It is hard being a sales leader

Off late, I have run into a lot of highly stressed out sales leaders – at work, at airport lounges and at assorted other places including at customer sites. It is real hard being a successful sales leader.

In most jobs, if you do well in current role – you are generally setting up yourself well for your next higher role. But I doubt that is true in sales . Many of the best sales people I know made mediocre sales leaders when they got promoted. And some of the top notch sales leaders I know today were just about average sales people in their prior life. While such things do happen in other job functions too – I have a strong feeling that sales kind of bucks the general trend.

To begin with – many organizations do not start grooming sales people into sales leaders early. They like sales people to be laser focused on quota and will not recognize the other skills they will need as they move up the chain. And compared to a developer or a finance person or something at the same level, the remuneration for a young sales person doing well in their job is pretty high. So the behavior patterns needed for narrow objectives of the organizations are rather strongly reinforced early in their life. I think this is also the reason why several successful sales people like to continue as individual contributors and not get promoted to leaders.

A developer who grows into an architect or development manager or a VP of development is not expected to code at that point. But  sales leaders have to occasionally take matters into their own hands and sell directly. That is not really the hard part – the real hard part is to resist the temptation of taking matters to their own hands too often in sales situation.

If you have an A team for sales, the chances are that they won’t sit patiently through a cadence call and take instructions and report status in a structured way. And many sales leaders are not very good at sales operations. It never ceases to amaze me on how long it takes for some of them to understand the need for good operations and hire a good COO . Good ops leaders are worth their weight in gold -once you find them, keep them close. However, you always need to watch out for where you draw the line on ops efficiency. End of the day – you need the sales to happen and reporting is an after effect. Don’t let controls screw up front line sales . It is a very hard balance to strike – especially for those sales leaders who totally hated controls when they were doing front line sales.

In  a big sale I did at IBM as an account partner – my deal strategy required a senior partner to come in as a “closer” to get the deal signed. I did not really need that given I had a great relation with the customer CIO and his staff, and we had done a good job in understanding each other. However, I was so tuned to having a closer in such big deals. Thankfully, when I pinged my boss to show up – he said ” this one is on you buddy, call me when you have it signed”. Words cannot express the sense of elation that balanced out my sense of panic. He was a senior guy and totally saw that the defined process is only a guideline – and I needed help in seeing that. Now, this is my guiding principle in any situation – sales or otherwise. Do not use “process” as a rigid mandate – use it only as a rough guiding principle. As long as you have the trust of the manager that you are ethical and responsible – you will have the support you need.

What is the most important asset for sales people? That would be the relations they have nurtured with customer contacts. This is also why a lot of Sales Force Automation systems get implemented by companies who want to keep that data. This is also the reason why most sales people do not care to put the information in these systems. It is hard to get the sales people to share those relationships. However, as a sales leader – your very success is dependent on your ability to share your relationships with your team so that they can go make the sale. This is the most counter intuitive thing for most sales leaders in their first leadership appointments.

As the size of the organization increases, there will be a number of over lay sales roles created to make sure there is sufficient attention on all important stuff. Too often – this results in lack of clarity and vast majority of leaders just become “checkers of the double checkers”. Eventually, everyone and no one is responsible for the actual sales or the lack there of. Over lay functions cannot be avoided when a company has a large number of products and vast geographic coverage for markets they serve. I have seen upwards of ten people “managing the spreadsheet” and “checking on status” for same sale in some situations in past life. It is a rough life to be at the receiving end of that mess. And this is only flavors of sales people. On top of that – there will be general managers of products, HR and assorted others who will need to be kept informed too. They cannot be blamed for asking “who is the customer here ? you folks or the company that actually is paying us?”.

Finally, there is the love-hate relationships with channels. Nothing demonstrates misaligned goals more than the goals set for direct sales and channel. Everyone loves channel up the chain – except the people held directly responsible for the quota for the same business. If you put direct sales and channel in conflict via goals and processes – you have no one else to blame for the resulting chaos. It is a hard lesson – with very few right answers. These are strategic goals to be set at the CEO level and lower level goals should be aligned perfectly to that strategy.

Despite all these things stressing them out day in and day out, all my buddies in sales leadership roles still keep their heads up and motivate (ok ok, occasionally even manipulate) their teams to achieve the big targets. I hope they have a less stressful 2014.




Published by Vijay Vijayasankar

Son/Husband/Dad/Dog Lover/Engineer. Follow me on twitter @vijayasankarv. These blogs are all my personal views - and not in way related to my employer or past employers

2 thoughts on “It is hard being a sales leader

  1. Hey Vijay,

    It is well known that good sales people often make bad managers. Their single-minded focus, results-driven approach and shunning of administrative process mean that not only do they not have the attributes for leadership but the best sales person no longer hitting the road as much.

    I would argue that whilst relationships are very important, relevance is perhaps becoming the number one asset. You need to be relevant, understand your customers’ business and deliver outcomes – and people who can do this will build new relationships very quickly.

    As you say, the best sales leaders retain high-level relationships and relevance at customers, whilst herding the cats that are excellent account reps, and delivering the operational efficiency that delivers results on time. That is an enormous amount to ask of any person.



  2. This is a very timely article for me, nailed it on the head. After working in Ops with Sales for five years I’m starting to consider next steps and am considering transitioning to Sales. The thing that scares me? As a planner and process lover I hate that most Sales people I know are driven by the current quota-focused on the battle instead of the war and that delivery is an afterthought.

    Given me something to think about Vijay.


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