Compassion and Accountability: A Hard Leadership Lesson | Peter Boolkah

Compassionate leadership does not mean abandoning accountability—and accountability does not require a leader to abandon compassion.

In this personal episode, Peter Boolkah reflects on a difficult workplace situation in which an attempt to support a struggling employee gradually created unclear expectations, additional pressure on colleagues and an unsustainable arrangement.

Peter examines what he would handle differently today and the wider responsibility leaders have to both the individual and the whole team.

You’ll discover:

• Why employee support needs clear expectations
• How informal arrangements can become difficult to sustain
• The difference between empowering someone and continually absorbing their responsibilities
• Why leaders must consider the impact on other team members
• How regular reviews can prevent temporary arrangements continuing indefinitely by default
• Why boundaries and compassion must operate together
• How unclear accountability affects morale and productivity
• Why leaders need an established process for responding to personal crises
• The importance of employee assistance and appropriate professional support
• Why avoiding a difficult conversation can ultimately fail everyone involved

For founder-led businesses, there is another important lesson.

When every sensitive people issue depends on the founder’s personal judgement and generosity, rather than a fair process supported by capable managers and appropriate professional advice, the company remains dependent on the founder.

Strong leadership means caring about people while also creating clarity, consistency and protection for the wider team.

IMPORTANT EMPLOYMENT NOTE

This episode describes Peter’s personal experience and provides general leadership perspectives. It is not legal, medical, mental-health or human-resources advice.

Employee health and personal information should be handled confidentially. Employers should obtain appropriate HR, occupational-health and legal guidance, consider any duty to make reasonable adjustments and follow the employment law applying in their jurisdiction.

CONNECT WITH PETER BOOLKAH

Website: https://www.boolkah.com
LinkedIn: https://www.linkedin.com/in/boolkah
Instagram: https://www.instagram.com/pboolkah/
Facebook: https://www.facebook.com/Boolkah
X: https://twitter.com/boolkah

ABOUT PETER BOOLKAH

Peter Boolkah is a business coach, author and speaker who has spent more than 20 years helping business owners build stronger, more valuable businesses that do not depend on them for everything.

He is the creator of The Hamster Wheel Trap® and author of Your Business Sucks: Build a Business That Works Without Destroying Your Life.

Peter works with founders and leadership teams on the issues that ultimately determine whether a business creates freedom or becomes another job: leadership, founder dependency, people, profit, execution, scaling, exit readiness and enterprise value.

His approach is direct, practical and built around one simple question:

Do you own the business, or does the business own you?

Learn more at https://www.boolkah.com

Transcript

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If you’re a business owner or leader, today’s video will be particularly relevant because we’re exploring a subject that inevitably affects everyone in our roles.

I’ll share a real story from my experience—a difficult situation with an employee that taught me invaluable leadership lessons. Those lessons have since shaped how I approach leadership.

Make sure you watch the full video to prepare yourself to navigate similar challenges.

Let me begin with the story.

A few months ago, we had an employee who was going through some difficult personal challenges. He was feeling overwhelmed and was having difficulty focusing on his work.

We had several conversations about his situation, and I suggested that he might benefit from speaking with a professional counsellor.

Despite his difficulties, he decided not to pursue that path. Looking back, it’s clear that his choice had a significant effect on everyone involved.

As a team, we genuinely wanted to be supportive.

We reduced his workload, extended his deadlines and covered for him whenever he couldn’t manage his tasks.

He was granted all the sick leave he needed, and we did our best to provide an environment in which he could feel understood and supported.

It genuinely seemed like the right thing to do at the time.

But what happened next taught me one of my most valuable leadership lessons.

Initially, the employee improved, but then came another difficult period. Over time, he became accustomed to being helped.

He began relying on the team to pick up the tasks he couldn’t complete. There was no visible effort on his part to regain control of his work or seek the help he needed.

I even moved him to a different project, where he could work more slowly and without being disturbed.

Then, after more than five months of trying to support him, he told me that he was leaving to work for another company.

He left without finishing his tasks.

The part that stung most was that he didn’t even thank us for the support we had provided.

He simply walked away, leaving behind a pile of incomplete work and a team that felt both used and unappreciated.

I worked for corporations for more than 15 years, and I know what it feels like to be shat on from a great height—to work under leaders who are disconnected and indifferent and who don’t give a damn about your needs.

I don’t want to be that kind of leader. It is something to which I’ve paid a great deal of attention.

That is why I try to offer as much support as possible.

Leadership during difficult periods is one of the most challenging but also one of the most defining aspects of our roles.

We have the difficult task of remaining balanced and avoiding becoming either overly compassionate or disconnected from our team.

Let’s break down some of the key lessons I learned and explore how you can apply them in your own leadership journey.

Lesson one: balancing compassion and performance.

One of the first things I learned was the importance of establishing clear boundaries when offering support.

According to Adam Grant’s book Give and Take, successful organisations thrive when they find the right balance between giving and taking.

As a leader, it is crucial to ensure that, while you support an employee through a personal crisis, the overall productivity and morale of the team are not compromised.

This is where the difference between enabling and empowering becomes important.

When we enable someone, we often remove the need for them to act.

Empowering someone means giving them the tools and support they need to help themselves.

In our case, we enabled the employee by continually picking up his work without encouraging him to seek professional help or take steps to manage his own responsibilities.

This affected his growth and placed an unfair burden on the rest of the team.

How can you strike the right balance?

Begin by establishing clear expectations.

Let the employee know that, while you are there to support them, there is also an expectation that they will take certain steps.

That might include seeking professional help, managing their workload within the limits of their circumstances or gradually accepting more responsibility as they begin to recover.

Another critical lesson I learned was the importance of understanding the boundaries of managerial support.

Brené Brown discusses the importance of vulnerability in leadership in her book Dare to Lead, but she also emphasises the need for clear boundaries.

As leaders, we need to show empathy and understanding, but we must also recognise when our support is no longer beneficial.

In our situation, we crossed the line between being supportive and enabling a cycle of dependency.

We didn’t establish limits on how long we would reduce the employee’s workload or make it clear that his continued absence from important tasks was unsustainable for the team.

As a result, we compromised the productivity of the entire team.

It is important to create a support framework that includes clear timeframes, regular check-ins and expectations for improvement.

This allows you to provide necessary support without sacrificing the needs of the business.

One practical approach is to establish a policy through which employees experiencing personal crises are offered a defined period of reduced responsibilities, followed by a review.

That review can assess their readiness to resume normal duties. Further adjustments can be made when needed.

However, it is crucial that these adjustments are communicated clearly and reviewed appropriately.

This experience also led me to reflect on the broader role of leadership during difficult periods.

Leadership isn’t simply about making decisions. It is about guiding your team through challenges while maintaining a sense of direction and purpose.

In Leaders Eat Last, Simon Sinek emphasises that leaders must protect their teams. But leaders must also make difficult decisions that ensure the organisation’s long-term health.

In my situation, I realised too late that, by failing to address the growing problem directly, I wasn’t simply failing the employee. I was also failing the entire team.

I genuinely believe that other people would have dismissed him immediately.

But do you know what? I thought that would have been too drastic.

One of the most difficult aspects of leadership is knowing when to be compassionate and when to be firm.

This experience taught me the importance of preparing for future challenges.

As leaders, we should have a clear plan for how we will handle personal crises within the team.

This includes having resources such as Employee Assistance Programmes, creating a culture that encourages people to seek help early and being ready to intervene with firm but compassionate leadership when necessary.

What about you?

Have you faced similar challenges during your leadership journey? How did you handle them?

I would love to hear your thoughts in the comments below.

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