Halloween Lessons for Negotiators: Tricks, Treats and Tactical Decisions

Siobhan Bermingham

by Siobhan Bermingham, a consultant at Scotwork UK, takes a deeper dive into her own childhood Halloween experiences, and how they have shaped her negotiation strategy in her career thus far

NEGOTIATION is a skill that bridges our personal and professional lives, and what childhood experience greater encapsulates our first memories of negotiation than trick-or-treating, where presentation, delivery and confidence can earn you the biggest bag of sweets, or an apple and some monkey nuts. 

As the excitement and anticipation of Halloween builds, I find myself reminiscing about the negotiation strategies I developed during my childhood Halloween adventures. Growing up as the youngest of six siblings, I eagerly awaited my turn to go trick-or-treating, observing my five older brothers returning with overflowing buckets of sweets. Finally, it was my chance, my inaugural foray into the world of trick-or-treating.

However, there was a catch—I couldn’t venture as far from home as my brothers did until I was a bit older. Time was limited, much like in negotiations, so I needed a clear strategy. My youngest brother and I decided to focus on the houses closest to ours to maximise our limited time before bedtime. Our goal was to visit as many doors as possible and fill our buckets with treats that we could proudly flaunt in front of our eldest brothers.

Armed with our Halloween costumes and a sense of pride, my brother and I believed that people would be astounded by how good we looked and would freely lavish us with treats, just as our older brothers had described. We knocked on the door of an elderly neighbour we frequently waved to, thinking it would be a great place to start. After excitedly exclaiming “trick or treat”, we waited with high expectations, hoping for an abundance of sweets. However, the elderly gentleman had a different plan; he asked us to perform ‘tricks’ and reminded us that nothing comes for free in life

Unprepared for this twist in our negotiations, we stood there clutching our empty buckets, desperately trying to come up with a compelling ‘trick’. With a sigh, he selected just one tiny sweet for each of us from his vast bowl of goodies, leaving us somewhat underwhelmed. Looking back, I realised that our high expectations had made that rather tasty sweet seem meagre when, in reality, on any other day, we would have been overjoyed to receive it.

This experience taught me a valuable lesson about negotiations: much like in trick-or-treating, different situations call for different approaches. Some houses gave fruit (much to my mother’s delight), while others handed out generous handfuls of sweets. Some specified that we could only pick one sweet from their pile. Just as in negotiations, there were those who freely gave concessions as goodwill gestures and those who taught us that we must give something in return, akin to performing a ‘trick’.

Our elderly neighbour was in the latter category—he would only trade a sweet for a ‘trick’, and the later we came in the evening, the less impressed he would be by our ‘tricks’. Thus, we developed a new strategy: visit him early each year with a well-prepared ’trick’. This approach paid off, and he rewarded our extra efforts with larger chocolates from his basket.

Over the years, I’ve observed different negotiation styles. Some negotiators offered ’goodwill gestures’ as free concessions, while others traded concessions for concessions. These unconditional gestures were warm and pleasant, but they set an expectation for future negotiations. I recall one partnering company that, due to budget cuts, suddenly ceased its generous goodwill gestures, shifting to a purely transactional approach.

Initially uncomfortable, we adapted our expectations and became more creative in our preparations, accumulating concessions to trade for items on our wish list. This change in approach led to more fruitful contracts for both parties, highlighting the importance of adaptability in negotiations. So, which type of negotiator are you? Do you freely hand out ‘treats’ without condition, or do you trade concessions strategically to achieve your goals? At Scotwork, we believe that “in negotiation, generosity generates greed”.

Another aspect of Halloween that can either delight or terrify is the decorations that suddenly come to life when someone approaches, often accompanied by screams and surprises. Much like in negotiations, you might encounter unexpected developments or possess information that the other party is unaware of. When it comes to disclosing information, timing and strategy are key. If sharing information strengthens your position, consider doing so strategically, as it can save time and bolster your negotiating power.

As for me, negotiating aside, I suspect my nieces and nephews will continue to relish watching me jump in fright at ominous decorations. So, I’ll be on the lookout for their excited squeals as I navigate the world of eerie decorations this year.

Siobhan Bermingham is a consultant at Scotwork UK

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