How to Find Sales Candidates Who Can Prepare, Organize, and Plan Complex Sales

We often associate sales and salespeople with character traits like spontaneity, charisma, and the ability to navigate the unexpected. Maybe you even think of competitiveness or drive in industries where salespeople need to manage transactional sales or do a lot of prospecting. Those traits are critical to push through what can otherwise seem like mundane daily tasks. 

But are they the only traits you should look for when hiring a new sales candidate? Are these characteristics really even necessary for successful sellers?

We’ve talked a lot about how to find the right traits like adaptability, grit, emotional intelligence, and resourcefulness. Each of these can help you find rockstar sales candidates who will take revenue generation to the next level. And while it would be great to find a candidate who had every positive trait needed for sales success, each of the skills above can vary in importance depending on your market and your company’s unique selling processes. 

So let’s add a few more traits to the list — planning, organization, and preparedness — and discuss why they’re important for your sales candidates and how you can uncover these traits during an interview. 

Why Planning, Organization, and Preparedness Matter

While it’s true the words “organization” and “sales” don't always seem like a natural fit, finding salespeople who can plan, organize, and prepare for a complex deal is critical. As deals become more intricate, sales leaders need to realize that these seemingly unassuming traits aren’t just strong characteristics for a successful employee — these traits can set the top sellers apart from mediocre sellers as your company navigates enterprise-level deals, or any deal that takes more than a few weeks to close.

If it’s not obvious why planning and organization matter in a complex sales process, picture this: a lengthy sales cycle, multiple decision-makers on the buying committee, and a team that needs hundreds of touchpoints to make a decision. These types of scenarios are pretty common, and not just in technology sales. Across multiple industries, the average buying team for a B2B company is 9 people. And on average, each member of a buying team reports 15 interactions with a vendor they’re evaluating. The average sales cycle for deals over $10,000 is around 11 months. 

Add in complex pressures on your end trying to get deals across the line, navigating competition, and meeting forecast and quota goals, and these deals can take on a life of their own. 

It's in this challenging terrain that you want to find people who can:

• manage expectations of your company and the prospective client.
• ensure they know who has been talked to and who still needs contact.
• manage the needs of multiple members of the buying team.
• identify pain points and competitive differentiators to share with this client. 

A sales team member who plans out the deal is organized and prepared, ensuring that every move is calculated, every interaction purposeful, and every resource optimally utilized. Without a meticulous plan and organizational finesse, the chances of success diminish significantly. It's not just about charisma; it's about piecing together a multifaceted selling machine with many moving parts.

So finding people who are good at planning, organization, and being prepared will help level up your sales deals. When it comes to interviewing candidates for sales roles, you need to know how to uncover these traits and see how candidates have demonstrated them in their past performance. 

Because let's face it: finding candidates with the right blend of strategic planning and organizational finesse is not just about ticking boxes. It's about securing the foundation for a thriving sales team that will keep revenue growing in complex and challenging sales environments.

Why Behavioral Questions Work Well in Sales

Research has consistently highlighted the effectiveness of behavioral interview questions, especially when it comes to hiring accuracy in complex roles, such as sales positions. Unlike traditional interview questions that might only scratch the surface, behavioral questions dive deep into a candidate's past experiences, offering valuable insights into their actual performance in challenging situations. 

When developing your interview questions for sales candidates, use this formula to build out behavioral-based questions: begin with prompts like, “Tell me about a specific time you faced a certain challenging situation.” This approach shifts the focus from hypothetical scenarios to real-life experiences, creating a more tangible and reliable assessment of a candidate's capabilities.

A note about hypothetical questions

If you use hypothetical questions, you don’t always get as reliable information from the candidate. These types of questions can be an attractive interview option because you can use hypothetical situations the candidate is very likely to meet in this role. But while hypothetical questions that gauge a candidate's intelligence in handling certain situations have their merits, they can be somewhat misleading. It’s a subtle but important difference to understand. 

For example, if you use a question like, “Tell me what you would do [in a certain situation],” you can get some valuable information. You can gauge the person’s ability to think through a problem and also get a really good idea of how well they’ve been coached to answer this particular question in an interview.

Why behavioral questions give you more information

What ultimately matters in a sales role is effectiveness. This is where the power of behavioral questions shines—specifically those that start with, “Tell me about a specific time when…” With this format, interviewers can simultaneously evaluate a candidate's intelligence and effectiveness. Then, as you work in questions related to planning, organization, and preparedness, you’ll be able to more effectively evaluate how the candidate thinks through problems and real-life examples of how they approached them in the past. 

It’s important to realize that the effectiveness of a candidate doesn't necessarily hinge on a story's happy ending. If a candidate shares a story about a problem they encountered and failed, interviewers should look beyond the final result to discern the candidate's commitment to planning and diligence consistently executed at a high level. 

Essentially, it’s all about reading between the lines. How well does the candidate know the company? Did they prepare for the interview? These seemingly subtle details can be telling indicators of a candidate's habit of planning, organization, and preparedness.

Charismatic sales candidates may be very good about winging it and answering hypothetical questions. But as your interview team gets better at digging into details, understanding what they’re looking for in a candidate’s response, and knowing how to evaluate for the characteristics important for success in your role, it becomes much easier to see which candidates are prepared and which ones will be consistently ready to engage with prospective customers. 

So, work behavioral interview questions into your list of questions. They will help you understand how a candidate’s past experience applies to your current role. They will also provide valuable insights into their intelligence, effectiveness, and commitment to planning and preparation. Using this approach, interviewers can move beyond surface-level assessments and uncover the nuanced qualities that make a candidate well-suited for the challenges of complex sales leadership roles.

Now, let’s dive into specific questions you can ask that will help you move beyond reading between the lines and into assessing a candidate’s planning, organization, and preparation skills.

What to Ask When Evaluating a Candidate’s Planning, Organization, and Preparedness

It can be tempting to ask a lot of questions. The more questions you ask a candidate in an interview gives you a lot more information you can use to evaluate them, right?

Not quite. When preparing interview questions, choose fewer, better questions with plenty of relevant follow-up questions ready to go, rather than asking more questions. This allows your team to deeply assess a few critical character traits in a candidate and see how well they demonstrate the traits that will be necessary to succeed in your particular role.

And remember: ask each candidate the same questions. It can be easy to let a conversation flow with a candidate and ask questions as they come up naturally in the conversation, but if you don’t ask candidates the same or nearly the same questions, it becomes impossible to evaluate candidates against each other consistently and fairly. Having a different set of questions for each candidate allows bias and intuition to unintentionally creep in, making your interview process less a predictor of the future success of the candidate and more a guessing game of how the candidate will perform. 

Here are some questions specific to planning, organization, and preparedness to consider asking:

• Tell me about a specific time you needed to prioritize how you worked the accounts in your territory.
• Tell me about a specific time you were mid-cycle with an opportunity, and they gave you an objection that was challenging to address.
• Tell me about a specific time you worked on an opportunity that had a complex negotiation.
• Tell me a specific time that you worked on an opportunity that involved coordinating a large group of internal resources.
• Tell me about a specific time you were behind the competition on a deal you were working on that was important to you and your company.
• Tell me about a specific time you changed course or revised your deal strategy for an opportunity after getting input from stakeholders.
• Tell me about a specific time you worked on an opportunity and learned that the initial buying criteria would make it so you could not win the deal.

Again, keep questions deep and focused on key traits. For a 45-minute interview, use only 3 or 4 questions. 

Here are some of the things you could be prepared to ask in follow-up depending on what you get in the initial answer:

• What are the specifics of the situation the candidate is describing?
• What actions did the candidate take?
• What were the results of the actions?
• What lessons did the candidate learn from the situation?
• How have they applied those lessons since then? 

As you work through your list of questions, listen to the candidate’s answers and see how the candidate demonstrates their ability to build and execute a plan to manage a complex sale.