How to Build the World’s Worst Sales Team | Proposify
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How to Build the World’s Worst Sales Team

Though every sales manager wants to create a dream team, the stress of hiring sales reps could have you losing sleep. How can you keep your hiring process from turning into a nightmare?

10 min. read

There’s no silver bullet for creating a perfect sales team. There are, however, many ways to muck it up.

A good sales rep hiring process has a lot of moving parts. As a sales manager building and growing a sales team, you have to make a series of decisions with a limited amount of information, while trying to avoid any biases, conscious or unconscious.

You also need to move the process along at a good pace so that your top candidates don’t get snapped up by another company. Then, even if you have a human resources department to help you out, you have to find some way to balance the hiring process with your regular duties and obligations.

When you’re hiring for a sales team, you can add the stress of a general high rate of sales rep turnover and the costs—money, time, and other resources—of a poor hiring decision.

While this might be enough to make you wring your hands and despair that you’ll never grow your sales team, relax. We’ve got tips to help you shape a thoughtful hiring process and build the sales team of your dreams.

Deep breaths. It’s going to be okay.

The not-to-do list

Hiring quickly and without a proper plan in place can lead to ill-fitting hires and high employee turnover. If your department becomes a revolving door with employees coming in quickly and out just as fast, it can also have a negative impact on the morale of those who do stick around.

How you set up your sales rep hiring process will depend on the kind of role or roles you’re hiring for, how many positions you’re filling, how established your team currently is, and whether you have access to human resources support. Of course, you also need to ensure your process follows any applicable employment legislation, as well as any company or industry best practices.

As you build or enhance your process, these are some common pitfalls to watch out for and avoid.

Hiring only ‘superstars’ or only ‘rising stars’

Your first instinct might be to hire only superstar salespeople. According to the Harvard Business Review, relying solely on sales reps with a reputation for putting up big sales numbers could be risky business.

Protect your sales team like the valuable glass egg it is.

Sure, at face value, it seems like a slam dunk. Who wouldn’t want more superstars on their team? The reality is that your company is not going to be the only one actively recruiting them and there are only so many of these superstars to go around. It’s likely that they will be in high demand and they can command top dollar.

Think about how this will affect the makeup of your sales team. Sales superstars may be great at what they do, but they are still only human. They have the same amount of hours in the day as anyone else.

For example, one superstar sales rep can’t single-handedly resolve a backlog of leads in your sales funnel that actually needs multiple salespeople to handle. If you’re overwhelmed with the volume of leads coming in, you might be better off adding two competent, but less experienced, sales reps to your team than one superstar.

This role fit is important in other ways. The candidate you’re considering is a superstar in their current position, but will their skills transfer if they join your team? Is it a similar kind of role?

Perhaps they consistently exceeded their quota in a job that required a lot of upselling and selling to existing customers, whereas the position you’re looking to fill would involve prospecting and new business development. Some people may perform well in both positions, but will it be to the superstar level you’re anticipating? It can be hard to tell without knowing all the factors at play in their previous role.

Aiming to increase sales rep performance across the board is a better way to achieve growth. Applied to hiring, this means you’ll also need to hire some less experienced salespeople, or, coachable rookies who can grow into the role.

It might be tempting to stack your team with these rising star sales reps. They usually command a lower salary and commission and are less likely to have bad habits or be stuck in their ways.

On the flip side, rising star sales reps will require more support, mentorship, and training. Their sales cycle might be longer than usual as they get used to the sales process and find their rhythm.

Benchmark the qualities that make a good salesperson at your company and hire based on those traits, not necessarily their numbers or previous experience. Having a balanced team of superstars and rising stars can provide you with the sales velocity you want and the mentorship that newer sales reps need.

Hiring a team of clones

Benchmarking the criteria for a superstar sales rep with your company can also show you where any gaps or weaknesses are in your team. When it comes to skills and strengths, which abilities and proficiencies do you have covered? Where could you shore up the team?

Maybe your team is great at closing but its numbers are weaker when it comes to prospecting or new business development. This will point you in the right direction for future hires and keep you from assembling a homogeneous team.

Just as a team of all superstars or all rising stars would be a liability, so is writing off candidates with experience outside your industry or the sales type. Don’t discount good general selling skills that are likely to transfer from one sales position to another, even if the roles don’t seem alike on the surface.

For example, someone with a retail sales background might be a natural at in-person sales presentations and demos for your software company because they are comfortable working with customers face-to-face.

Be just as wary of over-prioritizing a candidate’s experience in your particular industry. If you have comprehensive product knowledge training as part of your onboarding process, any candidate with solid sales skills should be able to hit the ground running.

And, watch out for unconscious biases in your hiring process. Studies have shown that we are naturally inclined to favour people who are similar to us, which can be a liability when hiring. Diversity is a strength, so make sure the people on your team have a range of skills and experience.

Being indifferent or married to the job posting

Now that you’ve spent some time cataloguing the qualities of a top-notch salesperson and the strengths and weaknesses of your team, you’re ready to tell the world you’re hiring and what you’re looking for.

Be as specific as possible.

List the qualities, skills, and experience in order of importance to the role and be precise. Many job postings have required, good to have, and nice to have sections, starting with the non-negotiable characteristics and moving down the list to assets.

You should also mention the main day-to-day duties of the role and add a little something about the company culture or any perks you might offer. This is your first impression with potential employees, so make sure it’s typo-free, reads well, and gives an accurate overview of the position and company.

Keep in mind that this is a list of ideals you’re hoping for—a ‘frankensteined’ list cobbled together from observing your current sales reps and identifying any gaps. Hopefully, you’ll attract candidates who possess some or most of them. Be wary of those who appear to check every single box; they could be too good to be true.

Once you start receiving applications, try not to focus on finding a ‘perfect’ candidate. Remember that you’re not unicorn hunting—there may not be someone out there who fits all the criteria. You’re aiming for someone to cover all or most of the required section, some of the good to haves, and then any additional skills or experience would be gravy.

Under-thinking the interview process

Once you have a shortlist of great candidates, the next step is usually the interview. Your questions for them should be designed to look for a history of initiative, hard work, and success.

Using a list like the one linked above is a great starting point, but make sure to tailor your interview questions to the role, your company culture, and the interviewee themself. You might to ask them how they would use the first 60 days in the role to achieve a company-specific goal or to expand on a particular detail from their resume.

Ask open-ended (can’t be answered with a quick yes or no) and non-leading questions. Posing a leading, closed-ended question like, “Our sales reps need to be resilient and own their mistakes. Do you take responsibility for your mistakes and then move on?”, will probably only return a chorus of yeses with zero elaboration.

You’ll prompt a more insightful answer by saying, “Tell me about a time when you lost a deal you should have won.” With a good open-ended question like this, you can get a sense of the situation, what the sales rep did, and what they took away from it.

Invite colleagues to join you in the interview process. This will give you multiple perspectives on each candidate and keep you from relying on your ‘gut feeling’ when making a decision.

Having an interview panel of two or more interviewers can also remove bias from the process. These could be positive biases, like preferring a candidate because they are similar to you, or negative, like excluding a candidate based on factors other than their answers. By making sure there are diverse opinions in the room, you can feel more confident with your selection.

Letting a poor decision worsen

Even the most confident hiring decisions, however, can turn out to be a bad fit.

Hiring and managing people is hard, and from time to time, it doesn’t work out, for a myriad of reasons. Sometimes people look great on paper or are really great at interviewing, but… sometimes you can’t find out what their performance will be like from resumes, interviews, and reference checks.

The first step to fixing a mis-hire is not letting the poor decision drag on longer than it needs to. Once you’ve identified that the person is not a fit for the role or your company, it’s time to officially let them go.

The longer you hem and haw, the more it costs your business. Of course, don’t press the eject button before you’ve given them a fair chance, but if you’ve had conversations and warnings and nothing’s changed, time’s up. No good manager enjoys giving someone the bad news that they’re being fired, but sooner is better if you’ve reached an untenable situation.

Not thinking beyond the present

So, you’ve hired an ace sales rep, one who fits great with the team. Your team is productive and growing. High five, you’re done, right?

Not so fast. What happens the next time you need to add to your sales team? And the time after that? Though there are some steps that need to happen each time, there are ways to streamline your sales rep hiring process with a longer-term hiring and growth strategy.

If you received promising applicants that maybe didn’t quite jive with the position this time around, keep them on file to check back with when you’re hiring again in the short term.

Take a look at optimal times for bringing a new person on board. Not every company’s sales will have high and low seasons, but try to time your hiring periods around those lower-volume times as best you can.

Onboarding and training is crucial and shouldn’t be rushed. There’s nothing noble about throwing a new sales reps right into the mix without providing some orientation. Customers expect to be guided, not sold, and a guide needs to be knowledgeable.

Once you’ve assembled a team of sales reps, you need to have an internal team growth strategy. Promotions and other opportunities for advancement are excellent employee motivators.

A lack of opportunity for growth within the company is one of the most-cited reasons for leaving a position. You don’t have to set anything in stone or make any promises, but let your sales team know that you’ll promote from within as much as possible as the department expands.

A good hiring process takes time to plan and execute, but when the return on investment is a confident, productive sales dream team, it’s definitely worth the effort.

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