Generational Selling

Executive Summary

In this 3,500 Sales Brief, we argue that the varying generations need handling differently by the modern salesperson if they want to achieve a win-win. He shares countless “use the very next day” tips and strategies to enhance your generational selling.

Invest 15 minutes in this paper now and be rewarded with some neat and clever ideas to improve your selling to the 4 varying generations buying now.

Why generational selling?

Saturday, shopping mall, my wife, credit cards hot with use…not my most enjoyable experience.

But for the sake of family harmony, I need to endure these moments periodically so how do I cope? Easy.

I comatose myself from the shopping experience and watch salespeople in action instead, noting positive and negative actions and skills.  It’s great fun.

This week I was fixed on the issue of selling to the four different generations. In the shopping mall there were people from all four generations shopping gleefully and how did the salespeople handle them?

Pretty much the same and this brought about some success but also some intense frustration on both fronts.

The plain fact is, we have to adapt our way of selling or handling customers and one way to achieve some success is to segment them according to the four recognised generations.

The purpose of this article is to give you “use the very next day” tips and strategies to help you sell more effectively to the varying generations.

So let me explore with you the four generations:

  • Matures born before 1945
  • Baby Boomers – born 1945 to 1965
  • Generation X – born 1965 to 1980
  • Generation Y – born 1980 to 2000


Matures are all pretty much into retirement now and have a very traditional, cautious attitude to buying.  They look for consistency and quality in the products they buy and aim to buy services that are tried and tested by others before them.  They are, and were, extremely loyal to their companies they work for and the companies they enjoy the products of.

They’re living much longer than anticipated and have a need for income to finance their spare time and of course, long term care.  The medicine popping generation, they spend more on healthcare than any other generation.

Baby Boomers

Baby Boomers are competitive, very hard working and tend to be in high levels of authority in the economy.  They are, as such, the wealthiest spending generation many sitting on high valued properties and assets particularly equities and funds.  They like to have trophies showing their hard work and success and they want their products to be a demonstration of this success.  Some have taken to technology and some haven’t.

As far as wealth is concerned, the Baby Boomers win hands down, they’re loaded.  Sitting on vast property and asset wealth. Many are retired and living off their final salary pensions and investments. Latter stage Boomers are in positions of authority in the workplace and are commanding large salaries and well protected fat pension pots.

Generation X

Generation X are quite different. The forgotten or bewildered generation. Financial scandal after scandal have affected their trust of Corporations and salespeople. Their boom years were in the nineties and naughties, then brutally cut down to size with the credit crunch. They believe in property and many have substantial wealth in this area, but also sizeable mortgages, numerous interest only.

The live for the moment generation have maxed their credit cards in more ways than one. Faced with alarmingly large University fees for their children and none of the big company benefits that the Boomers enjoyed, they have justification to feel hard done by. And jealous of the Boomers who enjoyed Woodstock and flower power, the 80’s boom years and always seemed to have it their way.

They have big protection needs and retirement planning goals. No longer members of final salary schemes, they feel they were abandoned by the pension authorities.

Generation Y

Finally Generation Y. The eldest is only 32, so haven’t had time to build up a store of wealth. Technology start-up millionaires are not common, so if you’re thinking of signing up the next millionaire, then think again, she’s taken. An exciting generation, IT literate, multi tasking, always on and instant gratification requirements stereotype them. Helicopter parented, attention seeking and individuality yearning, that’s the fresh young Generation Y.

Selling to Matures

Matures have an in built need to conform. They don’t need to “rock the boat” or to show their individuality like the Generation Ys. So they’ll often go with the off the shelf solution only so long as it’s tried and tested and oozes quality. No need to create tailored packages or solutions with the Matures.

Brought up with the rationing of war and post war austerety, Matures value quality and want whatever they buy to last and be proven. They’re not going to take up anything experimental, the latest fad. They respect proven quality and desire testimonials and referrals backing up our statements of quality.

Communicate with them the old fashioned way. Face to face visits are always welcomed, meetings, phone calls and letters. Ask about other mediums, some have taken to email and other electronic communications, most haven’t. Matures are not time strapped like other generations, they are mostly all retired so have the time to chat with you face to face or on the phone.

Follow the traditional sales process that you were taught in sales training school as the Matures will adhere to this conformity. Earn the right to present your solution by building a rapport, showing your credentials, referring to the mighty organisation behind you (if you have one). Matures generally have a fondness and trust for large institutions, the government, charities, the church. Traditional institutions give them a warm feeling.

Be prepared to work hard during the sales process. Matures are comfortable and willing to follow the whole sales process and will give you the opportunity to sell, only when you’ve covered the correct ground previously. Remember to ask for the sale, matures expect you to ask and will reward you with loyal business if you’ve been successful.

Earn their respect and trust first, share your experiences and above all, ask them how they like to be treated and handled, they all have a way for you to sell to them. Stick to it.

Under promise and over deliver is a good handle to use with Matures. They are looking to trust you and delivering on your promises within the timescales is vital.

Keep in touch with your Mature clients more than other generations. They don’t get email inbox fever, so use the postal system to make contact. Newspapers, information, birthday cards are all very acceptable.

Selling to the Baby Boomers

Boomers are ambitious and competitive, want to win and be successful. They want to show this success in material trappings.  Conspicuous consumption is quite common as they show how successful they are by having something slightly better than everyone else. Just take a look at the board’s car parking zone in corporate Britain. Cars showing their wealth and position.

You need to be subtle but don’t hold back on stroking their egos a little to air their hard work and success.

Known for their work ethic, Boomers will expect this from you as well. So don’t hide your work load on their behalf. Make visible what’s normally visible – the long hours, the reports, the meetings, the decisions – all on their behalf.  Make sure they know you’re working hard for them and going the extra mile to secure their business. You’ll be rewarded.

Use technology appropriately with Boomers. Many have adopted it and are using it progressively. You need to ask about their use and then match it but be willing to adopt their traditional communication methods such as face to face time, telephone calls. Bear in mind that boomers are adopting the technology in their droves now that it’s all getting easier. Smartphones and iPads that are always on and simple to operate are ticking their boxes. So be prepared to use modern technology to communicate more in the future.

Boomers like to fill their days with activities from work and home. This is the generation with the work/life balance predicament, other generations don’t seem to be too troubled by it. The reason is that they want to be the best parent possible for their children, to give them the face time they wanted, the “me” time. They’re constantly taxing them to swimming lessons, brownies and Judo and have big ambitions for their university education.

They like to be busy. It’s a sign of success. Remember they have always been surrounded by many other boomers so one way of being picked for promotion was to put in the long hours. As a result they are busy so anything you can do with your product to save them time, is most welcomed. Look for time saving angles, automated offerings that preserve their valuable spare time.

Boomers are not resistant to traditional sales practices in the same way as Matures. So approach them in the way you were trained – open, rapport, needs, solution and close – will work admirably with Boomers.

Coupled with time, Boomers like to be in control not as fetishlike as the Generation X, but they like to know that things can be done. They look for features that give them this control, help them with their priorities and provide efficiency.

Boomers, having been brought up around lots of other Boomers, are very comfortable in teams. Teamwork achieves great results. So make your product appear part of a team. Ensure they know about all the other people on your team who are contributing to the value you’re providing.

Remember your common courtesies with Boomers. Beware slang language and hip terms, they don’t like them. Don’t be overly casual or familiar unless you know them well.

Optimism, positivity, visible emotions are evident in Boomers. They were brought up to show their emotions unlike Matures and the younger Generation X and Y’s. Ensure you share this optimism and emotion when dealing with the Boomer.  A can do attitude will serve you well.

Selling to Generation X

So how do you sell to a Gen X?  You don’t, not in the traditional manner, if you do, you’ll fail.  Instead let them buy on their terms and in their timescale.  Don’t push them along a sales process designed by head office, they’ll see it coming and back off. After all, they don’t really need you to help them; they can and will, do it themselves.

Find their buying process, which usually involves huge amounts of research and checking with their network, stalking the products, checking facts and features, visiting stores, online and brick and then when they’re ready, they swoop in for the purchase.  Use this buying process and sell alongside it.

They are in control of the buying process, let them keep control and don’t take over and above all don’t use selling techniques with them, they’ll see a phony salesperson very easily.  Perhaps we should get rid of our sales in our titles because they want advisers, helpers, people who can smooth their buying process.

Last week I drove passed a new home development which said “Contact our sales representatives for information”.  As a Gen X myself, this puts fear and dread into me, I want to be in control and don’t want to speak with a sales rep.  Urggh.

Let them research. Because they will as they want to be in control.  They will end up knowing your product better than you.  They may even know you better than you know yourself. Help them to educate themselves provide links, sites, online content about you and your service.  Videos, White Papers, Blogs.  You’ve heard it all before but we must do it, as they want to educate themselves before they approach you to close the sale.

However Gen X’s are loyal to a brand once they’ve done all this research.  After all they don’t want to do it again and once they’ve proven that the product is right for them and you are trustworthy, they’ll stick with you religiously. Brand matters most to Gen X’s.  Remember they’re trying to be sure about you and your company.

Give them proof. They have cynical sensors built into their heads and will need proof, cold hard facts about your offering.

No need to build a relationship. I met a Financial Adviser recently who proudly announced to me that he “does business the good old fashioned way, face to face and I spend time building a relationship first”

The Adviser was in his mid 50’s and I bet most of his clients were too. Baby Boomer to Boomer this strategy works, but not with Gen X’s

This goes against the grain doesn’t it, but it doesn’t matter with Gen X’s.   They’re approaching only because they have to; they’d rather close the sale online. Don’t take it personally, but they’ve stalked you and your product for a long while, they just want to get the closing over and done with.

No need for chit-chat, get to the point quickly. Take your time with them, have many meetings if you have to, remember they don’t trust you initially. They are reserved with you.

If you’ve been brought up with relationship building sales practices, don’t use them with Gen X’s

Involve them. Gen X’s want to be in control and learn to trust you. Involve them along the way. Let them see your computer screens, let them input the details, share the processes you have to go through, make the sales process simple, not cumbersome. They don’t want to be there longer than normal. Someone tell Head Office please.

Gen X’s foresee problems happening at some time in the future so present Plan B’s in case Plan A goes wrong. Also give them options, be aware of forcing them down an alleyway.  It’s ok to make recommendations of course, but have a second option up your sleeve.  “Based on our discussion this route would be ideal for you both, but I also have some other ideas if you’re interested”

Don’t close them. Otherwise they’ll back off. Let them close themselves, they don’t want to be shoved into a corner by a pushy salesperson. Invite them to buy, give them space. Ask them if there’s any more information they need before you move onwards.  Give them thinking time, space to make their own decisions. They will.

Selling to Generation Y

Let’s look at how we get to speak with Generation Ys.  Self esteem is very important to them.  They don’t want to show it with physical trappings of success like their parents, the Boomers, they prefer to be acknowledged by people around them.  Ever since they were born they’ve been told how special they are and they have begun to believe it.  So if you’re prospecting for their custom, make them feel special and individual.

Approach them in the banking hall and literally hold their hands to help them make the purchase.  They’ve never had to make many decisions in their lives – their parents have done this for them – so help them to make the decision to talk with you.  Provide them with structure and outline the next steps with them.  Use signposting regularly.

It goes without saying but use new technology to reach this audience on an individual basis.  Start referring to Social Media as Soc Med and you’ll be accepted. They have totally accepted this as a way of communicating, it’s their way. Embrace it.  Think their world and put your message out to them.  Prevent using email – they just don’t get it.

So you get to sit them down and talk with them.  Generation Ys have short attention spans as they are the most over-scheduled generation and their friends come before you.  Dump the 2 hour interviews.  I know it’s difficult but we’ve got to find a way otherwise we won’t get this audience.  Go beyond 30 minutes and you’ve lost them so break down your interview format, use technology more before and afterwards to reduce the time spent face to face, and adapt your sale to them.  You’ll capture a massive market as a result.

Generation Ys strive to be happy.  They’ve delayed responsibility to enjoy themselves more choosing to have families later, mortgages later. They enjoy gap years travelling the world finding themselves, they have chill out times, they have “me” times.

Make your product make them feel good about themselves.

Let your product have an immediate effect on them since they’re used to instant gratification.  Offer them instant solutions as they live in an instantaneous world.  Give them the on the spot mortgage offer, use lenders that automate the valuation systems, and rely on web based employment checking, arrange for them to get their credit card that day, give them instant decisions by empowering sales staff more. Nothing irritates them more than having to go to head office for a decision.  Remember they have little loyalty to your company.

Individualise your product for them, provide customisation, make them feel individual and special.  Ensure your product can be tailored to their needs but don’t make the decision too onerous.  This will cause stress and they’ve never experienced this as their parents shielded them as much as possible.

Highlight any altruistic practices you or your company adopt.  Focus on ethical funds, have the points from the credit card go to Greenpeace, publish your firm’s recycling targets, show them that your firm is a good corporate citizen and thinks of others before profits.  Use recyclable paper, better still don’t use any paper – make it all electronic so it’s quick and instant and much kinder on the environment.

Be very very good with your technology. Don’t fumble with the laptop keys, you’ll get away with this from some generations – boomers and matures will sympathise with you, but Generation Ys won’t.

How do you ask for the business with a Generation Y?  Generation Ys are not skilled decision makers, they’ve never had to be as their parents have done it all for them.  With the close, you need to relieve the stress and hold their hands through the decision process.  Gain agreement through small bite sized chunks and staircase to the close.

Your next steps

You’re now considering your generational sales tactics to use. Here are some questions to help your transformation:

  • What steps will you take to identify and understand the generations you currently sell to or intend to sell to?
  • How will you distinguish your value proposition to each generation?
  • How do you plan to update your IT and use it appropriately for your generation?
  • What steps will you take to manage your reputation among the younger generation? Your brand online – is it safe?
  • How do you intend to win over your chosen generation?
  • What marketing methods and materials will you be adopting to appeal to your generation?
  • What new business practices will you be creating to appeal to your generation?

Back to my shopping mall

Are the salespeople adapting themselves according to the generations in front of them?  Not deliberately, by chance possibly, but relying on chance is not a positive strategy.  Use the ideas from this article and ensure you connect with all 4 generations at any given time. And has it made my shopping experience any more enjoyable?

Not really but it’s fun watching the lone Gen X customers checking their iPhones for a cheaper product at the till, the matures desperate for someone to connect with them, the Boomers enjoying the selling process and the Gen Ys hovering around in packs looking for peer testimonials on everything they want to buy.

Is the world stereotypical?  Yes it is, at least in a shopping mall.