How often have you found yourself enthusiastic about a new sales hire, only to discover that they weren't the right fit? The resulting costs, both in terms of financial investments and the expenditure of time and resources, can be substantial. Even worse, a significant portion of the year will be lost as a consequence.

How to Lessen the Chance of Wasting a Year on a Poor Sales Hire

How often have you found yourself enthusiastic about a new sales hire, only to discover that they weren't the right fit? The resulting costs, both in terms of financial investments and the expenditure of time and resources, can be substantial. Even worse, a significant portion of the year will be lost as a consequence.


  • Determine what you’re actually looking for (you’d be surprised how often this doesn’t happen)
  • Figure out what is non-negotiable
  • Create a framework for what good and great look like
  • Create questions that probe into these
  • Interviewing management has different nuances
  • Take 360o references to understand performance and behaviour

This is a recurring issue I hear often, especially when recruiting Account Executives. Making poor hiring decisions can be exorbitantly expensive, encompassing the recruitment process, onboarding, ramping up, offboarding, and then having to start the process all over again. This entire cycle can easily span a year and demand an extensive amount of energy.

Regrettably, when I speak with many founders, their approach to the interview process often appears rudimentary—consisting of a few conversations with different individuals within the organisation.

The conversations mostly being ‘gut feel’ or if they’re liked or feel like a culture fit. These Account Executives frequently serve as the initial point of contact for potential customers and play a pivotal role in generating revenue–the saying ‘you never get a second chance to make a first impression’ is very very true. Therefore it’s imperative to have a structured framework for conducting interviews to determine whether a candidate is a good fit for your company and your requirements.

There are lots of people I love having great conversations with. I have friends I can speak with for hours..but over my dead body would I entrust them with the responsibility of building, managing, and closing a sales pipeline. A compelling conversation alone does not suffice, so why is this the way most interviews are set up?  Some of the most successful sales representatives I've encountered have been natural introverts, and their ability to deeply comprehend and address customer challenges was their unique strength, distinct from superficial conversational skills.

The following discussion is tailored to sales but is applicable to all GTM functions.

First, it's crucial to consider the level of experience required. The criteria for assessing candidates and defining what constitutes "great" differ significantly between entry-level or transactional salespeople and senior enterprise representatives.

Second, intrinsic characteristics that are non-negotiable must be identified. These traits are essential for both success and cultural alignment. The presence or absence of these qualities is non-negotiable and are there or they aren’t, I can’t teach these. For me, there are four such characteristics:

  • Intelligence: This doesn't refer to the ability to solve a quadratic equation or degree from an Ivy League university. Rather, it means a natural curiosity, the capacity to explain intricate business concepts in terms of value, that they want to learn more about the market and their customers, emotional intelligence.
  • Integrity: I prefer not to micromanage, so it's vital that my team consistently acts in the best interests of the customer, the company, and their colleagues.
  • Hunger: Sales is a rollercoaster, and dedication in terms of time, effort, and thought is indispensable. It's about putting in the hard, often monotonous work that allows you to shine when it matters most.  We all know Christiano Ronaldo loves the game days, but what you don’t see that lets him appear effortless is the hard and boring graft–hours and hours and hours of training.
  • Coachability: I learn as much from my team as I hope they do from me. But they must be open to feedback, actively implement it, and continue to grow.

These are my personal criteria, of course there are others. I firmly believe that these qualities cannot be taught; candidates either have them or do not.

Third, determine the competencies necessary for success in the role. Some quick examples for sales include prospecting, pipeline building, deal orchestration, negotiation, business case development, effective communication with senior executives, forecasting, and handling adversity, among others.  These might be the same competencies for all levels, but what’s expected at a junior level is very different to that of someone more senior.

Now, the real hard work that must be undertaken before interviewing candidates is understanding what constitutes excellence and greatness in each of these competencies. This understanding will help you gauge whether your team member is "doing the right things." (see previous article here)

Fourth, formulate a set of questions that allow you to delve into each of these competencies and intrinsic characteristics. I particularly prefer "tell me about a time when" questions. Pay attention to the quality of their responses. Is their answer well-structured, or do they ramble on? While the STAR response framework (Situation, Task, Action, Result) is effective, not all candidates may be familiar with it. What concerns me more is when a senior candidate provides vague or unfocused responses; this is indicative of how they might interact with customers.

My favourite interview question is, "Tell me about a deal you lost." Every salesperson has encountered a painful loss, and it's crucial that they've learned valuable lessons from it. Blaming price or the customer is a major red flag.

A few others to get you started:

  • Tell me about a time when you received tough feedback and it ended up really helping you perform better?
  • How do you typically structure your week?
  • Have you ever walked away from a deal?  Why?
  • Tell me about your biggest deal ever, what were the customer’s challenges?
  • What do you think are the biggest challenges our company faces?
  • Tell me about your best manager–why did you work so well for them?
  • How many quarters/years have you hit your number? Why is that?

I strongly advise against just winging these interviews. For each competency, delineate what poor, good, and great performance looks like, and create questions that probe these areas. Providing interviewers with a structured framework for their conversations will lead to more meaningful and insightful interviews, demonstrating to candidates that your organisation is well-prepared.

Lastly, you’ll want to hear from others.  Of course the interviewing rep will showcase themself well (at least you’d hope!). That doesn’t mean they’re the most outgoing, it means they have thoughtful answers.  That they’re able to get their points across in a clear and compelling way.

But is that the actual truth?  Of course, if you can backchannel, that’s great. But many companies prohibit disclosing more information than just name, title and dates of employment.  (Which is still worth doing–LinkedIn is a great start but not always the truth). It’s great to ask for references, but who is going to give the name of anyone who they aren’t 100% positive will be a glowing reference?  Do you have any mutual connections? That said, even in references it’s worth having a few questions that allow you to dig deeper.  

  • What was the most challenging thing about managing this person that I should be aware of?  
  • What’s the best thing about managing this person?
  • How do they handle rejection?
  • What working conditions most help them thrive? Which were detrimental?
  • Are there any team members that you particularly saw them mentoring? Which roles and how did they impact that person’s growth?
  • How were they in accuracy at forecasting?
  • What one or two aspects of sales were they the weakest at?
  • Would you hire them for this role again?

In Summary

Will you get your hiring 100% right every time?  I wish. That said, I’ve seen people struggle desperately in one organisation, and then go on to become a rockstar in a different company. Some of it comes down to culture, chemistry, management and timing.  But what you can and should do, is make sure you’re not letting aspects that would have easily been uncovered slip by because you didn’t prepare.

These are going to be often the first people your business your prospects will engage with. Make sure you can say that you’re happy for that to be the case. 

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