Sales bosses, now that’s a tough crowd. They’re driven, persistent, and often relentless. Always pushing, always in your face, and rarely easy to convince. Why? Because they’re expert negotiators. Trained to challenge, question, and close. So, when you need to have a difficult conversation with one, it can feel like stepping into the lion’s den.
But what exactly makes a conversation difficult? It really depends. For some, it’s confronting performance issues. For others, it’s saying “no” or challenging unrealistic expectations. A conversation becomes difficult the moment it feels uncomfortable, risky, or emotionally charged for anyone involved.
Sometimes, we see it coming; a calendar invite titled “Quick Chat?” is all the warnings we get. Other times, it hits us out of nowhere. More often than not, we find ourselves playing both roles: the one raising the issue and the one receiving the blow.
In my experience, I’ve had my fair share of tough conversations at work, especially with sales bosses. In fact, I’ve had one in almost every job I’ve held. Most of the time, I was the one who initiated them. I can’t say I always “won” those conversations, but I’m glad I had the courage to speak up. And honestly, that’s half the battle.
A Few Difficult Conversations with bosses I can’t forget!!!
Pressure vs. Reality: A Lesson in Leading Up
I remember one particular job where I’d just moved to a new country to lead sales, and so had my boss. It was like the classic case of two blind men trying to find their way, except one of them had the power and knew exactly how to apply pressure.
He was one of those sales bosses who believed pressure alone could move the needle. And let’s be honest, they’re not rare. You’ll find plenty of leaders who think urgency and stress are the ultimate tools to drive results. The problem? That approach doesn’t always work, especially in a tough market.
At some point, I realized the only way to deal with him was to create a bit of counterpressure. I started taking him along to meetings with some of our most difficult customers. No sugarcoating, no filters, just a front-row seat to what I was dealing with. It worked.
After a few of those meetings, we sat down for an honest conversation. For the first time, he saw the ground reality. The market was tougher than he expected, and he finally understood that pressure alone wasn’t going to cut it. That conversation shifted things. We aligned on a more realistic and strategic approach, and from there, things improved.
When Loyalty Clouds Logic
Sales bosses often thrive on relationships. It’s one of the key reasons for their success, but also, sometimes, their biggest blind spot. When relationships run deep, they can overshadow logic, fairness, and even performance. I once worked for an organization where everything was going great. I was growing the business, hitting targets, and feeling like I was making a real impact until I had that conversation.
The issue was sensitive but important: one of the boss’s close confidants, or “buddies” as we used to call them, was actively slandering other team members. It was toxic and hurting team morale. When I brought this up, my boss didn’t want to hear it. At first, he ignored it. Then, when I took a firmer stand, things shifted, but not in my favor.
In the end, I became the collateral damage. Despite my performance and contributions, the loyalty he had to his buddy overrode everything else. I had to part ways, not because of my results, but because I stood up for what was right. It was a tough lesson, but one that reminded me how complex and emotional workplace dynamics can be, especially when relationships are involved.
The Paradox of Being Close to the Ground
One thing I’ve always admired about sales bosses is their strong last-mile connection. They’re not just sitting in ivory towers; they know the customers, they speak the language of the field, and they often have relationships right down to the sales executives working the floor. They don’t usually need extra data or reports to understand what’s happening; they live in reality.
But despite that strength, I’ve often found inconsistencies in how they judged performance. At times, they’d form strong opinions based on a single incident. Other times, they’d delay critical decisions indefinitely, even when evidence was piling up.
This was a recurring theme in my career, one I’ve discussed with nearly every sales boss I’ve had. I would bring up these inconsistencies, hoping to understand their reasoning. But while they always had a contextual explanation ready, I found myself struggling to make sense of the logic. They were so convinced by their gut, and their experience, their version of the story that I rarely, if ever, “won” those conversations.
Still, they taught me an important lesson: proximity to reality doesn’t always equal objectivity. Sometimes, being too close can cloud perspective just as much as being too far away.
How to Have the Difficult Conversations with Your Boss!
The Venue
I preferred to take my bosses outside of their office, say a conference room, so that it’s on neutral turf. Bosses, especially sales bosses, are a different breed when they sit in their chair of power. Alternatively, whenever I felt a more informal atmosphere would be appropriate, I took them to the cafeteria or a coffee shop to have this discussion. But, I should admit, not all the time do I get a favorable outcome in spite of the neutral venue.
Clarity & Composure
I have walked into conversations when I was high on emotions, and when I haven’t had much clarity in my head. In some of the instances, the lack of composure muddled my emotions and backfired on me. Confidence is a great ally; Whenever I was confident, I found my boss to be on the back foot and I came out a winner. But the sheer ability of a sales boss and the power seat they occupy can win over any confidence you wear.
Resolution & Relationship Orientation
All difficult conversations are never complete without a resolution. The ulterior motive of having a conversation or talk is to come to a resolution of an issue that is bothering. The talk may have conflicts, but you are not there to win a fight of words but to negotiate. I have been lucky that many of my bosses focused on the resolution rather than just my emotions or theirs in the conversation.
I have learned that having difficult conversations does not cost you relationships. In fact, it builds a new bond. Many of my Bosses knew how to make me comfortable after every such conversation.
Speaking Up, Growing Up
When I look back, I feel many of those arguments did not lead to a favorable verdict as far as I was concerned. But it allowed me to let my heart out rather than simmer within. These difficult conversations have helped me become a better salesperson and maybe a superior manager over the last decade.
Having an open and honest dialogue with your manager can be intimidating, especially if you don’t have an established relationship. This has been my situation most of the time; I have shot from the hip, whereas wisdom would have suggested waiting.
I continue to find myself in difficult conversations with my boss. And as luck would have it, I continue to get bosses who are brilliant salespeople. With age on my side now, I tell myself, “Be brave when you have to, but don’t get carried away and become Foolish.”
