Selling Across the Generations

By Cam Marston, President, Generational Insight

When is the last time you walked into a sales call and sold software to yourself? In today’s business environment, with many ages and background experiences at play, you are likely to be selling your products and services to people who are nothing like you. So how do you find that common ground? How do you present the information they want to know in the manner they want to receive it? One important starting point is to gain an understanding of generational dynamics.

With four distinct generations in the workforce today – Matures, Boomers, Gen Xers and Millennials – there is a growing need to customize sales pitches to not only the industry and business needs of your prospects, but to their generational perspective as well. Each generation has a shared history, common biases and core beliefs. In some cases, they are nearly consistent across the generations; in others, the differences easily get in the way of closing the deal.

It is human nature to sell and communicate from where we are most comfortable personally. However, that may not always be a match for your prospect’s comfort zone, especially when you have a different generational history. With older workers staying in the game longer and younger workers rising quickly through the ranks, it is less and less common to be selling to your peers. You are selling to everyone. And that means different value sets, different communication preferences, and different selling points at every turn.

Of course, generational biases are not ironclad and birth date does not dictate personality. It is quite possible for a Millennial to identify with the ideals of a Boomer, or vice versa. In general, however, the historical context of one’s place in the world does impart some shared definitions and expectations that are well recognized and deserving of consideration. Generational context is just one very important part of a fully-loaded sales toolbox, which must always include razor-sharp product knowledge.

Snapshot of the Generations

Matures: Born 1909 – 1945
The Matures came of age during the Great Depression and experienced Pearl Harbor, World War II and Hiroshima. As a result, they are driven by ideals of duty and sacrifice. Most Matures have worked for only one company, staying with that employer until retirement, and sometimes beyond. They are loyal to their employers and expect the same in return.

As consumers, Matures place great faith in the nation’s institutions: people, companies and the government. They value quality over speed and efficiency and do not require fancy options and customization. Though loyal, they are not afraid to shop around.

Baby Boomers: Born 1946 – 1964
Boomers are the original 'Me' generation, paving the way for a more self-motivated take on life. This generation led the Civil Rights Movement and experienced the assassinations of Martin Luther King, JFK, and Robert Kennedy. Many fought in or protested against the Vietnam War. They are a generation focused on prosperity and they remain largely in control today, though the wave of Boomer retirements has already begun. In the workplace, Boomers are champions of a work ethic measured in face time, sometimes at the expense of true productivity. Commitment to the team is paramount and relationship-building skills are critical to success.

As consumers, Boomers seek products that help them regain control of their time. Reflecting their Me Generation roots, Boomers are critically concerned with status and individuality; they seek products and services which can be customized and serve as a personal demonstration of their own success.

Generation X: Born 1965 – 1979
Originally disparaged as the slacker generation, Gen X has demanded compelling change from the national workforce. Raised in a world where the institutional powers – churches, presidents, families – seemed to fall apart at the seams, Generation X was inadvertently taught to question authority. And question they do. The result has been a carpe diem attitude that flies in the face of the long-term strategizing typical of Boomers and Matures. They eschew hierarchy, preferring instead open communication and a focus on efficiency over punching clocks. Perhaps most telling, Gen Xers invest loyalty in people, not companies. 

As consumers, Gen Xers pose a tough sell. They have been conditioned to spot a phony a mile away. They want to control the decision and the sale, selecting options that make sense to the way they live and work, not what someone has predetermined for them. They embrace technology, using it in most aspects of their lives – including competitive analysis for almost all purchases.

Millennials: Born 1980 – 2000
Millennials grew up in an uncertain world. While they have been coddled and protected from birth, they have also witnessed terrorist attacks on US soil. Until recently, they had lived their entire lives in a growing economy. They are extremely tech-savvy, never having experienced a world without cell phones, laptops, wireless, etc. In the workplace, Millennials seek personal fulfillment, aligning themselves with individuals who can help them achieve their goals. They seek open, constant communication with peers and leaders alike.

As consumers, Millennials are torn between a desire for individuality and the need to fit in. They want to be like their peers – but with a twist. They are loyal and altruistic customers who look at a company’s global impact as well as product features when making decisions.

Making the Connection, Closing the Deal
With just that basic information about each generation in mind, you can likely already see where the roots of some of your sales challenges may lie. Perhaps you can see the reason behind some of the seemingly bizarre experiences you’ve had with prospects or customers that don’t share your generational bias. The great thing about this information, however, is that you don’t have to share a history to understand it. Once you see why a generation has developed its particular idiosyncrasies, you will be better prepared to identify the correct approach, pitch and close to get results.

Matures: Search for Quality
With duty and sacrifice at the heart of the Mature mindset, it stands to reason that you must earn their business. Good intentions, snazzy packaging and a controlling persona will not sway the Mature prospect. You must respect their position of authority and ask how they prefer to conduct business – from the sales process to communications preferences, asking before assuming will earn trust. Likewise, ask the prospect how he defines success and quality, then identify where your software serves those needs – and back it up with proof. Matures respect proven authorities, so if your software is new, look to your leadership. If leadership is young, look to the historical development of the technology. Always find a way to demonstrate earned authority and highlight the core product features that meet his defined goals; place less emphasis on the bells and whistles.

After you are confident that you have positioned your product as the natural and proven solution for your customer, it’s time to close the deal. Summarize his expectations, recap how you met them, and then ask if you can have the business. The ‘ask’ is imperative with Matures, who continue to expect you to earn the business even if they are already sold.

Baby Boomers: Search for Control
Boomers yield tremendous purchasing power in today’s economy, and are often the final decision-maker, even when not the initial contact. When preparing to meet with a Boomer prospect, remember the value they place in teamwork. You are there to inquire about their challenges and determine how your software and service can add value to the team working to solve those challenges. Do not enter the conversation assuming you already understand their needs – ask. And then customize your solution to their needs.

Many Boomers are quite adept at technology, but they still value the human touch. When selling a software solution, take care to mention the people behind it, from designers to support staff, and explain their role in the team. Technology itself should not be the sole provider of efficiency or even the foremost benefit/solution. It is always part of a bigger picture, just as Boomers are part of the larger team. On the flip side, the ‘Me’ generation has a bit of ego to address, so if you are able to offer customization that allows the customer to sculpt the final software solution to fit their exact needs, you will have an edge.

To get to the yes with Boomers, you must demonstrate your willingness to compete for their business. Show your hunger – never desperation – by going the extra mile. Appeal sincerely to the sense of ego and then flat out ask for the sale.

Generation X: Search for Truth
And now we return to the cynics. As previously mentioned, Gen Xers were taught by their place in history to be skeptical of just about everything. Sales professionals are high on that list. So, your challenge is to view your encounter as an information exchange not a sales call. Xers crave knowledge and peer reviews. They will find out everything they want to know about your software and you will not be the primary source of that information. Instead of fighting that fact, embrace it. Be prepared to answer why and to refer them to additional, unbiased resources, including how your software stacks up to the competition.

When preparing your sales pitch, look to the short- and medium-term horizon. Xers are the carpe diem generation, who don’t want to wait for results. You will need to explain how your software will improve their jobs and lives the moment after it is installed, as well as a few miles down the road. Respond to their innate cynicism with thought-out back-up plans for the inevitable time when a problem arises. Xers expect the problem, they will be won over by your willingness to concede imperfection.

After you have provided all the information you have and answered all their questions, leave the ball in the Xers’ court. They need space to make a decision. It’s not the natural approach for sales pros, but it works. Once you have gained respect as an honest and valuable resource, Xers will remain fiercely loyal…as long as you continue to earn it.

Millennials: Search for Identity
Though not frequently in decision-making positions with regards to large-scale business purchases, Millennials are avid consumers and enjoy participating in the sales process. Build rapport with Millennials by recognizing their individuality and accomplishments. In other words, build up their self-esteem. Peer testimonial is critical to the successful sale with this generation, as is a company’s altruistic intentions. They want to feel good about their decisions within their peer group and on a global scale, so share that information wherever possible.

As a whole, Millennials have not had much practice being decisive – they never had to be. So position yourself as a trusted guide and help them find the information they need to make a decision that is good for them as well as the company. As Millennials move up through the business ranks, their buying power and habits may change, however they will likely remain grounded in a search for identity among their peers and the greater community.

Closing the Deal
When it comes to signing on the dotted line, people’s decisions are based largely on emotion, with a touch of logic thrown in. This is not to say that your software can be inferior if you are an engaging person – getting on the short list is a highly objective process – but closing the deal lies mainly in whether the decision maker feels good about the process, about you, and about him or herself. Being cognitive of the role generational biases play in the process can help you stand apart from the crowd and better pave the road to “yes.”