I'm scared of hiring my first employee, an email squabble, and more (2024)

It’s five answers to five questions. Here we go…

1. Was I wrong in this email squabble?

I have a question about a little email tussel I recently ended up in. I am a contractor for a professional services agency and was working on a project for a client. Part of my work includes using a third party to upload documents to a publishing site. This was my first time working with the third party in any capacity. Last week, I sent the required documents to the contact at the service (“Pat”) and asked for an update when the content was uploaded. They did acknowledge the email and said they would send an update once it was completed.

To make a long story short, Pat helped with uploading documents from a different (but related) project, and when I asked about the original request, I was met with pushback about never receiving documents related to the project (despite the email chain being named after the project). It was so blatantly wrong and strange that I began questioning myself, but a coworker also on the email chain acknowledged that Pat seemed disorganized, so I surmised that it must not be me. I sent the documents again to Pat two more times before the weekend, and each time was either ignored or they said that they did not receive anything from me when I asked for an update.

Eventually, on Monday morning, the client mentioned that they still did not see the documents uploaded. I reached out to Pat for an update, to which they said again that they never received anything from me and to send a new email with the attachments. I did as requested and included screenshots of all the emails I had sent to Pat the previous week with a note “in case they wanted to investigate.” It felt a little petty as I was sending it, but I was annoyed.

Pat replied back, “Obviously I am getting your emails but I never got one related to (Project name). Make sure you’re sending to the right recipient.”

Once they had confirmed completion of the upload, I sent them a screenshot of my original email including the “to” line showing that it did indeed go to them and said I appreciated their help. Pat’s tune changed significantly after that, and while they didn’t apologize, they said they would look into it more and they were glad we were able to complete the project.

If it matters, I am a woman in my late 20s and from what I can tell, Pat is a man in probably his 50s. While I felt petty sending screenshots of everything, this seemed like a very strange situation (could he not go back to the original email?) and I didn’t feel like being pushed around or apologizing for something I didn’t do. My director and coworker were also cc’d on all of the communications. Would love your insight on if I handled this appropriately!

Pat’s the problem, not you.

It’s one thing to miss an email, but before chastising someone to “make sure you’re sending to the right recipient,” you’d think he’d first go back and confirm that he really didn’t get the email.

I do think it was overkill on your side to send screenshots of all the emails you’d sent Pat the previous week, rather than just the one in question. Sending just the one in question probably would have solved the whole thing and not dragged out the interaction quite as much.

But again, you weren’t the problem.

2. I’m about to hire my first employee and I’m freaking out

I set up a nonprofit organization last year which has grown beyond the point where I can keep delivering everything on my own. There are two other directors on the board but they are both employed elsewhere, so other than quarterly board meetings I do the vast majority of the work. Thanks to grant funding and trading income, the organization can afford to employ someone part-time to take over some of the core delivery so that some of my time is freed up to work on developing and growing the business, and making it sustainable for the long term.

I’ve been through the recruitment process, I’ve got a preferred candidate and a second choice, interviews are done, references contacted, offer letter and contract (we’re in the UK) are all drafted with guidance from a HR consultant … and I am absolutely terrified of actually calling the candidate and making the offer.

I think I’m paralyzed by the weight of responsibility that being someone’s manager and employer involves. I have literally never been anyone’s supervisor or manager before. I’ve had a lot of managers, good and bad, and have a fairly good idea of what kind of manager I want to be, but the terror is getting in the way.

If I don’t hire this person, or at least A person, I will not be able to sustain the company. There’s so much potential and so much demand for what we offer, and the only way to realise that is to employ someone who is not me to do some of it. So why am I so scared? And what can I do? I told the applicants I’d make a decision last week. I’ve already updated them that there’s a delay, but I really do need to finalize the hiring decision this week, not least because I need them in role asap so that I can shift my focus to a large and important project starting in mid-July (which will involve hiring more staff).

This is hard to answer without knowing exactly what you’re afraid of, but if it’s really just the weight of being someone’s boss … well, honestly, you’re going to mess it up at some point, probably multiple points, because that’s what we all do. You’re not going to be perfect. You’re going to learn on the job, and it’s sometimes going to be messy. (This pep talk sucks, sorry!) But this is how you learn to do it. As long as you commit to a few basic principles at the outset — clear communication, getting aligned on expected outcomes, a coaching mentality, a bias toward transparency, and a view of the other person as a partner rather than a peon — you’re going to be fine. The other person is going to be fine. You’ll both figure it out. Commit to talking about it if that’s not happening.

But also, consider some training on how to manage people effectively — the nitty-gritty, “what does this look like day-to-day” of management. (I have conveniently written a book about exactly that and it’s even targeted toward nonprofit managers, so here you go.)

Also! Make sure you have a clear role description and list of outcomes the person will be responsible for achieving, and a training plan (at least an organized outline) for what you’ll need to cover with them to get them acclimated and equipped to contribute. You’ll feel better if you have those things. But from there … all you can really do is jump in.

Related:
advice for new managers

3. Interviewer asked, “What would your detractors say about you?”

I’ve interviewed twice for the same agency over the span of several years. Both interviews included the same question: What would your detractors say about you?

The question has actually turned me off a bit from working for that agency. How do you advise answering a question like that?

It’s really just the old “what are your greatest weaknesses?” in disguise — or at least you can answer it that way. If you’ve had 360 feedback and you’re comfortable talking about something from that, you can do that and cite it as the source. But either way, the framing should be the same as for the “weaknesses” question — something you’re not as strong in combined with what you’ve done/are doing to work on it.

4. Should I say my coworker is the reason I’m leaving?

I am planning to jump ship from my current position due to my hostile coworker. She belittles me and tokenizes my identity on a daily basis and reacts poorly to both constructive feedback on her poor judgement for managing relationships with outside community partners and simple requests such as turning off her phone volume in a shared office space or using Teams for work-related discussion instead of text. She is also a terrible writer (a key job requirement), so I end up having to rewrite much of her work.

I am 100% leaving this position due to her conduct and I feel it’s important to tell leadership. I already discussed my coworker’s behavior with my manager and there has been little change. Leadership’s main concern is finishing the project we were hired to implement. My coworker’s and my positions are temporary, project-based positions, so it is highly unlikely this coworker would stay on. Would I look like the petty, aggrieved employee for sharing my true reasons for leaving or should I keep it neutral and say, “I found a position that’s a better fit for my career goals”?

There’s no point in getting into a lengthy dissection of your coworker’s behavior, but if your manager is the one asking, there’s no reason you can’t say, “It’s no secret that I’ve found Jane very difficult to work with.” If the person asking is higher up, you can share, “I’ve encountered a lot of difficulties working with Jane, which I’ve shared with Manager. I don’t want to rehash it at this point, but it ended up seeming like the right choice to simply move on.” I wouldn’t get into it beyond that — you’re leaving, and that gives them enough bread crumbs to follow if they care to.

One exception: If I’m understanding correctly that Jane subjected you to harassment or discrimination based on your race, religion, sexual orientation, or other protected class, you should spell that out, along with the fact that your boss didn’t act on it when you reported it (that part is crucial). They need to hear that, even if they don’t care about the rest of it.

5. How to raise your rates as a freelancer

Is there a good way to raise your freelancer rates with your existing clients? I haven’t raised my rates in a long time because of The Fear of never getting any work ever again. I am now pretty sure that I am undercharging. My instincts are all saying “only raise by a really small amount!” “Give them three months notice before the rate rises kick in!” But those are the same instincts that led me to not raise my rates for years so I am not sure I should trust them!

Also, do I need to give a reason for raising my rates? Or do I just state that they are going up? I was planning to say, “Due to rising costs, I will need to raise my rates from 1 September to xxx/hour or xxx/day.” As I am a freelancer writer, they may ask what costs. But, honestly, the price of coffee, my most important business expense, has shot up so I am telling the truth!

In general, you shouldn’t raise your rates only by a small amount out of fear; you want to raise them to a level that’s in line with the market and which means you won’t be undercharging. At the same time, freelancers also have to be realistic about clients’ budgets and what price point they’ll accept, and how willing you are to potentially lose some clients over a price hike. (Ideally, you’d be willing to lose some, since it will open up space for clients who can pay what your work is worth — but obviously that gets into what you can and can’t afford, how much risk tolerance you have, and how large of an increase we’re talking about.) It’s more art than science.

You don’t need to give a reason and I wouldn’t say it’s “due to rising costs.” You can just let people know they’re increasing and to what. Giving two to three months notice is good practice. You can also note that you haven’t raised your rates in the X years you’ve worked together.