The 12 Most Useful Lessons I learned from 20 Years Coaching Sales Managers

Sales management tips you can use

I have been coaching and mentoring sales managers for 20 years. It all began by accident when I discovered the sales training program I was teaching did not always deliver the results my clients needed. There was nothing wrong with the program. It was, and it still is, one of the best sales training programs ever created.

What was the problem? Why wasn’t every salesperson who enrolled in the program not showing massive increases in sales? Why were some people producing awesome results, while others were not showing any improvement? This was a big concern.  I could not continue to sell something that wasn’t delivering results.

I figured out it wasn’t the content. I also figured out it wasn’t the trainer (I did a lot of soul searching on this and even used multiple trainers). That left only one conclusion … it had to be the people being trained.

More research showed the two biggest reasons sales training fails:

The number one reason … many salespeople are not trainable. No amount of training or additional sales skills will transform someone who won’t sell into someone who will sell. Dave Kurlan, founder of Objective Management, has documented this for years.

Even my ancestors in rural Ireland knew this …

“You can’t make a racehorse out of a donkey.”

The second reason … lack of follow-up by sales management. Companies send salespeople to sales training programs and expect miracles. It doesn’t happen. There’s no magic wand; no quick fixes.

As a society, we expect instant gratification. Doesn’t happen with weight loss, doesn’t happen with savings, and it sure as hell doesn’t happen with sales training. Just look at the following statistics:

  • “Without systematic, ongoing learning and reinforcement, 50% of the learned content is not retained within 5 weeks, much less applied. Within 90 days, 84% of what was initially learned is lost.”

  • Training Industry

  • “Firms where salespeople use the company’s methodology and get consistent coaching, see 73% quota attainment.”

  • CSO Insights

  • “90%+ will transfer new skills into practice as a result of theory, demonstration, practice, feedback and on-going coaching.”

  • Jim Stuckey Training & Consultancy

OK. It’s clear from the above. Two of the most useful lessons I learned over the years include having the right salespeople on the team and coaching them. I’ve listed all twelve below. By the way, I tend to learn better when I screw up and when there’s some pain involved. These lessons were learned the hard way … by experience. Hopefully, they’ll save you some angst and prevent you from making the same mistakes I did.

  1. Sales Management Tips

  2. Understand your role as a sales manager. Your job is to generate the sales and profits your company needs. You must do this through the salespeople. Everything else is secondary. Look, you’re going to have all sorts of demands on your time, people expecting you to perform a myriad of different tasks. There’s nothing wrong with that, provided you take care of your primary responsibility first. No sales and no profits equal a struggling company. Then why do they need you? Stay focused on your salesforce and stay successful.

  3. You must have the right salespeople on your team. Years ago, I was promoted to a sales management position and inherited the Vice President’s company car. It was a beautiful looking car and had all the bells and whistles befitting a senior executive. It had everything except power. That beast was so underpowered it wouldn’t get out of its own way. It failed to do the most important thing it needed to do … haul people from A to B safely and efficiently.

If you don’t have salespeople who will sell, you will fail. No amount of training or coaching will transform someone who won’t sell into a salesperson. I learned this the hard way. You may be good, but you cannot perform miracles. As another old Irish saying goes …

“You can’t make a silk purse out of a sow’s ear.”

Whether you’re a new sales manager, or you’ve been doing it for many years, evaluate your sales organization. Don’t try to do it yourself. Invest in a comprehensive sales force evaluation. You will recoup the investment many times over. For God’s sake, even the repair shop runs the diagnostics before working on your car.

  1. Set clear expectations for your salespeople. Most of us set sales quotas for our salespeople and that’s important. However, it’s just part of the picture. Salespeople have no control over the numbers. Only the customer controls those. Your salespeople do have control over their actions and their behaviors.

Set clear expectations for the activities that lead to the numbers. This will vary by industry, by company, even by individual salesperson. Closing ratios vary. Determine the number of calls each person must make to have a healthy pipeline.

Same deal with behaviors … what you expect your salesperson to say and do in front of the customer. Be very specific. You can’t assume anything.

  1. Track those expectations. I don’t care if you use, some other type of CRM system, or traditional old-fashioned paper reports. Just be sure to at least use a weekly tracking report. What gets inspected, gets done.

  2. Hold your salespeople accountable. This is an area where many sales managers get into trouble. Neither give or accept excuses. This is not a game. You have trusted your salespeople to perform the activities needed to grow sales. You have also trusted them to take care of your customers. It’s your responsibility to make sure they do it by holding them accountable for making the calls. If you don’t do this, you will fail.

  3. Provide ongoing training. Sit in on any Monday morning sales meeting and, in 90% of them, you’ll hear the same old crap. The sales manager will review the numbers and drone on about the challenges the team is facing. Then someone from marketing, or credit, or shipping, or a visiting factory rep will waste another half hour dealing with their own agendas.

OK. Maybe this stuff is important, but 99% of it can be handled by e-mail or memo.

Provide ongoing training in the following areas:

Product knowledge … updates on products and tips for selling them.

Industry and business updates … what’s happening in the market and how that creates sales opportunities for the company.

Sales training … This is vital. If you only have an hour a week, spend it on sales training. None of your people are so good that they can’t “sharpen the saw.” They may think they know it all. Believe me, they don’t. What they don’t know is costing you and your company business.

  1. Be a great sales coach. Every salesperson needs coaching. Some more than others. The biggest mistake I ever made in this area was assuming the top salespeople didn’t need as much help as the rookies. Wrong! Look at the ROI on your time and spend it accordingly.

If you’re not already a great sales coach, invest in yourself and become one. The payback will be incredible.

  1. Spend most of your time with your salespeople. You should be spending at least 75% of your time with your salespeople. You should be making calls with them, coaching, strategizing, debriefing, motivating and holding them accountable. Sitting at the computer, checking inventory, planning the company picnic, etc. does not count toward working with your salespeople. The US Marines coined a term for it … REMF. It’s not a term of respect.

  2. Be a champion for your salespeople. Look, you’re going to hold them accountable, make them do stuff they don’t want to do, and generally be a taskmaster. That’s your job. At the end of the day, you must always look out for them. You must nurture and support them. You must have their backs and protect them from attacks from customers or even people within your own company.

  3. Know when to cut your losses. There will come a time when a salesperson is no longer working out. It can happen for many reasons. You have done everything in your power to save them, but the situation is not getting any better. Stop screwing around. Your responsibility is to the entire company, not any individual salesperson. Cut them loose and move on.

11. Invest in yourself. Congratulations. You’re now the sales manager. Your job is to teach others the stuff that made you a successful salesperson. Understand a few things:

  1. The skills that helped you succeed in sales need constant updating.

  2. Managing salespeople requires a whole different skill-set than selling.

  3. You can’t afford to stop learning or growing. Invest in a good sales management coach. At the very least, participate in a sales management mastermind group.

12. Take good care of yourself. Managing salespeople is a tough job. It will take a toll on you mentally and physically. Eat right, exercise and get enough sleep. You can’t help others if you’re tired or stressed out. Remember the pre-flight announcement. Yeah, the one nobody listens to …

“Fasten your seatbelt, etc. In the event of a loss of cabin pressure, place the oxygen mask over your mouth before helping others.”

OK. That’s a dozen things you can do to be a good sales manager. There are others. You may have also noticed I didn’t mention any of the personal strengths or characteristics of highly successful sales managers … the things you need internally to help you perform the above activities. That’s a whole other story.

I’m Oliver Connolly, founder of Street Smart Sales Management. If you have any questions or if you want to explore how I might help you, please e-mail me at

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Oliver Connolly