Leading a Hybrid or Remote Team
How to Lead Salespeople Without Losing the Human Connection
Leading a sales team has always required trust, communication, and accountability. Leading a hybrid or remote sales team requires even more intentionality. When people aren't sitting in the same office every day, leaders can no longer rely on casual hallway conversations, walking by someone's desk, or simply observing the team to understand how things are going. The distance can create opportunities for greater flexibility and productivity, but it can also create isolation, disengagement, and uncertainty if leaders aren't intentional about staying connected.
One of the most important habits a leader can develop is having regular individual check-ins with team members. These conversations should happen throughout the year, not just during an annual performance review. This is especially important for new team members. A new salesperson may be trying to learn the products, understand the culture, build a territory, establish customer relationships, and figure out what success looks like all at the same time. Waiting six or twelve months to discover that someone is struggling is not leadership. Great leaders create regular opportunities to ask, "How can I help you win?"
That question represents a fundamental shift in leadership. Instead of making every conversation about what an employee has done wrong or what number they missed, focus on what they need to succeed. What obstacles are they facing? Where are they getting stuck? What customers are they struggling to reach? What resources would help them? What skill would make the biggest difference in their performance? Leaders should think of themselves as coaches whose job is to remove barriers and help each person become successful.
That does not mean leaders should micromanage. In fact, remote and hybrid teams can suffer when leaders try to compensate for distance by monitoring every activity. Constantly checking whether someone is online, counting every email, or demanding updates throughout the day may create the appearance of accountability without actually creating performance. Trust is essential. Give people clarity around expectations, provide the tools they need, and then give them the freedom to execute. Accountability should focus on results and meaningful behaviors rather than making employees prove they are busy.
For that approach to work, every team member needs to know exactly what winning looks like. The challenge is that winning may not look the same for everyone. A new salesperson building a territory may have different key performance indicators than an experienced salesperson managing a large book of business. One team member may need to focus heavily on prospecting and creating new relationships, while another may need to focus on retention, expansion, or strategic account development. Treating everyone exactly the same does not necessarily create fairness. Effective leaders understand the individual's role, experience, territory, and goals and establish KPIs that make sense for that person.
This is where leaders need to move beyond simply measuring activity. Telling every salesperson they need to make a certain number of calls each day may be easy to manage, but it doesn't necessarily produce better sales. Instead, identify the behaviors that lead to success for each individual. Maybe one salesperson needs to improve discovery conversations. Another may need to develop stronger follow-up habits. Another may need to spend more time with existing customers uncovering expansion opportunities. The objective is to create clarity around the behaviors and outcomes that matter most.
Hybrid teams also create an incredible opportunity for peer-to-peer mentoring. Every member of a team has strengths, experiences, and knowledge that can benefit someone else. One salesperson may be exceptional at opening new accounts. Another may be outstanding at building long-term customer relationships. Someone else may be great at presentations, negotiation, or using the CRM effectively. Instead of expecting the manager to be the source of every answer, create an environment where team members teach one another. When people are encouraged to share their strengths, the entire team becomes stronger and the person doing the teaching often gets better at their own skill as well.
Perhaps the most important thing leaders can avoid is the "sink or swim" mentality. Some organizations believe the best way to develop salespeople is to throw them into the territory and see who survives. While this may identify people who are naturally resilient, it does little to develop everyone else. Great leaders don't lower expectations, but they provide a bridge between where someone is today and where they need to be. They establish clear expectations, provide coaching, create opportunities to learn, and stay close enough to recognize problems before they become failures.
The best hybrid and remote leaders understand that physical distance does not have to create relational distance. In fact, intentional leadership can create stronger relationships than many traditional office environments. Regular one-on-one conversations, clear expectations, individualized KPIs, peer mentoring, and meaningful coaching create a culture where people know they are supported while still being accountable for their performance.
Ultimately, leading a remote or hybrid sales team comes down to one simple question: Are you managing people's activity, or are you helping people win?
Because great leadership isn't about watching people work. It's about helping people succeed.
Master the Art of Influence: Build Trust, Drive Sales, and Lead Effectively
Are you ready to become the magnetic force that attracts top performers and your best customers?
I’m Kevin Sidebottom—keynote speaker, sales trainer, and author—and I help organizations unlock the power of influence to achieve breakthrough results.
In this blog, I reveal why influence is the ultimate currency in business and leadership—and how you can use it to:✅ Motivate customers to stay loyal and buy again✅ Build trust and engagement with your team✅ Transform your leadership approach to inspire stronger performance
With decades of experience studying why people buy and how leaders earn loyalty, I equip sales professionals and executives to deliver lasting value, strengthen customer relationships, and drive higher revenue.
👉 Featured Resources to Grow Your Influence:
· Email: kevin@kevinsidebottom.com
Sales Management Strategies For Sales Growth
In the fast-paced world of sales, achieving consistent growth isn't just about closing deals—it's about fostering a high-performing team. This blog post delves into powerful sales management strategies that prioritize team investment through training, knowledge enrichment, and consistent communication. Let’s get into how you can achieve a solid team with strong sales growth.
Investing in Your Team
In the dynamic landscape of sales, knowledge is a potent weapon. Equip your team with the skills and insights they need to navigate the complexities of the market. Investing in regular training sessions and providing access to relevant books not only sharpens their sales acumen but also fuels a culture of continuous improvement.
When it comes to training programs, we need to make sure we address specific skill gaps or industry trends that our team is lacking in. Whether it's mastering new sales techniques or staying updated on product knowledge. Maybe the team could use an extra layer of negotiations training from a solid program to help them work with customers to a solid solution instead of having to escalate to management for every negotiation. An investment in education pays dividends in enhanced performance.
Encourage your team to delve into sales-centric literature. Books offer unique perspectives, fresh ideas, and invaluable insights. Create a reading culture within your team, fostering a shared knowledge that you can discuss as a team consistently to make sure everyone is grasping the knowledge. Sharing is caring in most cases and in sales hearing other’s perspective on a topic will open their minds to other options in their through process.
Temperature Checks
A successful sales team operates like a well-oiled machine. Regularly gauge the team's morale, challenges, and triumphs to identify areas for improvement. This temperature check isn't just about numbers; it's about understanding the heartbeat of your team. Fostering an environment where team members feel comfortable sharing their thoughts. Regular check-ins, team meetings, and one-on-one conversations can uncover hidden challenges and provide valuable insights for addressing issues promptly.
Consistency Is Key
Consistency is the bedrock of any successful team. Whether it's communication, expectations, or feedback, maintaining a steady course builds trust and loyalty. Team members thrive when they know what to expect and feel secure in their roles. Set clear expectations and communicate them consistently. Regular updates on goals, performance, and any changes in strategy keep everyone on the same page, fostering a sense of unity and purpose.
Most organizations only do once a year check in on goals or maybe a semi-annual check. We need to keep our teams moving forward so at a minimum quarterly check ins are required to keep goals fresh in the minds of the team and pivot if necessary to a new goal if needed.
Investing in your sales team isn't just an expense—it's an essential strategy for driving sustainable sales growth. By prioritizing continuous training, understanding the pulse of your team, and maintaining consistency in leadership, you're laying the foundation for a high-performance culture. In this environment, your sales team becomes not just a group of individuals but a cohesive force ready to conquer challenges and propel your business to new heights of success.
“Businesses wonder why it is still hard to be thought of as the brand of choice with the best customers and top employees. How can our business make more profitable transactions and stay out of the commodity battle with low profits? How can we land and keep top talent in our organization with the salary wars. Kevin teaches your sales and leadership teams how to build the key ingredient to be successful with their relationships and take your goals to the next level with high levels of engagement.
Kevin’s website: www.kevinsidebottom.com
Kevin’s email: kevin@kevinsidebottom.com
Alternative Sales Manager Titles
In today's fast-paced and competitive business environment, organizations need sales managers who can lead their teams to achieve extraordinary results. While all sales management roles are critical, the role of a Sales Leader is becoming increasingly important for organizations looking to stay ahead of the competition. In this blog post, we will explore why a Sales Leader may be better than other sales management roles.
Sales Leaders have a unique perspective on the market and customers. They are focused on building strong relationships with customers, identifying new business opportunities, and developing sales strategies that are innovative and effective. By building relationships with customers, Sales Leaders can gain valuable insights into what customers want, which can be used to develop tailored sales strategies that meet their needs.
Sales Leaders are highly skilled in managing and developing sales teams. They have a deep understanding of what motivates salespeople and how to create a high-performance sales culture. By setting clear expectations, providing ongoing training and coaching, and incentivizing performance, Sales Leaders can create a sales team that is focused on achieving extraordinary results.
Sales Leaders are visionaries and thought leaders in their field. They are constantly looking for new and innovative ways to improve sales performance and drive growth. By staying up-to-date with the latest trends and technologies in their industry, Sales Leaders can develop sales strategies that are ahead of the curve and deliver results that exceed expectations.
Sales Leaders are highly effective communicators. They are skilled at conveying their vision and strategy to their sales team, as well as other stakeholders within the organization. By communicating effectively, Sales Leaders can build support for their initiatives, create alignment across the organization, and drive success.
While all sales management roles are critical, the role of a Sales Leader may be better suited to organizations that are looking to stay ahead of the competition. Sales Leaders bring a unique perspective on the market and customers, are highly skilled in managing and developing sales teams, are visionaries and thought leaders in their field, and are highly effective communicators. By leveraging these skills, Sales Leaders can help their organizations achieve extraordinary results and drive growth.
Have a great week!
“Businesses wonder why it is still hard to be thought of as the brand of choice with customers. How can our business make more profitable transactions and stay out of the commodity battle with low profits? I equip your sales team to walk with the customer through the five buying decisions, and in the correct order to generate explosive revenues with greater profits!”
https://drive.google.com/file/d/1lWIVasmkFsoYL4h0AqIZgH6LC3qaw_gI/view?usp=sharing – client profile sheet
https://www.amazon.com/Sales-Process-Uncovered-Success-Influence/dp/0578421518 - Book