sales leadership skills

Growing a sales team isn’t hard. Growing a sales team that’s confident, comfortable and successful in their role… now that’s a challenge.

The effectiveness of any sales team starts with the sales leaders. It’s why many experts say any L&D spending should start (not end) with investing in your leaders. Simply adding more people to the team won’t deliver the scalability and dividends you’re looking for if your sales leaders aren’t willing to put in the work to create a culture of safety and empowerment that inspires confidence, continual development and genuine human connections.

In a tight job market where people have options — and in an economic environment that’s increasingly volatile and uncertain — salespeople want to work for sales leaders they can look up to.

Leaders who recognize that a silent room doesn’t always mean everyone understood what they just said.

Leaders who prompt a discussion to break the ice and confirm that everyone’s on board. 

Leaders who won’t push a sale when a customer’s goals and needs can’t be met (or even when a competitor is better suited).

Leaders who not only seek to understand each person for what they bring to the table but also tend to see more in their people than they might see in themselves — and then spend the necessary time with them to help them achieve new levels of personal and professional success.

Ultimately, this is the kind of leadership that transforms sales teams and elevates business results. The sales leader is able to reach into the relationships with the people on their team, find out their strengths and goals and align those things with the jobs that need to done in service of the customer. The question is, how well do your sales leadership skills measure up where it really counts?

How to Create a Psychologically Safe and Courageous Sales Culture

A recent podcast discussion we had with Karin Hurt, CEO of Let’s Grow Leaders, dove into how to create a psychologically safe and courageous culture that brings out the best in sales teams and allows them to grow to their full potential.

As Karin explained, when salespeople are juggling more responsibilities than they know what to do with, it can be hard as a leader to wedge culture change into the mix — especially when the definition of culture can be a bit nebulous. While it may not be easy, evolving the sales culture is still one of the best ways to keep top talent on your team.

So, how does a leader begin to approach such an ambiguous, and even somewhat intimidating, concept? It helps to get clear on what we mean by “culture.” Simplify things by thinking of it in terms of Seth Godin’s definition:

People like us do things like this.

It’s up to your sales leaders to decide what those ‘things’ are…

Get your sales leadership together and start asking the right questions:

  1. How do we want to show up?
  2. What values and ethics do we live by?
  3. What do our values look like in terms of behavior?
  4. How do we interact with and serve our customers?
  5. What do we ultimately want to be known for as a brand?

Here’s another simple tip: Give people two pieces of paper and have them draw the team as they see it now and then draw the team as they’d like it to be. The latter drawing is the culture you want. 

These aren’t complicated steps, but you’ll find that by doing these exercises, you’ll be able to quickly illuminate exactly how you want your team to act with customers (and one other) every day.

A great culture goes a long way toward helping you attract and keep top talent by helping you create a desirable and engaging employee experience. Those same benefits should also apply to the customer experience.

As you think about the internal culture you want to build, focus in tandem on the external culture — how your customers view the organization and what makes you the kind of company people want to do business with. Have your team start by creating a master list of what they think a truly great customer experience looks like. Then narrow it down into the top five ideas. Now your team has a blueprint of what they need to do and what steps they need to take to create an exceptional customer experience. 

The last element of the culture is one that isn’t always on a leader’s radar: personal relationships. Results are not just about numbers and meeting targets. They’re about how you arrive there (processes) and how you collaborate together to achieve them.

It’s no secret that the last few years have been difficult due to the pandemic and dramatic shift to more remote work cultures. When you pair that with regular day-to-day concerns, it becomes clear how necessary it is to check in regularly with each of your employees to see how they’re doing.  People need that human connection. They notice when they get it (and when they don’t). It translates into better engagement, which fuels greater energy, confidence and commitment to delivering even more value for customers. By making sure your team feels cared for and has a clear path to building a desired culture, you’ll have a significant advantage over the competition, both internally and externally.

Developing Stellar Sales Leadership Skills

But identifying a potential sales leader can be tricky. While it’s easy to think of the manager or leader position as the logical next step for someone who’s been successful as a salesperson, the two roles have vastly different responsibilities and require a different skillset and mindset. That’s not to say a top salesperson can’t excel as a sales leader. But they need to be aware of the differences and even the motivational mismatches that could derail their effectiveness.

For example, a star salesperson who’s used to a comp plan that rewards them when they close deals will face a stark change in how they’re compensated when they become a leader. As a result, you could be taking a highly motivated person and removing not just the financial incentives but also the personal satisfaction and fulfillment that fuels their motivation.

Don’t set a potential leader (and their entire team) up for failure by hiding the reality. Instead, focus on what their inner drivers are and help them get clear on what it means to be a leader and the different kind of fulfillment they can enjoy by helping others reach their potential.

Karin shares two first questions when considering someone for a sales leader role: 

What intrigues you about being a sales leader?

Do the people you want to be sales leaders have the values, will and commitment to leadership? Great leaders are driven by the actions and impact they have on other people. It’s so essential to understand why someone wants to lead. Individuals must be motivated to lead well beyond the title and paycheck that might come with it. Your leaders must model the behaviors and values the organization claims to hold dear. That’s a big responsibility. Does what they say match what they do every day? If not, mistrust and dysfunction can and will take hold.

Leaders with a high degree of integrity are genuinely interested in getting to know their people in order to grow them. They dedicate time to mentoring and exposing them to new responsibilities that will help them develop and grow.

The first time what a leader says and what they do don’t match will people will be confused. The second time? They’ll be disappointed. And the third time… they’ll be disgusted. Strong words, but it’s the truth.

People with great sales leadership skills- and the WILL to lead- will get their team to perform better and to ultimately win more customers and keep more customers.

The key is not in the telling. It’s in the modeling and in the asking. Some leaders have the mindset that their role is about catching mistakes and dictating how to solve problems rather than developing confidence, instilling a sense of ownership and maximizing employee potential and belief in themselves.

Which do yours have? And are you preparing them properly by having, for example, a clear definition of sales coaching? Without a common definition and clear coaching processes holding them accountable, sales managers can too often default to avoidance behaviors (“I don’t have time to coach”) and revert back to old habits (like taking over and closing deals themselves rather than supporting and nurturing talent).

Again, there are great sales leadership skills that must be taught. But without the clear will to lead, the entire team will suffer and potential is not reached.

Do you really understand what each person on your team needs?

A good leader will be able to identify the strengths and weaknesses of each team member, and balance each person to be the best they can be. As a sales leader, each coaching and development conversation should be unique because each of your people are unique. Their experience, level of confidence, communication style, appetite for risk and career ambitions will all be different. One of the most critical sales leadership skills is knowing what each person’s own style is and, most importantly, adapting to meet the needs of different people on the team.

If you help your people figure out their ‘why’, they’ll figure out the ‘how.’

The Six Competencies of Great Sales Teams 

Strong leadership and a positive culture are the foundation for sales team success. Once those are in place, development that focuses on building competencies across a few key areas will move the team to the next level.

Karin describes these six competencies as the ‘sandpaper’ that can help a sales team move forward:

Knowing when to walk away

If you don’t offer what the customer needs, have the courage, confidence and integrity to point them in the right direction.

The art of asking great questions

That means asking strategic, unbiased and open-ended questions at the right time. Some questions will draw out a customer’s wants and (often unstated) needs while others will just take you down a dead end. The more the customer talks and the more the salesperson actively listens, the more at ease the customer is, which elevates the trust level in the relationship.

Showing up with confidence and humility

Know and believe that you’re selling a great product or service with the understanding that every customer’s situation is unique.

Building great connections

Make sure that you’re engaging with customers and not just responding with fluff to get through the conversation.

Staying patient

Understand that customers need time and are in control of their own buying journey; follow up in a timely manner but never rush.

Giving generously

Be someone who genuinely wants to help even if you don’t make the sale.

Sales Leadership Skills and Trust

The ultimate sales leadership skill is engendering trust. And to build trust with others, it’s important to recognize something that trust is both a noun and a verb. How do you get more of the noun? By using more of the verb. Their first and foremost thought is “how can I serve and grow you?” And so a trust bond develops. They ask questions to understand and that enable that person to be successful.

Leaders must go first. They need to show up every day doing things that build trust, offering people the chance to do something new or outside of their comfort zone and allowing them to fail sometimes along the way. They listen more and remember that their team members need their ears more than they need answers.

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Integrity Solutions

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