Why is it sometimes hard to hire for Sales roles?

Let’s face it, all roles can be hard to fill in. They all have their challenges. However, as someone who has spent a large part of their lives doing sales jobs, hear us out. From our point of view.

Like all people we Sales guys are also people and no we are not special (or rather we are no more special than anyone else). However, we may have special skills that are suited to Sales related profiles  – like able to understand our products and services, potential customers, the market and able to articulate reasonably well – and of course, having the “closing” instinct. So, ultimately, hiring comes back to the question…

“What type of a person do I want?”

Note: Apart from the required skills. We will not go there today.

Now, this question directly reflects on

  • the type of person you are
  • the type of company yours is, and
  • the culture that you would like to harbour

Let’s look at these 3 points separately.

  1. Type of person

Personality compatibility is slightly more important in startups and smaller companies where everyone knows everyone. Especially, when you are the person who will be working closely with the new hire. A problem we see here often is hiring totally opposite personalities (other than job necessary skills) and being unable to work with counter cultures. This is totally fine (if you ask me). However, if you are going to be slightly (or largely) inflexible in certain things you GOT TO MAKE SURE that you talk about these points beforehand as well. A couple of examples to illustrate this point:

  • A CEO (or manager) who has defined everything on how things work would be hard pressed to work with a person who wants to change things around (maybe the process, or working style, or product future, could be many things). In this case all you would need is someone with the necessary skills and willing to follow in the predefined steps.
  • If you have defined most things and looking for someone to implement with their own additions, then you may be hard pressed to work with someone who follows but is unable to do anything new.
  • If things are still vague (in terms of perfect positioning, pricing, and so on) and you hire someone to do the thinking for you (with or without your help), be prepared to work with people who will consistently tell you what to do. And would want to make changes to so many things that you hadn’t thought of or you don’t agree with.
  • And so on…

2. Type of Company

The “type” of company you are will attract people who would like to be part of your “type” of company. For e.g.,

  • Startups generally attract people who want to make a direct impact in the growth and direction of the company. These are not people who would generally just “follow”.
  • And if you are a large company you will generally attract people who want “steady jobs” and may or may not want to contribute directly to the inner workings of the company.

So, it becomes obvious that how you portray and advertise about your company will make a HUGE difference. However, if you look for startup ready people and expect them to follow what you want them to do “exactly”… Ummm… you know what’s gonna happen, right?

3. Culture

Coming to culture, this sounds similar to “what type of company” you are, but not the same. Culture is related to the behaviour, mannerisms, etc of the people in your company – including you. This also becomes very important to inform potential hires in advance and is best to make sure there is some sort of compatibility. This could be as simple as – “in our company we would like all of us to work strictly from 9 AM to 6 PM”  or “breaks are strictly scheduled” and so on or as complicated as “we would like everyone to be friendly with each other professionally, and take all our breaks together and we do not hide anything work related” etc.

Culture is complicated. However, it may make sense for you to clearly articulate (and keep up) how you would like your company’s culture to be.

In the end my advise to anyone would be…hire for your and your company’s requirements and personalities and cultures rather than just skills. Else, be really flexible and focused on objectives rather than behaviour. Be open, discourage people who secretly come and gossip about everyone around them (they are highly opinionated and only care about their own skin), give credit where it is due (always and never waver) and be respectful when being a critic (with positivity) and so on.

Good luck! ๐Ÿ˜€

This is a two-piece article written by two different people. In general we believe in the same and in some ways different things as well.  Second part of the article below from a sales guy’s perspective.


Not knowing how to hire Sales teams is a common conundrum found amongst a lot of hiring managers. Particularly who did not have an active involvement in sales facing roles or have worked with one particular organisation their entire lives (it could potentially skew your opinion sometimes).

Poor implementation of GTM strategies are a major road block for great products. This gap needs bridging.

Let’s chalk out some common differences between Sales guys and Tech guys as I see it.

  1. Sales guys are adept to handle randomness while techies are more planned in nature.
    • We all face random outcomes in all walks of lives. There is a differentiator here. Techies are methodical in nature while sales guys are spontaneous. Techies aim at exception handling while sales is more focused on objection handling. Spontaneousness helps with the latter.
    • Let’s understand why with an example. When a techie prepares for an interview, she looks at the company. The website, products, performance on Glassdoor. Check out their tech stack on stackshare. As a sales person though, apart from checking Glassdoor, I have more steps I follow. An overview of the company’s website is good to have. However, we strike gold through their content on blogposts and social media. The most critical insight is the interviewer’s LinkedIn.
    • We do this for a very simple reason. It helps identify their personality. Personal biases and company’s content tells us about their thought process and roadmap. We use the same approach when we are engaging with a new prospect. Sales guys are more focused on the psychology of people than what meets the eye. Which leads me to my next point.
  2. We look beyond the offer letter.
    • This is controversial, but hear me out. We’re generally thrown a bone of performance based incentives and variables. This is standard industry practice. After chewing dust a couple of times, I can come to a conclusion. Money is a by-product of many moving parts. To be handled simultaneously.
    • We shift our focus to the product/service the company offers. We do that by checking customer feedback beyond the testimonials page. Competition analysis and product positioning are critical. These factors help us determine the odds of hitting the number.
    • So the next time you see a no show on an accepted offer letter, it’s time for a little introspection.
  3. Micromanagement is going to drive us out of the company.
    • Most people hate to be micro-managed. And most people also end up micro-managing others. It’s a human tendency driven by arrogance. There’s a voice in our head that keeps going I can do this better than her/him. Time to shut that voice up by putting a conscious effort.
    • As sales people, seeking approval is our second nature. Our performance depends on our mental health. Being judged all the time for making mistakes affects our mental health . Let’s understand this better with an example from football. The striker might’ve had 10 shots on target, but one missed penalty is going to haunt them for a long long time. Sales guys are only doing their job when a deal closes, but there is a proper interrogation when they lose a deal. I get it, these are attempts to revive a deal, improve the process/product bla bla.. and needs attention.
    • Carry out similar interrogations on a win. It might help improve the sales person’s performance. and the entire team’s too.
  4. Sales guys are going to act Stupid.
    • There is a thin line between bravery and stupidity You will find most sales guys deep in the stupid side. Come on, how else are you going to jump on a call with a complete stranger? Being friendly, start building a bond and gather insights about their company.
    • The tea/smoke breaks are going to be full of emotional rants rather than calm observations. It helps us maintain our sanity while talking to prospects.
    • We are going to obfuscate a lot. A sales pipeline is a mine-field. One wrong move and boom, we’re heading to the interrogation room. So every time we hit a wall, we’ll detour and try to trace back to our original trajectory. We are going to get caught most of the times. But we will keep reminding them to solve the larger problem, which the prospects also agree with.
    • You are going to find us everywhere, chilling with every team. Sales teams should discuss strategies and help their teammates hit their quota, right? Cut us some slack please. After spending days on calls and nights in terror, we don’t want to use this time to talk shop.

It’s a tough job like most other functions in a company. There’s a bunch of expectations from us. Driving revenue into the company, maintaining the brand image and stuff like that. Would a little empathy be too much to ask for?

P.S. Please read with a pinch of salt. There are always exceptions.

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