Negotiations in organizations have a tendency to go wrong. Requests for an exception get denied, proposals for the future get rejected, solutions to a problem get parked in the perpetual parking lot.

But why do so many of us find intra-organizational negotiating so hard? Put differently, is there something special about organizations that makes negotiations inside of them so difficult, or do difficulties like these simply reflect the difficulty of negotiating in general—the same types of challenges you’d face at the car dealer?

Having studied negotiation for 13 years and worked in organizations for longer, I’d suggest it’s the former. That is, I’d highlight a few special features of organizations that make negotiating within them a unique challenge. But luckily, knowing what they are can make organizational life more negotiable.

Consider five of the presumably most common reasons why negotiations in organizations fall flat. Specifically, imagine yourself making a particular request of your superiors. The request is likely to get rejected if it:

1. Creates a perceived inequity: I recently noted how bosses who adopt a win-win mindset with their employees (e.g., by granting a special exception) sometimes create a win-lose inequity for the employees who don’t receive the exception. Well, the flip-side is that your win-win suggestion may do just that. To mitigate the issue, perhaps take the boss’s perspective before making the request?
2. Doesn’t garner enough attention: It’s hard to redirect senior executives’ limited attention to anything outside the never-ending press of daily emergencies—especially unusual requests requiring less-than-immediate action. Add their limited attention to the risks of the telephone game, and you’ve got a recipe for inaction or outright rejection. To mitigate the issue, perhaps find a way to make your request especially vivid or enlist the help of someone who can call it to the executives’ repeated attention?
3. Sets a bad precedent: One way for a boss to avoid creating inequity is to grant your request and then grant the same to everyone else. But what would the organization look like if everyone enjoyed the same privilege—the same three days of virtual work, personally crafted benefits plan, or personally reimagined expense policy? If mass chaos would ensue, a wise boss is unlikely to grant your request. To mitigate the issue, perhaps imagine what the organization would look like beforehand (applying something like the categorical imperative)?
4. Calls a bad parallel to mind: Any experienced boss has heard every manner of request from employees. And inevitably, some of the granted requests have subsequently turned sour. Someone abused their virtual work, someone extracted crazy benefits and quickly quit, someone tried to get reimbursed for something you wouldn’t even purchase. If you’re unlucky enough to surface a request that calls such experiences to mind, you’ve got a tough slog ahead. The best I can suggest is stepping away to regroup, then reframing your request in starkly different terms than anyone’s ever requested before.
5. Gets stuck in organizational inertia: Organizations show massive inertia—marching methodically down well-trodden paths oriented around well-established policies and procedures. If your request somehow cuts against the inertia or, worse yet, threatens to disrupt it, good luck! But perhaps your fundamental need could be accommodated within the confines of the existing policies and procedures?

In sum, on the basis of issues like these, I think it’s fair to say that negotiators face particular challenges in organizations. But hopefully an awareness of these challenges, coupled with the tentative suggestions above, provides at least the contours of a roadmap for diffusing intra-organizational challenges. Good luck!