Handling The Difficult Sales Rep

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John Care


Apr 3, 2020


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We’ve all worked with one of those reps. One of those sales reps who makes the life of the Sales Engineer a complete and absolute misery. Lately my mailbag has been filled with questions about dealing with the ‘difficult” rep.

We’re not speaking about the professional, but demanding, sales rep – we’re speaking here about the rep, who through ignorance, inexperience or intent just kills the concept of a sales team.

Here are a dozen tips and techniques that may help you to improve both your relationship and working conditions with the difficult sales person in your life. Apply your own corporate, country and cultural filters to each.

1. Focus On Outcomes. One of the primary issues around selling is the establishment of control in the sales cycle. In most cases we examine that as it relates to the customer, yet it also influences how we relate to the sales rep. At its simplest, when discussing a sales call with the rep, you can either ask “what do you need me to do?” which immediately places you as a follower, or you can ask “what needs to happen as a result of this sales call?” That places you in charge of your part of the call by focusing on the customer outcome. Try it – it’s a simple change leading to big results.

2. Leverage the Sales Process. The CRM system you use can be your biggest friend. That is because it is no longer you asking for something, it is the sales process, and by extension – your boss and his boss. Admittedly there are few reps that seriously follow a process with all the steps and paperwork – yet it is leverage for asking for anything as simple as an opportunity id to something as complex as POC success criteria. It also supports the “always prioritize the forecasted deals” strategy.

3. Reverse Psychology. Acknowledge that the rep is better at pure “selling” than you are. This shouldn’t be a tough admission in most cases. The line of argument goes something like this “listen – you’re the rep, you’re supposed to be better at selling than I am. So when we disagree on something I expect you to sell me on it – but that doesn’t mean you’re always right.”

4. “Ask A Rep”. In some tough interpersonal situations, I’ve received better advice from another rep than I have from my manager or my peers. No-one can truly climb into the mind of a sales rep like another sales rep. An important distinction is that you are asking another rep for advice, not for intervention.

5. Use Your Materials. If you are working with a rep who doesn’t want to detail something like success criteria for a Proof Of Concept or start a presentation with a “What We Heard From You” slide/discussion (both common sources of conflict!) you can still create those slides or documents. Just use them for your own reference – who knows .. maybe the customer will ask for a copy of them? If enough customers respond positively you can use that fact to change things.

6. Shake It Up. Routinely make changes to your presentation or demo materials. Throw in a grabber slide at the start of your section. Simplify your slides; change the flow of your demo. Experiment and adjust based upon customer feedback. Keep the sales rep on his/her toes. This is a great way to have a rep pay attention instead of doing the email smartphone dance at the back of the room.

7. The Hit List. One of my favorite questions of a rep is “what is the single most important point we (not you) need to make in this customer interaction?” Sometimes you will get a single point answer; more often you will get a shopping list or a complete blank. Your most important task is then to accomplish the communication and understanding of that Very Important Point by whatever means possible. Your decision. If you cede responsibility for all strategy to the rep then you are getting what you deserve.

8. Proper Prior Preparation. Inadequate preparation before calls is one of the major sources of SE-rep conflict. It’s the reason SE’s commonly grade 40%+ of sales calls as “poor”. My experience is that asking reps to complete forms or fill out some computerized profile is not the way to go. Offer to have a conversation with the rep and you fill out the required information – making sure you ask many customer-related questions that she cannot answer. Focus on customer environment and requirements rather than classic sales questions like budget and approvals. Save those for a few months deeper into a troubled relationship. Challenging the rep on his “territory” is not the way to get started.

9. The Sales Debrief. The T3-B3-N3 methodology for sales call debriefs. That’s “what are the Top 3 things I did today you really liked? What are the Bottom 3 things I did, and what are Next 3 Things I should consider for future calls?” Take that feedback and use it to your benefit, selecting those items which align best to your view of the relationship. Then hold your breath – as about 20% of reps will ask for the same feedback from you.

10. The Conversation. Regardless of which of the Three I’s you are experiencing from the rep – Inexperience, Incompetence or malicious Intent you need to have a blunt conversation with the sales rep about the circumstances of your working relationship. Many reps may not realize the impact their behavior has upon you. Some may not care, but you still owe it to them to have the conversation. Note there is a strong correlation between poor rep skills and poor quota achievement – if a rep is at 50% of quota their behavior is to blame everyone but themselves. Get it on the table!

11. Negotiation. Despite the reputation of discounting everything, most reps are skilled at negotiation. It is their job to get the most for the least. The poor reps translate that into getting the most work from you for the least preparation and pre-work from them. That means always ask for more time, more customer discovery, and more rehearsal than you really need – as it will always be negotiated down.

12. Focus on Outcomes II. Outcome-based selling is the route to most successful Rep-SE relationships. It allows each of you to focus on those areas where you are the true professional in the team. There have been a few moments in my career when I’ve handed my laptop to the rep in the parking lot after a sales call and asked if he wanted to do the demo next time just to make my point. It’s worked the other way – there were times I asked about timing or budget when I shouldn’t have.


Most sales people – like most Sales Engineers – are professionals and take pride in their accomplishments. Most sales people – unlike most Sales Engineers – are heavily driven type-A personalities who like to be in control of everything. That is the nature of the relationship. Like most relationships, you need to put some effort into them. Some of these techniques may be viewed as a little manipulative, or else they may enable you to find a way around a “don’t do that!” so remember that one of the key skills in sales is being able to sell around a "No". You must do that internally, as well as externally with customers. Have confidence in your skills and capabilities and focus on the outcomes of the sales calls rather than on the details when preparing with the sales rep. Finally – look for opportunities to work with the rep in situations outside of direct sales; for example when conducting a pipeline review, or better still, when talking about a recent win!

"Never tell people how to do things. Tell them what to do and they will surprise you with their ingenuity” - General George Patton Jr.

John spent numerous years building world-class Sales Engineering organizations at companies such as Oracle, Sybase, Vantive, Clarify, HP, Business Objects and most recently Vice President and Area Manager of Pre-Sales at CA. He has a BSc with Honors in Chemical Engineering from Imperial College, London and is a former contributing member of the MBA Advisory Council for the Fox Business School of Temple University, Philadelphia. He has been published in such diverse media as CIO, InfoWorld, Touchline and The Wall Street Journal.

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