Ask around

by Dale Davidson March 18, 2026

A funny stick figure image depicting a business person who is nervous about asking someone for help, but the person he asks for help is happy to answer the question. The scene shows a stick figure business person sweating and biting their nails in hesitation, holding a question mark sign. Across from them, another stick figure, depicted as a colleague or a mentor, is shown with a big, welcoming smile, holding up a 'Happy to Help!' sign. The nervous business person is surrounded by thought bubbles filled with imagined scary outcomes of asking for help, like a 'No!' explosion or a 'Question Too Silly' sign. In contrast, the helper's space is filled with positive symbols, like light bulbs and hearts, indicating their willingness and happiness to assist. The background is a simple office setting, with a desk and a computer, adding to the workplace context. The style is exaggerated and humorous, focusing on the contrast between the apprehension of the asker and the positive attitude of the responder.

A friend recently asked me how to respond to a part of a sub-contract related to cyber security.

The form was basically asking what, if any, safeguards he had in place to protect sensitive data.

He was afraid if he didn't answer correctly, he would lose his sub-contract/1099 opportunity.

I didn't know what to write down on the form, so I gave him my usual advice: ask the prime's sub-contract administrator.

The subk administrator's job is to make sure all this paperwork is in order, and in my experience, are usually helpful in answering esoteric paperwork questions.

Even for myself, I've found that the fear of looking stupid or the fear of losing a deal if I ask a dumb question is unfounded.

People love feeling smart and helping others. So if you ask someone for advice or help, they'll often give it it to you.

In general, if you don't know something and can't research the answer, ask around.

Want the full playbook? Check out Going 1099.