how can I get my staff to figure things out on their own, asking about internal candidates, and more

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

1. How do I train my staff to be comfortable figuring things out on their own?

I’ve been a manager for a few years now, and I’ve been working hard to build my bench. I seem to keep running into assigning an employee a new task with as long of a lead time as I can manage, and the first response is “Can you show me, first?” Most of the time when I get tasks at my level, I’m not given 100{986d44274747a5c76dc1672921bbe0dd933450491f05a8d42739aa242512160b} of the information. I’m given a new report to run, or asked to find a piece of data. Most of the time I play around and figure it out, and if I get stuck, I’ll come back with “I tried A and B and those ways don’t seem to work, is there a different way to approach this or someone I can talk to?”

Nothing I’m assigning is outside the capabilities or bandwidth of the employees, and rarely when I’ve pushed them to try by themselves have they needed additional support. I just don’t always have the availability to screenshare and show you how to filter and copy a report. I’ve had success with letting them know if they want to check in with me after trying in a week, I can make some time, but not every task can come with an in-depth training. I’m spending my time with the more advanced tasks with even less information! I’ve made sure to include questions about what to do when you don’t have all the information to my interviews, and make sure my existing staff know that they have my support if there is a problem with the work the first time.

How do I get my team to get more comfortable swimming in the deep end?

Name it explicitly as something you want them doing, and something they need to work on. If you haven’t explicitly told them this is your expectation, they may not realize they’re out of sync with it. In fact, they may even see their requests for up-front demonstrations as conscientious, since they’re ensuring they’ll be doing something the way you want it done.

So say something like this: “With tasks like X and Y, I’d like you to try doing it yourself first. If you get stuck, you can come to me and let me know what you’ve tried and that you need help. But I have confidence that if you try on your own first, you’re usually going to figure it out, and that builds your skills and saves me time.”

You also need to let people know it’s okay if things take longer while they’re figuring it out, and that they won’t be penalized for mistakes in that process. (And then you really need to mean that — if you seem irritated or upset when there are delays or mistakes, people rightly won’t take you at your word about this.) You also should watch for how much time this really adds to people’s workload — if someone is spending days trying to figure something out when you could have shown them in 10 minutes, that’s likely not the right allocation of time.)

You also need to be judicious about it. You say that when you’ve pushed people to try on their own, they’ve rarely ended up needing additional support, which is great. But make sure that you don’t overlook times when people really do need more support up-front (like when something uses skills they’ve never had to employ before or when the work is very high-stakes — which are both times when you should provide more guidance).

2. Can I ask my interviewer if internal candidates are also applying?

I work in a field where mostly people are promoted from within. I’ve just applied for a lateral move to another organization, but I honestly don’t think it’s worth my time pursing if they have an internal candidate also applying. Can I ask about internal candidates during a phone screen?

You can, but it won’t necessarily tell you what you think it will. Sometimes there are internal candidates who have zero chance of being hired. Sometimes there are decent internal candidates, but the company prefers to bring in someone from the outside with a fresh perspective. Sometimes there are decent internal candidates but the company is going to hire the best person for the job, whether they’re internal or external.

It’s absolutely true that sometimes companies are already planning to hire an internal candidate and just go through the motions with interviewing other people. That’s rude and a waste of time, and it’s really frustrating to feel your time was wasted that way. But unless you have insider info about the situation (which you’re unlikely to be given in a phone interview), you have no way of knowing what the situation really is, and in many cases it would be a mistake to bow out of a hiring process simply because someone internal is also applying.

3. New employee fell asleep in meeting

I have a new employee who started on Monday. So far she seems great. But we were just in a kind of boring but important meeting with internal colleagues and she kept nodding off to sleep. She was trying to fight it, but it happened multiple times.

Is this something I should address with her now? Keep an eye on? Something else?

Any chance she wasn’t working for a while before she started with you or was working somewhere with a very different schedule? It’s possible this is just the initial adjustment to her new schedule and that she’s mortified it happened.

One option is to let it go and only address it if it happens a second time (at which point, address it privately right away). Alternately, you could say to her, “Are you doing okay? You looked pretty sleepy in that meeting.” That’s ideally said the day it happened though, and it doesn’t work as well to say it a few days later.

4. My awful former boss is terminally ill — should I reach out?

I spent over three years working for a small nonprofit before moving to a new company almost two years ago. When I was working for the nonprofit, my boss, Sansa, was diagnosed with cancer. If memory serves, she was in remission when I left. However, since then, the cancer has spread, and she has been given one to two years to live. It’s utterly heartbreaking. She is quite young, in her early forties, and she’s very good at her job.

Here’s the thing, though: Working for Sansa was unbelievably difficult. She was hypercritical well beyond what could be considered constructive, she was a chronic interrupter, and she had virtually no boundaries. She talked to me about her personal and sex life, made snarky comments about church-going colleagues (she was deeply metaphysical), and once told me I needed to “rethink my life” and my “attachment issues” when I went to retrieve a favorite pen I’d left in her office. Another time she raked me over the coals in front of a volunteer over a very small and easily accommodated change she wanted. Her moods were wildly unpredictable and she had a reputation around the office for being snarly and emotionally unstable on her bad days. Her toxic moods were so potent they had their own oppressive ecosystems that could put entire roomfuls of people on edge and leave me with anxiety stomachaches for the rest of the day. She made everyone on her team cry. I could go on, but you get the picture.

I have not kept in touch with her after leaving (all news of her illness has come through the grapevine). It took a month or two at my new job for me to stop getting a stomachache whenever my new (amazing!) boss came over to my desk because I was so used to getting dragged through the mud, and I needed a clean break to distance myself from that relationship. Sansa sent me a text maybe a year after I left, but it had strange vibes (and a friend who still worked there confirmed she was in a BAD mood that day), so I gave minimal answers and she left it alone.

So now we’re here. This woman made me utterly miserable for years, and she is terminally ill. So my question is … do I reach out? Should I try to see her? Would reestablishing contact under these circumstances even be appropriate? Is there anything to be gained in seeing her again, or is it better to just keep it a clean break? I’m not proud to admit this, but I wouldn’t even be considering reaching out to her if she weren’t sick. Am I insulting her by only considering it because of her health? Will I deeply regret not seeing her again before the inevitable? What should I do?

It doesn’t sound like you and Sansa have the sort of relationship where there’s a lot to be gained (for either of you) from you reaching out to her now. You don’t like her, she made your life difficult, you were glad to make a clean break, and it’s okay to simply feel sympathy and compassion from a distance. If you’d like, you could send her a card letting her know that you’re thinking of her, but this isn’t a situation where you’re a bad person if you don’t do more than that.

5. My employer will only get me a laptop if I give up my desktop computer

I have been working in my current job (as an early-career academic at a public university) for just over two years. During that time I have used my personal laptop whenever I work from home/outside office hours, or while travelling. We are expected to undertake work/conference travel and attend workshops etc where laptops are required. We are also encouraged to work from home one day a week to maximise research productivity/minimise student interruptions. I have a desktop computer in my office, which has greater storage space/processing power than the laptop. Two weeks ago my laptop broke and it cannot be fixed (it is more than 5 years old). When I spoke to the university about getting a work laptop I was told that they would only purchase one if I gave up my desktop computer or surrendered my personal laptop to them! Am I right in thinking this is unreasonable? If so, how do I push back on it?

The “give us your personal laptop” part of this is really weird (so weird that I wonder if they misunderstood and thought they’d purchased it for you), but the rest of it seems like they’re saying they have a policy of supplying one work computer per person. They’ll give you a laptop or a desktop computer, but not both. That’s not inherently unreasonable for an employer with limited funds (which is likely the case with a university).

It would be unreasonable if you needed a laptop for work (which you do) and they refused to provide you with one. But that’s not the situation; they’ll buy you one, but you’d need to use it for all your work things and let them reassign your desktop computer to someone else.

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