How Sales Teams Undercut Themselves with Longtime Clients

Three years. That is how long a multimillion-dollar project had gone unpaid at a large industrial manufacturer when I asked a question no one had considered: Why are you still delivering services to the client? The room went quiet. There was an air of slight embarrassment, the kind that comes from realizing the question had genuinely never been asked. Different departments were managing separate contracts with the same buyer, each in a silo. No one had a view of the full outstanding balance. No one had thought to use it as leverage. Every deal had been treated as its own isolated event, and the silence in that room was the sound of a company recognizing it had been negotiating against itself for years. This is not primarily a story about a difficult client. It is a story about what sales teams within organizations do to themselves, and how rarely they notice. When Long-Term Relationships Become a Liability When I advise sales teams and executives, I always ask: Have you ever lowered your price, changed your offer, or adjusted your terms before walking into a negotiation? Every time, 40% to 60% of hands go up, including those from seasoned professionals managing complex, high-value accounts. They have convinced themselves of three things: the client will not pay full price anyway, pushing too hard will damage the relationship, and a concession upfront will make closing easier. These are not always rational assumptions. In seven studies with more than 3,000 negotiators, George Mason University’s Einav Hart, Julia B. Bear of Stonybrook University, and Duke University’s Bella Ren found that people negotiating job offers consistently overestimate the risk that pushing back will end the deal. This fear is not unique to job offers. It shows up in nearly every relationship and negotiation we enter. Any time that a negotiator believes the other side’s commitment is fragile, and especially when they fear alternatives are scarce, that fear will drive premature concessions. Sales teams are particularly vulnerable when they assume the client can walk away at any time. This suggests that it is more often the fear of losing the deal than the actual risk of losing it that drives premature concessions. These concessions carry tangible costs: conceding before the other side asks trains clients to expect discounts, eliminates the opportunity to exchange value, and makes every future negotiation harder. The relational cost is equally real: when a team consistently signals that its own interests come last, the client learns exactly that. The industrial company I was brought in to advise was heavily dependent on one dominant buyer. Leadership wanted help strengthening the relationship. What I found was a company with no idea how much leverage it was sitting on, or that it had the power to stop going along with the client’s every wish. They described the client relationship as strong, built on a decade of history. When I pressed for specifics, a different picture quickly emerged. Multiple teams held separate contracts with the same buyer, each negotiated in isolation, with no shared strategy or leverage. They routinely lowered prices before the client asked, assuming they would not pay full value; continued to deliver services while significant invoices sat unpaid; and treated each contract as a standalone transaction rather than as leverage in a longer relationship. The costs compounded beyond any single contract. Every premature concession set a precedent, weakened pricing integrity across the team, and made the next negotiation harder to win. What began as accommodation became an expectation that the client had no reason to revise. When I brought the department heads into the same room, something shifted. As each team described their experience, which included delayed payments, pricing pressure, and scope changes absorbed without pushback, others nodded in recognition. They had been living the same story in separate rooms, assuming it was theirs alone to manage. What emerged was more troubling than poor coordination. The client had been counting on the fragmentation. Because each department had been negotiating separately, the client had a more complete view of the company’s overall position than any single team had. Concessions extracted from one group became the baseline in conversations with another. The isolation was not an internal failure that the client had stumbled into. It was a condition they had been actively exploiting. When I asked why they had never developed alternative clients, they admitted they had not seriously tried. The relationship felt too important to question. Nobody had stopped to ask whether it was strong or just old. What Makes a Relationship Healthy? Most negotiation training focuses on tactics: when to anchor, how to read a room, and when to concede. What it rarely addresses is the quality of the relationship you bring into that room. That quality shapes everything else. High-quality business relationships have two defining dimensions. The first is relational capacity: the ability of both parties to stay engaged through strain, disagreement, and ambiguity without shutting down or withdrawing. The second is subjective experience: a mutual sense of positive regard and genuine reciprocity. When both are present, they produce two conditions that change how people negotiate. Psychological safety provides confidence that raising a hard issue will not cost you the relationship. Integrity strengthens the belief that your counterpart is honest and principled enough that what you share will not be used against you, and what is agreed to will hold. My doctoral research at York University tested these dynamics across two studies. In the first, I surveyed 80 employed professionals, averaging nearly 15 years of experience, about a recent negotiation with a colleague with whom they had an ongoing relationship, ranging from contract and budget discussions to strategic initiatives and policy changes. In the second, I followed 58 pairs of MBA students through live, face-to-face negotiations over six months, using a multi-issue business simulation involving compensation, restructuring, and leadership transitions. While neither study was set in a sales context, both captured the conditions that define commercial relationships: ongoing partnerships, multiple issues to resolve, and stakes that extend beyond any single deal. Across both studies, I found that what determines how a negotiation unfolds is not how long you have known someone. It is the quality of the relationship that you have built. Negotiators in high-quality relationships shared more information, proposed more trade-offs, and solved problems collaboratively rather than defending fixed positions. But perhaps more importantly, they also reported significantly higher satisfaction with their outcomes, the negotiation process, and the relationship itself. MIT’s Jared R. Curhan, Hillary Anger Elfenbein of Washington University, together with academic colleagues, have shown in a series of papers that this subjective satisfaction, not the financial terms of any single deal, is the stronger predictor of whether two parties will collaborate in the future. A negotiation from which both sides walk away feeling good builds the foundation for the next one. A deal where one side feels ground down may close while quietly eroding what makes future deals possible. For sales leaders managing long-standing client accounts, this is the finding that should prompt a second look at every relationship you assume is solid: in my MBA study, relationship quality varied significantly among students who had all known each other for the same six months. Time was constant. Quality was not. Pairs who shared higher-quality relationships negotiated differently because of what they had built within that time. If the quality can diverge that sharply in six months, it can diverge just as sharply over 10 years without anyone noticing. The industrial company did not have a strong client relationship. They had a long one. The cost of confusing relationship length with quality went well beyond unpaid invoices. Collaborating with a counterpart who is negotiating transactionally does not protect the relationship. It strengthens the leverage they already hold over you. So, what can you do about it? How to Change the Relationship Dynamic Identifying the problem is a start. The harder work is in changing the behavior. In my advisory work with sales teams, I see consistently what the Hart, Bear, and Ren’s research describes: when negotiating deals, people are instinctively conflict averse. They are, therefore, reluctant to raise what they fear may be contentious issues; they look instead for ways to give customers what they ask for, even at a cost to the company, in the belief that flexibility is essential to creating a trusting relationship. This needs to change. Sales managers must instead realize that: Difficult conversations protect. When the industrial company stopped absorbing problems silently and named what was not working, the buyer’s commercial team did not walk. The escalation reached the CEOs on both sides, and the buyer’s commercial team began to cooperate. That is not the response of a counterpart who has written you off. My research confirms what that room demonstrated: in the MBA study, engaging directly in a negotiation increased integrity trust for all participants, regardless of baseline relationship quality. Hard conversations, handled with honesty, are a trust-building act. The fear that candor will damage a relationship is, in most cases, an overestimate of its fragility. Compliance is not trust. A sales team that consistently treats its own needs as secondary is not earning goodwill; it is training the other side to expect accommodation. Trust requires psychological safety on both sides of the table: the belief that either party can raise a concern and receive honest engagement in return. When only one side is accommodating, psychological safety does not exist. What defines the relationship at that point is dependency, and the dependent party usually does not negotiate. They comply. Flexibility without a goal is not a strategy. Arriving at a negotiation without a defined position is not open-mindedness. It is an invitation for the other side to set their terms. In the MBA simulations, negotiators in high-quality relationships did not succeed by being more yielding. They succeeded because they came prepared, knowing what they needed and willing to trade creatively to get there. Flexibility in service of a clear objective is tactical. Without one, flexibility is a concession the other side never asked for. Changing the dynamic at the table, however, requires more than a shift in mindset. It requires a shift in behavior to create a new kind of relationship. To ensure that happens: Articulate your value. Do not assume the client knows your value. The industrial company had a decade of operational reliability and technical depth that the buyer would have found genuinely difficult to replace. But the industrial company had never made that case directly. When they started leading negotiations with a specific account of their strategic importance to the client’s operations, there was significantly less room for the client to push for concessions that were never justified to begin with. Link your contracts. Leverage compounds across a relationship, but only when you treat the relationship as a whole. The industrial company had been negotiating each contract in isolation, with no shared view of what the other teams had agreed to or what remained outstanding. Once the company coordinated across departments and brought a unified position to every conversation, the dynamic shifted. When you have multiple agreements with the same client, connect them. What is agreed in one negotiation should reflect what is happening across the rest. Build real alternatives. The fastest way to stop making unnecessary concessions is to have somewhere else to go. The industrial company had not developed other clients because the dominant relationship had felt sufficient. It wasn’t: the dominant buyer had been extracting more than it returned for years, and when the situation required alternatives, none were in place. Viable options not only protect you in a crisis, but they also change your posture in every conversation before a crisis arrives. The industrial company eventually halted work on new contracts with the client until the outstanding balance was addressed. They restructured existing agreements, unified their negotiating approach across departments, and began building relationships with other buyers in their sector. The conversations were uncomfortable. But knowing what the relationship required gave them the basis to act, and they came across as more credible for having started those conversations. The results held financially, and the way the client engaged with them changed. Most of the leverage they needed had been available all along: across every outstanding invoice, every active contract, every year of institutional knowledge the client depended on. What they were short on was unity. . . . If your team is losing ground in negotiations with a big client, the reason may not be your client’s procurement process or the competitive landscape. Before the next negotiation, ask yourself: Is this a strong business relationship or just a familiar one, and do our strategies reflect the difference? Are we making the case for our value, or assuming the client already knows it? Are we negotiating from genuine strength, or from fear of losing what we assume is already ours? If your team cannot answer those questions clearly, your clients do not need to negotiate against you. You are already doing it for them.

How Sales Teams Undercut Themselves with Longtime Clients

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