Q: I work for a small company that doesn't have a lot of formal processes. My boss is retiring, and, while I know he has been happy with my work, there's no formal documentation of my performance. I'm concerned that my new boss won't have a good starting point to base her opinion of me on. What can I do?
A: Tell your own story, and make it easy for your current boss to provide his perspective.
The inner game
A lot of the effort for preparing for a new boss will be on you, so accept that and don't let it frustrate you. The fact is, you're not going to change your boss at this point. If you've asked for feedback and not received it, let it go, and engineer a last chance that will successfully get you what you need.
One way to imagine this is to think of a series of headlines about yourself. What would you like the topics to be? Are they about your knowledge? Determination? Collaborative skills? Whatever they are, take time to list them. Likewise, if you were envisioning a curriculum for your professional self-improvement, what areas would you want it to cover?
Narrow these lists to the most important, using criteria that are relevant to you. For example, if you are hoping for a promotion, move to a different area, learning new skills, etc., your goals will affect your priorities.
Taking your top tier (and maybe secondary ones, too), document your successes and opportunities for improvement in each. Be specific about what you did, how it worked out, the value to your company, and lessons learned. Try putting them on a timeline to bring your story to life; it's also an effective way to show promotions and informal increases in responsibility.
Finally, consider doing an informal "360" review. Ask for feedback from colleagues, direct reports and internal clients. Make it easy and safe, so that people will be comfortable giving critiques and won't feel burdened by the request.
The outer game
Once you've prepared your history, schedule time with your current boss. Establish a goal of getting his feedback on the material you've pulled together, as well as his endorsement of your strengths and contributions.