Dear J.T. & Dale: When I started my working life, I was drawn to small, entrepreneurial companies. Now that I’m older and have a family, I find myself with yet another startup that doesn’t provide benefits, and with an otherwise brilliant owner who just doesn’t make good business decisions. I’m at a point in my life when I would welcome the stability and benefits of a large corporation, but I feel I’ve “typecast” myself. How do I make the leap from a small organization to a larger corporate environment? — Maya

J.T.: Wow — can I relate to this. I did the very same thing early in my career.

Dale: And so you know that Maya’s concerns are not unfounded. Most corporate HR people have plenty of applicants to choose from, and have little incentive to take risks in hiring. The magic word is “fit,” and when they look at Maya they’ll have to wonder if she can handle the rigors of life in a big company. And they’re right to wonder — both types of employment have pressures, but not the same pressures.

J.T.: Therefore, Maya, you have to work to avoid being typecast. Large companies want to know that you work well in teams, that you are comfortable with office operations and processes, and so on. Consider putting together a transferable skills resume, one that showcases these elements of your skills and abilities. Also, be sure your communication, interview skills and attire match the environment you are headed into. “Conservative” and “professional” should be your themes. I’d suggest reaching out to a colleague who works in a corporate setting and seeking feedback. Ask if he or she will role-play with you to make sure your responses to the typical questions sound right. (”Why do you want to work for a firm like ours?” “How do you see yourself dealing with the structure we have in place?”)

Dale: But my guess is that you’ll get to actual interviews only by sidestepping the big stacks of competitive resumes. One advantage of having worked with all those startups is that you have a large network of former colleagues. While most of them might still work in smaller companies, you can go to them with your list of target employers and ask if they have connections. When you come in via an insider, you come in with the credibility you need for a great, big company to take a chance on you.