Tough Questions

You are always going to be asked tough questions that you may not want to answer or genuinely don’t have an answer for at that moment in time. Learn how to deal with these situations effectively and with confidence.


Investors love to ask you tough questions. They like to see how you reply to them and how you handle those tough questions. And one of the toughest questions that you will get is the question that you just don’t know the answer to, and it’s okay to say, “I don’t know.” It’s all in the tone of voice. You don’t want to just say, “Well, I don’t know!” That’s not confidence. But you can say, “Well, I don’t know, I will get you an answer by tomorrow.” So that gives you a perfect reason for follow-up. Sometimes when you don’t know the answer, it’s a perfect opportunity to do what they teach you in media training which is build a bridge to what you do know. Say, “I don’t know, but what I can tell you is,” and then you tell them what you can tell them. It’s as simple as that. Build a bridge to something you do know so that you just don’t stop with “I don’t know.” You might find that it actually directs the conversation into an easier area for you to respond to. And speaking of tough questions, I’ve compiled almost 40 of the toughest questions that you get from investors. I encourage all of you to look in the collateral here, and choose some of those questions that you may not be comfortable answering, and work on the answer.

Suggested Readings

Founders School || Powerful Presentations: Mastering Q&A || Tough Questions || Impact Guide (PDF).

Questions for You

When I do not know the answer to a question, how do I maintain credibility with my response?

Do I have a bridge ready to use when answering tough questions? Which ones work best for me?

How is the tone of my voice when answering a tough question?

What is happening with my facial expressions when answering a tough question?

Tools and exercises

Below, is a list of some of the toughest questions received by entrepreneurs from angel and venture capital investors. Feel free to take any or all of them and prepare yourself by rehearsing your answers in much the same way you rehearse your presentation. For those questions you do not know the answer for, simply say so and get back to them with an answer as follow up. It is quite human to NOT have all of the answers all of the time.

Tough Questions List (PDF)