • Identify any major organizational changes (mergers, layoffs, leadership transitions)
  • Review Glassdoor/LinkedIn for cultural insights

Industry Context:

  • What are typical pain points in this industry?
  • What compliance/regulatory pressures exist?
  • What technology stacks are common?
  • What’s the competitive landscape doing with AI?

Organizational Structure:

  • Get the org chart (official version)
  • Understand reporting relationships
  • Identify departments, team sizes, key roles
  • Note any unusual structural elements

Previous Initiatives:

  • Ask for documentation on past improvement projects
  • What tools were implemented in the last 2-3 years?
  • What change management initiatives happened?
  • What consultants have they worked with before?

Why this matters: Walking in cold wastes 20 minutes of every interview on context you could have learned yourself. Worse, it signals you haven’t taken them seriously enough to prepare.

Interview Logistics: The Details That Matter

Scheduling Strategy

Order matters:

  1. Start with the Executive Sponsor – Understand the political landscape, constraints, and real goals before talking to anyone else
  2. Middle managers next – They see both strategic intent and operational reality
  3. Department heads – After you understand the ground-level view
  4. Frontline staff last – By now you can ask very specific questions

Why this order? You’re building context progressively. Each conversation informs the next.

Timing:

  • Schedule 90-minute blocks (60 min interview + 30 min buffer for notes/synthesis)
  • Maximum 3 interviews per day (you need processing time)
  • Spread over 5-7 business days
  • Leave gaps for follow-up questions

Location:

  • Their space, not yours (they’re more comfortable)
  • Private setting (not an open office where others can hear)
  • Minimize interruptions (block their calendar properly)

Setting the Frame (First 5 Minutes)

Your opening script:

“Thank you for taking the time. Let me explain what I’m trying to accomplish here.

I’m not here to audit your department or evaluate performance. I’m here because we’re going to bring cross-functional teams together to identify problems worth solving, and I need to understand how work actually flows through the organization—not how the process manual says it should work, but how it really works.

Everything you share helps me ask better questions in those group sessions. I may take notes, but nothing is attributed to individuals unless you specifically want credit for an idea.

I’m looking for honest perspectives—what’s working, what’s broken, what’s frustrating. The more specific you can be, the better. Does that make sense?”

Why this works:

  • ✅ Removes defensiveness (not an audit)
  • ✅ Establishes confidentiality (safe to be honest)
  • ✅ Clarifies purpose (helps them help you)
  • ✅ Invites candor (we want the real story)

The Interview Itself: Technique and Tactics

The Funnel Approach

Start broad, narrow progressively:

Layer 1: The Big Picture (10-15 minutes)

  • “Walk me through what your team does”
  • “What does a typical week look like?”
  • “What are the 3-4 most important outputs your team produces?”

Layer 2: The Pain Points (20-30 minutes)

  • “What takes longer than it should?”
  • “Where do things break down most often?”
  • “What frustrates your team most?”

Layer 3: Specific Processes (20-30 minutes)

  • “Let’s dig into [specific process]. Walk me through every step.”
  • “Where do you get the data for this?”
  • “What happens when X goes wrong?”

Layer 4: Solutions & Ideas (10-15 minutes)

  • “If you could change one thing, what would it be?”
  • “What’s been tried before? What happened?”
  • “What would success look like?”

Question Techniques That Work

The Five Whys (Modified)

Them: "The monthly report takes forever"
You: "How long does it take?"
Them: "About 8 hours"
You: "What makes it take so long?"
Them: "We have to pull data from three different systems"
You: "Why three systems?"
Them: "Because sales uses Salesforce, operations uses the ERP, and finance uses their own thing"
You: "Why don't they talk to each other?"
Them: "They technically can, but nobody set up the integration and Finance doesn't trust automated data anyway"

Now you’ve found the real problem: Not the report itself, but data fragmentation and trust issues with automated data.

The Concrete Example Don’t accept vague: “Communication could be better”

Probe for specific:

  • “Can you give me an example from this week?”
  • “Walk me through exactly what happened”
  • “What should have happened instead?”

The Awkward Silence When someone gives a surface-level answer, don’t immediately ask the next question. Wait 3-5 seconds. People naturally fill silence with deeper insights.

The Hypothetical “If you were CEO for a day and could change anything about how this works, what would you do?”

This bypasses political constraints and reveals what people really think.

The Third-Party Frame “What do people in your department complain about when you’re not in the room?”

Easier to answer than “what do YOU complain about?”

The Workaround Detector “What do experienced people know how to do that isn’t in the training manual?”

Workarounds are treasure maps to broken processes.

Reading Between the Lines

What they say vs. What they mean:

They Say They Often Mean
“It’s fine” It’s not fine, but I don’t trust you yet
“That’s just how we’ve always done it” Nobody knows why we do it this way anymore
“We tried that before” Someone’s pet project failed and people are scared
“IT would never approve that” I don’t want to fight that battle
“Upper management wants…” I disagree but won’t say so directly
“It’s complicated” I don’t fully understand it myself
“We’re working on it” We’ve been working on it for 18 months with no progress

Body language signals:

  • Leaning forward, animated = real pain point they care about
  • Checking watch, short answers = either not engaged or uncomfortable topic
  • Long pauses before answering = political calculation happening
  • Vague, meandering answers = either don’t know or can’t say
  • Specific numbers/examples = they live with this problem daily

Handling Difficult Situations

The Rambler Some people will talk for 40 minutes without answering your question.

“That’s really helpful context. Let me make sure I understand the specific issue with [X]. Can you walk me through exactly how that process works today?”

The Defensive Some people think you’re there to blame them.

“I want to be clear—I’m not evaluating anyone’s performance. Every organization has processes that evolved over time and don’t quite work anymore. That’s not anyone’s fault. I just need to understand reality so we can help fix it.”

The Politician Some people only give you the corporate line.

“I appreciate the official perspective. But off the record, just between us—if you could wave a magic wand and change one thing, what would it make the biggest difference?”

The Overwhelmer “EVERYTHING is broken! We need to fix ALL of it!”

“I hear you. Let me ask this: if we could only fix ONE thing in the next 90 days, what would have the biggest impact on your team?”

The Skeptic “We’ve had consultants before. Nothing ever changes.”

“That’s exactly why I’m starting by listening instead of prescribing solutions. What happened with previous consultants? What should I do differently?”

(And then actually do it differently)

Documentation: Capturing What Matters

During the Interview

Use a structured note template:

INTERVIEW NOTES TEMPLATE

Interviewee: [Name, Title, Department]
Date: [Date]
Duration: [Actual time]

=== ROLE & RESPONSIBILITIES ===
[What they actually do daily]

=== KEY PAIN POINTS ===
Pain Point 1: [Description]
- Frequency: 
- Time cost:
- Business impact:
- Quote: "[their words]"
- Cross-functional dependencies:

Pain Point 2: [etc.]

=== CURRENT WORKAROUNDS ===
[Unofficial processes they've developed]

=== TOOLS & SYSTEMS ===
[What they use, how they use it, gaps]

=== CROSS-FUNCTIONAL FRICTION ===
[Which departments, what breaks down]

=== PREVIOUS INITIATIVES ===
[What's been tried, why it failed/succeeded]

=== IDEAS & SOLUTIONS ===
[Their suggestions]

=== POLITICAL/CULTURAL NOTES ===
[Sensitivities, relationships, sacred cows]

=== FOLLOW-UP QUESTIONS ===
[Things to explore in later interviews]

=== WORKSHOP IMPLICATIONS ===
[How this affects Phase 2 planning]

Don’t transcribe verbatim. Capture:

  • Key facts and numbers
  • Memorable quotes
  • Process steps
  • Your observations
  • Questions raised

Immediately After (Within 30 Minutes)

Brain dump while fresh:

  • What surprised you?
  • What patterns are emerging?
  • What questions did this raise for other interviews?
  • What political dynamics did you notice?
  • What should you ask next interviewee?

This is gold. Your immediate impressions matter more than perfect notes.

End of Each Day

Synthesis session (60 minutes):

  • Review all interviews from that day
  • Update master problem inventory
  • Identify emerging themes
  • Adjust remaining interview questions
  • Flag critical issues for executive sponsor

Pattern Recognition: What You’re Looking For

Cross-Functional Patterns (The Jackpot)

Example Pattern:

  • Finance says: “We can’t close the books on time because Operations is slow sending data”
  • Operations says: “We can’t send data faster because we’re waiting for Sales to confirm orders”
  • Sales says: “We can’t confirm orders because customers keep changing specs and there’s no version control”

The real problem: Not any single department, but a systemic lack of real-time visibility and version control across the order-to-cash process.

This is worth 10x more than department-specific complaints.

The Problem Typology Framework

As you interview, categorize problems:

Type 1: Data Problems

  • Data doesn’t exist
  • Data exists but can’t be accessed
  • Data exists in multiple places with conflicts
  • Data is manual/error-prone
  • Data is stale by the time you need it

Type 2: Process Problems

  • Too many steps
  • Unclear ownership
  • Bottlenecks/dependencies
  • Rework loops
  • Tribal knowledge required

Type 3: Communication Problems

  • Information silos
  • Unclear expectations
  • Missing feedback loops
  • Notification failures

Type 4: Tool Problems

  • System doesn’t do what’s needed
  • System does it, but it’s too complex
  • Multiple systems don’t integrate
  • Tool is deprecated but still used

Type 5: Knowledge Problems

  • Training gaps
  • Documentation doesn’t exist/is outdated
  • Expert dependency
  • Institutional knowledge loss

Why categorize? Because AI solves some of these (Types 1, 3, some of 4) but not others (Type 2 often needs process redesign, Type 5 needs knowledge management).

Impact Scoring During Assessment

For each problem, estimate:

Frequency:

  • Daily = 5 points
  • Weekly = 3 points
  • Monthly = 1 point

Scope:

  • Affects entire company = 5 points
  • Affects multiple departments = 3 points
  • Affects one team = 1 point

Time Cost:

  • 10 hours/week wasted = 5 points

  • 3-10 hours/week = 3 points
  • <3 hours/week = 1 point

Business Impact:

  • Direct revenue/compliance risk = 5 points
  • Customer experience impact = 3 points
  • Internal efficiency only = 1 point

Solveability with AI:

  • Clear AI application = 5 points
  • Possible but complex = 3 points
  • Probably not AI = 1 point

Total Score = Frequency + Scope + Time Cost + Business Impact + Solveability

Anything scoring >15 is Phase 2 priority material.

Red Flags That Should Pause Everything

Deal-Breakers (Consider Walking Away)

🚩 Blame Culture If every interview is “it’s [other department]’s fault,” the organization isn’t ready for collaborative problem-solving.

🚩 No Executive Buy-In If the sponsor can’t articulate why they’re doing this or what success looks like, you’re being set up to fail.

🚩 Magical Thinking “AI will automate everyone’s job and we’ll cut headcount 50%” = unrealistic expectations you can’t meet.

🚩 Recent Major Trauma Layoffs, failed merger, leadership upheaval in last 3 months = organization is in survival mode, not improvement mode.

🚩 Tool Graveyard If they’ve implemented and abandoned 3+ systems in the past year, they have an adoption problem, not a solution problem.

Yellow Flags (Proceed with Caution)

⚠️ Analysis Paralysis History Lots of studies, no action. You’ll need to build in forcing functions for decision-making.

⚠️ Turf Wars Department heads protecting their domains. Phase 2 facilitation needs extra focus on psychological safety.

⚠️ Change Fatigue “Not another initiative” sentiment. You’ll need to differentiate this from previous efforts.

⚠️ Technical Debt Overload Systems held together with duct tape. Any AI solution may require infrastructure work first.

⚠️ Compliance Complexity Heavily regulated industry with risk-averse culture. Solutions will need extra vetting.

Special Interview: The Executive Sponsor Deep Dive

This interview deserves its own section because it’s the most consequential.

The Real Questions to Ask

Beyond the stated goals:

“What prompted this initiative right now? Why not 6 months ago or 6 months from now?”

(This reveals the real driver—pressure from board, competitive threat, new executive mandate, etc.)

“What happens if this doesn’t produce results? What happens to you personally?”

(Tells you how much political capital they’ve invested)

“Who internally is skeptical about this? Why?”

(Identifies resistance you’ll face)

“What would cause you to kill this project midstream?”

(Defines real failure criteria)

“If we identify high-value problems that aren’t AI problems, how do you want me to handle that?”

(Tests intellectual honesty)

“What past initiatives have you championed? What happened to them?”

(Track record matters)

The Budget Reality Check

Don’t just ask budget size. Ask:

“If we identify a solution that costs $X but delivers $Y in value, who makes that decision? What’s the approval process?”

“What’s already budgeted vs. what would need additional approval?”

“Are we optimizing for quick wins or long-term transformation?”

This tells you whether to focus on cheap wins or swing for the fences.

The Political Landscape Map

“Who are the internal champions I should build relationships with?”

“Who might block implementation? What are their concerns?”

“What’s the real decision-making process here—not the official one, but how things actually get approved?”

“Who has veto power even if they’re not officially in the approval chain?”

This is pure gold for Phase 2-4 success.

The Synthesis Process: Making Sense of Everything

After All Interviews (8-10 hours of analysis)

Step 1: Problem Inventory Consolidation

Take all your individual interview notes and create master problem list:

MASTER PROBLEM INVENTORY

PROBLEM #1: Monthly financial reporting takes 8 hours of manual work
- Mentioned by: Finance Director, 2 Finance Analysts, Operations Manager
- Root cause: Data fragmentation across Salesforce, ERP, manual spreadsheets
- Frequency: Monthly (12x/year)
- Time cost: 8 hours × 2 people = 16 hours/month = 192 hours/year
- Dollar cost: $75/hr × 192 = $14,400/year
- Business impact: Delayed financial visibility, occasional errors
- Current workaround: Friday all-hands data compilation session
- Potential solution: Automated data integration + templated reporting
- AI applicability: HIGH (data aggregation, report generation)
- Priority score: 18/25
- Workshop topic: Yes - cross-functional data flow session

Repeat for every problem identified (you’ll typically have 30-50).

Step 2: Pattern Clustering

Group related problems:

Cluster A: Data Fragmentation

  • Problems #1, 5, 12, 18, 23
  • Common theme: Multiple systems don’t talk to each other
  • Affects: Finance, Operations, Sales, Customer Success

Cluster B: Manual Status Tracking

  • Problems #3, 7, 14, 22
  • Common theme: No real-time visibility into work status
  • Affects: Operations, Customer Success, Executive team

Cluster C: Customer Onboarding Delays

  • Problems #2, 9, 15, 19
  • Common theme: Handoffs between departments cause delays
  • Affects: Sales, Implementation, Customer Success

This clustering reveals systemic issues, not just point problems.

Step 3: Impact vs. Effort Matrix

Plot each problem cluster:

HIGH IMPACT, LOW EFFORT (Do First)
- Automated financial reporting
- Customer status notifications

HIGH IMPACT, HIGH EFFORT (Strategic Projects)
- Complete CRM integration
- Real-time inventory visibility

LOW IMPACT, LOW EFFORT (Quick Wins)
- Automated meeting notes
- Email templates

LOW IMPACT, HIGH EFFORT (Avoid)
- Complete system replacement
- Custom-built ERP module

Step 4: AI Suitability Assessment

For each high-priority problem:

Is this actually an AI problem?

✅ Good AI Candidates:

  • Repetitive data processing
  • Pattern recognition
  • Natural language tasks
  • Personalization at scale
  • Prediction/forecasting

❌ Bad AI Candidates:

  • Requires human judgment on edge cases
  • One-off custom work
  • Problems caused by poor process design
  • Issues with accountability/ownership
  • Tools that already exist for this

Be honest. Half your credibility comes from saying “this doesn’t need AI, it needs better process design” when that’s true.

The Deliverable: Landscape Assessment Document

Structure (15-20 pages total)

1. Executive Summary (1-2 pages)

  • Organizational context
  • Assessment methodology
  • Key findings (3-5 major themes)
  • Readiness for AI initiatives
  • Recommended next steps

2. Organizational Overview (2-3 pages)

  • Departments interviewed
  • Current technology landscape
  • Previous improvement initiatives
  • Cultural observations
  • Change readiness assessment

3. Problem Inventory (4-6 pages)

Organized by cluster, not by department:

Cluster 1: Data Fragmentation & Reporting Problems identified: 8 Total annual time cost: 450 hours Departments affected: Finance, Operations, Sales Priority: HIGH

[List of specific problems with details]

Cluster 2: Customer Communication & Status [etc.]

4. Cross-Functional Insights (2-3 pages)

  • Where silos cause friction
  • Hidden dependencies
  • Common workarounds
  • System integration gaps
  • Knowledge transfer issues

5. Opportunity Assessment (3-4 pages)

High-Priority Opportunities:

For each:

  • Problem description
  • Current state vs. desired state
  • Business impact (quantified)
  • Affected stakeholders
  • Preliminary solution approach
  • AI applicability
  • Implementation complexity
  • Estimated ROI

6. Phase 2 Recommendations (2-3 pages)

  • Recommended workshop participants
  • Specific topics for facilitated sessions
  • Potential sensitivities to manage
  • Success criteria
  • Timeline and logistics

7. Appendices

  • Interview participant list
  • Process flow diagrams
  • Memorable quotes (anonymized)
  • Detailed problem scoring
  • Technology inventory

Presentation to Stakeholders

Don’t just send the document. Present it.

30-minute executive presentation:

Slide 1: Recap methodology Slide 2-3: Key themes (the patterns you found) Slide 4-6: Top 5 priority opportunities Slide 7: What this means for Phase 2 Slide 8: Next steps and timeline

Then facilitate discussion:

  • “What surprises you here?”
  • “What did we miss?”
  • “Which of these resonates most?”
  • “Are there political considerations we should know about?”

This discussion often reveals the final 10% you didn’t get in interviews.

What Success Looks Like

You know your Preliminary Landscape Assessment was successful when:

✅ Stakeholders say “this nails it” rather than “that’s interesting”

✅ People you didn’t interview reach out asking to be involved in Phase 2

✅ The executive sponsor sends the document to their peers unsolicited

✅ Problems are specific and quantified, not vague and aspirational

✅ You have clear, defensible priorities for Phase 2 facilitation

✅ You’ve identified 3-5 clusters of related problems, not 50 disconnected complaints

✅ You can confidently explain why each priority matters to the business

✅ You know who the champions and blockers are for each initiative

✅ You’ve identified at least 2-3 problems that shouldn’t be solved with AI

✅ Phase 2 participants are excited (or at least willing) rather than resentful

Common Mistakes and How to Avoid Them

Mistake #1: Treating It Like an Audit

What it looks like:

  • Checklist mentality
  • Evaluative tone
  • Focus on what’s “wrong”
  • People get defensive

Fix:

  • Collaborative inquiry, not investigation
  • “Help me understand” not “Why don’t you”
  • Focus on obstacles, not blame
  • Appreciative framing

Mistake #2: Accepting Surface-Level Answers

What it looks like:

  • “Communication could be better”
  • “We need more transparency”
  • “The system is slow”

Fix:

  • Always ask for specific examples
  • Probe for the problem beneath the problem
  • Use Five Whys technique
  • Request quantification

Mistake #3: Ignoring Organizational Politics

What it looks like:

  • Taking org chart as reality
  • Missing hidden power dynamics
  • Proposing solutions that step on toes
  • Surprised by resistance in Phase 2

Fix:

  • Ask about informal influence
  • Notice who defers to whom
  • Understand previous failures
  • Map stakeholder interests

Mistake #4: Falling in Love with Technology

What it looks like:

  • Every problem looks like AI opportunity
  • Ignoring process/training solutions
  • Solution-first thinking
  • Losing credibility with practical teams

Fix:

  • Honest assessment of AI suitability
  • Recommend non-AI solutions when appropriate
  • Focus on business value, not tech coolness
  • Build trust through intellectual honesty

Mistake #5: Analysis Paralysis

What it looks like:

  • Perfect documentation before moving forward
  • Wanting to interview everyone
  • Endless refinement of findings
  • Delaying Phase 2

Fix:

  • Set hard deadline for assessment completion
  • Accept 80% confidence is enough
  • Some questions can only be answered in Phase 2
  • Ship the document

Mistake #6: Skipping Validation

What it looks like:

  • Delivering document without review
  • Surprises in executive presentation
  • Missing obvious considerations
  • Political landmines

Fix:

  • Share draft with executive sponsor first
  • Quick check-ins with key stakeholders
  • “Did I miss anything?” conversations
  • Soft-launch findings before hard presentation

The Meta-Lesson

The Preliminary Landscape Assessment isn’t really about collecting information.

It’s about:

  • Building trust so people will be honest in Phase 2
  • Understanding politics so you can navigate resistance
  • Identifying champions who will carry initiatives forward
  • Learning the culture so you know how to communicate
  • Establishing credibility so your recommendations land
  • Creating momentum so Phase 2 has energy behind it

The document is the artifact. The relationships and insights are the real deliverable.

Done well, this phase makes everything else easier. Done poorly, no amount of brilliant facilitation in Phase 2 will save you.

What specific aspect would you like to explore further? Interview techniques? Documentation templates? Political navigation? Synthesis methodology?