In his Pulitzer prize winning play Death of a Salesman Arthur Miller presents a sobering vision of the fear and isolation confronting an ageing salesman, struggling to come to terms with his declining fortunes, in an industry that is rapidly evolving beyond his sales strategies.

In my almost 20 years in the enterprise sales industry, I’ve witnessed my fair share of Willy Loman style declines, as high performing salespeople I knew and admired slowly withered on the vine. A few suffered a fate similar to Loman and are now selling their wares in the big sales warehouse in the sky, but many suffered a plight almost as ignominious.

They were fired or quietly managed out of companies, told there was a skills mismatch or the company was heading in a different direction with its sales strategy. They had their targets dramatically increased or their territories dramatically reduced, whatever it took to ensure they were no longer part of the customer-facing sales team. They took jobs at lesser known companies, with tougher patches to cover and people who neither knew nor cared about their past successes. Eventually and inevitably they walked away from the sales industry all together.

In recent years I’ve seen many once-great salespeople (the so-called ‘elephant hunters’ of the 90’s and early 2000’s) become surplus to requirements. Rendered increasingly obsolete in an industry that used to place their achievements on a pedestal and elevate them to the status of demi-gods of the sales fraternity.

200% percent achievement of target, annual trips to the Caribbean, I’ve even seen a top performing salesperson receive a brand new Porsche for his troubles.

Let’s not kid ourselves though, in the last few years the enterprise sales industry has changed forever. Prospective customers have become ever more well-informed, sales cycles have become increasingly commoditized. The existing skill-sets and experience of many 40, 50 and 60-something salespeople with plenty of petrol left in the tank have become increasingly obsolete or irrelevant in this brave new world of sales.

Is that how it has to be I wonder? Should these great salesmen and women simply hand back their laptops, cut up their frequent flyer cards and resign themselves to an early retirement or the daunting prospect of skilling up in a brand new career? My personal view is that this would represent a criminal waste of experience and hard won knowledge, and that we in the sales industry would be poorer for the loss of these individuals from our talent pool.

So what can we do about it, you may well ask? Well, I’ve spent quite a bit of time mulling it over and have come up with 6 strategies for staying at the top of the sales game for those older salespeople amongst us, keen to stay at the forefront of their industry for at least another decade or two!

Disclaimer: This is by no means an exhaustive list and these are my personal opinions, but as someone who has trained thousands of salespeople across Australia and the Asia Pacific region, I’m happy to stand by my list … until of course I get some better suggestions from you.

To avoid overloading I’ll share 3 strategies today and the final 3 next week … I’d love to hear from those older salespeople who might read this article with ideas or strategies that work for you and of course any younger salespeople out there, regarding the value you’ve received from the older or more experienced colleagues you’ve worked with.

1. Become consciously competent

Symptom – Far too many experienced salespeople rely on instinct, muscle memory or plain old gut-feel in their day-to-day sales activities. Why do they do this, its simple … they’ve been in the sales game for years and have always been pretty successful so why mess with a proven formula?

Cure – Focus on what you’re doing each day, be specific and write things down. When you’re preparing for a client presentation capture:

  • What you do before hand
  • Where and how you do your research,
  • Who you speak to (internally and externally),
  • Whether you do a dry-run, if so how long before the presentation
  • Whether you invite your internal customer sponsor to participate.

Once you’ve captured this information follow the same process for capturing your prospecting process, your discovery meetings, the way you respond to tenders, how you prepare for a negotiation.

Get this information out of your head and down on paper. You may think you run the risk of giving up your secret sauce or letting folks get a peek behind the Wizard of Oz’s curtain, but what you’re really doing is quantifying the value you bring to the organisation and providing another outlet for your skills and knowledge. You’re also ensuring your hard won knowledge can be quantified and have value placed against it, which its much harder to do when it resides between your ears!

2. Find yourself a reverse mentor

Symptom – Whenever we hear the word mentor, we inevitably think of a single directional flow of information and knowledge. An experienced, wily industry veteran taking a young and enthusiastic recruit under their wing and helping to guide and advise them as they build their careers. This is a wonderful tradition in many organisations and despite the often high-stress, occasionally cutthroat nature of the enterprise sales world, it’s a tradition that continues to flourish today.

Cure – The problem with this old mentoring model is that all of the value flows in one direction. The experienced industry veteran dole’s out their Yoda-like pearls of wisdom that their acolyte gratefully accepts. Demand some value in return I say. Take a leaf out of former GE Chairman Jack Welsh’s book, one of the first champions of the reverse mentoring phenomenon. Become a mentee, ask these young people stupid questions, it will encourage them to ask you stupid questions in return (remembering of course that there’s no such thing as a stupid question) and break down the awkwardness that can sometimes exist at the beginning of a mentoring relationship. Try asking the following:

  • Where do you go to access news content?
  • If you were going to buy a new car or a new computer, what process would you go through to research it? Who would you speak to, where would you go for information?
  • Who or what do you believe represent trustworthy sources of information?
  • Find out what they like to read in their spare time, what technology platforms they spend most time on, who they admire in business or just in life.

Don’t just do this because these individuals are the customers of the present and the future, do it because it will keep you relevant, connected and most of all because it will keep you learning.

3. Stop ignoring social media

Symptom – You either pay lip service to social media or ignore it completely. The average senior salesperson (I’ve undertaken extensive research in this area … a total of 14 salespeople I know who are all over 40) are active on LinkedIn, Facebook and about 20% on Twitter.

That might sound like a pretty good cross-section of the social media spectrum, so what’s the problem? The problem is that many of us are floating along the surface of the social media river, without really getting wet. In a recent Pew Research Center study they found that “Just over one quarter (26%) of internet users aged 18-29 use Twitter. Most notably, those 18-29 represent nearly double the usage rate for those ages 30-49”.

Cure – Start taking an active interest in the communication platforms of the present and the future. Recognise where your customers and prospective customers are going for information, for research and peer-to-peer review. Be there waiting for them with valuable information they can use, in a format they can quickly consume, with an insight or point of difference that will make you remarkable:

  • Don’t be afraid to have an opinion and express it
  • Become a human content aggregator, find interesting and relevant content and share it with your network (the key words here are interesting and relevant, over-sharing or poor content is a no-no)
  • Dip your toe in the water, join a new LinkedIn Group and start to actively engage rather than passively read
  • Sign-up to Twitter and find some thought leaders or industry experts that interest you to follow
  • Take a leaf out of Ashton Kutcher’s book (@aplusk) who has a simple mantra for the Tweets he sends out. He believes everything you post online has to ‘Inspire, Connect, Entertain or Educate’ and with 16.3 million followers and counting, he must be doing something right.

Authors note: Having recently turned 39, this isn’t just theoretical concept for me, these strategies and the ones to follow next week are some of the ways I’m hoping to stay relevant and at the forefront of my industry for a few more years to come!

Photo Nick Walton

Cian McLoughlin is the Amazon #1 bestselling author of Rebirth of the Salesman, a regular keynote speaker at sales kick-off’s around the world and one of the Top 50 Sales bloggers in the world for the past 2 years. He is a passionate proponent of an ethical, honest and authentic approach to sales. His company, Trinity Perspectives, is committed to helping sales organizations unlock the latent potential of their customers’ insights with their Win Loss Analysis and Sales Transformation services. To read more of Cian’s sales articles visit

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