What Do I Do When Someone Keeps Disappointing Me?

Most of us can accept the occasional disappointment. A friend cancels lunch, a colleague forgets to do something, or someone close to us lets us down. These things happen.

It becomes more difficult when the same thing happens repeatedly. We may start wondering whether the person cares, whether we can rely on them, or whether we are expecting too much.

At work, the consequences can be more serious. A colleague who repeatedly misses deadlines may affect our own work. A manager whose team member does not follow through on commitments may find the problem increasingly difficult to ignore.

When someone disappoints us repeatedly, we naturally try to make sense of it. We may decide that they are inconsiderate, unreliable or simply unwilling to change.

Sometimes we may be right. But there may be more to the situation than we can see, and it is worth being careful about the conclusions we reach.

Looking at what is happening

A friend cancels plans for the third time, and we conclude that we are not important to them. A colleague takes several days to respond to an email, and we decide that they are uncooperative.

Those explanations may be accurate, but they are interpretations rather than facts. It can help to look at what has actually happened. What was agreed? What happened instead? Was the expectation clear to both of us?

We sometimes expect people to know what matters to us without having explained it. A colleague may not realise that a delayed response is holding up our work. A friend may not understand how disappointing repeated cancellations have become.

Making an expectation clear does not guarantee that someone will meet it. But it gives both people a better chance of understanding the situation.

It is also worth considering whether the expectation itself is reasonable. We may be asking someone to do something they have neither agreed to nor understood to be their responsibility.

None of this means that we should dismiss our disappointment. It simply gives us a clearer starting point from which to decide what to do.

Understanding the other person

We cannot always know why people behave as they do. We can ask, listen and try to understand, but we should be careful about assuming that we know their motives.

Consider a manager whose team member repeatedly misses deadlines. The manager may reasonably conclude that the employee is careless or does not take the work seriously.

A conversation might reveal something different. Perhaps the employee has competing priorities, is unsure which work matters most, or has been reluctant to admit that the workload is becoming unmanageable.

That information could change how the manager approaches the problem. Priorities may need to be clarified, or the employee may need help raising difficulties earlier.

But suppose the priorities are made clear, support is offered, and the deadlines continue to be missed. The manager then has a different problem to address.

Understanding what is happening does not remove the employee's responsibility to do the work, or the manager's responsibility to deal with the consequences.

The same applies in our personal relationships. We can understand why a friend struggles to keep commitments without pretending that repeated cancellations do not affect us.

Understanding someone does not mean that we have to accept everything they do. It helps us respond to the situation as it is, rather than relying on assumptions about the person.

When something needs to be said

Not every disappointment needs to become a discussion. Sometimes we can adjust our expectations. If a friend has shown us that they are unreliable when making plans, we might arrange things differently rather than repeatedly having the same conversation.

In other situations, particularly where the relationship matters or other people are affected, it may be worth talking about what is happening.

It is usually more helpful to describe the behaviour and its effect than to make a judgement about the person.

Instead of saying, "You are so unreliable," we might say:

"We have made plans a few times recently, and each time they have had to change at the last minute. I enjoy spending time with you, but I find it disappointing when this happens. Is there something we need to talk about?"

At work, a manager might say:

"We have spoken about these deadlines before. I would like to understand what is getting in the way, but we also need to find a way of making sure the work is completed when it is needed."

Neither conversation guarantees a particular response.

The other person may explain something we had not considered, disagree with our understanding, or become defensive. We may learn something useful, or the conversation may leave us with questions that remain unanswered.

The purpose is not to force an admission or secure a promise. It is to make the concern clear, hear the other person's perspective and see whether a way forward can be found.

There are situations, of course, in which a direct conversation may not be safe.

If there is a real risk of intimidation, aggression or harm, it may be better not to engage directly or to withdraw from the situation. Safety comes first, and appropriate support may be needed.

What happens next?

A conversation can help, but it does not necessarily resolve the problem. Sometimes the person understands our concern and makes a genuine effort to change. At other times, there is an explanation, an apology or a promise, but little changes.

Over time, what people do may tell us more than what they say.

If the problem continues at work, a manager may need to set clearer deadlines, monitor progress or take appropriate formal action if performance does not improve. In a personal relationship, we might stop relying on someone for particular things, change the arrangements we make with them, or reconsider how much time and energy we want to invest in the relationship.

These decisions need not be punishments. They may simply be a response to what we have come to understand.

We cannot make another person change. We can explain what matters to us, listen to their perspective and give them a fair opportunity to respond. What we cannot do is make their choices for them.

Repeated disappointment can leave us frustrated, hurt or uncertain. We may want the other person to understand, to change, or to become the person we hoped they would be. Sometimes that happens. Sometimes it does not.

We may then have to accept that the situation is unlikely to be different from what it has become.

Acceptance does not mean approving of the behaviour or remaining in a situation that is not good for us. It means recognising what we are dealing with, rather than continuing to respond to what we wish were happening.

Perhaps the question is not only why someone keeps disappointing us, but what we now understand about the situation that we did not understand before.

And, from there, what we want to do.