My name is Jason Winkler, I’m the VP of Sales & Business Development at Device Authority.

In this article, I'll talk about leading with CARE. I learned very early on in my career how to lead and empathize with my people.

Here’s our main talking points:

  • What is CARE-based leadership?
  • CARE-based leadership vs. fear-based leadership
  • CARE flywheel continuum

Let’s go ahead and dive in 👇

What is care-based leadership?

The real point of leading with care, and the reason why you build teams, is to accomplish big audacious goals.

We're going to talk about the differences between groups of people and pro teams, and how to build a high performance culture where creativity and contribution are encouraged in today's remote based work environments.

It's very difficult to do, but it can be done.

Care-based leadership isn’t about keeping people in their comfort zone, it’s quite the opposite. It's about challenging people to get outside of their comfort zone.

"Help people get what they want and you will get what you want". "People don't care how much you know until they know how much you care" - Teddy Roosevelt. Care -> leads people out of selfishness to selflessness.

Working with teams and building teams, you have to learn how to not be selfish. As human beings, we're innately selfish.

It's a defense mechanism we have, but you have to care about other people and help other people get what they want, and ultimately, you get what you want.

People don't care how much you know as a leader until they know how much you care”.

That’s a quote by Teddy Roosevelt, and it's something you can't remind yourself of too much as a sales leader.

In everything you do and all the actions you take, if you keep that top of mind you're going to be a much better leader.

Care-based leadership vs. fear-based leadership

Care-based leadership is the complete opposite of fear-based leadership.

Many of us have worked for leaders leading by fear and that's not a great long term working environment and it also causes a lot of turnover.

It's difficult to accomplish big goals when a leader rules by fear because it causes a lot of stress which is an extremely potent, negative feeling.

As a sales leader, you have to be mindful of everything you say and do amongst your team. There's certainly times as leaders where we have to be able to lead people, give them direction and be firm but there's a big difference between leading by fear and leading by care.

At the end of the day, it's all about shared commitment towards the vision the team shares to accomplish extraordinary goals, shared accountability for the results, and hopefully transparent communication amongst everybody on the team.

As a leader, it's all about helping the people you're working with to become the best versions of themselves.

CARE flywheel continuum

CARE flywheel continuum. 1. connect, 2. achieve, 3. respect, 4. empower. "Unstoppable Teams" - Alden Mills

This CARE flywheel continuum is from a podcast by Alden Mills called Unstoppable Teams.

In case you don’t know anything about flywheels and engines, it's a loop that stores energy and that's very much the same thing in business with our people.

When you show care and if you can commit to these steps (connect, achieve, respect and empower) as a leader, you're going to store this energy which is going to be used by your people and you get a multiplier effect amongst your organization if you're trying to accomplish something big.


Connect (create & build trust). 1. Communication, 2. credibility, 3. commitment, 4. consistency.

The first step of the care continuum is how to show care towards your people – so connecting with them, creating and building trust. Trust happens over time but there's a couple of key steps to connecting and building trust.

First is communication. Things get lost with written communication in today's busy world and this can derail the team's overall goal and mission as well as yourself as a leader.

So be intentional about your communication and understand that communication goes beyond just the words you say.

55% of communication is done through your body language, 38% through your tone and only 7% is through words and diction.

Meeting 1-on-1 with your team, asking them questions about their personal lives outside of work shows you care about them beyond the eight hours that you're working with them.

Understanding what their professional and personal goals are, not every leader does that necessarily in today's world and it’s very difficult to do through team meetings and zoom calls as there's little time for interaction with our team members on a personal level.

Second is credibility. As a leader, are you accountable? How proficient are you and how reliable are you?

Third is commitment. As a leader, are you all in for some people or for everybody? Do you motivate and lead everybody on the team, not just the people most like you?

Lastly, the fourth is consistency. Are you consistent with your words and your actions through this connection phase and in other phases of your leadership? Are you leading by example?


Achieve. 1. Aspire, 2. Assume, 3. Assessments, 4. Assure, 5. Appreciation. "If we manipulate people they will give us exactly what we pay for. If we inspire people they will will give us more than we ask for" - Simon Sink

You don't necessarily have to have all the answers, but you have to be able to inspire people right into whatever the goal of the team is.

Then, you're going to help. Once you've provided the vision, direction, and goals, you're gonna allow your people to fail and succeed.

You're gonna allow them to go on their own path and you're not going to micromanage them.

Nobody likes to work in that type of environment where somebody is constantly over them so you're going to trust them and that's how you're going to get trust back as leader.

You should assess how you’re doing as a team, as individuals, and how you’re doing as a leader. Getting 360 degree feedback is important for a leader, as well as for the individuals on the team, that's how you’re going to gauge progress.

In business, we're attacking some large goals and we're gonna have some setbacks. We're going to take two steps forward, one step back. As a leader you have to assure your people that we're gonna make mistakes and failures but that at the end of the day we're going to learn.

The biggest piece here is appreciation.

Constantly sharing your appreciation for the people – the whole person – not just the eight hours they’re at work, that’s the key here.

There's a great quote by Simon Sinek that says:

If we manipulate people, they will give us exactly what we pay for. If we inspire people, they will give us more than we asked for.

At the end of the day, getting them to be a better version of themselves and helping the team walk through walls for each other is what we're trying to do as leaders.


Respect (fostering the care environment & culture). 1. Realize, 2. Recognize, 3. Require.

Quite often managers stop after the achieve step but this third step is where leaders really transform their organizations because there's a big difference between being a manager and being a leader.

Care-based leadership is about fostering the CARE environment and the culture. You're not going to accomplish big things without a strong culture and you’re not going to have a strong following from your customer base.

You want to create an environment where willingness to contribute is innate in your team.

If people don't feel like they can contribute, they're not going to be motivated for very long.

We've got to be able to respect the differences and understand the power of diversity – and diversity of thought is what we're going after. We want different opinions and thoughts and we want people to be able to express those opinions, that's how teams accomplish more together than as individuals.

The goal is to get those differences of opinion to solve the business's largest problems.

You have to recognise the actions of others.

Do you take the time to recognise the strength of each individual on the team? Do you publicly promote the strengths of your people?

We are all motivated by public recognition and it's something leaders can take for granted because it's that person's job but you have to be actively thinking about ways you can engage your people and publicly recognise them.

If you don't, you're going to lose people.

If somebody isn’t exhibiting the team mentality and the culture you’re going after, you have to remove the person from the team. As a leader you sometimes have to have those tough conversations.


Empower. 1. Educate, 2. Enable, 3. Engage. "The more you care, the more they will dare".

Empowering your people comes down to three things:

  • Education: You have to train them on the job you want them to do, and give them vision in terms of directions and goals (short-term and long-term).
  • Enablement: You have to help them succeed, have knowledge checks and check-ins on a consistent basis with your people.
  • Engagement: They have to feel like you care about their success (short-term or long-term) and you have to engage them. This is an active process of testing, educating, challenging and improving them and doing that individually as well as within the team environment.

To sum up

If you're able to do all four of these CARE steps, people get bought-in and will want to share it with other people.

Leading with care is so much more powerful than any other type of leadership. By leading with care and showing care towards your people on a consistent basis, you'll get reciprocity.