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The Biggest Challenges of First-Time Sales Managers & How to Overcome Them

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Sales Manager Facing Challenges

Congratulations, you are now a Sales Manager!

It is now time to cultivate the necessary skills to lead a sales team of your own.

As a first-time Sales Manager, you will likely experience a steep learning curve.

Do you sometimes feel as though you are expected to already know the ins and outs of this new role?  Does it seem like you are working harder than ever, without seeing results? 

If so, you are not alone.

Keep reading to learn about the top five challenges of first-time sales managers, and how to overcome them to lead your team more effectively—starting today.

Top 5 Challenges of First-Time Sales Managers

1. The Increased Pressure to Perform

As a brand-new sales manager, it is natural to want to demonstrate that you are equal to the task and ready for this new opportunity.  It can certainly be nerve-wracking!

Remember, there is a very good reason you were chosen for this role: the decision-makers in your organization believe in your abilities.  Developing your leadership skills is a journey – the more experience you gain, the more you will learn and grow.

For now, it is important to lay out clear goals and standards with your supervisor.  When everyone involved knows what to expect, you are much more likely to meet your goals.

2. Developing a New Set of Soft Skills

In your past position(s), you may have only been in charge of yourself and your own tasks.  Now, you have taken on the role of a leader who’s supposed to motivate others to accomplish their goals.

As you guide your team, it is important to stay one step ahead and discern the kind of attention and support each of your employees require.

It is your responsibility to actively listen and read between the lines so each team member can feel supported and make their best contributions to the team goals.

Your employees want to hear from their sales manager on a regular basis, and they want to feel heard. To facilitate clear communication with your team members, always be direct and very specific.

One way to support your team members and keep them focused is to hold brief daily meetings.  When everyone presents their daily tasks to the team, they set their daily focus and cultivate an understanding of how everyone’s tasks fit into the overall team goals.

Also, consider scheduling one-on-one meetings to regularly connect with each team member.  The frequency that works best for each employee for these meetings will probably be different, so ask what works best for them.

3. Managing Your Time

One of the most common challenges for first-time sales managers is learning to juggle their own tasks with the seemingly-endless responsibilities of overseeing their new team.  Over time, you will learn how best to split your time, but always keep in mind that your team comes first.

Be sure to position yourself as someone who is always available to your team.

Start by setting aside blocks of time in your calendar for your own tasks and letting your team know when you will be unavailable.  This signals that being available for your team is your default, and they will appreciate knowing what to expect from you and your schedule.

When you are open and available for communication with your employees, they will feel more comfortable coming to you to talk something through.  This also keeps you from slipping into the role of the dreaded micromanager.

4. Making the Transition from Co-worker to Supervisor

If you have been promoted internally to your new sales manager role, you will likely have former co-workers reporting to you.  Even among the many challenges of first-time sales managers, this one can feel particularly awkward.

It can be tempting to treat some co-workers differently based on who you connect with most naturally.  For example, do not fall into the trap of letting your former co-workers (or your top sellers, for that matter) get away with using their own sales techniques rather than your company’s established selling protocol.

Consistency is a key to effective management.  Your employees will quickly notice they are being treated differently than their colleagues, which erodes morale.

Be sure to address your team members directly about your new role as sales manager, and assure them you are still part of the team while establishing yourself as a communicative, consistent leader from the very beginning.

5. Hiring and Firing

Bringing new team members on board, and knowing when to let them go, is one of the more significant challenges of first-time sales managers.

When making hiring decisions, it is important to evaluate possible candidates holistically.

From past sales experience to their ability to fit into the company culture, always view your candidates as the unique and evolving people they are.  What can these candidates bring to your team beyond their skill sets?

Also, consider giving candidates a small project to see how well they perform, communicate and interact with your team.

When you have decided to let someone go, prepare everyone as best as you can to fill in the gaps in your team’s workload.  Be as transparent as possible and encourage a culture of open communication when addressing your team about the termination. Also, invite your employees to come to you privately with any concerns or feedback.

It is natural for a first-time sales manager to have questions about hiring and firing, so do not hesitate to ask other managers or your company’s HR team for help or advice.

While these 5 challenges are common, the biggest opportunity for first-time sales managers is to make sure they have the right team working for them. This starts with building a sales team correctly and onboarding your new hires effectively.

Let’s dig into both now.

Business People Talking Challenges First-Time Sales Managers

The New Sales Manager’s Guide to Building a Strong Sales Team

Building a strong sales team is not solely about making wise hiring decisions – it is also about learning how to coach your current salespeople in a way that helps them achieve better results.

As the new sales manager, it is your job to do both. Otherwise, you could end up with a team of salespeople who are unmotivated and, therefore, incapable of selling to your standards.

Evaluate your current team.

If you are not satisfied with your new sales team’s results, you should evaluate them to determine how you can help them sell more. Here are a few reasons your current team could be failing:

  • Their leads have not been qualified properly. Even the best salesperson will find it difficult to sell to someone who is unlikely to be interested in her product/service.
  • They lack basic sales knowledge, like how to close and how to overcome objections. Fortunately, you can resolve this issue with a bit of training and role playing.
  • They are slowed down by administrative tasks. If this is the case, consider hiring administrative support employees to free up more time for your salespeople to talk to customers and work on other revenue-generating tasks.

If you are unsure of why your team is producing poor sales results, consider asking them about which challenges at work hold them back from selling more. You can use the insight from their answers to determine the best ways to help them improve.

Improve your hiring process.

Too many sales hiring managers rush into the interview process without a plan of action. As a result, they often end up hiring low-performing salespeople.

Does that situation sound familiar?

If so, it is time to improve your hiring process. Here are a few suggestions:

  • Get a second opinion on every candidate. That way, you can make sure your judgment is not being clouded due to the fact that you like the candidate’s personality.
  • Start using a sales personality test. Doing so will allow you to take the guesswork out of hiring and learn more about what kind of salesperson the candidate will be.
  • Ask the best sales interview questions. Instead of working off of a list of ineffective interview questions, dig deeper and ask candidates questions that will uncover their true sales potential.

When making hiring decisions, consider attributes over experience.

You may find it tempting to hire a candidate who has many years of experience over one who is Driven and motivated to succeed. After all, an impressive resume says a lot about a candidate’s ability to succeed at work.

However, sales managers should always hire for attributes over experience. That is because sales skills and product knowledge can be taught, while attributes cannot. Here are the top 3 non-teachable attributes you should look for in each candidate:

  • Need for Achievement
  • Competitiveness
  • Optimism

Make sure your sales interview questions help you uncover whether or not candidates possess these attributes. However, you should not directly ask a candidate whether she possesses these traits – instead, ask questions that indirectly help you find out the truth. For example, to uncover a candidate’s Need for Achievement, you could ask her:

What do you want to accomplish in your first 30 days here?”

If the candidate has a high need for achievement, she will likely talk about the impressive sales results she plans to produce. On the other hand, she may seem indifferent about producing impressive results if she has a low need for achievement.

Provide coaching and training.

You cannot expect your salespeople to grow their skills and improve their results if you do not provide them with coaching and training that helps them do so.

Here are a few ways you can coach/train your team effectively:

  • Provide tailored, one-on-one coaching. “One-size-fits-all” coaching is often ineffective because each salesperson struggles with a unique set of challenges based on her skill set and personality traits. That is why you must tailor each coaching session based on a salesperson’s specific challenges and traits.
  • Have a set training system in place for each new salesperson. Successful onboarding involves making sure each new salesperson understands the product/service being sold and has enough industry knowledge to sell it. Keep that in mind when creating your onboarding process and consider using e-learnings or group training sessions to make sure everyone is up to speed.
  • Provide your salespeople with detailed feedback. It is not enough to tell a salesperson that she is not selling effectively. You must tell her why she is not selling effectively and work to help her improve her sales process.

While training and coaching may take up a significant amount of your time, you should still strive to do it consistently. Your efforts will pay off when you see that your team is more motivated and well equipped to sell than ever.

Give your team the resources they need.

The last thing you want is for your salespeople to produce poor sales results because they do not have access to the resources they need to sell effectively.

Make sure they can easily and quickly access any product information sheets, sales scripts or other relevant documents that could help them when they talk to customers.

Cultivate a good company culture.

A good company culture will attract high-performing salespeople, while a poor company culture will repel them. That is why you must focus on creating a company culture that attracts the Driven salespeople you want on your team. Here are a few tips to help you make it happen:

  • Provide salespeople with a fun, enjoyable atmosphere to work in. You can do this by creating fun sales competitions, providing free food on occasion and making the office look inviting.
  • Always hire salespeople who are a good culture fit. This is important because just one salesperson with a bad attitude could negatively affect the morale of your entire team.
  • Be the kind of boss you would want to have. When your salespeople feel like you genuinely care about helping them improve, they will be more receptive to your feedback and more likely to work hard every day.

For more on building a winning sales team, check out Sales Psyched!, our online video membership platform designed to provide sales professionals with hiring and management best practices rooted in psychology, psychological selling tips and six masterclasses. Videos are sent three times per week and our goal is to help you elevate and lead your sales team to peak success.

Now that you know the basics of building a successful sales team, let’s look specifically at tips for onboarding new hires. The first 90 days are critical, with expectations and excitement at its highest on Day One. You want to have a structured process in place to onboard your new salespeople effectively. Remember, new employees bond (or do not) emotionally with their new company and co-workers within the first 90 days of being hired.

6 Tips for Successfully Onboarding New Hires in the Sales Department

A 2012 Allied Workforce Mobility Survey showed that it took one year or longer for most new employees to get caught up to speed in about 30% of companies.

As a sales manager, you might find that statistic concerning. A year is a long time for a person to work at a company without completely understanding their job. For salespeople, slow progress translates to a lowered ability to sell productively.

Can you imagine how much your team’s sales results could improve if every single salesperson went through an effective onboarding process?

Chances are, their results would improve quite a bit. To learn how you can make that happen, check out the following tips for sales managers who are onboarding new hires.

1. Ease new salespeople into their role

You cannot expect a new salesperson to immediately understand the way your sales department operates on a daily basis – it will take some time for them to adapt.

To support your new reps during that time, avoid overwhelming them with unnecessary tasks or disciplining them when they do not produce top results as quickly as you would like. Instead, let them know that you are available to answer any questions they might have and provide as much guidance as possible.

2. Provide proper training and resources

It might seem obvious that you must teach new salespeople about your products and services, but many sales managers fail to do this in some way.

For example, they might offer outdated resources that are not conducive to learning, or they might expect their new salespeople to figure out the details of the products and services on their own.

Avoid doing either of those things. Instead, communicate openly with your new salespeople and determine their learning style so you can provide them with a training experience that is well-suited to their preferences if possible. By doing so, you will not just help the new hires – you will also help your team’s results as a whole.

But you cannot only teach your products and services – you also need to teach new salespeople about your company culture and the common procedures in your sales department. That way they can get used to how things are done quickly and become a productive member of your team in no time.

3. Assign a mentor for each new sales rep

In addition to providing training and resources, you may want to assign one of your seasoned sales reps to sit down with the new salesperson and go over all of the applications they need to use. The seasoned rep can help the salesperson learn how to use those applications in a day-to-day setting and address any questions.

This is a great way to onboard a new salesperson successfully and gives your top sales reps an opportunity to take on a leadership role by serving as a mentor.

4. Set challenging (but achievable) goals

If you set goals that are too challenging, you will find new sales reps feeling burnt out, discouraged and overwhelmed. They may even consider leaving their new position with your company, which will contribute to costly employee turnover.

On the other hand, if you set goals that are not challenging enough, you will fail to motivate your salespeople to achieve top sales results. They may also feel underutilized and start questioning their decision to work for you.

To combat these issues, set goals that are challenging but achievable. Also, make sure the goals you set are concrete so the new salespeople know exactly what they must do. That means you must avoid any vague statements and instead outline goals that are easy to understand and measure.

Keep in mind that the goals you set should not all be centered around sales results – you should set learning goals too. For example, you might let a new salesperson know that they should show mastery of your CRM in 30 days and give them an outline of exactly what “mastery” entails so they are aware of everything they need to know to meet their goal.

Whatever goals you decide to set, make sure your timelines for achieving those goals are realistic. The last thing you want is a sales rep who feels like they do not have enough time to reach their goals because then they will feel like you set her up to fail.

5. Check in every week

More often than not, people leave their managers, not their companies.

As a new sales manager, that means you need to establish yourself as a trusted leader by showing that you genuinely care about the well-being of your team. Maybe you already have a great relationship with your current salespeople, but you are not quite sure how to make a good first impression on a new salesperson.

If that is the case, you will be happy to learn that it is easy to build a healthy professional relationship with new salespeople after they are hired. Other than following the previous tips outlined in this post, you just need to make sure you check in with the new salesperson every week to provide helpful feedback and answer questions.

Doing so will help your new salesperson adjust to their new role more quickly and it will also decrease the likelihood that they will quit unexpectedly. Checking in allows you to quickly identify any challenges the new rep is struggling with so you can work together to overcome them.

Keep in mind that your weekly check-in does not have to be extensive. Something as simple as a 10-minute phone call or an in-person meeting can work wonders for a salesperson’s morale and productivity.

6. Ask for feedback on your onboarding program

One of the best ways to determine the effectiveness of your onboarding process is to directly ask your salespeople what they think about it.

However, you should not perform this task yourself or have another sales manager handle it – if you do, your sales team’s answers may not be honest due to fear of the repercussions they might face for making negative comments. Instead, have a neutral party, like a human resources employee, address it. That way, your salespeople will be more likely to provide an accurate assessment that details the good and bad aspects of the onboarding process.

Once you have feedback from several salespeople, do not be afraid to make changes to your process for onboarding new hires based on that feedback.

It may take some time to implement these changes, but it will be worth knowing your new salespeople are empowered to adapt to their new job more quickly and start achieving top sales results.

In Summary

We have covered a lot in this post, but above all, never be afraid to ask for help. You are likely feeling significant pressure to have all the answers in your new role from the very beginning, but it is perfectly okay if you do not.

Remember, company culture is not just about fun perks. Even sales departments with attractive amenities like game rooms can repel top performers if the work environment is toxic. That is why your new job as a sales manager is so critical – you must cultivate a good company culture with structured processes if you want to attract and retain a team of sales superstars.

As you take on this new professional challenge, never stop seeking out knowledge you need to help your sales team succeed.

For more resources on being a great sales manager, check out Sales Psyched! We cover everything from finding and attracting top talent to interviewing, training and motivating your salespeople to peak performance.

Sales Hiring Simplified!

Hire top-performing salespeople with The DriveTest®. Get started now with one free test.

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