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Empathetic leadership — the path to better business results

Empathetic leadership is key to delivering resultsThe Sales Enablement Society Boston Chapter met to discuss the role of empathetic leadership, and share ideas on meeting today’s challenges.

It was fantastic!

A summary of our conversations is below; we all hope that the rest of the Enablement community finds value and can learn from our discussions.

How do you know you need to take a step back?

We started the conversation looking back at the bravery of Simone Biles in the last Olympics.

An athlete at the top of her game.

An athlete who was expected to win it all.

And she chose, for her well-being, not to compete.

She recognized that her head, and therefore her timing and execution, were off.  Whether than risking injury, she stepped back to take care of herself and not negatively impact the rest of the team.


As a result, others on the team rose up and delivered.

As a result, she avoided injury and gave herself permission, and time, to work through the challenges.

Relating this to our own lives

As Enablement professionals, coaches, and leaders, how often do we see one of our teammates struggling?

Perhaps a sales rep who is failing to hit their numbers, or a manager who seems unengaged.

Are they bad employees or simply going through a rough patch?

We have these challenges in our business every day, and how we choose to react and then coach our teammates makes all the difference.

  • Our leaders, including ourselves, need to be able to have tough conversations. 
  • Leaders need to validate everyone’s feelings and recognize that we are human beings first and employees second.  To achieve outstanding results, we must recognize and balance how we support each other.
  • Everyone is looking for a better work-life balance — but organizations are looking for ever-increasing results.  Validate their feeling — enablers must create a healthy environment.
  • We arm our sellers with more and more technology to support or monitor their efforts.  It can be overwhelming, and we must do a great job building their comfort with these tools to ensure our teammates’ success.  Are there things you can do to offload non-sales activities from their plates?

Business demands vs. life demands

Providing safety and space through empathetic leadership

Some companies are creating wellness days during the month.  A day where people are expected not to work, but to unplug from technology and focus on themselves and their families.

Is your business building in safe spaces and times?

In some cases, employees are not allowed to use slack, email, or any corporate technologies on those days, to ensure they are not creating disparities between employees taking the time to themselves and other employees who are powering through.

This health day could be a day a month, a half-day a week, or multiple other approaches that support the employee’s break from the day-to-day work.


If you are building this environment, ensure leaders are role models for what you expect.  Don’t have them blasting people with emails, slack messages during these quiet days.

Some companies are taking other or additional paths, offering meditation classes and slack channels for non-work topics where people can chat about hobbies.

Empathetic leadership – Lowering expectations or…

With work demands increasing, we explored multiple approaches to support this balance.

Lowering targets.  Is it feasible to reduce sales targets?

Focusing on the right areas.  Can sellers concentrate on the areas where sales are easier by selling different products to existing customers?

Giving the sellers more time to sell.  Can you hire an admin to create decks, perform data entry into the CRM?

There is a multitude of options.

Ultimately, businesses and employees must find the right solution for their business — just make sure you seek the answers as the problem is not disappearing.

Final thoughts

In a survey of almost 800 sellers, almost 3 out of 5 (58%) salespeople struggle with mental health today — and 52% say their mental health is worse today than before 2020. – 2021 State of Mental Health in Sales Report

Depression and anxiety impacts employee health (lost work time), effectiveness (lower outreach and lower win rates), reduces cognitive performance (missing opportunities to best support customers).

If you are not convinced that your teams have the right to better health, I hope you are convinced that finding solutions will positively impact your bottom line.

-The Board of the Boston Chapter of the Sales Enablement Society

Amanda Maddox, Bob Lucas, Bob Dozois, Matt Cohen, John Moore – The Collaborator