Sales leadership and wellbeing

For a long time stress and pressure have been seen as par for the course in everyday sales.

Our environments have shifted dramatically over the last six months and the usual stress indicators and access to support look entirely different.

With a lot of peripheral pressure gathering, how can we ensure our teams – and ourselves as sales leaders – are coping sustainably?

What is wellbeing, how does it translate to the current working conditions, and how do you measure it?

We’re joined by four experts in the field with authentic advice for leadership.


Lauren Cartigny, Leadership Coach & PCM Trainer

Simon Scott-Nelson, Founder, Wellity

Alexandra Damgaard, Head of People & Culture, Sales Impact Academy

Tamara McMillen, Board Advisor, CSO UK

Join us for the next live broadcast!

What is wellbeing?

It’s hard to define something uniquely personal and regarded differently on an individual-to-individual basis. 

However, you can be confident that without the right care, consideration, and support, people will be unable to perform at a high-level healthily.

Working in sales comes with a culture of expectation. 

It’s ingrained, sometimes damagingly, into our everyday processes, conversations, and compensation to continuously strive forward. 

You made a great deal or had a good month. Great, how do you improve on that?

When things aren’t going well in sales, you’ll likely feel it hit you in the pocket.

Wellbeing could be seen as the gap between how you’re performing in sales and how you’re feeling in yourself. 

When that gap gets wider you’re more likely to encounter burnout, stress, struggle with your workload, and encounter the negative consequences that come with all of these.

It’s the role of sales leaders, and the difference between a boss and a leader, to help those you manage to adapt to the recent changes in a balanced way that is mindful of that gap.

What to look for with sales wellbeing?

People won’t always ask for help, so make it part of your routine. 

The typical indicators that we might have picked-up on in the office are largely hidden, which is why we need to be extra vigilant of changes.

You might have noticed when people stopped showing up for work, arrived in the office earlier than usual, or burnt the midnight oil.

  • Overworking can mask damaging behaviour

Routine has been turned on its head and visibility of what we’re doing relies on being at the end of a video call and reporting accurately on activity.

Seeing that your reps are constantly on Slack, or clearly recording more hours might be a good signal for you to engage with them.

  • Dips in performance should be cues for conversation not condemnation.

Everyone is reacting differently to an unsettled work climate and it’s important to balance how people are adapting with your knowledge of how they are capable of performing.

Look out for bunched pipelines, muddled forecasts, catastrophizing, gambles, and mistakes. 

  • Don’t lose sight of the individuals

Employee output could be doing well on the whole, but your employees might not.

Size allows wellbeing to be masked and it’s harder to spot a lack of messaging, availability, or withdrawal from individuals.

Leaders need to look past the figures to remember that we’re human first and that right now empathy, compassion, and communication are fuel and a very necessary lifeline.

Sale leaders aren’t trained for this

It’s ok to not be ok yourself and conversations with your team are just as important for you as they are for your team.

You have to find time to decompress and leave the baggage of a bad call, report, or management meeting before the dial of your next call.

Be self-aware of your own wellbeing and acknowledge that resilience does not mean suppression, it can store up longer problems for what is a sustained duration of being unsettled.

Sales is not a solo sport and neither is wellbeing. 

Lean on each other and bring those that are resilient together with those that are more sensitive to each other to develop the rounded support that you can’t provide as individuals.

We don’t have the moments by the water cooler, or a lunchtime coffee, and many of us don’t have that important engagement in our personal lives either.

There are a lot of difficult conversations arising and leaders need to be factual of the situations, mindful of the legality, and then connect emotionally in a human way. 

Honesty breeds honesty

Someone has to be the first to share.

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