Having Trouble Sharing Performance Expectations? (Part 2) Ask Madeleine


Dear Madeleine,

I was promoted to VP of sales a few months before the pandemic hit. I feel like I have been in an industrial washing machine ever since, and am just starting to come up for air. There was a lot of training at the beginning but then our entire book of business and go-to-market strategies shifted. It has been mayhem, but things are starting to settle now.

I have an amazing team. I physically moved in order to take over a new region, so all of my people are relatively new colleagues, which is nice. About two years ago, our company changed CRM (Customer Relationship Management) systems. [Note: This is the system that sales leaders and marketing use to gain visibility into prospects, contact info, opportunities/pipeline, forecasting, account plans, competitive intelligence, etc.]

The new system is fine; not any worse or better than the old one. My people have figured out how to make it work for them and comply with requirements. But there are exceptions.

One sales rep, who creates amazing relationships with his customers and crushes his quota, cannot for the life of him get his info into the system. It’s great when he suddenly brings in huge projects, but then there is a scramble to deliver on the contract. Then there’s another rep who puts everything into the system beautifully but can’t seem to get anything done other than that—and she certainly can’t close.

My boss is giving me a hard time about both of them, but very little guidance on how to get them to where they need to be. Thoughts?

CRM Conundrum


(If you missed last week’s blog, Part 1 of the response can be found here. This is Part 2 of the response.)

Dear CRM Conundrum,

Last week we discussed how to deal with the rep who won’t use the CRM. Now let’s take a look at the other two situations you are dealing with.

  1. One rep who is very good at CRM management but doesn’t seem to know how to actually sell.
  2. A boss who isn’t very helpful.

Your rep who can’t sell probably needs some training on mechanics as well as a ton of support to boost her confidence. If she already has been through training, and can tell you what she should be doing but can’t seem to do it, you have a confidence issue. Perhaps she used to be good at selling and something happened that made her start doubting herself.  

However, if she’s never been successful, she probably doesn’t know exactly what to do and how to do it. Whatever your company’s sales training is, she will need to attend. She will also need super clear direction from you, and then extra time. If you can attend some of her sales calls with her as a fly on the wall and then give her feedback, that would be ideal. Or, if she could tag along with some of your superstars and see how they do it, that would also be great.

In the last post, I floated the idea that this rep might apprentice with your sales rock star who can’t (or won’t) use the CRM, and they could tutor each other on their strengths. Role play is also a terrific tool—it is much easier to say certain things if we’ve practiced.

If she was once great and lost her mojo, you’ll need to ask some open-ended questions to help her talk things through so that you can gain some insight into what is getting in her way. Ask questions like:

  • What happened that shook your confidence?
  • What do you think might be going on?
  • What might help you get back on track?
  • What would be helpful to you right now?
  • What kind of help would feel right?

Make sure your employee knows that you are on her side, you really want her to win, and you’ll do anything in your power to help her get there. Help her build a step-by-step action plan that will get her to her goal.

If there is still no improvement over time, just as with your other situation, there will need to be consequences. Not everyone is cut out for sales and it won’t serve you to belabor things. If that is the case, the faster everyone comes to terms with a mismatch, the better off everyone will be.

Now. Let’s talk about the fact that your boss offers neither direction nor support, just a “hard time.” That isn’t a shocker, but it does mean you are probably on your own. If you are like most managers, you were promoted because you were an amazing salesperson, not because you demonstrated skill at managing people. The sad and kind of scary fact is that most managers are in their jobs for ten years before they get any kind of training. You sound like you have great instincts, but why learn by trial and error if you really don’t have to? There is no shortage of brilliant advice out there for new managers. Of course, I think ours is top notch, but I wouldn’t want to limit you. I guarantee your organization has some kind of training available. Attend. Pay attention. Take notes. Formulate intentions and practice new skills.

You are probably thinking you don’t have time. You won’t remember the opportunity cost of the time you took, and you will remember three or four tidbits that will change your work life. Your people will thank you and you won’t regret it. I promise.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.


About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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