They don’t get along.
She questions everything.
He’s a good worker, but managing him is exhausting.
These are the kinds of concerns that bring business owners and managers to us. By that point, they have often tried informal chats, reminders about teamwork and asking everyone to communicate better. Things might improve briefly. Then another missed deadline or tense email brings the same frustrations back.
When we start unpacking what is happening, we look at the behaviour and how the work is organised. Who sets priorities? What instructions have people received? Can they make the decisions their role requires? Have they been shown what good performance looks like?
Sometimes the person labelled difficult is working around a problem the business has never properly resolved. That does not excuse poor behaviour. It does mean leaders need to understand what is driving it before choosing a solution.
Karlie Cremin explores this issue in her book Don’t Lead Like a Jerk, which places proficiency alongside people and profit in effective leadership. It is a useful lens for leaders before deciding an employee is the problem, examine whether they have the clarity, skills and support to do their job well.
A familiar scenario – the manager, the administrator and the owner in the middle
The following example brings together common workplace issues. It is an illustration, rather than an account of a particular client.
An owner contacts us about friction between an experienced administrator, Sarah, and a new operations manager, Mark. Sarah won’t accept that Mark is in charge, the owner explains. She questions his decisions and keeps coming to me. Mark is getting frustrated, and I’m tired of being in the middle.
Sarah knows the customers and how the business operates. Mark has been employed to introduce structure and take pressure off the owner. On paper, their roles should complement each other. In practice, Sarah feels her experience is being dismissed. Mark feels his authority is being undermined. The owner wants them to sort it out.
When we work through a recent disagreement, several gaps emerge.
Mark changed the order process in a team meeting, but there was no written follow-up or agreed start date. The owner continued giving Sarah separate instructions. Sarah was expected to resolve customer concerns but needed approval for almost every exception. Everyone was working from a different understanding of how things should happen.
A conversation about attitude would leave much of that untouched. Our starting point is to make the work clear, address the behaviour and help the owner stop unintentionally reinforcing the confusion. Here is what that looks like in practice.
They should know what’s expected by now
We hear this when a manager has explained something several times and feels the employee is not listening.Our first question is, What, specifically, has the employee been asked to do? Expectations such as take ownership, be proactive or show more initiative leave considerable room for interpretation. We help the manager turn the concern into an observable expectation.
Be more proactive with customers becomes Check outstanding enquiries each afternoon and Follow up anything unanswered for more than one working day and flag issues you cannot resolve before you finish. We then check whether the employee has the time, access and authority to do that.
What leaders can do
Before your next performance conversation, write down what you would see or hear if the employee met the standard. Use that description in the discussion. Then ask them to explain how they will approach it. That gives you a better understanding of their knowledge than a quick Does that make sense?
They keep going around the manager
Sometimes an employee deliberately bypasses their manager. Sometimes the business has taught them that going to the owner is the quickest way to get an answer. We look at what happens when they raise a question through the expected channel. Does the manager respond? Can they make the decision? Does the owner regularly override them or give a different answer?
In our example, Sarah has learned to go directly to the owner because that is how decisions have always been made. Mark’s appointment has changed the reporting line without fully changing the working habits. We would help the owner clarify the arrangement and support it consistently.
Mark is responsible for operational priorities. If you raise something with me that falls within his role, I’ll bring him into the discussion. Mark also needs to provide timely responses so the new arrangement works. What leaders can do for the next fortnight, notice how often you answer questions that belong with someone else. Redirect them appropriately and check whether there is a genuine blockage.
Everything needs checking
A manager tells us they cannot trust their team to complete work properly. They review every email, approve routine decisions and correct tasks themselves. The team, meanwhile, says the manager is controlling and never lets them get on with anything. We look at why the checking started.
There may be a genuine skill gap. There may also be an unclear standard, inconsistent feedback or a manager who has never learned to delegate. Our approach is to establish what good work looks like and where checking adds value.
For a newer employee, an early checkpoint may prevent substantial rework. For an experienced employee completing a routine task, reviewing every step may create unnecessary delays. We help the manager agree on the outcome, decision-making limits and review points before the work begins.
What leaders can do
Choose one recurring task. Explain the required result, provide a good example and agree on a checkpoint. As the employee demonstrates capability, reduce the oversight. Trust becomes easier when both people understand the standard.
Nobody takes responsibility
We often hear this after something has fallen between roles. A customer has not received a response. An employee has started without the right paperwork. A deadline passes while everyone assumes someone else is handling it. We ask the people involved to walk us through what happened. Frequently, several people completed individual steps, but nobody owned the overall outcome.
This does not need to become a lengthy procedure. A short checklist or shared task can be enough. What leaders can do pick a task that regularly falls over and ask each person who they believe owns it. Different answers tell you where to start.
They can’t manage their time
Before we recommend a conversation about time management, we check the workload. What was originally assigned? What was added? Who changed the priorities? Was anything allowed to move? An employee may have missed a deadline after covering an absence and handling urgent customer work.
If nobody adjusted expectations, the business may have created competing commitments that could not all be met. We help managers make those trade-offs visible. Instead of adding another task with can you fit this in? Maybe question what would need to move for you to complete this by tomorrow? That gives the manager useful information and allows them to make a clear decision.
What leaders can do
Hold a short weekly priorities check. Agree on the main outcomes, identify dependencies and confirm what can wait if urgent work arrives. When priorities change, update the people affected.
We’ve told them, but nothing changes
Repeated instructions can be a sign that someone is unwilling to follow a reasonable direction. They can also indicate that the employee has not learned the skill. This is particularly common when someone moves into supervision. A capable trades person, clinician or administrator becomes responsible for a team. Their technical knowledge is strong, but delegation, feedback and difficult conversations are new territory.
We help identify the particular management skill that needs development, then practise it using real situations. For example, rather than broadly telling a supervisor to improve communication, we might help them prepare for a conversation about missed deadlines what happened, the impact, the employee’s explanation, the required change and the follow-up.
What leaders can do
Ask yourself, have I taught this skill, or have I only pointed out the disappointing result? Choose one skill to coach over the next fortnight and review how it is being applied.
The process is there; they just don’t follow it
A documented process is only useful if people can find it, understand it and use it in the actual work. We ask someone to demonstrate the task while using the procedure. That can reveal an outdated instruction, a missing approval step or a workaround everyone uses but nobody has formally considered.
In Sarah and Mark’s situation, we would test the revised order process against actual examples, including an urgent request and a customer exception. This helps establish whether the process works before treating every departure from it as an employee problem.
What leaders can do
Ask, where does this process become difficult to follow? Listen for recurring obstacles, fix them and explain the final agreed approach. After that, there is a clearer basis for accountability.
But their behaviour still isn’t acceptable
Sometimes it isn’t, and we address that directly. Understanding the source of frustration does not make personal criticism, shouting or disrespect acceptable. We help managers separate the legitimate concern from the way it was expressed.
The missing information needs fixing, and we will address it. Speaking over your colleague and making a personal comment was unacceptable. Next time, explain what is missing and the decision you need. The employee leaves knowing that their concern has been heard and that the behavioural expectation remains firm. Serious concerns need an appropriate response. Leaders should not postpone addressing them while trying to perfect every process.
What leaders can do
Explain what needs to stop, what should happen instead and when you will review progress. Avoid vague instructions to be more professional.
How we bring the pieces together
Returning to Sarah and Mark, the aim would be a workable arrangement that both can understand and follow. That means clarifying Mark’s authority, Sarah’s decision-making limits and the owner’s role. It means documenting the order process, checking that it works and setting expectations for respectful communication.
We would then agree on a review date and look for practical evidence of improvement fewer unresolved orders, less repeated chasing and concerns raised through the agreed channels. If difficulties continue, the business has a stronger basis for identifying the remaining issue and deciding what further action is appropriate.
Start with one recurring frustration
You do not need to overhaul the business to make progress. Choose one problem your team keeps revisiting. Ask the people involved to walk you through a recent example. Look for unclear expectations, conflicting instructions, missing skills or delayed decisions. Agree on one change, assign responsibility and review whether it helped. Before deciding someone is simply difficult, make sure you have given them a clear and workable way to succeed.
Need help working out what is driving the friction?
HR Cornerstone helps business owners and leaders address workplace conflict, clarify responsibilities, build management capability and manage employee performance. If the same issues keep returning despite repeated conversations, we can help you understand what is happening and put practical changes in place. Contact us to talk through a challenge in your team and identify the next step.