5 Small Business Leadership Habits of Effective, Compassionate Sales Teams

As a small business leader or a midsize business executive, it’s your job to consider what you and your sales teams can do for customers. Answering questions on products or services may lead to a sale, but you’ll have to do more than that to earn long term trust and brand loyalty. To strengthen solid and deep relationships that lead to repeat sales, your team must be there for customers at every turn – anticipating their needs and supporting them with the tools and insight they need. Sales teams in the growing enterprise often have the advantage of more flexibility and a faster response time – both a huge boon for customers. How else can you lead your team to success? 

Here are five simple and effective small business leadership tactics you can use to lead your SMB with compassion, and help you sustain real customer relationships both now and in the future.

1. Small and midsize sales teams help, rather than sell

Lead with trust, empathy, and flexibility during the sales cycle. Encourage your sales teams to make  personal check-ins with customers to provide a compassionate ear. If a customer has an urgent business need that translates to a sale, that’s great. Use this phone, Zoom, or fact time as an opportunity to guide with value and align with customers’ needs and interests. 

In my decades of experience in small business sales, I’ve always encouraged our sales teams to speak to customers about balancing current circumstances with future risk mitigation and technology strategies. The ultimate priority is to be there for your customer in a time of need and help them navigate any challenge  with the intent to build and strengthen long term relationships.

2. Treat stabilizing and growing customers differently

Ask questions about your customers’ priorities to help you get a better sense of where they’re at. Are they in  stabilization mode? Or are they ready for the next step? Once you understand their point of view, take a two-prong approach:

1. For stabilizing customers, spread some positivity. In our latest Small and Medium Business Trends Report, we found out that 72% of SMBs are optimistic about the future of their business. Extend that philosophy of optimism to your daily conversations with customers and colleagues. Share how you’re personally supporting fellow small businesses, or even personal highlights from your day. 
2. Help growth-minded customers reach their full potential. In your customer conversations with those ready to move forward, offer support by helping them overcome fear and doubt. Our research found that growing SMBs are 65% more likely than their respective counterparts to report acceleration in technology investments. Help your customers realize that this is an opportunity to be better than before. You can also start pointing them to online training resources, share best practices, or help them develop new business ideas and strategies. This, in turn, can expand your sales playbook to use your broader expertise to help however you can. 

3. Encourage your team to practice self-care and wellness

Helping others can be a powerful form of self-care, but be sure to take care of yourself, and your team, too. Stay focused on communication and transparency. On my sales team, we’re working to improve as individuals and as a team. Set aside a budget for fun activities like virtual happy hours or company-wide mindfulness activities. It’s important to keep your team grounded and communicating. Our team has started Growing Together, a podcast-style interview series. It’s a place where our sales leadership can share personal stories to connect, learn, and inspire the team. We’ve also been encouraging time off. Just because we are at home doesn’t mean we can’t step away from the screen for a few days.

Consider these points as you think about how to lead and care for the people you work with every day: 

• How are you staying in touch with the needs and challenges of your sales team? 
• Are you plugged into areas where a team member may need help? Is there a gap you and your leadership team need to assess? 
• Make sure you have processes and check-ins in place to keep your team supported and plugged in. Remember that structure and routine can be powerful tools. Consider adding daily huddles, one-on-one check-ins, and organization-wide all-hands calls. 
• How can you ensure everyone is taking some time off? Consider enacting an organization-wide day off, or requiring employees to take a certain amount of days off every quarter.

4. Sell with compassion

Customers want experiences that make them feel a sense of community.Sell compassionately to your customers by helping foster community at the same time. Partner closely with your marketing team to see if you can host online events that enable creative business conversations and thought-provoking discussions between your customers. For example, we’ve been setting up virtual mixology and wine tasting events for groups of customers. These create an opportunity for roundtable discussions for them to collaborate, share the state of their business, help each other move forward during this time, and foster space for tangible connections. 

5. Be open-minded and flexible with customers’ finances 

Flexibility — the ability to bend without breaking — can go a long way with customers. In fact, 49% of growing SMBs have admitted they’ve offered more flexibility to customers since the pandemic began. What can you do to make things easier for customers without jeopardizing your operations? 

We’ve adopted a two-step process to build more flexibility into our playbook:

1. Arm our sales reps with the confidence to listen to their customers and seek to understand their financial challenges.
2. Partner closely with our sales operations (SOPS) and billing partners to create more lenient options within our business practices.

Step one is pretty universal: talk with your reps and encourage them to just listen. Help them help their clients by gaining an understanding of their financial situation. Gather real-time data on what your customers are facing right now. Then look at what organization-wide steps you can take to support them.

Being flexible with payment plans and helping your customers manage their expenses can go a long way. And, of course, you can offer to brainstorm pricing strategies with clients to help give their businesses a needed boost. Customers want salespeople to be more engaged. They want positivity — or even to be respectfully challenged — and they want you to create more experiences that take them out of their home. Compassionate selling is one way to help them get there.

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