There’s a ritual that happens when someone new arrives — a consultant, an advisor, someone brought in to help. They schedule meetings. Thirty minutes each, across the organization. “Tell me what’s working. What’s not. What would you change?”
Two weeks later they’ve talked to forty people and feel like they understand the landscape.
They don’t. They understand the version of the landscape forty people felt safe presenting to someone who showed up last Tuesday with a title and a mandate.
The Outsider’s Disadvantage
I do this for a living. I walk into organizations where I might not know the domain, don’t know the people, and have no history with the decisions that shaped whatever I’m looking at. Sometimes I have relevant experience. Sometimes the industry is new to me and I’m learning the business and the people at the same time.
Either way, the hardest thing to internalize — even after decades — is how little you actually know when you first arrive. You might have a strong instinct about what’s wrong. But instinct built on pattern recognition from other companies isn’t the same thing as understanding this company, these people, this particular tangle of decisions and trade-offs and personalities that got them here.
The temptation is to arrive with answers. Clients want that — they hired you because you’re supposed to know things. And you do know things. But the gap between general expertise and specific understanding is where most consulting engagements go sideways.
Early in my career, I watched a consulting team redesign a warehouse layout for efficiency. They had data — units sold by product category — and they used it to allocate space. High-volume products got the prime real estate with the largest pick areas. It looked rigorous. Except they’d optimized around the wrong metric. The products moving the most units were small items, individual picks. The large pick areas they’d built were designed for bulk orders that didn’t match how those products actually shipped. The internal team — the people who worked the floor every day and understood order patterns, not just sales volume — had to quietly rework the layout after the consultants left.
The consultants weren’t wrong about the data. They were wrong about what mattered, because they hadn’t spent enough time understanding how the work actually moved through that building. That’s the gap. General expertise gets you in the door. Specific understanding is what keeps you from rearranging the furniture in the wrong direction.
Why Asking Isn’t Enough Either
The discovery phase is supposed to fix this. Instead of arriving with a playbook, you arrive with questions. You schedule the meetings. You genuinely want to hear from people. And that impulse is right — it’s a world better than the warehouse consultants who never thought to ask.
But think about it from the other side of the table. Someone you’ve never met — someone your boss brought in, someone who might recommend changes that affect your work, your team, your budget — sits down and asks you to be honest. You have thirty minutes. You don’t know what they already believe, who they’ve already talked to, or what they’re going to put in a deck next week.
So without really thinking about it, the conversation drifts toward safe ground. The problems that are easy to explain, the wins that are easy to see — and the harder stuff just doesn’t come up. It’s not deliberate. Most people don’t even realize they’re doing it. It’s just what happens when the stakes are unclear and the audience is unfamiliar.
I’ve been on both sides of this. When I was newer to consulting, I mistook the consistency of those answers for consensus. Everyone seemed to agree on the problems, so I figured I had a clear picture. It took a while to realize the consistency wasn’t consensus — it was caution. People had gravitated toward the same safe ground without coordinating it.
What Workarounds Tell You
Every organization has workarounds, and they’ll teach you more than most meetings will. The spreadsheet that exists because the system doesn’t track what people actually need. The Slack channel where real decisions get made because the official process is too slow. The person everyone calls when the documented procedure doesn’t cover the situation.
Nobody brings up workarounds in a scheduled meeting with an outside advisor. They’re embarrassed by them, or so used to them they’ve stopped noticing. Either way, they’re not coming up in a scheduled meeting. But workarounds tend to be more honest than anything you’ll hear in a meeting. They show you where the official story and the actual work diverge.
You find workarounds by being present, not by asking questions in a conference room. Shadow someone through their actual Tuesday. See what tools they have open on their screens — not the approved ones, the ones they actually reach for. Ask someone to walk you through a specific task from start to finish, and watch their hands, not their explanation.
Earning the Real Conversation
There’s a moment — and it’s never in the first meeting — when someone decides you’re worth figuring things out with. It usually happens informally. A side conversation after a meeting runs long. A hallway comment. Someone testing the water with a small, deniable criticism to see how you react.
If you react well — listen instead of defending, resist the urge to jump to a solution — the door opens a little wider. Next time, they tell you something harder. Eventually you get to the conversation that actually matters — where the real friction is, and what could genuinely change if someone had the room to rethink it.
This can’t be compressed into a two-week engagement kickoff. Trust doesn’t run on a project timeline. The advisor who treats discovery as a phase with an end date is inadvertently announcing a deadline — and deadlines are the enemy of candor.
Immersion Over Interviews
The most effective consulting relationships I’ve been part of didn’t start with a round of interviews. They started with showing up and joining the work — asking questions in context, while the thing was happening, rather than in a conference room after the fact.
Covey had it right — seek first to understand. But understanding isn’t something you get from asking. It’s something you get from being there. Learn the systems. Hear what customers actually complain about — not the summary, the unfiltered version. Attend the recurring meetings, but don’t try to run them yet. Be the person learning, not the person evaluating.
I started volunteering at a local food pantry this way. Didn’t walk in with suggestions — just showed up and loaded boxes. The process was straightforward: stage food from storage into a packing area, pack the boxes, then return the leftover food to storage. After a few sessions of doing the work, something clicked. What if we pre-calculated the exact quantities needed and only staged that amount? No leftovers to put back. I had a brief conversation with the leader — not a presentation, just “could we try this?” It took a small amount of upfront work to figure out the numbers, but once we tried it, the time volunteers spent on the whole activity dropped substantially.
That insight came from loading boxes long enough to feel where the process was wasteful. The warehouse consultants had better data than I did. I just had better context — because I’d been doing the work.
This may feel slow when the client’s expecting deliverables. But the alternative — making recommendations based on answers that never got past the surface — is how advisors end up confidently solving the wrong problems. And it’s how organizations end up skeptical of the next consultant who walks through the door.
The Relationship, Not the Report
There’s usually a line on the project plan where discovery ends and “the real work” begins. As if understanding is something you finish.
But organizations shift. What people told you in week two may not be true by month three. The workarounds evolve. The frustrations change shape. The person who didn’t feel safe enough to be candid in February might be in July — if you’re still around. If you’ve earned it.
The best outcomes I’ve been part of didn’t come from a thorough discovery phase. They came from people who never stopped paying attention — who kept showing up in the work and built the kind of relationships where you end up solving the right problems together.
You can’t schedule that in thirty-minute increments. And you can’t finish it — you can only keep showing up.