Boldr CX Blog

Let your people use their judgement: the case for healthy escalation cultures

Written by Elen Veenpere | Jun 25, 2026 2:06:15 PM

A huge amount of friction in support starts with somebody trying very hard not to escalate.

 

 

A customer reaches out with a problem that lives in the operational equivalent of international waters. The policy sort of applies, the documentation sort of helps. The team member responsible is reasonably sure they shouldn't make the decision alone, but not quite sure enough to escalate immediately. So they start digging.

 

First, the knowledge base, then old tickets. Then Slack. Then the colleague who somehow remembers every policy exception approved since 2022. Two hours later, five people have weighed in, three conflicting opinions have emerged, and the issue gets escalated anyway.

 

Everyone has now spent more effort avoiding the escalation than the escalation would have required in the first place. The actual problem here is not the escalation itself; it comes down to the relationship people have with escalations.

 

Most organizations would tell you they want team members to use “good judgment”. They want people to take ownership, solve problems independently, and make decisions confidently.  All reasonable goals, and all great things to say and enforce. The trouble starts when people begin to believe that asking for help and demonstrating good judgment are somehow different things.

 

That's where hesitation creeps in, that's where people start carrying issues longer than they should, and where small customer problems can become much bigger operational ones.

A refund request that needed a five-minute conversation with Finance somehow survives three follow-ups, two shift handovers, and a long weekend before anyone finally asks them. Unsurprisingly, they still give the same answer they would've given on Monday.

 

The weird signals companies send about escalation

Nobody puts "plz avoid escalating issues" in the onboarding materials, yet plenty of organizations accidentally build exactly that behavior (whether they do it knowingly or not).

 

A team member gets praised to the high heavens and back for handling difficult situations independently. Escalation rates show up in performance discussions. Folks hear words like ownership, autonomy, and empowerment so often that they start treating escalation as evidence they've fallen short of those specific expectations.

 

Nobody explicitly says this, and nobody has to, because culture is very efficient at filling in the blanks in our brains. Over time, people start making tiny calculations every time they encounter uncertainty. Can I solve this myself? Should I ask somebody? Will escalating make me look less capable? Will my manager wonder why I couldn't handle it?

 

Most people don't answer those questions consciously; they just feel the weight and pressure and adjust their behavior accordingly. That's how companies end up with teams that are technically allowed to escalate but reluctant to do so.

 

The fake hero problem

Almost every support organization has a hero; you know the one. They're the person who somehow knows everything. They somehow remember the policy exception approved eighteen months ago, know exactly which engineering lead needs to be involved in a specific situation, and can still tell you where an undocumented process lives despite nobody updating the documentation afterward.

 

People love working with them because they're incredibly helpful, and leaders love them because they seem capable of solving anything. The problem is that many organizations mistake this for operational excellence; that “one person knows everything” means “the system works”.

 

From a distance, it might look like expertise, but up close, it's usually a knowledge management problem. The hero becomes the unofficial escalation path. Questions that should move through a structured process instead flow through direct messages, side conversations, and institutional knowledge that exists almost entirely inside one person's head.

Everything feels efficient right up until that person takes a vacation, changes roles, or leaves the company. Then, suddenly, everybody discovers just how many critical decisions were being routed through a single human being.

 

Healthy support organizations don't scale by finding more of these heroes, they scale by making expertise accessible, creating clear escalation paths, and ensuring people know exactly when and how to use them.

 

When empowerment becomes abandonment

Few ideas are more popular in customer experience than empowerment. Support professionals should absolutely have enough authority to solve customer problems, exercise good judgment, and take ownership of outcomes without needing approval for every minor exception.

 

The problem is that some organizations stop halfway through the empowerment thought: they give people responsibility, and then they forget to give them support. Somewhere along the way, empowerment becomes "good luck."

 

Team members end up navigating increasingly complicated situations with unclear guardrails, incomplete context, and only a vague understanding of where their authority begins and ends. They're expected to demonstrate excellent judgment while operating inside an environment that makes judgment unnecessarily difficult. The result is a team that's accountable for increasingly complex decisions without having the visibility, context, or support needed to make them confidently.

 

Real empowerment looks different; it looks like people understanding what they can decide on their own, what requires additional visibility, who to involve, how to involve them, and what information needs to travel with the escalation.

 

Most importantly, they know that escalating an issue won't be treated as any kind of evidence that they somehow “failed” and that sometimes the smartest decision available is recognizing that somebody else should be involved.

 

Experienced people don't escalate less, they escalate better

One of the myths in customer support is the idea that more expertise naturally leads to fewer escalations. In reality, experienced support professionals often become much better at recognizing situations that deserve additional visibility.

 

They've seen enough edge cases to know where risk tends to hide. They understand which issues can create compliance concerns, legal complications, customer trust problems, or operational headaches if handled incorrectly. They've learned that confidence isn't always the same thing as competence and that a fast decision isn't necessarily a good one.

 

A newer team member might spend forty-five minutes trying to solve a complicated issue because they don't want to bother anybody, while an experienced one might escalate after five; not because they know less, but because they've seen what happens when people wait too long. One of those behaviors often looks more impressive on paper, but the other usually creates better outcomes.

 

The best support folks also understand that a good escalation isn't just about getting an answer, it's an opportunity to sharpen their own judgment. Instead of handing the issue off and moving on, they pay attention to how it gets resolved. They ask why a particular decision was made, what signals they missed, and what they'd do differently next time. Over time, that turns escalation into one of the fastest ways to build expertise rather than something to avoid.

 

Escalations are information

Support leaders sometimes treat escalations as something to reduce, which is a mindset that misses one of the most useful things about them: escalations are information.

They're often one of the earliest indicators that something inside the operation isn't working the way it's supposed to. Imagine a support team suddenly starts escalating far more conversations related to a specific product feature. The immediate assumption might be that the team needs additional coaching. Maybe?

 

Or maybe customers are running into the same confusing experience over and over again. Maybe documentation hasn't kept pace with recent product updates, or maybe a workflow that made sense six months ago is now creating friction for both customers and support professionals.

 

When dozens of people are struggling with the same thing, it's worth considering whether the issue lives with the people or the system surrounding them.

 

The danger of turning escalation into an isolated KPI

At some point, usually during a quarterly business review, somebody notices the escalation number, and the room collectively decides that fewer escalations would probably be better. Sounds about right, until you remember that support professionals don't stop coming across uncertainty just because a dashboard tells them to. The uncertainty doesn't disappear, it just finds other ways to move through the organization.

 

Questions migrate into Slack DMs, decisions get made with partial information, and people spend an impressive amount of time playing "who knows the answer to this?" The dashboard looks healthier, which is excellent news for the dashboard, but nothing meaningful actually changes.

 

Like most operational metrics, escalation volume is a signal, not a verdict. A rising escalation rate can point to all sorts of things, from training gaps and outdated documentation to product friction that customers keep running into. Sometimes it's just evidence that people trust the escalation process enough to use it. Without context, the number doesn't tell you nearly as much as people think it does.

 

What healthy escalation cultures look like

Healthy escalation cultures aren't defined by how often people escalate, they're defined by how confidently they do it. Rather than guessing their way through greige areas and playing a game of operational hot potato, people understand what they own, what they don't, and how to involve the right people when a situation falls outside their lane.

 

Most importantly, they don't waste energy wondering whether escalating will make them look incapable. Once that hesitation disappears, people can focus on solving the problem instead of worrying about what asking for help might say about them.

 

The customers benefit from this, too. They don't care whether an issue was escalated; they care whether it reached the right person quickly, whether the answer was consistent, and whether someone took ownership instead of passing them from one uncertain conversation to the next. Customers rarely notice a healthy escalation, bu they almost always notice when one should have happened sooner.

 

How to actually do this

Creating a healthier relationship with escalation requires more than good intentions. People take their cues from what gets measured, rewarded, discussed, and modeled throughout the organization.

 

Stop treating escalation as a performance problem by default

Escalations often get terrible PR. They're usually discussed after a customer complaint, a process failure, or a metric review, so people naturally start connecting escalation with things that have gone wrong. Before long, asking for help feels suspiciously similar to admitting fault.

 

If you want people to view escalation as a normal part of good decision-making, you have to talk about good escalations too. Review them in coaching sessions. Call out examples where someone recognized risk early. Celebrate situations where a team member pulled in the right expertise before a problem became more complicated. People pay attention to what gets recognized.

 

If the only escalations anybody hears about are the bad ones, they'll eventually conclude that all escalations are bad ones.

 

Make the boundaries obvious

A surprising amount of escalation hesitation comes from uncertainty, and not about the customer issue, but about the process. People don't know:

 

  • when they're expected to escalate
  • who owns the next step
  • whether they're allowed to involve another team
  • how their decision will be judged afterward

 

When those boundaries are fuzzy, people tend to wait too long. Aim to remove as much ambiguity as possible: define escalation triggers clearly and make ownership visible, so team members spend less time wondering what they're supposed to do and more time actually doing it.

 

Teach judgment, not just procedures

The trouble with training people to memorize answers is that customers have a habit of asking questions nobody thought to include in the training. Policies change, products evolve, and edge cases appear out of nowhere.

 

The organizations that handle those situations best tend to focus less on pure rule memorization and more on helping people develop sound judgment when the playbook runs out.

 

Make leaders model the behavior

This might be the most important one. People notice what their leaders do far more than what leaders say. If managers ask questions, seek input, and pull in expertise when they encounter uncertainty, teams learn that escalation is a normal part of responsible decision-making.

 

If leaders behave as though asking for help is a sign of weakness, everyone else will too. Culture tends to follow example much faster than instruction.

 

The outcome matters more than the handoff

The goal shouldn’t be to eliminate escalations, it’s to make sure that issues reach the right people quickly enough to create the best possible outcome. Sometimes that means solving the problem independently, and sometimes it means pulling somebody else into the conversation immediately.

 

Both require judgment. Both require confidence. And both become significantly easier when people aren't carrying the additional burden of wondering whether asking for help will be held against them.

 

Good support organizations aren't built around knowing everything, they're built around making it easy to surface uncertainty before it creates bigger issues for customers, teams, or the business.