SIL Masterclass for Entrepreneurs

Don’t label them.
Diagnose them.

An employee may repeatedly miss deadlines, resist feedback, avoid responsibility, disagree with colleagues, or fail to meet expected performance standards. This SIL Masterclass, “How to Handle Difficult Employees: Here Is Our Answer!!”, breaks down five practical steps for turning a frustrating situation into a fair, structured process.

SIL

School of Inspirational Leadership

Leadership Development & Business Consulting

Five Pointers for Handling Difficult Situations

Every business leader will eventually face a challenging employee situation.

An employee may repeatedly miss deadlines, resist feedback, avoid responsibility, disagree with colleagues, or fail to meet expected performance standards. Some employees may have the right attitude but lack the required skills. Others may possess strong technical knowledge but display behaviour that affects the wider team.

When such situations continue, managers may feel frustrated. They may begin asking:

  • Why does this employee require repeated follow-ups?
  • Why is the employee not responding to feedback?
  • Is the issue related to attitude or capability?
  • Should we provide more support?
  • Was the person unsuitable for the role from the beginning?
  • At what point should we take a firm decision?

The SIL video “How to Handle Difficult Employees: Here Is Our Answer!!” recognises that difficult employee situations can result from several possible causes, including attitude, skill limitations, knowledge gaps, or an unsuitable hiring decision. In the video, Dr. Yogesh Pawar shares five pointers for handling such employees effectively.

The first responsibility of a manager is not to label the employee as “difficult.” It is to understand the specific behaviour or performance problem, identify its cause, and follow a fair process for improvement.

Prefer watching? View the SIL Masterclass on handling difficult employees, or continue reading for a practical five-step framework for business owners and managers.

In this masterclass

  • 1Identify the Real Cause of the Problem
  • 2Address the Issue Early and Directly
  • 3Listen to the Employee's Perspective
  • 4Create a Clear Improvement Plan
  • 5Review Progress and Take a Fair Decision

Prefer watching? Jump to the full SIL masterclass session below, or keep reading for the detailed breakdown of all five steps.

Before You Label Anyone

What Is a Difficult Employee?

The term “difficult employee” can mean different things to different managers. It may refer to an employee who:

  • Regularly misses deadlines
  • Resists instructions or feedback
  • Avoids taking responsibility
  • Creates conflict within the team
  • Demonstrates a negative attitude
  • Fails to follow workplace processes
  • Communicates disrespectfully
  • Delivers inconsistent work
  • Refuses to cooperate with colleagues
  • Repeatedly makes the same mistakes
  • Does not possess the required skills
  • Disregards organisational values

However, managers should avoid using the term as a general label. Saying that an employee has a “bad attitude” does not explain what the person is doing or what needs to change. A more useful approach is to describe the specific behaviour.

Vague label

“This employee has a bad attitude.”

Specific observation

“The employee missed three agreed deadlines and did not communicate the delay in advance.”

Vague label

“This employee is disrespectful.”

Specific observation

“During the last two team meetings, the employee interrupted colleagues and dismissed their suggestions without allowing them to complete their points.”

Specific observations make it easier to have a fair and constructive conversation.

01

Step 1 of 5

Identify the Real Cause of the Problem

The behaviour visible to the manager may be only a symptom of a deeper issue. For example, an employee who appears unwilling to take ownership may actually lack authority. An employee who repeatedly delays work may not understand the priority or may be handling an unrealistic workload.

Before deciding how to respond, determine whether the issue relates to:

  • Attitude
  • Skill
  • Knowledge
  • Role clarity
  • Workload
  • Resources
  • Motivation
  • Communication
  • Management support
  • Workplace conflict
  • Personal circumstances
  • Unsuitable hiring or role allocation

The SIL video specifically notes that difficult employee situations may arise because of attitude, skill, knowledge, or an incorrect hiring decision.

Distinguish between capability and willingness

Managers should determine whether the employee cannot perform or will not perform.

Capability problem

The employee is willing to perform but does not have the required knowledge, skill, experience, tools, or support. A capability problem may require:

  • Training
  • Coaching
  • Additional resources
  • Clearer instructions
  • Process documentation
  • More frequent guidance
  • Temporary supervision
  • Realignment of responsibilities

Willingness problem

The employee understands the requirement and has the necessary capability but repeatedly chooses not to follow it. A willingness problem may require:

  • Direct feedback
  • Clear consequences
  • Closer performance monitoring
  • A formal improvement plan
  • Disciplinary action where appropriate

Applying the same solution to both situations will not work. Training may not correct deliberate non-compliance. Similarly, strict performance action may not solve a genuine knowledge gap.

Review the manager’s contribution

Before assigning complete responsibility to the employee, the manager should ask:

  • Were expectations communicated clearly?
  • Was the deadline realistic?
  • Did the employee have the required resources?
  • Were responsibilities clearly assigned?
  • Was the priority changed midway?
  • Did leadership provide decisions on time?
  • Was previous feedback specific?
  • Did the employee receive sufficient training?
  • Were signs of difficulty ignored earlier?

This does not excuse poor employee behaviour. It ensures that the manager evaluates the complete situation fairly.

02

Step 2 of 5

Address the Issue Early and Directly

Managers sometimes avoid difficult conversations because they hope the issue will resolve itself. They may continue giving informal reminders, compensate for the employee's performance, or ask another team member to complete the pending work.

This may create short-term convenience, but it can make the problem more difficult to address later. It can also affect other employees. Responsible team members may feel that performance standards are not applied consistently. They may have to manage additional work because one employee is not delivering.

Difficult employee situations should therefore be addressed early.

Prepare for the conversation

Before speaking with the employee, gather:

  • Specific examples
  • Relevant dates
  • Agreed expectations
  • Actual performance
  • Previous feedback
  • Business or team impact
  • Relevant workplace policies
  • Required improvement

Avoid beginning the conversation when emotions are high. The objective should be to understand the situation and define corrective action, not to win an argument.

Use facts instead of labels

Avoid saying

“You have a negative attitude.”

Use instead

“During the last two project reviews, you interrupted team members and rejected their recommendations without listening to the complete explanation.”

Avoid saying

“You are irresponsible.”

Use instead

“The customer update was due on Monday. It was not shared, and the delay was communicated only after the customer followed up on Wednesday.”

Facts reduce ambiguity and help the employee understand exactly what has created concern.

Explain the impact

Employees may not understand how their actions affect others. Explain the impact on:

  • Customers
  • Project timelines
  • Team workload
  • Work quality
  • Costs
  • Revenue
  • Employee morale
  • Organisational trust

For example

“When the customer update is delayed without communication, the customer loses confidence in our ability to manage the project. It also requires other team members to respond without complete information.”

This connects the employee’s behaviour with a meaningful business consequence.

03

Step 3 of 5

Listen to the Employee's Perspective

A performance conversation should not become a one-sided lecture. After presenting the facts, give the employee sufficient opportunity to respond. Ask:

  • What is your understanding of the situation?
  • What prevented the work from being completed?
  • Were the expectations clear?
  • Did you have the required information and resources?
  • Is there any challenge affecting your performance?
  • What support do you require?
  • What could you have done differently?
  • How do you propose resolving the issue?

What the manager may not have known

The employee may reveal information that the manager did not previously know. For example:

  • Another department may not have provided the required data.
  • The employee may be managing conflicting priorities.
  • A process may be unclear.
  • The employee may lack technical knowledge.
  • The person may be experiencing conflict with a colleague.
  • The role may not match the employee's strengths.
  • The employee may not understand the business impact.

Listening does not mean accepting every explanation without evaluation. It means understanding the employee’s position before deciding on the appropriate action.

Separate explanation from excuse

An explanation helps the manager understand why something happened. An excuse is repeatedly used to avoid responsibility without proposing corrective action.

Avoiding responsibility

“Nobody reminded me, so it was not my fault.”

Taking ownership

“I misunderstood the deadline and should have clarified it earlier. I will complete the work by tomorrow and use the project tracker to confirm future deadlines.”

The manager should listen carefully but continue to reinforce ownership.

04

Step 4 of 5

Create a Clear Improvement Plan

Once the issue is understood, the manager and employee should agree on what must change. Statements such as “improve your attitude,” “be more responsible,” or “work harder” are not sufficiently clear.

The improvement plan should define:

  • The behaviour or performance requiring improvement
  • The expected standard
  • Specific actions
  • Measurable outcomes
  • Required support or training
  • Review dates
  • Improvement timeline
  • Consequences of non-improvement

Example of a performance improvement expectation

Improvement expectation

Issue
Customer updates delayed and not communicated proactively
Expected standard
All priority updates shared by the agreed deadline; delays communicated in advance
Measurement
On-time %, uncommunicated delays, customer feedback, manager review
Support
Communication template, weekly planning review, escalation clarity
Review period
Four weeks
Expected outcome
Consistent, timely communication without repeated manager follow-up

This structure reduces misunderstanding and creates a basis for fair evaluation.

Provide suitable support

If the problem relates to knowledge or capability, the improvement plan may include:

  • Technical training
  • Process training
  • Job shadowing
  • Mentoring
  • Coaching
  • Written guidelines
  • More frequent reviews
  • Access to tools or data
  • Temporary reduction in work complexity

Support should address the identified cause. Training on its own will not solve an unclear role, unrealistic workload, or deliberate unwillingness to follow workplace standards.

Document the discussion

Important performance conversations should be documented. The record should include:

  • Date of discussion
  • Specific issue
  • Examples reviewed
  • Employee's response
  • Agreed expectations
  • Support provided
  • Review timeline
  • Next action

Documentation helps both the manager and employee maintain clarity. It also supports a fair and consistent process if formal action becomes necessary.

05

Step 5 of 5

Review Progress and Take a Fair Decision

An improvement plan will work only when progress is reviewed consistently. Managers should not wait until the end of the review period to discuss performance. Schedule regular check-ins to understand:

  • What has improved?
  • What remains unchanged?
  • Is the employee following the agreed actions?
  • Is the support sufficient?
  • Are there new challenges?
  • Is the team or customer experiencing improvement?
  • What should happen next?

Recognise genuine improvement

When an employee responds positively, acknowledge the progress specifically.

For example

“During the past three weeks, you have completed all customer updates on time and informed the team early about possible delays. This is the level of ownership we expect.”

Recognition reinforces the improved behaviour and communicates that the manager is reviewing performance fairly.

Address repeated non-improvement

If the employee does not improve despite:

  • Clear expectations
  • Direct feedback
  • Appropriate support
  • Reasonable time
  • Regular reviews
  • Defined consequences

the manager may need to take a firmer decision. Depending on company policy and the situation, this may include:

  • Formal warning
  • Role reassignment
  • Reduced responsibility
  • Extended improvement monitoring
  • Disciplinary action
  • Separation from the organisation

Employment-related action should always follow applicable company policy, HR procedures and legal requirements. The objective is not to retain every employee regardless of impact. It is to provide a fair opportunity for improvement while protecting the team, customers and organisation.

Watch the Session

See the full masterclass on handling difficult employees

Everything covered here comes from this SIL Masterclass session with Dr Yogesh Pawar. Watch it in full, or continue reading below.

Behaviour, Not Personality

How to Handle an Employee With an Attitude Problem

Managers often describe an employee as having an attitude problem. However, the conversation should focus on observable workplace behaviour rather than personality. Possible behaviours may include:

  • Disrespectful communication
  • Constantly dismissing team suggestions
  • Refusing reasonable instructions
  • Blaming colleagues
  • Displaying hostility
  • Ignoring workplace processes
  • Spreading repeated negativity
  • Resisting necessary changes
  • Avoiding accountability

Use the following process:

  1. 1Describe the behaviour — explain the exact statement or action that created concern.
  2. 2Explain the impact — show how the behaviour affects colleagues, customers or execution.
  3. 3Clarify the expected standard — explain what respectful and professional behaviour should look like.
  4. 4Listen to the employee — understand whether there is a workplace concern contributing to the behaviour.
  5. 5Agree on corrective action — define what must change and by when.
  6. 6Review consistency — one positive interaction is not enough. The improved behaviour should continue over time.

A manager should remain professional and avoid responding to difficult behaviour with anger or personal criticism.

Willing, Not Yet Able

How to Handle an Employee With a Skill Gap

A skill gap exists when the employee is willing to perform but lacks the required capability. Possible signs include:

  • Repeated technical mistakes
  • Difficulty completing specific tasks
  • Dependence on colleagues
  • Slow performance despite effort
  • Limited understanding of tools or systems
  • Inconsistent quality
  • Difficulty applying feedback

Before creating a development plan, identify the exact gap. Avoid general statements such as “the employee needs more training.” Define:

  • Which skill is missing?
  • What proficiency is required?
  • How will it be developed?
  • Who will support the employee?
  • How will improvement be measured?
  • What is the expected timeline?

The solution may include training, mentoring, supervised practice, job aids, certification or role adjustment. Managers should also evaluate whether the employee has the potential to meet the role’s requirements within a reasonable period.

What They Know vs. What They Can Do

How to Handle an Employee With a Knowledge Gap

Knowledge and skill are related but different. Knowledge refers to what the employee understands. Skill refers to the employee’s ability to apply that knowledge. A knowledge gap may involve:

  • Product information
  • Business processes
  • Customer requirements
  • Workplace policies
  • Industry regulations
  • Reporting standards
  • Quality expectations
  • Safety requirements
  • Commercial understanding

A knowledge-development plan may include:

  • Structured onboarding
  • Process documentation
  • Product training
  • Refresher sessions
  • Knowledge assessments
  • Shadowing an experienced employee
  • Access to standard operating procedures
  • Practical review discussions

When several employees have the same knowledge gap, the issue may require an organisational solution rather than individual correction.

When the Fit Was Never Right

How to Respond to a Wrong Hiring Decision

Sometimes, performance problems continue because the employee was not suitable for the role from the beginning. Possible causes include:

  • The job description was unclear.
  • The interview process did not assess the required skills.
  • The candidate's experience was not verified.
  • Behavioural fit was not evaluated.
  • The role changed after hiring.
  • The employee was selected urgently.
  • Expectations were not communicated during recruitment.
  • The employee's strengths are better suited to another role.

Before concluding that the hire was incorrect, evaluate whether appropriate onboarding, clarity, training and support were provided. If the employee has useful strengths but is unsuitable for the current position, role reassignment may be considered where a genuine organisational need exists.

However, avoid creating an unnecessary role only to avoid a difficult decision. The business should also improve its recruitment process so that the same mistake is not repeated.

Look Beyond the Individual

Difficult Employee or Difficult Workplace?

Not every employee problem begins with the employee. An organisation may unintentionally create difficult behaviour through:

  • Unclear responsibilities
  • Conflicting instructions
  • Inconsistent management
  • Unfair performance standards
  • Excessive workload
  • Weak communication
  • Limited growth opportunities
  • Lack of recognition
  • Delayed decisions
  • Poor workplace culture

If several employees demonstrate similar issues, leadership should consider whether the problem is systemic. For example:

  • Repeated deadline failures may indicate unrealistic planning.
  • Frequent conflict may indicate unclear responsibilities.
  • Low ownership may indicate insufficient authority.
  • High turnover may indicate poor management.
  • Resistance to change may indicate inadequate communication.

Managers should address individual accountability while also reviewing organisational causes.

Learn From Others

Common Mistakes Managers Should Avoid

01

Labelling the Employee

Focus on behaviour and performance rather than describing the person as difficult, lazy or negative.

02

Avoiding the Conversation

Delaying feedback allows the issue to continue and makes later action more difficult.

03

Giving Feedback Without Examples

General feedback can make the employee defensive or confused.

04

Criticising the Employee Publicly

Sensitive performance discussions should take place privately.

05

Acting While Emotionally Frustrated

Managers should prepare and respond professionally.

06

Providing Responsibility Without Authority

Employees cannot be accountable for outcomes they cannot influence.

07

Taking Over the Employee's Work

This may solve the immediate problem but create further dependency.

08

Ignoring Good Improvement

Acknowledge when the employee responds positively.

09

Applying Standards Inconsistently

Different treatment can damage trust across the team.

10

Retaining a Harmful Situation Indefinitely

Leaders must protect the wider team, customers and organisation when reasonable improvement efforts fail.

Put It Into Practice

A Simple Difficult Employee Management Framework

This process helps managers remain objective while giving the employee a reasonable opportunity to improve.

  1. 1

    Step 1: Diagnose

    Identify whether the issue relates to attitude, skill, knowledge, clarity, resources, motivation or role fit.

  2. 2

    Step 2: Discuss

    Present specific facts, explain the impact and listen to the employee's perspective.

  3. 3

    Step 3: Define

    Clarify the required behaviour, performance standard and measurable improvement.

  4. 4

    Step 4: Support

    Provide suitable training, coaching, authority, resources or managerial guidance.

  5. 5

    Step 5: Decide

    Review progress and make a fair decision based on demonstrated improvement.

Check Yourself

Difficult Employee Management Checklist

Define the Problem

  • What specific behaviour or performance has created concern?
  • When did it occur?
  • How frequently has it happened?
  • What is the business or team impact?

Identify the Cause

  • Does the employee understand the expectation?
  • Does the employee have the required skills?
  • Is there a knowledge gap?
  • Does the employee have sufficient authority?
  • Is the workload manageable?
  • Is the employee suitable for the role?

Conduct the Conversation

  • Have factual examples been prepared?
  • Is the discussion being conducted privately?
  • Has the employee been allowed to respond?
  • Has the impact been explained clearly?

Create the Plan

  • Is the expected improvement specific?
  • Is it measurable?
  • Is the timeline clear?
  • Is suitable support available?
  • Are review dates agreed?
  • Are the consequences understood?

Review and Decide

  • Has performance improved?
  • Has improvement remained consistent?
  • Has the support been effective?
  • Is further development reasonable?
  • Is a formal decision required?
Final Thoughts

Handling difficult employees requires more than repeated reminders or disciplinary warnings.

Managers must first understand whether the issue relates to attitude, skill, knowledge, unclear expectations or suitability for the role. The SIL video emphasises that difficult employee situations may have different underlying causes and that business leaders need a practical solution. Dr. Yogesh Pawar presents five pointers intended to help leaders handle these situations effectively.

A fair and effective approach should include five actions:

  1. 1Identify the real cause of the problem.
  2. 2Address the issue early and directly.
  3. 3Listen to the employee's perspective.
  4. 4Create a clear improvement plan.
  5. 5Review progress and take a fair decision.

Not every employee issue will end in separation. Some employees improve when expectations become clear. Others require training, coaching, better resources or a more suitable role.

However, when an employee repeatedly refuses to improve despite clarity, support and reasonable opportunity, the organisation must protect its customers, team and workplace standards.

Effective employee management requires both empathy and accountability.

Managers should support genuine improvement without allowing one unresolved situation to harm the wider organisation.

Frequently Asked Questions

Quick answers, before you go

A difficult employee may repeatedly miss deadlines, resist reasonable feedback, avoid responsibility, create workplace conflict or fail to meet expected performance and behaviour standards.

A manager should identify the specific issue, discuss it privately using factual examples, listen to the employee, define the required improvement, provide suitable support and review progress regularly.

A skill problem usually exists when the employee is willing but unable to perform. An attitude or willingness problem may exist when the employee has sufficient capability but repeatedly chooses not to meet the agreed standard.

Feedback should describe the specific behaviour, explain its impact, clarify the expected standard and allow the employee to share their perspective before agreeing on corrective action.

An improvement plan should include the performance concern, expected standard, measurable actions, support provided, review dates, completion timeline and consequences of insufficient improvement.

Training is appropriate when the performance issue results from a genuine knowledge or skill gap. Training may not resolve repeated unwillingness, negligence or deliberate non-compliance.

If the employee does not improve despite clear expectations, suitable support, reasonable time and regular feedback, the organisation may need to consider formal performance or disciplinary action in line with its policies.

Businesses can improve hiring by creating clear job descriptions, assessing technical and behavioural capability, checking references, discussing expectations honestly and using realistic role-based assessments.

Build a Stronger and More Accountable Team

Managing difficult employee situations requires clear expectations, constructive feedback, suitable capability development and consistent performance reviews.

SIL works with entrepreneurs and growing organisations to strengthen leadership capability, improve workforce accountability and build high-performing teams.