My top 10 from 1 on 1 Meeting Questions

If you are a manager of any kind, save this list of 1-on-1 Meeting Questions. This will definitely save a bit of your brain power when you most likely need it. Pretty sure you can get a meaningful conversation by selecting these questions at random, but better would be to select the questions in advance. Especially because some of the questions in the list are really dumb.

But anyways here is my top 10 of the questions without any order or preference. I will comment them from a perspective of an employee and give advice to a manager. I will also focus in my reasoning on the Software Development area. With that in mind let’s go

What have your past managers done that you’d like me to also do or not do?

Almost all the other questions in the “About Manager” section are open questions — unless an employee is specifically prepared for them it’s often hard to come up with a reasonable suggestion. This one however narrows down the selection quite a lot and also it’s much easier to come up with an answer when you are asked to compare things. Keep in mind however that the answer might be biased.

Do you feel like you are learning at work? What are the new things you learned lately? What are the areas you want to learn about?

Okay here are three questions but one of them is at utmost importance: “What are the new things you learned lately?”. If your answer is “nothing” then it’s a symptom of some problem at work – it’s like a 37°C fever that indicates that your body doesn’t function effectively.

When asked “why?” people often mention deadline pressure but I think the real reason is one level deeper. It’s that you have an endless stream of bugs or routine problems to solve and you don’t have time to stop and sharpen the saw. In big companies it’s not bugs but process requirements to follow which might consume too much time.

When people constantly learn new things they will have this fire in their eyes, and that will keep them moving. People even value this more than getting extra money from the promotion. But once it’s gone it’s very hard to light it up again – if you don’t find anything exciting for them, such a person is much more likely to move out to another company.

Small disclaimer: it’s not a bulletproof symptom, it’s also not always possible to figure out the real reason for this, but it’s something I would keep an eye.

If you were to create your ideal position, how would it differ from what you are currently doing?

This is a bit boring but the important thing is that it reveals the hidden wishes of an employee. Whatever they answer they must deal with the potential responsibility they can take. If they answer “My ideal position is CTO” then the obvious next question is – “What do you know about what CTO daily job look like”?

I made a survey some time ago and noticed that lot of developers would like to have a position where they spend time on improving some internal tools. I think that it’s very often a case that developers have some impediment which they aren’t allowed to solve by managers because “they don’t bring value to customers”. So if you ask this question and get an answer “Same as what I do now + also improving XYZ” then maybe it’s time to dedicate resources to it. Again this question is good because it’s a comparison question, so it’s not that hard to come up with an answer.

What about this goal is important to you and what will be different when you achieve the goal?

This one is pretty nasty! I mean the second part. This is a great question to ask before setting the yearly goals, recording the answers and then reviewing the answer in a year. Somehow I expect most of the time the true answer will turn out to be not quite what it was expected. Still as long as it’s not “nothing” it’s good. The question is brilliant because it can reveal a goal that’s not worthy to pursue. One of the good answers to this question is “I will be the first in the company to ever do X”. It is an incredible self-motivator.

What are some of the work projects you’re most proud of, and what do you think you might want to do next?

Ask that from time to time and keep looking for results. Sometimes I find myself dragged into a boring demotivating routine of tasks. It’s important to keep a mental list of great things you achieved. This list might get stale — “oh, that time 3 years ago when I implemented that thing and everyone is still using it and is thankful to me for that“, but still it reminds you that you are not just a bag of meat with bunch of synapses on top — you can do awesome things, and maybe it’s time to look if you can do them in your current environment. And if not — analyze together with the manager how to fix that.

What are your super powers? What powers would you like to develop?

That’s just a perfect ice-breaker. In a training for iSAQB SOFT module we had the blind spots exercise when you are given a list of people qualities (energetic, shy, smart, thoughtful, lazy etc.) and you choose the ones that you think apply to you. Then you ask a colleague who knows you to select the qualities they think you have. And finally you compare these lists. In the end you reveal the qualities that you have but you might not be aware of them and also the things about you that aren’t clearly visible from outside.

This question is quite similar to that exercise but is open-ended. I would ask it and then check with that person’s colleagues if the answer holds. Again the goal here would be to find the blind spots and use the working time better.

What skills do you have that you think are underutilized?

For me the single big reason of people leaving the company is realizing that their skills are underutilized. The other one is money but they often go together hand in hand. Here is why.

Some people are really great coders, they love code, they can easily read it, they can create it really fast. They have tons of github repos and they commit every day. Now let’s suppose that 60% of your professional brain-space is configured for software engineering and the other 40% have grown to be good at art (or soft-skills, math, analytics, writing etc.). You will never produce the code as good and as fast as the people who are 99% focused on programming. You will be slower, make more mistakes and write more bad code. Compare that with chess — unless you’re trained from childhood you can never become a Grandmaster. In programming it’s not so strict but the overall rule still has big influence. So if you’re not getting value from those additional 40% by e.g. taking management position, moving to design department, becoming an architect and so on, then you will be stuck. You manager will only see that you are worse than other developers when it comes to the number and complexity of tasks solved and you will see that too. You will be unhappy.

There must be some exercises to reveal these skills but probably even a simple trial-and-error could work. I’d like to have a success story here but there is none I know of. If you have, write and I’ll add it.

Who in the company would you like to learn from? What do you want to learn?

We love to be near really smart people. We love to learn from the best teachers. We want to go to the best university to be among the most talented people in the world. These people will inspire us, show us the true meaning of the world, they seem to know everything. We want to be like them.

I read some interviews from successful developers and very often they say something like “it was my first company, the salary wasn’t great but there was a guy who taught me how do X and he was really a master and I am forever grateful to him”. The masters/trainers like that are incredibly important to your company – they will attract more talented people to your company and they can unleash the potential of them. And if you lose them, you’ll lose a lot of company morale.

And you will lose them eventually because usually there is not enough challenges for them and the CTO role is already taken and you can’t just raise their salaries without limit. The only solution I know is to make them share their knowledge — like the kung-fu masters of the past who trained great warriors to take their place, this is the only hope you get — that some young padava developer will eventually become as good as they are.

This question also serves as a survey to identify these people in advance or to realize that you don’t have many of them.

Are you on track to meet the deadline?

Just wanted to add it here as a terrible conversation starter. But honestly all of the questions listed in the article in this section are bad. In my opinion the manager should already have some information about the employee and build the conversation based on what they know. I imagine the best conversation starter as “You mentioned you like X, do you know that recently Y happened in this area?” – this doesn’t put any pressure on an employee but immediately gives some topic to start from. This also implies the manager needs to have an employee profile at hand to ask a related question.

I’ve noticed X about the project… Can you help me understand that better? Talk me through your process.

A lot of questions in the “Job satisfaction” are repeating the ones mentioned earlier. Also these questions can be asked and analyzed by an automated tool like Officevibe. This one requires in-person asking and it’s a great conversation starter — you will likely hear a lot about what its going on and if any problems exist on a project without even asking another question.

What part of your job do you wish you didn’t have to do?

Really easy to answer, identifies places where the company can automate something or streamline the process. Collect responses, identify the weak spot, dedicate resources, rinse, repeat.

When is your next vacation?

Another very good conversation starter. People generally like to think about vacations and making plans so it’s easy to go from there. Although in a pandemic year when this article is being written this is a bit of a joke.

If you reached this point you might say, “hey, that wasn’t top 10”, that was more. Well, yes, I tricked you, I’m sorry. Hope you still got some stuff from it.

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