Mastering Enterprise Relationships Without the Bullshit: The Psychology of Enterprise Success
Enterprise success is a mix of trust, politics, and people. Win by being honest, kind, and sharp.
On my mind this week
I talked to a former colleague this week, and she asked how I’m liking working with enterprise brands, especially since most of my career was spent in startups or smaller companies.
It wasn’t love at first sight, lol. But it grew on me.
When I think of myself, I think of this rebel, punk-rock chick with a strong personality, outspoken and direct. Been like that for as long as I can remember. Naturally, the startup world felt like home.
But as I told her, I genuinely enjoy working with enterprise brands now. And it’s not because of the prestige or the resources. It’s because, at its core, enterprise success depends more on understanding human psychology and internal politics than anything else. As a former salesperson, I find that fascinating.
Most standard advice you hear about enterprise sales is basic:
“Reply quickly.”
“Be professional.”
“Build relationships.”
Sure, true. But that’s table stakes. Not a competitive advantage.
Enterprise deals rarely fail because of bad tech or lack of talent… or bedside manners.
They fail because stakeholders act in predictable but misunderstood ways; protecting their roles, preserving the status quo, or avoiding risk. To win, you have to understand those hidden motivations early and manage them well.
I also think a lot of people who want to sell to enterprise brands get lost in the sauce. They see the $$$ and forget that these companies are made up of people, people just like us, trying to figure it out and do their best. That thirst? It shows. And when it’s not backed up by real value or excellence, it puts people off.
So this week, I’m sharing some observations and learnings from working solely with enterprise brands for almost three years now. Whether you work in one, consult for one, sit agency-side, or want to sell into one, this might help.
Of course, this is my experience, my lens. Your mileage may vary.
Beyond The Mean
The Hidden Psychological Dynamics at Play
Enterprise sales aren’t complex because companies are big, they’re complex because humans are.
Sure, the process is longer, and the buying cycle feels endless. That’s to be expected when decisions have to pass through layers of stakeholders, departments, and priorities before you celebrate a closed deal in Salesforce.
The real challenge isn’t navigating the process. It’s navigating the people.
At the end of the day, you’re not dealing with logos or org charts. You’re dealing with egos, fears, biases, and carefully guarded turf. Every stakeholder comes into the room with psychological baggage, and your job is to unpack it gently, strategically, and without setting off alarm bells.
One dynamic I see all the time is status quo bias.
Stakeholders aren’t afraid of your new tool, or even your pricing. They’re afraid of uncertainty.
The spreadsheet everyone hates? It’s familiar.
The legacy platform that crashes twice a month? Still less threatening than staking their credibility on something unproven.
Your real job is to help them realize that staying where they are is actually the riskier move.
Then there’s loss aversion.
Humans are wired to hate losing more than they love winning. Even if your product clearly creates value, stakeholders often fixate on what they might lose: control, reputation, budget, influence.
In the enterprise world, “no” is a safe bet. Read that again. And again.
Nobody ever got fired for saying, “Let’s wait.” So your task isn’t just to pitch benefits. It’s to neutralize perceived risks.
Another big one is territorial defense.
Departments in big orgs operate like kingdoms. With moats, drawbridges, and gatekeepers.
If your proposal even hints at stepping on someone’s turf, you’ll get quiet resistance: passive delays, strategic silence, or endless alignment meetings.
You can’t tear down someone’s castle. But you can reposition your solution so it supports their stronghold instead of threatening it. The best consultants don’t “invade”, they align.
If there is one thing I want you to take from this section is this: Don’t wait for internal politics to derail your project before you take them seriously.
Anticipate the psychology in the room. Speak to it directly. Show how your work helps stakeholders win, without making them feel exposed or replaceable.
You're dealing with people, not personas. And people, especially in high-stakes environments, act in predictably irrational ways. Mastering enterprise work means mastering those dynamics.
Identifying and Navigating Internal Politics Early
Big organizations come with complex relationships and carefully balanced interests. That’s just how things work when many people have skin in the game.
When internal stakeholders hesitate or stall, it’s rarely because they’re being “difficult.” More often, it’s because they have valid concerns, competing priorities, and real consequences tied to the outcome.
It’s easy for consultants or vendors to blame the business when things go sideways: lost deals, stalled roadmaps, last-minute resistance. But enterprise work isn’t about playing hero or painting the client as the villain.
Like any human relationship, it’s about trade-offs, perspective shifts, and understanding that most people are just trying to protect what they’ve built.
Yes, I can already feel some of you rolling your eyes, and fair. It’s not always sunshine and “alignment”😂
Enterprise politics can be cutthroat, and kindness does get taken advantage of quite often. But letting that harden you doesn’t serve you long-term.
You don’t have to play games (although sometimes, it does happen, and God, I personally do not like that one bit, as it doesn’t fit my character), but you do need to play smart, and not lose your kindness. Staying grounded in empathy, even when it's hard to, it’s just the best way forward. As my friend Shiva always says, circle of positivity.
Back to internal politics.
Enterprise decisions rarely move cleanly through official channels. Org charts don’t show you influence. Informal networks, built on trust, credibility, and history are where real power lives. Instead of blindly following the process, map the people behind it:
Who are the trusted internal advisors?
Who do others go to for reassurance or informal sign-off?
Who has successfully championed projects like this before?
Find those people early. Watch who people defer to in meetings. Pay attention to who isn’t speaking but clearly matters. Influence is rarely loud.
And most importantly: respect the quiet concerns.
If someone doesn’t immediately embrace your proposal, don’t assume it’s resistance. As said, more often than not, it’s caution, earned through experience. Enterprise stakeholders have watched big ideas succeed and crash. Their hesitations are rational, even if they seem excessive from the outside.
Quiet hesitation isn’t rejection. It’s an invitation to understand more deeply.
Ask direct but empathetic questions like:
“Are there concerns we haven’t addressed yet?”
“How might this affect your team’s priorities?”
“Is there additional context we should know before moving forward?”
This is where empathy comes in, not as tactic, but as thoughtful understanding. Actually care. Give grace. Ask yourself: If I were them, what would worry me? What would make me feel secure enough to move forward?
Every concern is a signal. Use it. Stakeholder objections are often a roadmap to earning trust, if you listen well enough.
Make the solution feel like a win not just for the business, but for the individual and their team. When people feel understood, they’re far more likely to stick their neck out and back you.
How to Actually Navigate Internal Politics and Psychology: Practical Scenarios (RFPs & RFIs)
Let’s get practical.
One of the best ways to decode enterprise politics in the wild is by responding to RFPs (Requests for Proposal) and RFIs (Requests for Information). These documents are more than procurement exercises, they’re windows into how a company thinks, how it operates, and who really holds power.
Quick refresher:
RFP (Request for Proposal): The company knows the problem and wants detailed solutions, pricing, and execution plans.
RFI (Request for Information): Earlier stage, more exploratory. They’re trying to understand the market, compare options, and test how vendors think.
I have to admit, I LOVE RFPs and RFIs. Not just because I enjoy a good challenge, but because these processes, if you know how to read between the lines, reveal everything:
who’s influencing the decision
where internal alignment is missing
which team is quietly trying to drive change without ruffling feathers.
Every RFP or RFI is a case study in enterprise psychology.
If you treat them like “paperwork,” you’re missing the opportunity to build relationships that outlast the procurement cycle.
I will give you three real-world tactical examples:
one vendor-side
one agency-side
one selling AI (because, well, that’s where the fun and chaos lives)
Scenario 1: Responding to an RFP as a Vendor
Before an enterprise brand sends out an RFP, someone inside has already spent months justifying the need for this purchase.Maybe they’re stuck with a vendor that underdelivers. Maybe they’re using a legacy system that’s become a liability.
Either way, someone’s credibility is on the line, and your job isn’t just to win the deal at all costs. Your job is to help them confidently advocate for you internally.
They need ammunition. Give it to them.
How You Can Help:
Make it shareable. Yes, a slick deck helps. But a clear, concise one-pager tailored to their exact needs is gold. It’s easier to forward, easier to digest, and more likely to circulate inside the company.
Preempt objections. Anticipate the tough questions: budget, IT, compliance, integration, etc; and answer them up front, directly and empathetically. Don’t wait to be asked. Bake this into the one-pager.
Arm them with talking points. Don’t make them translate your pitch. Give them language they can use in their internal conversations. Be their invisible ally.
Practical Example:
Let’s say you know IT or Compliance will have concerns. Don’t wait for it to come up in round two. Address it head-on:
“We understand compliance is a top priority. Our solution aligns fully with your company’s current security standards and mirrors the protocols already approved for vendors like [insert trusted partner].”
This way you acknowledged internal realities, removed friction, and made your champion’s job easier. You are equipping the real decision-makers behind the scenes to feel confident putting your name forward.
Scenario 2: Responding to an RFP as an Agency
Creativity matters. Stakeholders don’t want only the boldest idea, but care about whether they can confidently defend that idea inside their organization.
These are people with reputations to protect, teams to manage, and internal politics to navigate. What they really need is reassurance that choosing your proposal won’t backfire.
How You Can Help:
Address internal risks explicitly. Budget sensitivity, brand safety, political landmines…don’t tiptoe around them. Acknowledge them head-on.
Offer collaboration, not disruption. Propose ways you’ll actively support internal alignment. Show that your agency delivers bold ideas and helps make them executable.
Map to their internal goals. Don’t assume your creative brilliance will speak for itself. Show how your proposal fits into their existing objectives and language.
Practical Example:
Use language that signals connection, understanding and lowers perceived internal risk:
“We recognize this campaign is ambitious. To support your internal alignment, we’ll lead stakeholder sessions early in the process, tying our creative direction directly to your brand guidelines and KPIs. Internal buy-in is a top priority.”
This way, you’re not pitching your idea,sure, but you’re also making it safe to say yes. That’s the difference between getting shortlisted and actually getting selected.
Scenario 3: Selling AI Products/Services to Enterprise
AI makes a lot of stakeholders nervous even if they love innovation. AI makes them expect unmanageable complexity, hidden risks, or unexpected failures. And to be fair, most AI sales pitches validate that fear by leaning on vague buzzwords like “revolutionary tech” or “advanced algorithms.”
What I prefer? Radical transparency. 0 hype. Build trust.
But let’s be clear: transparency doesn’t mean underselling.
If you’re asking someone to take a risk on AI, the product better be good. When someone is already cautious, don’t bring them half-baked tools. Bring them the best damn thing you’ve got, and show them exactly why it’s worth betting on.
How You Can Help:
Be brutally clear about what your AI product/solution does, and doesn’t do. Ambiguity breeds resistance. Precision builds confidence.
Reinforce human control. Enterprise leaders aren’t afraid of automation, they’re afraid of losing oversight. Show them exactly where the human stays in the loop.
Start small, on purpose. Pitch low-risk pilots that surface challenges early and build internal confidence, instead of pushing sweeping transformation out of the gate. It’s the best move for everyone.
Don’t settle for mediocre. If you're selling AI, it has to be legit. Don’t just rewrap a rules engine and hope no one notices. Enterprise clients are smart and skeptical. Respect that.
Practical Example:
Use language that reassures, not overwhelms:
“Our AI product/service doesn’t replace your team’s decision-making, it makes it better. Every step includes human oversight, keeping your analysts in control. We also recommend starting with a focused, low-risk pilot designed to surface internal blockers early. That way, your team gains confidence before scaling.”
This way you’re showing respect for your buyer’s caution, and proving that you’ve brought something worth trusting.
Five Bonus Tips for Mastering Enterprise Relationships
People Remember How You Protected Them
Enterprise buyers remember who made them feel safe. If you reduce internal risk, you're seen as an ally, not just a vendor.
Never Underestimate the Power of Autonomy
Stakeholders fiercely protect their autonomy. Make your solution feel like it empowers them, not replaces them, and they’ll advocate for you internally.
It’s Always Personal
Even at enterprise scale, decisions have personal stakes. Identify how your solution affects stakeholders personally, not just professionally, and speak directly to those hidden stakes.
Clarity Beats Complexity Every Time
Complicated language signals risk. Clear, simple explanations build immediate trust, especially with cautious stakeholders in Legal, Finance, or Compliance.
Be a Translator, Not Just an Expert
Your real competitive edge is your ability to translate your expertise into the language stakeholders already use internally. If they don’t have to translate, they don’t have to hesitate.
Enterprise Work Isn’t Playing The Game. It’s Understanding the Rules Of The Game
Working with enterprise brands isn’t chasing prestige or scaling creativity. Enterprise means navigating real human behavior: ego, fear, trust, caution, and doing it with empathy, strategy, and clarity.
If you want to succeed here, you don’t need to be louder. You need to be sharper. That means:
Anticipating power dynamics without making people feel exposed
Building trust by making others look good internally
Translating complexity into confidence
And showing up with actual value, not just decks and buzzwords
The best enterprise relationships aren’t transactional.
They’re built on mutual respect, emotional intelligence, and a shared desire to not screw it up. If you can become the person who helps stakeholders win, without making them feel like they’re gambling their credibility, you will close deals, and you will stay in the room because you provide value.
And if you're selling AI? please, for the love of compute and what’s sacred in enterprise procurement: Don't show up with an OpenAI API wrapper and call it innovation.😭😭😭
On my radar (a lot of stuff going on)
Hope you guys enjoyed this week’s newsletter, I had tons of fun writing it.
Some quick announcements:
I will be in Hamburg this November with Simo Ahava doing a LIVE, in person, recording of the Standard Deviation Podcast, on the stage at the Analytics Summit. Can’t wait to have you all that will be there as part of our episode. BTW, we reached 20K downloads this month!! That for me is still insane given we are doing bare minimum promotion LOL.
Doing SMX Advanced Berlin this autumn and I will talk about my ex-partner: Customer Lifetime Value. You don’t want to miss that reunion. Also, boy I love me an SEO/PPC conference, after doing the first SMX last year in London, I am hooked.
OK, so I am working on a framework, well, working on making it generally usable for you all, called Stakeholder Sanity Sheet for CRO. Basically I’ve reworked Craig Sullivan’s Hypothesis Kit, into a commercial first, stakeholder friendly, framework to transform your hypotheses and tests from ugly to sexy and potentially implementable experiments. If you are curious to understand more about this, listen to this podcast episode I recorded with Shiva Manjunath, on the From A to B Podcast.
I will be at Experimentation Elite in June, talking about my framework Insights, Intent & Impact, where I am going to give people obsessed with optimizing interfaces a bit of a cold shower of where the experimentation and brand perception forming is actually happening. NOT ON INTERFACES, LOL.
OHHH, and if you missed the fun this week, me and Bhavik Patel, launched the most revolutionary AuraTech tool, for those of you who are tired of stupid numbers and stats - The Vibe A/B Testing Calculator. Because who needs stats when you have vibes ✨✨✨ (PS: This is a joke)
PS: Andreas Cederband actually showed me that he built also a calculator for A/B Tests, but unlike mines and Bhav’s, his is real. Check it out here.
Until next time,
x
Juliana
PS: if you liked this newsletter, please hit that reply button and let me know :) I am needy.