Note to CEO's: Why Sales Training Fails


Twenty-five years of working with sales teams, with varying degrees of success, has taught me why attempts to improve sales succeed or fail. Progress has been satisfying, but I don’t have all the answers. I do have some, though, so I thought I’d post them here on LinkedIn to invite your comments.

Training salespeople alone won’t fix sales.

When there is visible senior leadership from the CEO, the odds of success skyrocket.  I recommend that your initial actions include:

  • Let the team know you are in for the long haul. Change occurs only with sustained effort.
  • Harness the power of your lead buffalos. Select top performing salespeople and managers to help customize the program. If they build it, they will love it. If they love it, they will use it. If they use it, others will follow. If they don’t help build it, unfortunately, they will scoff and resist. Their innate leadership will undercut your effort.
  • Accountability. Let your first line sales mangers know that they are the backbone of success. Ensure they accept the responsibility to lead by example. George Patton said, “They do what you check.” If you want your managers to lead from the front, you will need an ongoing way to check progress. If you keep them on track, they will keep the salespeople on track.

Most sales training is endured and forgotten.

Salespeople approach training with cynicism, because they know from experience that the training is just the corporate flavor of the month. Somebody at corporate headquarters picks whatever program seems acceptable at the time, and runs the entire sales team through it. It feels a bit like sheep being dipped.

One size fits nobody.

It’s not that salespeople don’t want new sales strategies. But if the message is stale and generic, no one listens. As a veteran sales trainer, I see programs that claim to be “customized,” but customization stops at the cover sheet.

Start with customization by thought leaders and the result is a message that is targeted, specific, and immediately applicable to your team’s real world. And it is supported by your top-performers.

Message x Messenger = Impact.

Once the message is right, you need the right messenger.

A salesperson asked a sales trainer how to get to decision-makers.

The trainer said, “Word it in a way that does not offend the current contact or ruin the relationship, but in a way that will get the right answer.”

The salesperson remarked later, “When you get an answer like that, you know the trainer has no more idea than you do, which is why he is longer in a sales role.”

Shoot the messenger.

Trainers that don’t have real answers are not credible and will not earn the respect of your salespeople.

Training should be led by someone who clearly walks the talk. When a salesperson is not buying in to a concept, the trainer should say, “Let’s role-play. You are the buyer. I am the seller. Let’s go!” That sort of no-holds-barred interaction will earn the respect of the most skeptical sales audience.

Training should be engaging and fun.

And the trainer ought to have answers, not platitudes.

Knowing how is not enough.

Mastery of selling is like mastery of golf, or playing a musical instrument. It is about knowledge, but also skill-building. Optimum selling is counterintuitive. We all naturally try to swing the club too hard. We also sell too hard.  Success requires adopting a paradoxical approach. A level of discomfort naturally accompanies the implementation of any new approach. We give it a try, and if it doesn’t feel right, we abandon it. Once the novelty wears off or the first obstacle is encountered, salespeople will fall back into their old habits. At a sales moment of truth, we all revert to habit or instinct. These automatic responses lead to automatic failure.

An ongoing practice regimen ensures that your salespeople move beyond knowledge to mastery. So when they’re under pressure, they are unflappable.

Anything else is a Band-Aid.

Following initial training, I suggest a series of weekly mastery sessions, using call recordings, like game film, to coach. It is a period of intensive habit reformation and skill building to support and reinforce the adoption of the concepts. Each salesperson focuses on one of the concepts at a time, working every day to master that skill. Once they demonstrate mastery in a live selling situation, they move on to the next step. The standards for each step are established in the initial training and they are documented in a customized Perfect Sales Call Check List. In that way, they progress at their own pace to achieve mastery. Stronger salespeople succeed more quickly and their example pulls the rest of the team along. It typically takes twelve months to get everyone to demonstrated mastery.

I work myself out of a job.

The mastery phase is training at two levels: your salespeople master selling, and your first line managers master coaching. Once that is done, they can do it without me. Straight and level flight is easy. Take off and landing is the hard part.

The impact is not monitored.

Visible success is a key motivator for salespeople, yet sales training is usually conducted with no method for measuring the impact of the program beyond the evaluations. If you let your team know you are going to check, results will follow. We all read with more attention and retention if we know there is a quiz at the end.

Select metrics to establish a baseline, to determine if you are moving the needle. But QUANTITY-only measurements will not work. We all know if we demand more deals in the pipeline, we get more. QUALITY must be measured, if you hope to impact quality of sales conversations. Use of game film is an example of a quality measure.


It’s trite but true: feature and benefit selling is ineffective. We know it, but we still do it.

As I work with clients, baseline assessments show that most SAS and software companies still train their sales teams primarily on the capabilities of the technology. So the sales team dutifully goes out and delivers the message, only to find that they have trouble keeping the attention of senior decision makers. Demos are seen as the main selling event. Since all the options sound the same to the buyer, price is the only differentiator.

I am often asked why this is true. Here’s one observation.

Most sales training is done by product managers. I love ‘em, but a person with no sales background isn’t going to produce the right training. A solution? Cross train. Send the product managers to sales training. I have had many product managers in my bootcamps. They find it eye-opening. They leave excited. If they come from a technical or marketing background, sales is new to them.

Premature Presentation Syndrome kills sales.

Knowledge of your products and services is important, but used the wrong way, at the wrong time, it will do more harm than good.

Good sales training delivers an understanding of:

  • why it is smart to hesitate dispensing your knowledge,
  • why the presentation that convinces a buyer can’t be given by the seller,
  • how to use knowledge effectively, and
  • how to ensure that THE solution is not YOUR solution, but the BUYER’S.


The following six steps will ensure the money you invest in a sales training program comes back to you through increased sales.

  1. Lead from the top: visible senior management focus and support, from the beginning and throughout.
  2. Customize the program for top performers, to engage them and their thought leadership.
  3. Senior leaders must require first-line sales managers to become sales leaders, who lead from the front.
  4. Ensure the messenger has “street cred.”
  5. Define quantity and quality metrics, and hold reps accountable for applying new techniques in real buyer/seller situations.
  6. Measure the impact of the program and celebrate successes along the way.