Dealing with challenging customers

Wouldn’t sales be a ‘walk in the park’ without challenging customers? Why is it that some customers are so difficult to please, so quick to call ‘foul’ at the slightest blip and so mean with their gratitude after we’ve bent over backwards to accommodate them? Whether we are looking at prospective or existing customers, there is a toolkit for dealing with the most challenging of them and by learning and deploying these skills you and your team can:

  • Take orders from people that your competition shy away from
  • Take customers into an ‘adult’ behaviour state by skilful questioning and listening
  • Build trust and credibility with people who are reluctant to trust salespeople

Learning objectives

This course will help participants:

  • Use broad open questions to give the customer a platform for their opinions or issues
  • Improve listening skills to really understand what’s behind the customer’s challenging style
  • Probe specific phrases to show listening and earn deeper disclosure
  • Use silence to let challenging customers ‘blow off steam’
  • Understand the negative impact of certain phrases on a challenging customer
  • Summarise effectively and reassure the customer of our understanding of their needs
  • Recognise the ‘behaviour cycle’ and avoid emotional escalation
  • Understand ‘transactional analysis’ and how to bring people from ‘child’ to ‘adult’ state
  • Create loyalty in customers who are slow to give trust

Who should attend?

This very practical and interactive course is geared towards salespeople at all levels. Participants will have the opportunity to deal with a ‘live’ challenging customer and the degree of ‘stretch’ can be specifically tailored to each participant’s experience level.


A highly practical and interactive one-day session for a maximum of 12 people. Activities throughout the day will include a ‘Forum Theatre’ session where participants take turns to sit in the seat opposite a challenging customer (the trainer) and their colleagues can stop the action and suggest alternative tactics whenever the conversation takes a downward turn. There will also be training on ‘transactional analysis’, the ‘behavioural cycle’ and the different personality styles that make a customer ‘challenging’.


The course structure will not be cast in stone and there will be opportunities to flex around the needs of the participants in the room, eg, dealing with challenging customers on the telephone.

Special features

The majority of the training we deliver is either tailored or completely bespoke. This workshop can therefore be delivered entirely as advertised, or it can be tailored to your particular requirements, or we can simply take it as a starting point for a conversation with you before we draft a completely bespoke programme for you – the choice is yours. As a rule, there is no additional charge for this service.

Expert trainer

Alun is a very experienced and entertaining deliverer of sales training. After sixteen years of sales and sales management – ten of which were in a telephone environment – he became a professional actor, attending Drama School in 2000/2001. Since 2002 he has become a highly skilled corporate role-player and for the last seven years or so has focused on sales training, using his role-playing experience to make training highly interactive and, above all, fun.

He has trained salespeople in numerous industry sectors and in markets as diverse as India, China, Pakistan, USA, Brazil, Morocco, Thailand, Malaysia and many countries in Europe. He has even written and performed at the Edinburgh festival a one-man show, ‘Salesbears!’, lampooning the ‘boiler room’ tactics occasionally found in the telesales industry.

‘Stacking the pain has been one of the most effective ways to close a sale for me, whether in person or on the phone, but to experience it within a role play scenario was the trigger to starting using it.’ Mark Collingwood, Director, Digitally Engaged

‘Alun demonstrates that you never know it all and equipped with easy “how to’s” you can improve the outcome of any sales meeting… I have used his methods over the past 9 months with great success and I have easily won over 10% more business. There are not many things that deliver that return.’ David Millward, MD, Pebble Web Design Ltd

‘Alun has been very helpful providing sales advice for myself and some of my clients. The difference that he brings to any training is that he ticks all the important boxes. He is extremely personable, he knows his subject and he can explain and deliver concepts and techniques in an easy to understand manner. His ability to get everyone up to speed without seeming to leave anyone behind in a training session is to be applauded. I continue to use his services and often seek his advice on how to position and explain services that we offer. I have no hesitation in recommending him.’ Angus Grady, Owner of Customeyes Media Ltd

1 What makes a customer ‘challenging’?

  • Why customers challenge us – understanding their drivers
  • ‘Wearing their shoes’ – seeing things from their perspective
  • Understanding our own personality style
  • How to flex with a style that is different from our own
  • Ways to quickly recognise a customer’s style
  • The benefits of flexing with a challenging customer’s style

2 Practical exercise – forum theatre

  • Participants take it in turns to deal with the trainer (who plays the role of the challenging customer)
  • Observers stop the action when they hear or see something they deem wrong
  • The participant in the seat gets a chance to use a suggested alternative line
  • The participant who makes the suggestion has the chance to occupy the seat and deliver it themselves
  • Frequent feedback from the trainer as to how the participant’s words are making him feel
  • Opportunities to rewind the action if an ill-advised line is suggested and delivered
  • Flipchart for capturing what worked, what didn’t work and why
  • Mehrabian principle – the importance of body language and tone over words used

3 Questioning and listening skills

  • How to use open questions to get the customer talking
  • What questions to avoid and why
  • The use of pauses and silence to reduce tension and build trust
  • What listening is and what it isn’t
  • Question funnelling – how to earn deeper disclosure through probing
  • The power of summary

4 Transactional analysis explained

  • What is transactional analysis (TA)?
  • Exploring the TA states and why people behave in that way under pressure
  • How to bring challenging customers to ‘adult’ state to reduce tension
  • How ‘parent’ or ‘child’ behaviours can be inadvertently triggered
  • Understanding the ‘behavioural cycle’ and how to break it
  • Mini-role play ‘vignettes’ to demonstrate real time impact of ill-chosen words

5 How to build trust with challenging customers

  • Techniques for placating current challenging customers
  • Methods that the participants have already used effectively – understanding why those methods worked and how other participants can model them
  • Participants’ experiences of trust having been lost – understanding why those experiences had that negative outcome
  • How to ‘go the extra mile’ with challenging customers

6 Bringing a ‘real’ challenging customer to life

  • Participants give the trainer a brief profile of a specific challenging customer of theirs
  • 5-10 minute roleplay in which the trainer brings that individual to life
  • Observing participants – without interrupting – make notes on what is and isn’t working
  • Trainer stops the action half-way through to give feedback on how he is feeling
  • Participant goes back into the roleplay having recalibrated their approach based on feedback
  • Observers give feedback on what did and didn’t work
  • Trainer comes out of character to explain the impact of the participant’s words and behaviours

7 Wrap-up

  • Key learnings from each participant
  • Individual action planning – steps that can and will be implemented in the workplace

Any questions? Please just give us a call on 01582 463463 – we’re here to help!