"The Navigator" News Blog

How to Manage a Long Sales Career

This week’s Navigator is inspired by one that I wrote twelve years ago, and actually incorporates part of it.  That post was called, “When Salespeople Get Older,” and it was inspired by a true story – you’ll read that in this article.  When I read my Google Analytics this month, I was shocked to find out that it was my most-visited page on my website, and that in fact it’s been one of the most visited pages on my site for a long time. It seems like a lot of people want to know how to manage a long sales career. What makes that resonate so much?

Well, being “of a certain age” myself, I think that there are a lot of us right now who are looking ahead at our careers, working hard to stay relevant, and at the same time, there are a lot of managers out there working on keeping their more seasoned salespeople ahead of the learning curve.  And, yes, there are a lot of salespeople who are now thinking about a well-deserved retirement.  For the record, I’m not one of them – I’m having WAY too much fun now to think about retiring! Still, this is a topic worth discussing.  How do salespeople stay relevant in the present, finish with a flourish, and retain the fruits of our labors?  Within this article will be (hopefully) great advice for salespeople in every phase of their careers.

Sales can be a tough career – mentally, emotionally, and even physically.  As you probably know, I worked in the car business for three years at the start of my career. In that time, I worked for three different dealerships (one long engagement, two short ones) before pointing myself in another direction. Since then, I’ve rarely crossed paths with people from back then; the car business tends to be a bit insular. But there are many, many people who have a long sales career in that business.

On the morning that inspired “When Salespeople Get Older,” I had received a resume’ from the owner of one of those dealerships.  He didn’t remember me; I only worked for him for a few months (his dealership was the one that convinced me that the car business wasn’t my long term gig). That guy had, at the time, a pretty profitable business. He had a great house, a ’58 Corvette (which I still would love to have), and was making money hand over fist – which is why the tenure and tone of the resume’ was so shocking. Since selling out over 10 years previous, he’d bounced from job to job, mostly in one year or shorter engagements, and in a downwards direction. His “job objective,” as stated on the resume’? “A stable living for my family and some means for retirement.” It made me sad, even though I didn’t particularly like the guy. But here’s the kicker; this is the career trajectory of entirely too many salespeople.

Entirely too many salespeople peak many years before they retire, and then they ride a spiral of unsuccessful short engagements to – where? I honestly don’t know.  Many salespeople tend to peak, in terms of performance, about 15-20 years into their selling career. Then they hit the wrong side of the bell curve, and go downward faster than they went up.

My question is, “why?” I still sell, after 33 years, and to be honest, it’s more fun for me now than it ever was. Part of that is because I’m self-employed and doing something that I truly love, but part of it is that the zest for the sales call has never left me. I’ve interviewed enough of the previous types of salespeople to know that this is the key issue. For many of the salespeople that are on a downward spiral, something happened – some event or turmoil – that knocked the pins out from under them. Psychologically, they’ve never been able to recover. For others, they simply stopped learning and growing at some point in the past, and they’re just trying to coast and collect. Let’s talk about how to make you NOT be one of those people.  Here are a few ways to keep your sales career vibrant and productive until YOU decide that it’s time to ride into the sunset.

  1. Fall Back in Love With Selling. What I find, in talking to them, is that they literally can’t remember what they loved about selling; they have too easy a time focusing on the negative things that have happened. This typically leads to call reluctance (low quantity of activity) and poor call performance (low quality of activity), which leads to repeated failures. Since selling success is so mindset-dependent (I can’t think of any other discipline in business where enthusiasm is so critical to performance), a poor mindset equals a declining career. Worse, motivation is so individually based, it’s extremely difficult for others to re-energize a salesperson who has lost their zest for the job.
  2. Keep Reminders of Successes. One common thread of many of the people I’m describing is that they can’t remember details of past successes very well; they are able to focus on recent failures. So, here’s my advice to you: start keeping reminders of your success NOW. Keep a journal, and make sure to put in plenty of details about WHY, and HOW, you are successful. Basically it will be your own training and motivation manual, and it will help you get back on track. I still have trophies, letters, and awards that I won 20 or more years ago.  Why?  Because every now and then, looking at them puts me back in that place and mindset when those trophies were placed into my hands.  They are very personal to me, to the point that I don’t take pictures of them or share them on social media, but they’re important.
  3. Never Stop Learning. There are few things more gratifying to me than giving presentations or Webinars and seeing salespeople in their 60s, 70s, and even beyond who are still involved, still engaged, and still want to do better and learn more so they can be a better help to their customers and be valuable to their companies.  Those are people who are still in love with sales.  I talked to a salesperson last week who is 78 and learning how to use AI.  In fact, he sent me a short follow-up email thanking me for our conversation.  About 80% of it was written with ChatGPT.  He’s just starting with it, but I guarantee you that in a few months, he’ll be really good at it.  That’s a guy who still loves this profession.  Continuous learning not only helps you to stay relevant, it keeps you excited about what you do.  Stagnant salespeople stop learning – and that infects every part of their game.
  4. Don’t Fall For “Toy Motivation.” I am a bit of a contrarian in my profession, because I break with a lot of the old ways of managing and motivating salespeople.  One of those ways is called “Toy Motivation,” and it’s still being practiced today.  The idea behind “Toy Motivation” is that the manager finds out what “toys” the salesperson really wants – a new Cadillac, a jet ski, a boat, whatever – and then influences the salesperson to buy those things as soon as humanly possible. The idea here is that in the short term, the salesperson lives beyond his or her means, which makes them “hungrier,” and therefore motivated to sell more.  What it usually does is lead to financial disaster – which can be one of those events that knocks the pins out from under a salesperson.  I’ve seen this many times. Frankly, I find it immoral for a manager to knowingly urge a salesperson to make bad financial decisions, and even more immoral for a trainer to influence a manager to do so.  A pox on all their houses.  While you are saving reminders of the successes in your long sales career (see #2 above), don’t forget to save some of the actual fruits of your labors as well.  Make good financial decisions, and if a manager tries to influence you otherwise, find another job where you are respected as a human being.  I have no leeway on this one.

And finally, if you truly lose your zest for selling and can’t get it back, find another way to make a living. It’s a big old business world out there, and there are many rewarding spots for people other than salespeople – and your long sales career can give you a leg up in any discipline. There’s no shame in leaving the profession; there are other ways to have success.

When I started my first sales management job in 1998, my boss, Darren Pearce, told me that I had the most fun job in the building – if I did it right.  “Troy, your job is just to produce success and be a hero.”  I’ve never forgotten that.  I hope none of you forget that, either.