There are times where it makes sense to provide direct feedback and discuss a hard truth. There are also times where the answer doesn’t matter, and it is more helpful to provide the supportive role to get through tough times.

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When to be direct

First, the entrepreneur has to want to receive feedback. If they have been trying things that have not been working, it can be helpful to be more direct on suggesting a different path. Even when being direct, I find it is usually helpful to ask questions to go down that path together versus just directly saying what to do. Even in saying what to do, I find it far more productive to share specific past experiences that can be discussed instead of hypothetical situations. This may not be what the person wants to hear, but in the right frame of mind can help sharpen their thinking. I find you can also be more direct when you have already built a trusted relationship with the other person and they believe you have their best interests in mind.

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When to be supportive

There are times when the entrepreneur is emotionally drained, and just needs someone to be a cheerleader or ear to listen. In these situations it is often more productive to listen and encourage. Entrepreneurship is a tough journey; don’t be afraid to allow some time/space to reflect and make decisions. Being supportive can give them the confidence and clarity to move forward.

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Pay close attention to who you are speaking with, the relationship you have, and the situation they are in. There are times to be direct on a difficult topic as well as times to just listen and encourage (for anyone married you understand!). Be observant and apply the right dialogue to each circumstance to help move things in a positive direction.

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