When I dress up in a suit, I often wear a pocket square. It’s something different. A flash of colour captures people’s attention, to stand out and be a little bit more memorable.

The key to pulling off a good pocket square is to make sure it compliments the rest of the outfit. If the colour or pattern clashes with the shirt, tie, or jacket, it can be jarring. The entire outfit may look slightly awkward – like there’s something wrong. If people perceive something wrong with my appearance, they will think there’s something not quite right about me. I become memorable for the wrong reasons. As a result, the trust and rapport I can build is compromised.

The reality is that just because my pocket square may be a poor choice, it doesn’t mean that the rest of the outfit is terrible. It doesn’t mean I should change my suit, shirt or shoes. It doesn’t mean I should abandon pocket squares as clothing accessories altogether. It certainly doesn’t mean I’m a lousy person or leader. It simply means I should make a small adjustment and change my pocket square, so it complements the outfit.

Suit pocket square

In a similar way, when we find ourselves struggling in one particular area of our work and leadership, it doesn’t mean we are a failure, that we are no good, and that we should throw in the towel. Yet this is often where our mind goes when we ask ourselves the ‘Am I good enough?’ question. When we ask ourselves this question, fear erodes our confidence and we are tempted to throw in the leadership towel altogether.

That’s unnecessary. We simply need to make a small adjustment to the question.


Fear operates in the macro. Yet we take control in the micro.

The “Am I good enough?” question is general in nature and therefore operates at the macro-level. Because the question is so general, we apply it to our whole selves. Not just our skills and abilities – those things that triggered the question in the first place – but our character and identity as well. Fear operates at this macro level. When we begin to worry we aren’t good enough at a thing, thinking at the macro level makes us fear we aren’t good at anything.

So often it is our ability to employ a specific skill or ability in a specific situation that prompts us to ask the “Am I good enough?” question. Even though the catalyst to question ourselves may be specific, we ask ourselves a general question. In so doing we shift our thinking from specific and micro to general and macro.

If we are to take control of our fear and limit it from eroding our sense of self and our confidence, we need to avoid this shift. If the catalyst to question ourselves is specific, we need to answer specifically. We need to stay at the micro level.


To avoid shifting from micro to macro in our thinking, we need to reframe the questions that we ask. If we ask general questions, we get general answers. If we are more specific in our questions, we inspire specific answers.

The easiest way to reframe the ‘Am I good enough?’ question is to simply add a two-letter word at the end. That word is ‘to.’ Thus, the question becomes, ‘Am I good enough to…’ You get to finish the question by inserting the specific skill, ability, or behaviour that is relevant to the specific situation you find yourself in.

Rather than asking whether you are good enough as a leader and as a person, you ask:

  • Am I good enough to deliver a presentation confidently to the board?
  • Am I good enough to resolve this conflict in my team?
  • Am I good enough to negotiate the terms of this deal?

By adding ‘to’ and reframing the question in this way, we focus our thinking on our capability. We separate ourselves from the specific skills, abilities, and behaviours in question, creating what is called psychological distance. This allows us to make more objective assessments rather than subjective fear-riddled ones.

We can take this one step further by adding ‘yet’, ‘right now’, or ‘in this unique situation’ to the question. The more specific we make it, the more distance we create between our core selves and our potential shortfalls. Even if we decide no we aren’t good enough yet, it means we aren’t questioning our identity and the rest of the good leadership work we are doing. Additionally, it provides mental scope for us to get good enough in the future.

When we focus on our specific skills and abilities in a given situation, it also allows us to more easily identify capability gaps that we can address. Once identified, we can develop a plan to upskill in these areas. If we decide our negotiation skills aren’t good enough, we can easily develop a plan to improve our negotiation skills. Answering the specific question, ‘How can I develop negotiation skills for the upcoming deal?’ is much easier than answering the general question of ‘How do I become a good leader?’

We may never be able to stop ourselves from asking the ‘Am I good enough?’ question. But by leaving the question general, it’s harder to answer, it erodes our sense of self and therefore our confidence. By making it specific, we empower ourselves to take action and build our confidence.