Compassionate Clarity: Navigating Tough Leadership Decisions

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CEOs have to make tough calls. It’s part of the job. Discover how one leader struggled with, then handled the delicate decision to let a long-time employee go, balancing compassion with the needs of the business.

Sometimes the decisions we face can be very uncomfortable. Especially those that impact a person’s life or livelihood. Personal feelings can cloud our judgement, and our desire to avoid emotional discomfort can drive us to freeze or to make unwise decisions.

The Dilemma of the Empathetic CEO

The imperative:

  • Be aware of the feelings brought up by the situation (this is important “data”)
  • Address our feelings in a healthy way
  • Assess the situation from a place of clarity
  • Choose the wisest path forward
  • Act with compassion

The Story of William the CEO & Mary the VP

Mary, 62, has been with an innovative company for 22 years. When she started, there were 30 people on staff and an HR director was needed. Over time the company has grown to 1,400 employees.

Quoto: As conscious leaders, it's important for our hearts to be engaged as we lead —  so that our ommunication, our choices, and our actions carry the blended synergistic wisdom of our hearts and minds.

She has not kept pace with the professional growth required to manage a company of this size. Her old-school policy initiatives, attitudes and approach don’t match the dynamics of today’s ever-changing workforce.

It has become clear that the job has been beyond her capacity for years and a resulting company-wide agitation is negatively impacting performance.

William, my client, has been CEO for the last 10 years and has grown increasingly frustrated with Mary’s subpar performance. He has wanted to let her go for a while but has been unable to get himself to do it.

Every time she doesn’t deliver as needed, he starts heading down the termination path only to put it off once he cools down. He needed to shift his approach to save time and energy to prevent further damage.

What's in William's Way of Taking Effective Action?

William knows how much meaning Mary’s job has for her. She is the company’s longest-serving employee and has been a central part of the company culture. He’s aware that she’s a widow, has no children, and that for her, the company is like family.

He and Mary have shared many conversations about their lives so there’s a personal connection. And she’s only three or four years away from retirement.

William said to me, “I have got to get rid of her, but I just don’t have the heart to do that to her.” And THIS is the crux of the issue.

Yes, caring about our employees and taking into account how our decisions impact them is essential in conscious leadership.

But where William went off the rails was in making the situation about himself, what he would be “doing to her”, and what this would mean about him as a person.

That is not a healthy place to lead from, nor is it a wise place from which to make sound business decisions.

Tackling Difficult Decisions: A Step-by-Step Approach

Quoto: Leading from a place of being truly authentic — demonstrating that our actions are aligned with our words and philosophies — will lift and inspire all those around us.

There are situations in our businesses where people we like, people we care about, people who have worked hard for the company, are no longer the right fit.

What do we do when we’ve objectively assessed that there is misalignment between a team member’s skill or ability and their roles or functions—even though they’re a great person and dedicated employee?

As conscious leaders, it is important for our hearts to be engaged in our decision-making process, and to choose our course of action wisely.

Here is how William and I approached finding a resolution that felt right for him. Play with this; use it as a model you can test out in your own tough situations.

  • We started by laying out the issue: VP of HR blocking the company’s forward movement.
  • William acknowledged the obvious solution: Bring in a stellar VP of HR to replace Mary.
  • Next up was a brief discussion of company values. They’re not meant to sit in a document for posterity. We want our decisions and actions to always be rooted in and aligned with those values (which may need to evolve as we do).

In order for William to get to clarity, we needed to process how his thoughts and emotions were blocking him from effectively managing the situation.

Three of his insights were:

  • Growing up, his business-owning father used to gloat about how he took advantage of “those poor suckers” (his employees), and William had vowed he would never be like that.
  • William saw how his need to be seen as a “good guy” was overpowering his ability to see the larger picture—that while he was avoiding addressing Mary’s exit, hundreds of other employees were suffering from her policies and attitude.
  • He saw that it had been Mary’s responsibility to grow with the company, rather than allow the times to pass her by while she coasted to retirement. This situation was, in part, a consequence of choices she made. He realized that ultimately this was a performance issue and that he was not “doing this to her”.

William knew he wanted to bring an element of compassion into his choice on how to proceed.

That guided him to determine his top three options for Mary:

  • Move Mary to a consultative role in a division with 300 employees working on a $200 million project that currently was having a lot of HR issues
  • Immediate termination with some type of parachute
  • 3- or 6-month transition out of her position with some type of parachute

These insights and the work we did with each one allowed William to release the tension, see through the unwinnable game of needing to be the good guy, and find clarity.

Proceeding with Compassion

Quoto: We make the wisest decisions when we allow ourselves to feel —  providing we don't  get caught up in emotions, which can cloud our judgement.

Bringing compassion to such situations requires taking the whole picture into account and recognizing that perfect solutions are rare.

In this case, at the very least, Mary, the team members, morale, and productivity must all be assessed. William and I evaluated his three paths forward.

Having Mary bring her failing HR approach to a division in strife did not appear to be a winning proposition for the company or for Mary. That team was already under Mary’s broad HR umbrella.

William considered whether a smaller group would be more manageable for her, but in the end he realized setting Mary up with another opportunity where she would likely fail herself, the team, and the company was neither compassionate nor wise.

He decided he was fine with either of the other two options: for Mary to leave immediately with some form of parachute for all of her years of service; or to allow her to stay in a consultative transition role for up to six months.

Parting Ways, with Compassionate Clarity

Compassionate consideration led William to meet with Mary off-site to give her the space to react without having to face anyone else on the team. With the internal processing he had done, he found himself to be grounded with his heart open.

This allowed him to be direct but caring in breaking the news and laying out the options. He also created the opportunity for her to feel somewhat empowered by giving her time to consider the options and to choose what felt best for her.

Further, he was able to tell her that no one else in the organization knew this was happening, so that if she wanted, she could announce she was leaving on her own accord. This eased the potential for the humiliation such circumstances can bring out.

The Irony

Though Mary was shaken and tears were flowing, she smiled at William and told him how relieved she was. She shared that for the last few years she felt like she was in over her head but didn’t want to let him or the company down, so she just kept plugging away.

That surprised William, but nowhere near as much as when she said, “You are such a good guy for handling it this way. I’ll never forget this moment.”

Infusing Compassion into Leadership

There is a purity to true compassion that has to do with selflessly acting to relieve suffering. And bringing compassion to our teams is certainly a tenet of conscious leadership.

For instance, seeing a person trip and fall in the office, we’d likely feel “moved” by compassion to see if they’re okay, or if we can assist. Our heart opens, we act with care.

Or if we become aware that we’ve under-resourced our teams to the point where their stress levels are skyrocketing, compassion can connect us with our desire to help ease the suffering that our choices have helped generate.

Quoto: Out of touch with compassion, we might convince ourselves that our employees' stress is just part of  the job, or worse — tell them to suck it up and be glad they have jobs.   But they'll not create, produce,  and thrive if we carry that attitude. I'm not suggesting that we coddle them, but a bit of compassionate understanding can go  a very long way.

Out of touch with compassion, we might see that they’re still producing the desired results, and be able to fool or convince ourselves that their stress is just part of the job, cheer them on, or tell them to suck it up and be glad they have jobs.

As conscious leaders with compassion, we’ll naturally care enough about our team to creatively find ways to better support them. This is important in and of itself.

It’s also wise because quite often a “side effect” of treating teams with respect and compassion is greater productivity, improved morale, dedication, and loyalty.

But remember, this is not about pretending to act as though we’re compassionate in order to get those results. That would be manipulation – putting ourselves first to get our own needs met at the cost of others.

That type of faux compassion will ultimately be seen through and is destined to fail. Acting with compassion must be heart-felt and authentic.


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