Encouraging unsure employees

When employees doubt their abilities, it might be interpreted as a sign of weakness but can be a question of preparation. They might be your strongest employees. How you as the leader encourage them to take the assignment makes all the difference. Here are three possible responses by the leader:

  1. Full encouragement: OF COURSE YOU CAN DO IT! Don’t even doubt! Just get on with it!
  2. Support, often in private: I know it’s a difficult task, but I will help you succeed in it. The organization will give its support and you’ll get the help that you need.
  3. Apparent agreement: You have a point. Perhaps I should ask someone else. As you engage in the discussion, you may find out what the real worry is and you may overcome it.

Depending on the situation, each one of those three types of responses may cause your employee to perform at their best and get the job done wonderfully.

You choose your type of answer based on the personality of the person you are dealing with, your common history of tasks and successes and failures, and the moment. Think of how YOU would like to receive encouragement, and do the same to your team.


It’s easy to think that unsure employees are weak employees, but many times it’s the opposite. The unsure ones just need some encouragement and they’ll be your best employees.

As a leader, you’re in charge and responsible for making all employees perform at their best. When you delegate a task to somebody who’s unsure and they say, “Boss, I’m not so sure. I’m not sure I can do it. I’m not sure I’m the right guy.” Then how you respond makes all the difference in what the outcome is.

Here I have three particular ways of responding. There are situations where you’re going to say, “Of course, you can do it. You are our champion. You will do it. Don’t even doubt it. Just go for it.” You make it very vocal and you say it perhaps in front of the whole team. You make it obvious that there’s no question about the abilities of the person and no doubt will be tolerated and they’ll just push for it. That’s one method.

The other method is a softer one where you say, “Okay, I’m hearing you.” Maybe you say it in a one-on-one setting and not in the group. You say, “Okay, I understand that you have your doubts and maybe you haven’t done it before but I believe in you. I trust you. I know you are good. I know you can do this. I will give my support. The organization will give its support and you’ll get the help that you need.” Then you encourage them in this way. But it’s a softer encouragement and typically done one-on-one, not in a group.

The third way is also very useful in certain situations. When you’re trying to delegate the tasks and the employee says, “Boss, I’m not sure.” Then you say, “Yeah, maybe you do have a point. Maybe you haven’t done it before. Maybe you lack something.” You engage in that discussion and you acknowledge the doubt that the person is having. But as you do that and you engage in the discussion, you may actually find out what the real worry is and you may overcome it. By giving this apparent agreement to the doubt of the person, you actually figure out a way to manage around it and get the person to do it.

Whichever of these methods you choose, the goal is to get the person to feel trusted – feel that you really believe in the person and to know that it’s okay to do your best, it’s okay to try. And if there’s a failure, the whole group will learn together. Nobody will get killed for a failure, but you need to encourage everybody to do their best because they will do their best. And in most cases there will be no failure at all.

As I said, it’s very important for the leader to encourage the people to do things and encourage them even though they may initially be unsure.

Iceberg and fish

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