The Messy Part of Leadership…

Hello ingagehr community, 

April has a way of bringing everything to the surface; while we’re hoping this means grass, flowers and the sunshine, that is not the case in the workplace. The year is no longer “new,” the pace has picked up, and leaders are often deep into the real work of managing people, performance, and the occasional workplace curveball. I do love me a good curveball.  

And let’s be honest: nothing tests leadership quite like a challenging employee situation. It might be navigating a medical leave. Responding to an accommodation request. Working through a challenging compensation discussion. Addressing a complaint involving questionable behaviour in the workplace. These are not easy, tidy, textbook moments. They are human, nuanced, and often layered with legal, emotional, and operational complexity. 

These situations can leave even the most seasoned leader can feeling uprooted and uncertain. 

Part of the challenge is that these moments rarely show up one at a time or in a perfectly convenient format. In some cases, there is no strong policy in place to guide the response. In others, leaders worry about overstepping personal or protected boundaries, especially when medical information or other sensitive details are involved. Without even realizing it, leaders often overlay their own perspective, tolerance, or past experience onto a situation. When that happens, the matter may not initially be approached through the lens of fairness, consistency, and organizational responsibility. Let me be clear; this isn’t failure, it’s what it means to be human.  

When I’m called, my initial conversations with leaders and managers begin with some version of ‘I’.  

“I cannot believe that…” 

“I’m shocked.” 

“If it were me…” 
“What I would do is…” 
 

And while those instincts are human, they do not help in resolving and addressing the matter. This is why it can be so valuable to reach out to a third party; someone removed from the emotion and day-to-day dynamics that can influence how sensitive matters are handled. Approaching the issue with the right mindset, the right process, and the right supports in place helps get to the root of the issue more quickly and move toward resolution with greater confidence. If you have a trusted advisor, they will quickly hold up a mirror to any personal biases in a respectful but helpful way.  

Sadly, I can’t provide a perfect textbook answer, and this is not something AI or a quick Google search can fully solve for you. We are gloriously messy humans. I can offer a few effective tools that stem from a combination of sound judgment, practical skill, and yes, real in-the-trenches experience. 

Here are five core skills every leader should lean on when navigating a difficult workplace situation: 

1. Separate fact from fiction. 
Start by gathering factual information from the appropriate source, which may include medical documentation, eyewitness accounts, or market analysis, depending on the situation. Hearsay and unreliable sources are the death knell of any sound investigation. Research and investigate appropriately and thoroughly, ask relevant questions, seek documentation where needed, and avoid assumptions. A leader’s first job is to understand what is actually happening or required; not what is rumoured, implied, or emotionally assumed. 

2. Understand the legal requirements. 
Not every situation is purely an internal people issue; many also carry legal obligations. Whether it involves leave, accommodation, workplace safety, or respectful workplace concerns, leaders need to understand employer responsibilities and the boundaries they must work within. This is where expert guidance matters. 

3. Lean on policy and process. 
Yes, I’m mentioning policies again. Because this is exactly where they matter most. Good policies and clear processes support fair, consistent, and appropriate responses. They are established to set clear expectations and parameters. They also help ensure there is shared understanding between the employer and employee about rights, responsibilities and next steps. 

4. Appropriate Resolution 
Not every situation has a perfect outcome, but every situation should aim for an appropriate one. That means considering what is reasonable, what needs to be addressed, where compromise may be possible, and how to reach a resolution that is consistent, fair, and respectful for everyone involved. 

5. Stay solution-focused 
What is the end result both parties are trying to achieve? When leaders stay focused on the desired outcome, conversations tend to become more constructive, grounded, and productive. It also helps build confidence, because leaders are not relying solely on their own moral compass to guide the response, but instead are anchored in facts, outcomes, and process. 

The reality is that challenging workplace situations are part of leadership. No one gets to skip this chapter and in fact, learning to navigate through the messy but human elements of leadership builds confidence. You also do not need to face these situations ill-equipped; when organizations have the right policies, the right advice, and the confidence to respond thoughtfully, these situations become far more manageable. Not always easy. But manageable. 

A FINAL THOUGHT 

Strong leadership is not measured by avoiding difficult situations. It is measured by how those situations are handled; with clarity, fairness, sound judgment, and the willingness to pause, assess, and respond in a way that protects both people and the business. 

If your team is facing more complex people situations, or if your policies and processes are not quite keeping pace with the realities of your workplace, this is a good time to reset. Quiet preparation now can prevent much louder problems later. 

Christine 
ingagehr