Helping Employees Overcome Self-Doubt

Have you ever worked with someone who is capable of doing the job but hesitates whenever a new responsibility comes along? They may have the experience, knowledge and skills, yet still question whether they are good enough. When offered an opportunity to lead a project, present an idea or take on a more challenging assignment, their first response might be, “I’m not sure I can do it.”

As managers, we sometimes respond with encouragement: “Don’t worry, you can do it. Just be confident.” Although well-intended, reassurance alone may not address what is making the employee uncertain.

Self-doubt can affect anyone, including experienced employees and those who have performed well in the past. Understanding what lies behind that uncertainty is often the first step towards helping someone move forward.

Recognising Self-Doubt in Employees

Self-doubt occurs when someone questions their own abilities, judgement or readiness to handle a situation. It may become more noticeable when employees face unfamiliar responsibilities, higher expectations or situations where they feel their performance will be closely evaluated.

For example, an experienced salesperson may be comfortable managing existing customers but hesitate when asked to present a proposal to senior decision-makers. A newly promoted supervisor may know the team’s work very well but feel uncertain about giving direction to former colleagues. These situations involve different challenges, yet both employees may question whether they are ready.

Some possible signs include:

• Hesitation when taking on new responsibilities. The employee may repeatedly question whether they have the necessary experience or ability.
• Frequent requests for reassurance. They may seek repeated confirmation before making decisions that are normally within their responsibility.
• Reluctance to share ideas. The employee may hold back during discussions because they are concerned about being wrong or criticised.
• Excessive checking or preparation. They may spend more time than necessary reviewing work because they worry about making mistakes.

However, these behaviours do not automatically mean an employee lacks confidence. Someone who remains quiet during meetings may prefer to listen before contributing. An employee who checks their work carefully may simply be thorough. Hesitation may also reflect unclear instructions, limited authority or a genuine lack of experience. Managers need to understand the circumstances before drawing conclusions.

A useful starting question is: “I’ve noticed you’ve been hesitant about taking on this assignment. What’s concerning you most?”. The answer may reveal something quite different from what the manager initially assumed.

Building Self-Trust to Overcome Self-Doubt

Confidence develops when people begin to trust their ability to handle situations, make decisions and learn from experience. For employees experiencing self-doubt, this trust may be weakened by past setbacks, unfamiliar expectations or fear of disappointing others. Managers can help by encouraging employees to examine their experiences more realistically.

Consider an employee who has been asked to coordinate a cross-departmental project for the first time. The employee says, “I’ve never managed something like this before. I’m worried I won’t be able to handle everyone.”

Instead of immediately replying, “Of course you can!”, the manager could ask: “Which part of coordinating the project concerns you most?”. The employee may explain that they are comfortable organising tasks but unsure how to handle disagreements between departments. Now the manager has a clearer understanding of the concern.

The conversation can focus on the employee’s existing strengths, relevant past experiences and areas where additional guidance may be needed. The employee may still feel uncertain, but they can begin to see the challenge more clearly. Self-trust grows when employees have opportunities to test their abilities, learn from experience and recognise the progress they are making.

Supporting Employees Through a Coaching Approach

Managers have an important role in helping employees work through self-doubt. The way they respond can either encourage employees to speak openly or make them more reluctant to share their concerns.

Here are four practical approaches.

1. Understand Before Offering Advice

When an employee expresses uncertainty, resist the urge to provide an immediate solution. Ask what is making the situation difficult. Is the employee concerned about making mistakes? Do they lack experience? Are expectations unclear? Have they received discouraging feedback in the past?

Different concerns require different forms of support. Listening carefully helps the manager understand what the employee actually needs.

2. Help Employees Recognise Their Strengths

People experiencing self-doubt may overlook experiences that demonstrate their abilities. Managers can help them reflect on relevant achievements. For example: “You mentioned that you’re worried about handling difficult stakeholders. How did you manage the disagreement between the sales and operations teams last month?”

This allows the employee to recall a specific situation where they handled a similar challenge. The purpose is to help them recognise evidence of their capability. Managers should also acknowledge genuine development needs. An employee can have useful strengths and still require additional preparation.

3. Make the Challenge More Manageable

Sometimes employees lose confidence because the responsibility feels too large or unfamiliar. Breaking the assignment into smaller steps can help.

An employee preparing to lead their first customer presentation might begin by presenting one section, receiving feedback and gradually taking responsibility for the full discussion. A new supervisor might start by conducting individual check-ins before facilitating a larger team meeting. These opportunities allow employees to build experience at a manageable pace.

4. Provide Support Without Taking Over

When employees appear uncertain, managers may be tempted to step in and complete the work themselves. Although this may solve the immediate problem, it can reduce opportunities for the employee to gain experience.

A more useful approach is to agree on what the employee will handle independently and where support will be available. For example, a manager might say: “Why don’t you prepare the first proposal? We can review it together before you present it to the customer.”

The employee remains responsible for the task while knowing that guidance is available.

Coaching Questions to Help Employees Work Through Self-Doubt

Good coaching questions encourage employees to examine their concerns, recognise their capabilities and identify practical next steps. Managers do not need a long list of questions during every conversation. Choose those that fit the employee’s situation and allow enough time for reflection.

Understanding the Concern

1. “What is making you feel uncertain about this situation?”
2. “Which part of the responsibility concerns you most?”

Recognising Existing Strengths

3. “When have you handled something similar successfully?”
4. “What strengths or experience could help you here?”

Exploring Possibilities

5. “What would help you feel better prepared?”
6. “What support or guidance would be useful?”

Taking the Next Step

7. “What’s one manageable step you could take to get started?”
8. “How will you know you’re making progress?”

These questions are intended to guide a conversation, rather than become a checklist.

An employee may need time to think, and some conversations may reveal practical obstacles that require the manager’s attention. The manager should remain open to both possibilities.

From Self-Doubt to Taking Action

Helping employees overcome self-doubt requires more than a reassuring conversation. They need opportunities to apply what they have discussed and gradually build confidence through experience.

Consider a Sales Executive who is reluctant to approach a major prospective customer. The salesperson has handled smaller accounts successfully but worries about meeting a larger customer’s expectations. After discussing the concern, the sales manager discovers that the salesperson is particularly uncomfortable dealing with multiple decision-makers.

Instead of asking the salesperson to manage the entire opportunity immediately, they agree on a practical starting point. The salesperson will research the customer’s business, identify the likely stakeholders and prepare questions for an initial meeting. The manager will review the preparation and provide guidance before the customer discussion. Afterwards, they will reflect on what happened and what the salesperson could improve.

The salesperson may still feel nervous during the meeting. That does not mean the coaching has failed. What matters is whether the salesperson is beginning to take appropriate action, develop relevant skills and become more comfortable handling the responsibility. Over time, these experiences can provide a stronger foundation for confidence.

Conclusion

Self-doubt is something many employees experience, particularly when facing unfamiliar challenges or greater responsibilities. As managers, we may be tempted to encourage them with positive words or remind them of their past achievements.

While encouragement can help, employees also need the opportunity to understand their concerns, recognise their strengths and develop the capabilities required to move forward. A thoughtful coaching conversation can help them see their situation more clearly. Practical assignments, appropriate support and regular reflection can then help them build confidence through experience.

Managers should also recognise that persistent self-doubt may involve concerns beyond what a workplace coaching conversation can resolve. In such situations, sensitivity and appropriate additional support matter.

The next time an employee tells you, “I’m not sure I can do this,” consider asking: “What is making this difficult for you, and what would help you take the first step?“. Their answer may tell you more about the support they need than another reminder to be confident.