I bombed in an interview I asked for, employee wants to skip lunch and leave early every day, and more

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

1. I bombed in an interview I asked for

I’m in a customer-facing role at a large company, and I’m interested in advancing into a management role. I’ve held management positions in the past, but happily took a “step back” in this job because it’s a great company, good job in itself, and it supported a family-related interstate move.

I recently asked my grand-boss for a 1-1 meeting to discuss advancement opportunities, and he was very supportive of the conversation. Knowing this was effectively a job interview, I came prepared to discuss staffing, training, expectations, client engagement, priorities and goal setting, etc. Unfortunately, what my grand-boss wanted to discuss was systems, metrics, repeatability — more of the systems-thinking side of the job than the human-thinking side of the job. And it’s a job that I tend to approach in a very human-thinking sort of way. That was reasonable of him, but I wasn’t remotely ready for that conversation, as I’d been very focused on the people side of it.

It wasn’t the worst professional conversation I’d ever had, but it was easily in the top three. He even left me with the advice “If you ask for a meeting like this, you really should prepare for it, which is impossibly embarrassing to hear. That he thought I needed that advice feels like I may as well have needed to hear “don’t drop your pants in front of the CEO. Of course I know that, but I’ve clearly made a terrible impression.

My gut reaction was that I’d blown any opportunity at advancement (and my current job is great, but it’s not a career). But I didn’t, exactly. Grand-boss left the door open, offering another shot at a “career development” call with him, suggesting we talk in a few weeks. He’s been gracious about the whole thing, even while reinforcing the message that the conversation itself we did have was completely unsuccessful in promoting my candidacy. (If I hear “you really should prepare…” again, I’ll probably die of shame.)

How do I recover from this? I doubt my aspirations will survive another disaster-meeting. I feel like I shouldn’t wait too long to reengage, but this has become the only interview I’ve ever been hesitant about. I normally delight in job interviews, but this was my worst interview failure ever, and I’m feeling bruised and full of self doubt. How do I approach the next round? Do I address my past failure as incorrect rather than absent preparations, or just let it go? Is it reasonable to stall for a month or two while I collect my thoughts and my confidence, or should I get back on the horse quickly? There’s no open position currently on the table, so it’s all about putting myself in position for when a seat opens up — which could be soon or could be well into the future.

I’m a big fan of just putting it out there, on the theory that if they don’t like your thought process on something like this, that might be a sign that they won’t like it on other things too, and better to just be transparent and figure out if that works for them or not. So I’d just be candid about what happened. And it doesn’t need to be a big deal (shouldn’t be, in fact). It can just be something like, “I want to be up-front with you that I’d prepared for a different conversation last time. I’d come prepared to talk about staffing, training, expectations, client engagement, priorities, and goal setting. I’m ready this time to talk about systems and metrics.” And then move on quickly — you don’t want it to sound like excuse-making, just quick context, and then move right into what you’re there to talk about. In fact, you could even could address it when you reach out to schedule the next meeting instead — as in, “When we talked, I’d prepared to talk about X — and I appreciate you refocusing me. This time I’m going to be prepared to talk about Y. Would the first week of May work for you?”

On the timing of the meeting, don’t stall — the sooner you have the second meeting, the sooner you can recover from the first. And you’ll show that you’re able to take criticism, incorporate it, and move right along without being rattled by it. (I mean, don’t reschedule so quickly that you don’t have time to thoroughly prepare — but don’t stall just because it feels awkward.)

2. Replying to the wrong optional emails on vacation

My colleague, “Sophie,” is on holiday. In our office, there is no expectation that staff should check their emails when on vacation but many people do. Sophie has been replying to emails, but only non-urgent or even trivial ones that could easily wait until she gets back. I also know that there are some more urgent requests she has received and not responded to (not necessarily labour intensive, some just need a confirmation from her).

Our manager is frustrated but doesn’t know what to do. She doesn’t want to encourage anyone to work while out of the office, but since Sophie is already taking the time to get work done, our manager would prefer she redirects her efforts.

Do you think it is worth even bringing it up? If so, how would you approach this?

I’d leave it alone. Any attempt to address it is going to undermine the idea that people aren’t expected to check email on vacation. At most, I suppose someone could reply to one of her non-urgent replies and say something like, “If you’re checking email, I’d love your thoughts on the message about X — but no pressure if you’d rather wait until you get back.” But even that is signaling that you want her to do work on vacation. And who knows, maybe she’s answering trivial emails because they’re an easy break for her brain, but she doesn’t want to deal with things that require more stress or more thought.

3. Two people giving notice at nearly the same time

I am hoping to get your perspective on how my colleague and I should handle giving our notices, when it looks like we are both going to be a leaving our professional services firm at nearly the same time.

We both work for a small company (<30 people) and have both been here for about five years, which is relatively long. We are both senior managers with some but not all overlapping responsibilities, and we both report directly to the CEO. It is likely that if only one of us was leaving, the other would assume most if not all of the other’s responsibilities, including taking on direct reports and client accounts.

We independently decided to search for new positions for various reasons, both personal and because of some concerns about the direction of our current employer. Not coincidentally, we are both good friends outside of work who are at similar stages of our careers and with similar family situations, work styles, and personalities. We are both nervous to tell our current boss we are leaving because he has taken resignations personally in the past and because we recognize the short-term disruption we will cause with our timing. We have already discussed with each other where all our work could be reassigned without overloading the team, as it has been a slow time for the past few months.

So, how do we handle giving our notice? Do we go one at a time and the first person pretends not to know about the second? Do we speak to our boss together even though our decisions were independent? What is the least hurtful way to break the news?

Don’t talk to your boss together; that’ll be weird and it will look like you coordinated more than you actually have. Hopefully you won’t get job offers on the exact same day or need to give notice on the exact same day, so whoever accepts an offer first will give notice first, making no mention of the other person. Then when the second person accepts an offer, they give their notice at that point and can say something like, “I know the timing isn’t ideal with Lorraine leaving as well, but I have some ideas for how to reassign work that might make the transition go more smoothly.”

If for some reason you both do end up having to give notice on the same day, you should still do it separately. In that case, whoever gets to go first (and thus sticks the other one with a more awkward conversation) should probably buy the other one several drinks.

4. Employee wants to skip lunch and leave early every day

I have an employee who often doesn’t eat lunch. He sometimes stays at his desk and plays on his phone, or sometimes visits with friends on their lunch hour, but seems to rarely eat lunch himself.

It is common knowledge on my team that if you need to leave early for the day, you’re allowed to skip your lunch break and leave early. This team member asked me if he could skip lunch every day and leave early. I am hesitant to agree to this as an every day option because in the past I’ve read multiple articles saying that skipping lunch breaks or working through lunch is bad for productivity, and often leads to burn-out (and I have some personal experience with this as well). Additionally, we work in a collaborative environment and while I don’t dictate set working hours, I do like people to generally be available to their teammates for questions, help, etc. I allowed this policy because I really try to be as flexible as possible for my team, but I just don’t feel right about making it every day. Am I overthinking this?

If it will inconvenience your team to have him unavailable for the last hour of the day every day, it’s perfectly reasonable to say no to this, and to explain that it’s fine to do occasionally but not every day.

But I wouldn’t base it on worries about burn-out. Some people do fine with working through lunch; others don’t. You don’t want your reason for banning this to be that it can be bad for some people, when others do just fine with it and even prefer it. Keep the focus on how it impacts what you and your team need from him.

5. I’ve been asked to give a reference for two people for the same job

I work in a fairly competitive, but still small, field, where getting a job is all about who you know. There is an opening at the company I work at that two people who I have worked with in the past are going to apply to, and both want to put me as a reference. I think both would do a great job, and I had agreed to be a reference in the past, not knowing that both would be applying for the same job at the place I am working.

Is that weird? Do I need to talk to my HR manager and explain? Should I tell them not to use me?

It’s not weird. When you give a reference, you’re not saying, “Definitely hire this person over all your other candidates.” You’re ideally saying “Here is a detailed assessment of this person’s strengths, work habits, and challenges, and it’s up to you to decide how this person fits in with your needs.” So you can definitely give a reference for two people for the same job.

The exception to this might be if you think one is significantly stronger than the other — especially since this is for a role at your company, meaning that you’ll want to be very candid. In that case, it might be fairer to say to the weaker person, “I want to be up-front with you that I’ve been asked to be a reference for someone else applying for this same job, and I think they’re a really strong match with the role. I’d still be glad to be your reference as well, but I wanted to be transparent about that in case you’d prefer to use someone else.”

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