Get Better at Disappointing Others

It was the last day of school for everyone — my primary school was closing down. We took all the decorations off the walls and packed them into boxes. 

As we peeled the paper off the display boards to reveal the bare hessian underneath, one of my classmates grabbed a permanent marker and drew a smiley face. 

One child picked up a pen, then another and I too grabbed a marker and drew a giant face (with a funky hairdo) on the wall. Soon, we were surrounded by marker pen smileys.

Hauled into the headmaster’s office for my first serious non-parental telling off 4 years into my education, I was told how I’d disappointed the teachers I looked up to. 

Worse still, I was instructed to go and get a list of all the other children who had been involved in the graffiti incident. Double disappointment. 

The feeling of disappointing my teachers and my classmates at the same time was mortifying. I didn’t know whose names to put on the list.

This moment has parallels with the tougher moments in working life — disappointing up, disappointing down and being disappointed in oneself and one’s team.

According to leadership development expert John Eades, “disappointment is a part of life unless you have depressingly low standards.” Fail to experience that sinking feeling of disappointing others and you’re selling yourself short. But how we deal with it when it comes up isn’t always obvious.

We should disappoint more often

“The chances of you disappointing others are high” warns Leah Aguirre LCSW. So why do we feel uncomfortable about the inevitable gap between expectations and reality?

However uncomfortable it feels, a world where we disappoint no one is a world where we prioritise nothing.

In brand strategy, we talk about the power of “brand rejectors”. If no one rejects your brand because they feel it doesn’t resonate with them, then you stand for nothing. You’re “nice”, but no one hates you and no one loves you. You’re stuck in the murky middle. 

In fact, the best brands often offend large swathes of the population (think Europe’s Ryanair) with their polarising yet memorable positioning and their infamous disappointing experiences.

Sarah Epstein LMFT sums it up well: “Disappointing others means learning to say “No” to things beyond your capacity and sitting with the discomfort of others feeling disappointed by that.”

Put this way, seeing we’ve disappointed someone is a signal that we’ve made a significant trade-off and chosen to prioritise something else. If we’re comfortable with that decision, sitting with the disappointment becomes easier.

Refuse to disappoint, and like the “nice” brand we end up in the murky middle, unable to assert ourselves or stand for anything meaningful. 

A lot of us spend more time here than we think, because we’re bad at letting people down. Think about the last time you sat on the fence, was it because choosing a side would mean disappointing someone?

Inevitably, we all have to land on one side or another. Why drag out the inevitable disappointment?

Learning to live with disappointment means we must embrace more honest, transparent communication, avoid delaying the inevitable and behave with more respect towards those we ‘let down.’

How to do it better

Imagine you’re turning down an invite — someone really wants you to be there but you have a commitment you need to prioritise. As you start to explain you can’t attend, you see they are disappointed.

Be Kind but Firm

Express feelings of warmth that help them see you empathise with their situation and show your gratitude for being included.

Resist the temptation to take the warmth so far that it softens the “no” to take the edge off the disappointment. Phrases such as “If anything shifts I will do my best to make it” risk leaving your options open and creating false hope, promising a second wave of disappointment down the road.

Instead, hold firm: “I’m sorry I can’t make it, I have another event I need to prioritise.”

Sit with the discomfort

Did that firm and direct line of communication make you feel a little uncomfortable? Learning to sit with it is key to disappointing people better. Like ripping off a band-aid, it’s more pleasant for the individual to have it over-and-done-with.

If you easily read others’ feelings, it can be challenging to shift the burden that comes with this discomfort. One way to approach this is to remember it’s their disappointment, not yours, and ultimately not your burden to bear.

Be Punctual

Delivering the message clearly, firmly and all at once (versus creating false hope) goes hand-in-hand with punctuality. Many of us avoid disappointing people with the excuse that we’re “waiting for the right time”. Most often, we fail to realise that now is the right time.

Exceptional circumstances such as personal emergencies aside, communicating your message immediately conveys respect.

Communicate “What For”

In choosing to disappoint someone, you prioritised something else. Clearly communicating the reasoning behind your decision can help someone understand the purpose behind your disappointment.

This is most appropriate in a work context — it creates a culture of transparency to make those around you aware of the reasoning behind your decision, especially as a leader.

In a personal context, it’s worth considering whether the person you’re disappointing sees eye-to-eye with your priorities and will understand your “why”. If in doubt, empathise with their situation without expanding on your own reasoning at length.

Share the learnings

Imagine the company didn’t hit their sales numbers this quarter, and it’s up to you to tell the team.

Sharing what you’ve learned and how you and the team could adapt your offer as a result softens the blow of disappointment by activating people’s growth mindset and presenting new opportunities.

Navy SEALs use a strategy they term “full benefit” to ensure they focus more on the learnings than disappointment. Read more here.

The best “disappointers” earn respect

Accepting that disappointment is inevitable is a critical step on the journey to clear, honest communication.

Those who communicate early, kindly, firmly, explaining why and what they’ve learned are much more likely to be respected in their decisions than those who drag out communications and create false hope for fear of being unkind.

What if we spent less time avoiding disappointing others, and more time getting better at it?

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