Sales head is a challenging position to hire for. We see a lot of churns in this role and in several cases quite quickly. 

Founders often debate whether it’s better to groom a sales head internally or hire from outside. Should one look for someone who’s built or grown a similar size team or one who’s managed a large team in their previous role? Do they need to be from the same industry or should they have experience selling similar products?

These are all valid considerations. Coupled with the fact that there aren’t many suitable profiles available, makes this a particularly challenging role to hire for. Hence once you find a suitable profile it’s important to evaluate them thoroughly.

The following list of questions is by no means exhaustive. Nor do they have a unique correct answer. However they will help you understand how the candidate thinks and you might pick up something in the conversation which might be a dealmaker/ breaker for you and your team.

What is the toughest client escalation you’ve had to deal with?

Sales heads frequently have to deal with escalations. This requires them to handle multiple stakeholders: clients, salesperson and her immediate supervisor, other teams like finance, compliance etc. Maneuvering through an escalation requires astute judgment and their answer will give you a good sense of how the candidate thinks through vis a vis customers, sales team and the larger organization goals.

What difference have you seen in a good vs an average team leader in the previous role?

Sales leaders generally are pretty good at evaluating frontline sales people. At the very least, they will have a good answer to the question. 

When it comes to team leaders ( Area sales managers, group sales managers etc.) things get complicated. A sales leader has to look not just at target achievement & activity numbers, but also at training capabilities, spread of performance, ability to motivate etc.

This question will help you understand how the candidate manages his team, evaluates them and if he’s able to identify gaps and opportunities. 

A salesperson has been chasing a deal for sometime. Another salesperson comes up to you and mentions that he knows someone and can close the deal. How do you deal with such a situation

Conflict is innate to all sales teams. Be it for leads, territories, discounts etc. you will have people in your team staking claim to those. A good sales leader needs to be able to resolve these quickly and move forward taking the team along. 

Resolving such cases is usually a balance between achieving sales numbers and maintaining fairness. You’d want someone who thinks similar to you in such situations though extreme on either side is usually problematic in the long run.

What would you ‘not’ like to see in an organization that you are joining?

Sales heads are important members of your leadership team. They are also the one of the primary drivers of your initiatives. Having a working relationship with your sales head is critical for early & mid stage startups. 

Beyond the basics like integrity, mutual respect which every one expects, this conversation helps you understand the candidates views on things like dealing with uncertainty, managing product changes, speed of execution etc. which are critical to an early stage business.

What is the most critical feedback you’ve received from your team?

People often ask candidates for previous feedback from superiors. In this role however, feedback from your team both immediate reportees as well as the larger team is often more critical. Irrespective of whether there was a formal process for collecting this feedback, this will give you a sense of how connected the candidate was to her team, whether they had a pulse of what was happening in their sales team and if they are open to feedback and course correction.

What is a red flag for you when you are interviewing candidates?

Hiring is an important part of a sales head’s role. In the course of your conversation, you’ll explore several things related to hiring. One important thing you must check is what are the red flags for the candidate while interviewing a potential candidate. An experienced sales leader will have many insights to share on this based on his experience. This will allow you to understand the depth of her experience as well as compare notes on your  

Once again, there isn’t a ‘correct’ answer to any of these questions. It is also unlikely that you’ll like all the answers that a candidate gives. This does not mean that the candidate isn’t a good hire. These questions will however give a fair idea of what you are getting into right upfront.