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Your Ultimate Guide to Sales Leadership in 2022

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Posted in:  Best Practices, Sales, Sales Training

We’ve all had experiences with sales leadership. And most of us could list the benefits of working with a good sales leader — like the fact that their average annual quota attainment sits around 105% or that by offering dynamic training, they can boost their reps’ win rates by 28%.

But being effective as a sales leader isn’t exactly a walk in the park. It takes a unique set of skills, competencies, and characteristics.

In this post, we’ll dig into the nuances of sales leadership and show you what you need to know and do to become one, answering questions including:

What Is a Sales Leader?

Sales leaders are just that — the leaders in the sales department. They’re strategic decision-makers, coaches, sales experts, and change managers, all rolled into one. As a result, they’re the ones responsible for setting sales goals, charting a clear path to success, and scaling winning sales behaviors across the organization.

But successful sales leaders don’t just guide sales teams as a unit. They also play a role in each sales rep’s professional development by mentoring them one-on-one, doing annual performance reviews, and offering constructive criticism to help them reach their full potential.

Traditionally, sales leadership was reserved for senior leadership positions like sales directors and VPs. But with growing expectations for exceptional performance and explosive growth, sales managers are joining this exclusive club as well.

Why Is Sales Leadership Important?

Without real sales leadership, sales teams tend to just go through the motions. Yes, they still work through the sales process, manage their sales pipeline, and communicate with leads and customers. But they rarely break new ground or make pivotal changes that achieve explosive growth. And few work for any reason other than to get their paycheck.

But with true sales leadership, that paradigm changes. Sales reps work with more enthusiasm and they actively look for ways to improve and innovate. Why? Because sales leaders are inspirational. They’re motivational and visionary. As a result, they can pull their sales reps out of the daily grind, set their sights on bigger organizational goals, and give them the tools and techniques they need to achieve them.

Sales Leadership vs. Sales Management

There are many ways to do the same job — some bad, some good, some neutral, and some best. And sales manager positions are no exception.

While some sales managers may be content to simply manage the status quo — maintaining positive sales numbers and keeping their team from making big mistakes that would impact the bottom line — sales leaders see a lot more potential in their teams. As a result, they approach their role as a people manager and strategic decision-maker differently.

Here are some of the differences between sales leaders and sales managers:

Sales Leaders Sales Managers
Set inspirational SMART goals and spark intrinsic motivation in their sales reps to achieve those goals. Set KPIs to benchmark rep and team performance, but require reps to perform at a high level rather than inspiring them to do so.
Coach and mentor employees personally to help them improve their performance and get better outcomes as a team. Conduct regular performance reviews and direct reps to work on techniques and behaviors they struggle with.
Focus on big picture success, like sustainable business growth. Focus on reaching short-term and mid-term sales KPIs (monthly, quarterly, yearly), sometimes separately from big picture goals.
Encourage their sales reps to try new things and think outside the box. Expect sales reps to follow the game plan, dotting every “i” and crossing every “t” along the way.
Facilitate sales reps’ professional development and career advancement. Maintain the status quo, focusing more on team performance than their sales reps’ growth and career development.

How to Become a Sales Leader

Whether you want to make the jump from a sales rep to a sales leader or exchange your manager title for that of a sales leader, there are some skills you need to develop. Let’s walk through them one by one.

Master the Basics

First things first: you need to make sure you’ve mastered all the major pieces of the sales process, including prospecting, cold calling and emailing, upselling, cross-selling, and closing deals, to name a few. This will enable you to effectively coach and train your sales reps regularly.

In addition, you need to understand different sales methodologies — such as SPIN, Challenger, SNAP, and Sandler System — so you know when and how to use each sales model to move closer to your sales goals.

And to top it all off, you need to be familiar with your business’ core sales platforms (like Salesforce or HubSpot) and know how to vet and choose new ones so you can improve your sales performance.

This bank of knowledge and skills is the foundation of successful leadership in sales, so it’s important to start here.

Get Experience Managing People

This point is a bit of a conundrum for most people. You need management or leadership experience to land a management or leadership position. But you can’t get that experience unless someone gives you the opportunity to manage or lead a team in the first place.

So what do you do? You find creative ways to lead, manage, or mentor in your current role. You might do this by mentoring a teammate on a technique or skill you’re good at, helping your boss train a new hire, or taking on some additional responsibility that your manager is willing to offload to you.

Not only will doing so help you learn how to interact with employees who will report to you, but it will also enable you to help them improve their performance, support them in their professional development goals, communicate the executive team’s vision clearly, and collaborate to solve problems and scale winning behaviors.

Develop Soft Skills

Hard skills and experience are valuable, but there’s much more to leading a team than sheer experience. It takes a particular set of skills and traits to energize your team and get them to follow you.

This includes reliability, trustworthiness, and empathy — as well as dedication to deadlines, a passionate desire to communicate clearly both within your team and cross-functionally with other departments, and a willingness to work collaboratively with other people.

But the reality is, these are skills you can’t really teach. They can be learned, but you have to discover and practice them on your own. That being said, you can ask your teammates and manager for feedback and get their perspectives on gaps in your soft skill repertoire.

Pro Tip: Be prepared to not always like the answers you get. And remember that sometimes the least palatable feedback is the most useful.

Identify Your Leadership Style

As a sales team leader, you need to understand your leadership style (i.e. how you manage, coach, and support your employees on a daily basis), because every word you say and action you take has an impact on them.

Not only does knowing your leadership style allow you to capitalize on your strengths, but it also raises awareness about your weaknesses and flaws as a leader. And that makes it possible for you to change more easily and build stronger relationships with your reps.

Complete Relevant Sales Training Courses

When you’re learning the ropes for your first sales leadership role, it’s helpful to complete a few online sales training programs on the subject. Besides giving you the inside scoop on what you need to know to be a great sales leader today, they also provide a risk-free way to practice new skills and competencies.

In partnership with leading providers, Highspot offers dozens of interactive sales training programs that you can use to brush up on sales leadership skills like coaching your sales reps, hiring top talent, creating a sales playbook, and more. Here are just a few of our options:

  • Template: Sales Process Playbook by Sandler Training
  • Improving Strategic and Critical Thinking by Ignite Selling
  • Sales Behavioral Assessments by SalesMatch
  • ValueSelling Framework by ValueSelling Associates

As a bonus, Highspot offers pre-built courses and allows you to create custom learning pathways by blending content from different programs and weaving in interactive elements like quizzes and video challenges. This means you can continue using Highspot when it comes time to start coaching and mentoring your own sales team. Find out more at Highspot Marketplace.

Find and Enlist a Mentor

While you can make a lot of headway on your own, it doesn’t hurt to have a mentor who can coach you through the process of becoming a sales leader. In fact, those who are currently filling sales leadership roles can streamline the process significantly by giving you relevant resources and mapping out a path for you to follow. And once you get started, they can mentor you personally, providing feedback on your development and giving you insider information on their role and responsibilities.

Pro Tip: Find a sales leader who is part of your organization because they’ll also know what upper management is looking for.

There’s more than one way to be a good sales leader, but typically, those in sales leadership roles embrace similar leadership styles. To give you some idea of what your leadership style might be, we decided to break down a few in detail.

The Coach

The coach leadership style is all about growth and improvement. Leaders who embrace it focus on enhancing their sales reps’ strengths and improving their weaknesses. But they don’t do either one of these things with a heavy hand. Instead, they inspire their reps to actively seek mentorship and professional development opportunities.

Does it Work? Yes — the coach leadership style lends itself perfectly to the role and responsibilities of a sales leader.

The Autocrat

Autocratic leaders in business are mirror images of autocratic leaders in government. They make decisions without any input or feedback from their teams and they tend to micromanage employees as they do their jobs. While these leaders may mean well — their firm belief that they know best can demoralize sales reps and eventually lead to turnover.

Does it Work? No. This leadership style, in many instances, can actually be more harmful than helpful.

The Democrat

As the polar opposite of autocratic leaders, democratic leaders are all about collaboration. Team members, no matter their experience level, get to have a say in important decisions. And leaders tend to be more open in sharing their reasoning for the decision they ultimately make. As a result, sales reps are more likely to be on board with the direction the sales leader takes.

Does it Work? Yes. Sales teams tend to appreciate this type of leadership since it gives them a voice and allows them to work closely with their leaders.

The Laissez-Faire

While this term is often associated with economics and finance — laissez-faire is also a common leadership style. Here, leaders are relaxed and hands-off, allowing their teams to have more ownership over their own schedules, performance, and professional development. However, it does come at a cost. When leaders are laissez-faire in their approach, less is directly expected of employees. As a result, there’s a risk that growth will slow or stop altogether.

Does it Work? It can if you have a team of true self-starters that are intrinsically motivated to improve their performance and take charge in decision-making. But even if that’s the case, this style can be problematic for those looking for further mentorship and training.

The Transactional Leader

The same way a seller and buyer might come to the table to exchange goods for cash, transactional leaders trade incentives — like bonuses, gift cards, and recognition — for performance. And by all appearances, this may seem smart. After all, it’s a fair trade for employees to go above and beyond. However, when sales leaders operate under a transactional paradigm, they can actually demotivate employees to push themselves, as it’s difficult to offer a valuable reward every time reps do something laudable.

Does it Work? To a certain extent. But extrinsic motivators aren’t enough to consistently motivate sales reps, so this shouldn’t be your sole or primary leadership style.

8 Top Skills that Effective Sales Leaders Have

Becoming a sales leader is one thing. But if you want to be effective, there are certain characteristics and techniques you need to master. Let’s look at just eight of the most important ones to have in your arsenal.

Communication

Being able to communicate clearly is valuable for many reasons. For one, it allows you to share the company vision and goals with your sales representatives. And two, it plays a key role in your interactions and relationships with stakeholders, including senior executives like the Sales VP and Chief Revenue Officer (CRO), and upper management in other departments, like marketing and customer success managers.

To be considered an effective communicator, you need to be able to:

  • Present complex sales data and strategies in simple ways
  • Focus on information that’s relevant to your audience
  • Find a way to reconcile your sales reps’ perspectives with the executive leadership team’s vision
  • Be authentic in your presentation (fake enthusiasm doesn’t have the same effect as the real thing)

Empathy

It’s hard to motivate your sales reps if they feel like you’re disconnected from their situation. That’s why great sales leaders make it a priority to develop and showcase empathy for their team members. By drawing on their shared experience as sales reps and offering insight into their own journey (both their triumphs and struggles), these leaders become more approachable and trustworthy.

Here’s what it takes to have empathy for your sales reps:

  • A high degree of emotional intelligence, so you can perceive and respond to your employees’ emotions, effectively
  • Ability to honestly acknowledge and validate your employees’ feelings
  • Finesse to bridge the gap between the top-down direction from the executive team and the sales reps’ perspectives
  • Willingness to be vulnerable about your own experiences that are relevant to their situation

Strategic Thinking

Since sales leaders are responsible for creating the sales team’s game plan, strategic decision-making is a critical skill for them to have in their repertoire. With it, good sales leaders can pinpoint problem spots in the sales cycle and use that information to refine their approach or adopt a new methodology altogether. And they can identify winning sales strategies among their top performers and devise an effective way to scale them across the team through a relevant training program or mentorship.

Here are a few things great leaders do when developing an action plan:

  • Consider customer value proposition canvases (i.e. pains and gains), product positioning, market conditions, competitors (current and future), and pricing
  • Set SMART goals
  • Decide how to allocate the budget to get the sales performance they want
  • Pick training programs that will help salespeople execute chosen sales strategies and methodologies

Persuasion / Inspiration

Having a vision for your sales trajectory is great, but it’s only useful if you can execute on it. Naturally, that means sales leaders need to have the ability to inspire and mobilize their teams to perform at a high level. And the best ones do. Here’s how:

  • Devise a vision that sales representatives will actually want to get behind
  • Set a SMART goal for their entire sales team to accomplish
  • Develop a persuasive argument for the vision and the goal
  • Present it to your sales team in a compelling way

Data-Driven

Sales professionals at all levels need to be able to work with data. But it’s especially important when you take on a leadership role. It enables sales leaders to make good strategic decisions, pair up top and bottom performers for peer mentorship, pinpoint team weaknesses in the sales cycle, refine best practices, and find the best training program to improve rep performance.

When they’re data-driven, sales leaders:

  • Deeply analyze team and sales rep performance (via KPIs) to figure out what’s working and what isn’t
  • Discover the “why” behind good and bad performance
  • Identify strategies and techniques that can improve current outcomes
  • Mentor and train employees on their chosen techniques and strategies (sometimes personally)
  • Rinse and repeat

Coaching

Sales leaders spend lots of time mentoring and coaching sales reps. So naturally, knowing how to coach effectively is a must. This includes coaching on specific sales methodologies and a wide range of sales techniques, as well as best practices for each stage of the sales cycle.

Here’s what a successful coaching relationship might look like:

  • Ask sales reps about their career goals and help them chart a path (including a timeline and list of skills) to achieve it.
  • Identify weak spots in their skill set and offer resources (like training programs) they can use to work on those weaknesses.
  • Suggest resources that will help them broaden their skill set or learn a new methodology or strategy.
  • Answer tactical and strategic questions as they come up
  • Help them find the balance between their work and personal life
  • Offer opportunities to practice new sales techniques before sales reps have to use them in high-risk customer conversations

Integrity

Trust is one of the most important skills you can have as a sales leader. Without it, you may be hard-pressed to get your employees to follow your lead, and in some cases, stick around altogether. But having integrity is much easier said than done. When push comes to shove, not everyone stands by it.

Here are some ways that the best sales leaders show integrity:

  • Work alongside their team and lead by example
  • Follow through with commitments (and don’t make promises to upper management or sales reps that they don’t intend to keep)
  • Apologize when they make a mistake or forget to deliver on a promise they made

Humility

The best sales leaders don’t just direct, coach, and correct. They’re also active learners, seeking constructive criticism that will help them get better as a salesperson and a sales leader. And they’re willing to accept this feedback from anyone in their organization, regardless of title and responsibility. If someone has useful sales experience or knowledge, they listen and internalize it. And they give credit where credit is due.

Having humility as a sales leader might look like this:

  • Asking upper management and sales reps for feedback on your game plan and leadership
  • Listening carefully to suggestions that are made and analyzing them for their merits
  • Constantly looking for opportunities to learn from the expertise of others, including new hires
  • Acknowledging when you’re wrong and making a positive change as appropriate
  • Giving credit to the people who suggested a successful course of action

While becoming a sales leader isn’t easy, it’s incredibly rewarding. You get to have an impact on your company’s growth and help your sales reps move closer to their career goals at the same time.

Whether you’re new to sales leadership or simply want to get better at it, developing the characteristics and skills listed in this article will help you get started on the right foot.

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