pushing for better work from someone who’s having a rough time, getting salespeople to get to the point, and more

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

1. How much should I push for better work from someone who’s having a rough time?

I supervise a promising person who has room (need, really) for improvement in some important areas, but we are in a sector that has been hugely impacted by all the USG directives and funding cuts.

When I hired Sage, they came highly recommended from a well-reputed partner organization that was cutting the entire department. I know from others who worked there that it the several months prior to the dissolution of the department were incredibly challenging and destabilizing. In the interview process, I noticed some things I’d want to work with Sage on but overall the rest of the hiring panel and I felt they were the best candidate for the role.

After just a few weeks of working together, my concerns from the interview process were borne out — nothing egregious but some ways I would want their approach to communication and attention to detail to improve. I was giving feedback on items as they came in, but preparing to have a bigger-picture conversation about it. Then the stop work orders came, it obviously was not the time to hold that conversation, and we both wound up getting laid off.

I’ve now been hired back and was able to hire Sage back for a more limited scope under a consultancy. I feel overall they are again the right person for the work, and I am glad to be able to get them some income and an active thing on their CV in this awful time, but still have the same concerns coming up around communication and elements of performance.

I’ve been trying coach as things come up, but haven’t had a macro conversation with them. They are still looking for full-time work and feeling financial and other pressures, especially as they have serious family support obligations. Our field is totally decimated and job prospects are slim. I really feel for Sage, who is passionate and hardworking and smart, and has clearly been cut down by the past years. It doesn’t seem like a good time to try to critique even in the spirit of helping someone grow. At the same time, they’ve expressed interest in mentorship, and I find myself annoyed by some of the repeated, if not huge, issues I’m seeing that make more work for me, especially when there are so many other good people now needing work in the space. And I don’t want to inadvertently hurt their confidence more with a constant trickle of small criticisms.

Is it worth a bigger check-in conversation now to share my concerns/requests for change, or better to keep addressing as issues come up and save a larger convo for a hopefully less fraught time when they are emotionally a bit more stable?

Have the bigger picture conversation now. It’s fine to address things piecemeal when they’re one-offs, but once it’s clear something is a pattern, you owe the person a “this is a pattern” conversation, since patterns are more concerning. Often managers assume employees will realize something is a pattern on their own and so it doesn’t need to be spelled out (you’re pointing similar things out over and over! surely they must see the pattern!) but very often, people don’t realize that issues they might have viewed as minor on their own add up to a more serious concern when viewed all together.

It’s a kindness to Sage to do that — not only because they’ve explicitly requested mentorship, but because this has the potential to influence how enthusiastic you are about keeping them on in the long-term (or giving them a full-time role if that possibility opens up), and it could influence their security in future jobs as well. You can do it in a supportive, rather than critical, way; approach it as collaborating on what will make the work better / what the work requires rather than “you are a failure,” but do talk about it.

2. How do I get salespeople to get to the point?

I’m on the receiving end of a lot of sales pitches both in my paid job and as a person who has influence on decisions in volunteer organizations, sometimes officially and sometimes not. The sales folks all seem to follow the same pattern or script that I’m really uninterested in sitting through/participating in. Why do vendors do this to the rest of us? Is there anything I can do to cut through all of that to get to what I want to know about whether or not I’m interested in whatever it is that they are selling? I don’t need a song and dance with a bunch of boring lead-up, I just want the nitty-gritty about how what you do could benefit my organization.

You definitely don’t need to let the salesperson control how they’re using your time! It’s fine to jump in right at the start and say, “I only have a few minutes and the things I’m most interested in knowing are XYZ.” Or, “Before we go any further, can you tell me X? It doesn’t make sense to continue if we’re not aligned there.” If they avoid answering direct questions like that and try to stick to their spiel anyway, interject again and say, “It really doesn’t make sense for us to talk before we cover XYZ so can we talk about that first?”

Good salespeople will tailor their approach if you make boundaries like that clear. Bad ones won’t, and at that point you should feel free to say it doesn’t sound like it will make sense for your org and end the conversation. (For that matter, you don’t need to talk to them at all, but it sounds like these are potentially people you’re interested in hearing at least a little from.)

As for why they do it, they’ve been trained that they make more sales with this approach. But you don’t need to lend them your time to do it.

Related:
how to deal with cold-calling salespeople who won’t take no for an answer

3. Did I lie by omission to my boss?

I was reading through your archives today and stumbled on this letter from someone whose assistant let them believe she had a key certification that she didn’t actually have. It brought to mind something that happened very early in my career I am now curious about. In that post, you advised that it was a pretty big deal that she didn’t correct a mistaken impression when it was central to the reason she was being hired. I am curious if you would say the same about my situation.

I went to university for a BSc and studied for four years but technically did not graduate because I was three science credits short of a BSc. I could either take a BA or do the extra three credits, and I (naively) told myself I would just take a course online, but never did. Fast forward a few years to when I applied for a job with a major bank, and as part of their application process it asked for post-secondary, where I put in the school and then ticked “did not graduate” instead of entering a graduation year. I get an interview, and the manager says, “I see you went to [school]?” and I said, “Yes.” He replied, “I really like to see that. A degree isn’t a requirement by any means as a teller, but what it shows me is that you’re someone who when you start something, you finish it” and he then moved on to discuss banking/teller stuff.

I ended up getting the job, and by the time I showed up for work a few weeks later post-background checks, he had bragged to everyone about how he found “a smart person with a [STEM field] degree” to join the team, so that ended up following me for years there despite me never actually confirming it to anyone.

Do you think I should have spoken up in the interview, despite the fact he made it clear it would impact my candidacy and the fact I had explicitly ticked “did not graduate” in their application? (If it matters, I’m now 10+ years at that bank and did eventually realize I was procrastinating going back for too long so got my BA in that field a few years ago.)

In the letter you linked, the person was hired specifically because she let people think she had a certification she didn’t actually have, and one that was key for the job. I suppose we could argue that you were hired specifically because your boss really liked your degree even though it wasn’t a job requirement, but they seem like two really different situations to me. What’s more, you were clear when you applied that you didn’t graduate; you weren’t trying to obfuscate.

I do think that ideally you would have spoken up in the interview and corrected his misimpression — but it can be hard to know how to handle that on the spot.

Once you started the job and he kept bragging about your degree, at that point you ideally would have clarified with something like, “I want to make sure you know I don’t actually have the degree yet; I’m three credits shy of it. I did check ‘did not graduate’ when I applied and I want to make sure there’s no confusion about that!” But also, your boss was being pretty weird and, either way, it’s a different situation than the one in the earlier letter.

4. I was blindsided when my director joined a performance meeting with me and my manager

I’m having some performance issues that have been addressed, and I have been implementing all feedback as soon as I receive it. My manager and I had a planned meeting today to go over the week’s progress and, as we were beginning, our team director joined. It was never mentioned beforehand that he would be joining, and my meeting went terribly because of my anxiety about the sudden addition. I feel like I should have been given some sort of heads-up, or am I incorrect in that thinking?

You’re not really entitled to a heads-up on that sort of thing, although thoughtful managers will give you one if they can. It’s also possible, though, that your manager didn’t know the director would be joining you until just before, or even that she figured it would stress you more if you had a lot of advance warning about it. I’d say it falls under “ideally you’d get a heads-up if possible, but it’s not outrageous if you don’t.”

5. How to address a hiring manager in a cover letter

I am a Gen X mother of several teenage children. My youngest is applying for various apprenticeships while in high school. His high school teachers have given him a list of companies who hire high school students. The list includes the name of the company, the name of a contact (for example, Jane Doe), and the email for each contact. The applicants are required to send their resume and a cover letter (generally an email, not an actual letter).

How do you address the individual to whom you are sending this email? Ms. Doe? Mrs. Doe? Miss Doe? I advised my child to address the email to Ms. Doe but worried that my advice may be outdated (as is my usage of two spaces behind a period of which I cannot let go) and he may be misgendering this contact. What advice would you give an applicant? If it would be any different, what if the contact’s name was listed as Sam Doe. Is that Samatha? Samuel?

Yep, Ms. Doe is correct. Mrs. and Miss both assume marital status; the point of Ms. is that it does not. So Ms. is the correct form unless you know for a fact that person you’re addressing prefers Mrs. or Miss. With gender-neutral names, it’s fine to use the full name (“Dear Sam Doe”) or just the first name on its own.

Related:
how should I address my interviewer in application emails?

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