Old bosses can be valuable resources for new jobs, especially if you had a good working relationship and kept in contact. Rekindle the connection by finding a reason other than the job to get in touch. For example, “I saw in the newspaper that your company won a national award for your advertising campaign -- congratulations!”
Research the Position
If you hear about a job opening with a former boss, find out as much as possible about the position’s requirements. Contact the human resources office and request a job description, or, if the position is with a company you used to work for, get in touch with a former colleague and ask about the role. If your old boss is with a new company, do some research so you can talk intelligently about how you see yourself fitting in and benefitting the business.
Talk in Person
If it's geographically possible, and you had a friendly, personal working relationship with your former boss, call and invite her to lunch or for coffee. If you have a more formal business relationship, a personal phone call is your best bet. In either instance, say you're interested in catching up and are excited to hear there’s a job opening you might be qualified for. Your former boss’s response will give you an indication of your potential for the position. If the job is in someone else’s department, you might be referred to a different manager or director. If that happens, follow up with the appropriate person and say you were sent by your former boss.
Even if you stayed in touch with your boss, ask about how her career and family are doing and give her an overview of what you’ve been doing professionally since you last worked together. Describe new skills and experience you have, particularly traits that are necessary for the job you’re seeking. Note specific accomplishments and achievements that highlight the professional strides you’re making in your career, and give your former boss an updated resume that describes your most recent positions and responsibilities.
Ask for the Job
Tell your former boss why you're interested in the position and ask her what the company is looking for. Listen closely and match your abilities to the requirements of the job. Talk about how your experience will work for the company and reiterate how much you’d enjoy the opportunity to work with her again. Ask your boss if you meet the requirements, and if she’ll consider you for the job. She might have to consult others or conduct interviews, but her feedback will tell you if you’re a potential candidate. Thank your former boss for her time, ask when you should follow up, and send her a thank-you note after the meeting.