Difficult Conversations with Sales Bosses

Sales Bosses are tough nuts to crack, They are always pushy and on your face all the time. They are also difficult to convince as they are trained and experienced negotiators themselves.

What conversations do you find difficult with this genre of bosses? This answer might be different for each of us, but we’ve all experienced…difficult conversations. And what is a difficult conversation?… Well, if it’s challenging for at least one of the people involved, then it’s difficult.…Some difficult conversations are planned, and we know it is coming.…And many are spontaneous and catch us by surprise…Sometimes you might be the initiator of difficult conversations, either…delivering bad news or confronting someone about a problem.…And most of us have been on the receiving end too.…as we up against people who have power and sometimes superior skills.

I have been in many or can I say in all my Jobs I had Difficult conversations with my Boss. Most of them initiated by me, I wouldn’t have won most of them, But, Happy that I asked those questions.



    I was in a new country to lead sales and so was my boss to the role and the market. It was like two blind men except that one of them knew how to pressure the other guy and was in power. Sales bosses who get the work done only by building pressure are common to find. The only way to deal with them was to build counter pressure. I ended up taking him to some difficult customers for him to realise that it was a tough market. We then had an honest conversation and he was convinced that we needed a different strategy to build sales.
    Sales Bosses are also highly relationship driven that they can get blind to anything rational. Their success also comes from relationships and also makes them break few others due to the loyalty they breed within. Once I was working for an organisation where I successfully grew business and was performing really well. The times were really good till the time I had a Difficult conversation with the Boss. One of his buddies, as we used to call him, was indulging in slandering other colleagues. When this was brought to his notice he turned a blind initially until I took a tough stance. I became the collateral damage and had to part ways as their relationship prevailed over any professional context.
    Sales bosses have a great last mile connect, They tend to have connections with customers, sales executives at the bottom of the pyramid. In a nutshell, they are always close to reality and need no extra information related to situations and people. However, I found some inconsistencies in their judgement on performances. Sometimes they would make calls on just one instance and many a time they would wait forever while taking calls on performances of people. This was a conversation I must have had almost with every boss of mine. I felt they found it easy to explain in the context and myself difficult to comprehend their inconsistencies. But, they would be so convinced that I never won any of those arguments.



    I preferred to take my bosses outside of their office say a conference room so that it’s in a 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 times I got a favourable outcome in spite of the neutral venue.
    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 backfoot 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.
    All difficult conversations are never complete without a resolution. The ulterior motive of having a conversation or talk is to come to a result of an issue which 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 focussed on the resolution than just my emotions or theirs in the conversation.

    I have learnt 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.

    When I look back I feel many of those arguments did not lead to a favourable verdict as far as I was concerned. But, it allowed me to let my heart out 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 times, 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”


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