A reader writes:
I just started a new job at a nonprofit organization, taking over for a beloved employee who was here for 20 years and is still a big part of our organization’s community.
He was very successful, but I am coming across a lot of pretty substantial errors he made. A good example is a grant proposal in which he basically ignored the guidelines, although we got the grant anyway. Now I am working on this year’s proposal for that grant; I have to follow the guidelines and I think I really ought to tell my boss about the discrepancies and about what I am doing differently this year. But I am hesitant to do so, because this would be about my 10th time alerting her to something I came across that he kind of messed up. I don’t want to seem as though we have a pattern of “now look at THIS thing Joe screwed up,” and really I don’t want to speak ill of him at all, especially when there never have been negative consequences (such as missing out on a grant). But she is the executive director and she should be aware of everything, especially when I am doing things very differently than he did. Any advice on how to navigate this?
Well, when you say he was “very successful,” what exactly does that mean? If it means that he achieved unusually good results, then it’s important to keep that mind when you’re assessing the mistakes you’re coming across. The grant application might be a good example of this — he didn’t follow the guidelines, but the organization got the grant anyway, so it seems like he did something right. Sure, it’s possible that that was a fluke, but if the outcome was successful, you’re probably going to have a hard time convincing people that it was a problem that he didn’t follow the guidelines. (And yes, of course it’s possible that if he had a habit of not following grant guidelines, there were other grants he applied for that the organization didn’t get … but it’s also possible that he was good enough at the job that he knew what could be ignored and what really mattered.)
Is it possible that the other mistakes you’re finding fit this profile? If something is technically a mistake or not a best practice but he got fantastic results anyway, it might be worth considering that he knew other, different ways of being effective.
Of course, maybe that’s not the case at all and the grant application example is just misleading me. If in fact you’re uncovering things that were genuinely messed up — things where the long-term results were not as good as they could have been because of his mistakes — then that’s different. But start by making sure that you’re really being objective about whether that’s the situation or not.
Either way, it’s not uncommon that you’d do things a bit different from your predecessor. So when you feel that you need to bring something to your manager’s attention — whether it’s because there’s a problem he caused that she needs to know about or because you want her to understand why you’re handling something differently — approach it as simply keeping your manager in the loop. For example: “I wanted to let you know that I’m doing the grant proposal a little differently than it was done in the past, because I’ve found that they’ll sometimes reject you if you don’t follow their guidelines to a T.” You could even ask, “I noticed that Joe didn’t strictly follow them, and I wonder if that’s because we had a more informal relationship with this foundation or whether there’s any other context like that that I should know about?”
As long as you’re not presenting this stuff in a tone of “here’s another thing I’ve uncovered,” your manager isn’t likely to think you’re being unnecessarily hard on Joe.
But what you don’t want is to find yourself in a situation where your predecessor was successful precisely because he knew when he could and couldn’t break the rules and then end up coming across yourself as someone who doesn’t have that nuanced level of understanding. So be sure that you’re assessing what you’re finding not just as “is this done correctly?” but rather as “did this get good long-term results for the organization?”