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What are the five rules for conducting tough sales management conversations?

I'm not going to sugarcoat this. As someone who leads salespeople (or leads others, who lead sales people), tough conversations may be the most difficult part of your role, and involve heavy lifting. These truths will not go away as you advance in your career.

At times, an employee will test your authority. Some salespeople will even test the boundaries of what is acceptable. Unfortunately, it will be up to you to correct unprofessional or inappropriate behavior.

There will be moments when you must develop people. This means pointing out how they need to modify their behavior, improve their performance, or find ways to contribute to the team… beyond reaching their sales quotas.

And part of your responsibility to the business (meaning your employer) is that you do not avoid these difficult conversations. You must conduct them in a timely manner, and ensure that they are productive for both sides. Meaning you, and the affected employee.

While this is not happy talk... it's part and parcel of your role.

Tough Sales Management Conversations must be faced, embraced, and COMPLETED. Here’s WHY:

  1. lack of performance, behavior inconsistent with stated expectations and negative influence on the team impede your ability to make quota, keep churn low, and avoid drama. (As stated in: The Sales Management Triangle)

  2. the tone and tempo that your team operates under can be vulnerable to attack from the outside (competition, recruiting of your people, shifts in the market). You can not afford for the team to be brought down (or negatively impacted) from the inside, by having someone act out, act up, or act inappropriately.

Now, here’s HOW:

  1. Focus on Facts, and be Firm

  2. Avoid Tangents

  3. Remove Unnecessary Words (be clear, succinct, and to the point)

  4. Deflect Hypotheticals


Tough conversations are heavy lifting for leaders. People who want to continue to BE leaders need to stretch, take their vitamins, and (to continue the metaphor) lift with their legs.

Be smart. Prepare. Understand that you may not be able to get in and out of these conversation comfortably, so:

  • Triple - check your facts!

  • Don’t go into a tough conversation relying solely on your gut, or hearsay. Bring the reason for the meeting, and have it verified as factual in advance.

  • Be Clear

  • Avoid “I think you…”, or “I don’t like when you…” This is a professional encounter and discussion, not to be left to chance. Your opinion may be relevant, however whenever you begin with “I” focus the conversation on yourself, or your feelings and opinions, none of which are relevant. What IS relevant is the misstep or incorrect act, or behavior of the person you are counselling, and your approach must focus on:

  • The specifics of the issue

  • HOW it is inconsistent with company policy

  • What is Inappropriate

  • SPECIFICS of what was Out of line with the expectation of the ROLE.

  • Practice what you will say IN ADVANCE. Plan (and rehearse!) clear, uninterrupted, “Ummm” - free language. (When you use fillers such as “Ummm”, “Uhhh.”or “You know”... you appear to lack conviction. You seem uncomfortable.) You MAY actually BE uncomfortable, but you cannot allow that to seep into the environment and tone of this conversation.

  • Free time on your calendar for 7 minutes before, and 5 minutes after these meetings

  • BEFORE your meeting, You need to attain calm and clarity. Calm to brace for an uncomfortable few minutes, Clarity to ensure that you are not distracted.

  • AFTER your meeting, clearly and accurately document what transpired.

  • Plan to cover no more than three key concepts, incidences, or infractions.

  • Each incident, concept or infraction must be followed by a recommended approach to remedy or discontinue said action or infraction. (Sounds like an attorney wrote that… and it SHOULD. This is not to be taken lightly.)

Ok, let’s get human here for a moment. No one likes uncomfortable conversations, least of all the person being brought to task. (Or, called on the carpet. Or Called out…) You want it to be over much as the person on the other side of this does.


Not all Tough Conversations are initiated solely because the Sales Person has done something wrong. You will change expectations and measurements. You may reassign a sales person's territory or change their market focus. We will expand on these instances in a future blog post.

So, to create your preferred future condition with as little pain (and drag on your energy) as possible, keep two things in mind:

  1. Sales People will go out of their way to convince you that their actions and choices are justified and righteous.

  2. Sales People, unfortunately, sometimes need correction and guidance.

Of the folks who NEED correction and guidance, only some will actually take what you say to heart and change how they think, act or interact. Do not take this personally. YOU are not managing YOU. The fact that you would never act this way is immaterial.

In one of my books: “The Ultimate Sales Managers’ Guide”, I share the Hobson Principle, which states: “You will never find someone to work FOR YOU… who will work LIKE you.”

The approach people take to their work, their “at - work” relationships, and / or their ability to keep personal issues out of the workday conversation - all vary. I can not count the different ways people can (and will!) act out in the working world.

  • Focus on Facts, and be Firm

Unapologetic? Yeah, that works, as long as you understand that unapologetic does not equate to being overpowering or rude. It means that you deal in facts. Being Firm means that you do not get caught up in emotional indicators, outbursts or your own potential desire to “clear the air”. Remember the old adage: “You can be RIGHT… or you can get what you want.” What you want is for someone who works for you to adjust their behavior, and work towards being a better contributor going forward.

  • Avoid Tangents

The topic is this person’s behavior, not the temperature of the food that was catered yesterday. FOCUS.

  • Remove Unnecessary Words

This is great editing advice, and editing is necessary in advance of Tough Sales Management conversations, (yes, there will be more than ONE) and may be needed afterward. Clarity is your friend, tool, and watchword. See the first point in this list : FFF! Now, read it again.

  • This is NOT the time for hypotheticals, nor is it the time for you to be cornered by the person you are counselling. (Example: The person you meet with says something like: “So, if I go and make these changes, does that mean that you will tell So and So to stop doing ‘x’?”) Your response: “We are here to address specific actions and behaviors that have come to my attention, that are important for you to correct in order for this to work.”


The word DOCUMENT, in this instance… is a VERB. Do it. Document what you hear. Alert the employee that they will receive a copy of your notes. As will HR. This is a Tough Conversation, remember? Not a casual cup of coffee. This is serious, and should be handled seriously, with professionalism, tact, poise, and compassion. And directness.

Tough sales management conversations are:

  • Heavy lifting

  • Part of your role as someone who leads sales people, OR if you have Sales Leaders who report to you!

You can do this. And you will have to, more than you would like. Welcome to the profession known as Sales Leadership.

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