How to ask dumb questions, follow up on feedback, and convince your boss

I keep track of the themes and various questions that come up in conversations with my friends and here is a summary of three questions that have surfaced repeatedly

Over the past few weeks, I’ve continued to use my newfound free time to catch up with old and new friends. One theme that came up across a few conversations was the idea that often, we don’t vocalize advice or other knowledge because it feels really obvious to us, when in fact it might actually be quite valuable to others. This is a common struggle I have when deciding what to write about here, as I worry that some of you readers may see a post and think, “How silly for Isabella to mansplain that to us.”

Having spent some time reflecting on this, I’m going to write about a few topics that may feel obvious to some readers. As always, skim or skip past the parts that don’t feel helpful to you. My goal in writing has always been to put something into the world that resonates with someone, but not necessarily (and highly unlikely) with everyone.

Let’s start with how to ask dumb questions

One of my close friends started a new job last year and early on, we talked a lot about how she suddenly felt like she was given a lot of rope from her manager and often felt a bit under-managed. We spent a while going back and forth on strategies for how she could ask her manager for more support without coming across as incompetent. 

One of the first things I asked her was if her manager was stretched thin across many responsibilities and didn’t have a lot of time as a result. She said that was her guess for the root cause. I put myself in her manager’s shoes and thought about what would frustrate me the most: if a direct report did something wrong and I needed to spend precious time fixing it.

With this in mind, I suggested that my friend frame her requests to her manager around making sure that she was doing her work correctly, to avoid her manager needing to spend time fixing it later. This was a very proactive framing, which, if I were her manager, I’d be appreciative to hear and see as a sign of forward thinking from my team member.

In general, I’d venture a guess that managers tend to be pretty busy. Being asked dumb questions can be frustrating at times, but if it’s presented with the caveat of trying to save the other person time and avoid yield loss, it can fundamentally alter the tone of a conversation.

Tl;dr: Ask the question even if it feels dumb but frame it around making sure you’re doing the right work / looking to avoid yield loss / making sure other people don’t have to clean up after you if you do the wrong thing.

Next, how to follow up after receiving feedback

In my experience at work, I’ve always been given a lot of feedback but not really coached on what to do after receiving it, other than vaguely knowing that I was supposed to just “do the thing differently.” I always wondered, “Is this going to be evident to other people?” and “Is my manager going to remember what they told me and see that I’ve changed?”

Unfortunately, it is rarely enough to just act on the feedback. Most systems are set up to overindex on giving feedback with relatively little to support you after the feedback has been given. Whether you’re receiving it as part of a formal process or informally in 1:1s with your manager or other teammates, here are the steps I figured out for myself, to make sure that other people see me improving.

First, figure out what to do differently: Align with the feedback giver on what you should do differently on a very tactical level. For example, if the feedback was around providing more progress updates, you can propose a Slack message template for a daily end of day summary.

Next, do the new thing: With the same example, once you’ve both aligned on the template, set aside time at the end of each day to fill it out and send it. If you might forget, set yourself a reminder. Send the message every day.

Then, check if it was received well: At your next 1:1 with the feedback giver, check in. Ask, “Hey, how is the new template working? Is it giving you everything you’re looking for?” Make any tweaks as needed.

This is a moment to let the other person know that you’ve taken action and you’re doing something differently. Without discussing the change, it could be taken for granted and go unnoticed, or perhaps it doesn’t hit the spot and leaves the feedback giver waiting for more. You don’t have to – and probably shouldn’t – frame the conversation as, “Hey, look at me kill it! I did the thing!” Instead, you should frame it as, “Hey, I took your feedback and started doing this differently, and I wanted to check how that’s going for you. Does that address your feedback, or is there anything still missing?”

Lastly, if needed, keep track of the changes you’ve made: If you’re near a review cycle or need to put together a self reflection, you can keep a simple log of commitments you’ve made and new actions you’ve taken. This can be great to share with your manager and other teammates to jog their memories on how you’ve improved.

Finally, how do you convince your boss to let you work on specific projects

Note: This could also be framed as: “How to convince someone to pay you to do something for them.” 

This one comes with several caveats. I’m going to trust that you, reader, are going to take this advice only if you have something that you actually believe is important and valuable for your team / the company / the business where you work. Please don’t take this advice and try to convince your manager to let you work on something just because it’s fun. Or try, but don’t come back to me when it doesn’t work…

Let’s say you have found a project or an area of investment that you believe to be really important. Perhaps your boss has already resourced you to work on something else, or they just don’t see why this other direction matters against other existing priorities. I feel like in most scenarios, the stereotypical solution here is to write out the business case and make a ton of slides to present to your boss.

However, before you go deep into creating all sorts of collateral, I believe it’s really important to stop and understand the results that your suggested project would deliver. What will be accomplished, and how will that tie that into the bigger picture? How will your project help advance the company or the team’s overall goals? Tie it into any metrics that your team is actively tracking. It may be as easy as crafting a narrative that you can share with your boss that consists of 3-4 bullet points. “I believe I should spend x weeks on y project, because this will allow us to increase z metric by x%, which is a key metric for the team this quarter. If we don’t invest now, this problem will increase and drag down y metric next quarter.” 

Remember this: ultimately, your manager is accountable for certain results. If you want to ask for time to work on something, show them how your effort will be spent on something that also supports the results they need to deliver. 

Finally, an added bonus is if you can tell your manager what you will learn along the way and which skills you’ll hone. Then you can make the argument that this will help make you and your team better at doing your work on an ongoing basis. If you can introduce or test out new tools as part of this project, address that there may be a slower learning curve but also explain how this will contribute in the long run to team productivity. In general, you’ll want to frame things in terms of ROI, but that doesn’t mean you have to quantify all of it.

Tl;dr: Whatever you share with your manager, and in whichever format you choose, make sure you tie it back to what they’re working towards.  

Closing thoughts on the overall theme: empathy

The underlying theme here is empathy. A lot of these approaches centre around taking a step back and thinking about what other people may be trying to achieve. At the end of the day, we all have limited time and energy and we’re all trying to accomplish certain goals. If you need someone else to support you – which they may do, out of the sheer goodness of their hearts, but they also may not – then you need to make sure your incentives are aligned. You need to think about the other person’s situation and setup and figure out what will make them tick. You should ask yourself, “how can I make it as easy as possible for this person to help me accomplish what I want?” and “how do I make sure that they see that what I’m doing is also going to help them with their goals?”