Holbeck College

Cognitive strategies for assertiveness

Published 23 November 2022. Written by Chris Worfolk.

Nervous woman talking to her boss

Many people want to be more assertive. In this article, we will look at a common example people find difficult: asking our boss for some time off.

Blocks to assertiveness

What might be difficult in this scenario?

The primary worry is probably that our boss will say no. Why is this scary? One of the most common reasons is the anticipated emotions: we may feel embarrassed, ashamed, disappointed, sad, or some other emotion that we would rather avoid. Therefore, to protect ourselves, we decide not to make the request.

Other reasons may play a part, too. We may be worried that our boss may become aggressive. Or maybe we are worried that our boss will be upset because it means extra work for them of re-arranging the schedule. Or that our boss saying no is saying something about our worth as a person: i.e. our boss will not give us the time off and that means they do not value us.

We may also worry about what it says about the future. We may think that if our boss says no and we do not stand our ground, that will show we are weak and it will be easier for our boss to walk over us in the future.

What can we do about it?

If we want to troubleshoot these feelings, a good first step is to explore what it is we are worried about. Are there any automatic thoughts cropping up? How would it feel if we made the request and our boss said no?

Once we understand why we are worried, we can explore the worry further.

If we are worried about anticipated emotions, we might ask ourselves how we will feel if we do not make the request at all. Chances are we will feel bad anyway. We might also ask ourselves if we can deal with those emotions even if they are unpleasant. Chances are that we can.

If we are worried about our boss's reaction to the situation, whether it is aggressive, annoyed or hurt, we can remind ourselves that we are not responsible for how other people feel. They are an adult and it is their responsibility to treat people with respect, process their emotions and sort out holiday requests.

If we are worried that we are setting a precedent for the future, we might consider what precedent we are setting if we do not make the request at all. Or we can remind ourselves that each situation is different and that our boss is likely to consider each on its merits. Especially as they may feel guilty for declining our previous request.

Focus on the benefits

Up until now, we have looked at potential worries and how we can combat them. But it is also important to consider the potential benefits of making the request.

If we do not make the request, we will not get the time off that we want. If we do make the request, we may also not get it. But it opens up the other possibility: our boss may say yes and we may get the time off!

It is worth remembering that being assertive is not the same as always getting what we want. But sometimes we do. And when we open ourselves up to the risk of getting hurt, we also open ourselves up to the possibility of getting what we want.


In this scenario, we have considered making a request for time off. But this situation can be applied to many others. Both identifying worries and putting them in perspective, and focusing on the potential gains, can make it easier for us to find the confidence to assert our needs. We may not always get our way, but by being assertive, we at least open up that possibility.