How do I build trust with a client who’s had a negative past experience?
First, find out the history behind their opinion. Is it based on a prior (negative) experience with your organization? Is it because they favor another firm? Is it based on second-hand information they received? Once you understand the reasons, it will be easier to decide on a strategy. It’s better to put things on the table and talk openly about the basis for their opinions than keep quiet and guess why they are upset.
For example, if they had a bad experience with you five or ten years ago, you can talk frankly about how the firm has changed over the last ten years and how they would be working with an entirely new team. If there has been a service or quality failure in the recent past, you may need to offer guarantees going forward and have your senior management get involved in the discussions. If there is a personality conflict, you will have to deal with that forthrightly, potentially by changing some key players on your side. Also, see if there is another member of the client’s management team—someone who is very positive about your company—who could be the one to influence this person. When a trusted colleague says “We should give them another chance” it’s more convincing than you saying the same thing.
Remember that you earn trust with someone like this in the same way that you earn trust with any client: One small step at a time, not through broad pronouncements.