How to Have Difficult Conversations with Your Sales Reps

By Tim Rockwell

Difficult conversations are part of any sales leader’s job. In fact, your ability to successfully execute them can either make or break your effectiveness as a leader.

As a sales manager, you need to have confidence that you are actually doing your team a great service by having tough conversations with them. Can it be awkward and maybe uncomfortable at times? Yes. On the other hand, you’re also showing them that you care enough to invest the effort to help them grow and learn.

Accountability is a gift to your salespeople. We are often blind to our own shortcomings, but most of us have the desire to grow. Whenever you tactfully and thoughtfully communicate opportunities for your salespeople to improve and grow, you can actually change their lives.

Of course, one clear risk when giving constructive criticism is that your efforts could fall on deaf ears. To help your team truly receive and grow from your constructive criticism, you need to build trust. Employees need to know that you are for them, you fight for them, and you genuinely believe the best in them.

Personally, I sit down every one of my employees on day one and tell them that I am on their team and that I will be fiercely loyal to them. Words are cheap but, over time, I do my best to prove it to them. When the time comes to have a difficult conversation, it is always received much better because they know I have their best interest at heart.

Knowing the importance of having difficult conversations and keeping the challenges in mind, here are a few tangible steps to consider.


Before you initiate a hard conversation with someone, you should write down exactly what you want to communicate. Opener, meat, and conclusion. Write it all down. In the heat of an awkward or difficult situation, our mental capacity is often monopolized by our emotions instead of the substance of the issue. When you have notes, you won’t forget anything or regret something you communicated poorly.

Additionally, it can be therapeutic for you to write down how you feel about a certain topic. You may even omit or add something after seeing it on paper that you would have otherwise forgotten. Besides helping you remember what you want to say in the moment, the practice of writing things down will force you to give meaningful thought to an issue instead of just saying what comes to mind in the moment.

Of course, a difficult conversation will evolve outside of your planned words – but you can plan for that as well. Anticipate three different reactions from the person with whom you are having the conversation. Put yourself in that person’s shoes and begin to imagine how he or she might react. It will allow you to prepare for any rebuttal and it will also give you a perspective outside of your own.


Before you begin a tough conversation, ask the other person for permission to speak to an issue. Then, if given the green light, ask for permission to be direct. Although you may not “need” permission to speak to a subordinate, it is a strategy that makes them feel involved in the process and can help bring their walls down. Also, if you receive their blessing to be direct, it allows you to not have to dance around the issue and get right to the point.

Stephen Covey famously says: “Seek first to understand, then to be understood.” I’m convinced that the most successful and effective leaders in this world are the best questions askers. That theory carries over into having hard conversations. Don’t assume anything – especially the worst in a person. At all costs, try to avoid speaking to character deficiencies as that will initiate the fiercest of defense mechanisms. It’s amazing what you can learn and how much better you are received when you approach a hard conversation by asking questions first.   

Follow Up

There is a good chance that, at the end of a hard conversation, one or both parties will feel frustrated or hurt. That is okay. If the relationship is meaningful, whether professional or personal, it was worth it. End the conversation with a pleasantry like, “I really respect you and I appreciate the opportunity to work this out,” then schedule a time to follow up.

A follow-up conversation will allow the two parties to take some time to gather their thoughts and bring back anything they forgot to say or wish they would have said differently. This ultimate step may seem like overkill, but it is the final healing agent to prevent a feeling from festering into a grudge. The healthiest business relationships keep “short accounts” and move forward after successfully executing a hard conversation.

Tim Rockwell is national sales manager at Imperial Blades. A version of this post was published originally on LinkedIn.