The Questions Doc

This is part of the Bag of Tricks series.

I’m starting a new series of blog posts about my “bag of tricks” or “toolkit.” The list of stuff I’ve learned from other people that I’ve remixed into my own DevRel and management style. I hope others will take these ideas and modify them to fit their own approach to tech and life.

The Question Doc

A lot of people think remote and distributed management is hard. It is all I’ve ever done so I don’t know any different, but I’ll trust folks that say that in person management is easier. One of the few times I’ve caught myself saying “I wish we could just work together in person for a couple weeks” is when I’m helping new folks onboard and ramp up. I want to be able to just come over to their desk and help them through some of the weirdness that is a new job. I want to be able to draw things out on the whiteboard.

I always tell folks as part of their onboarding that they’re going to have a lot of questions and they need to ask them. I use the rule of thumb I learned at Seattle.rb that new folks shouldn’t stay “stuck” on anything for more than 30 minutes. After 30 minutes they need to take a break and ask for help, or move onto something else. And this works great for folks who are willing to ask for help.

But a lot of folks aren’t willing to publicly ask questions. Sometimes cultural factors are impacting people’s behavior. Sometimes it is impostor syndrome. Sometimes folks think that they’re bothering their super important and busy teammates with “stupid” questions. As a manager you can reassure folks that questions are welcome, but even so I’ve found many people just won’t ask.

Enter one of my favorite tools, the questions doc.

This is based on an idea my partner has used in person, but I’ve adapted for a 100% remote environment. Here’s how it works:

A manager or mentor creates a shared document that only the mentee and the manager and/or mentor can access. Obviously I use Google docs but any collaborative editing software cloud work. You could even use something like a wiki I guess.

After the doc is created the mentee’s job is to write down a question every day. I ask folks to put the date and then their question. And yes, I really mean everyday.

The everyday part is important. Requiring a question everyday helps break the habit of saving up all your questions for your 1:1. Or sitting on questions because you don’t think your questions are good enough. Requiring a question everyday also encourages curiosity and makes it clear that on this team it is expected that you won’t know things.

Usually the early questions are logistical about how the team operates. Then they move to technical questions about our products or our industry. Eventually the mentee starts running out of questions and you may end up with things like “what’s your favorite color?” or “why do customers do ?”

The manager or mentors job is to visit the doc once a day and answer any questions that have been added since the last time they looked. In Google docs I usually reply inline with purple text to make it clear that I’ve answered the question. I prefer having two “question answers” when I use this technique. Usually a mentor and a manager. With two folks answering a questions you can model that there are often multiple right answers. You can model respectful disagreement. And you can model deferring to an expert. It also communicates that there are multiple people on the team that want the new hire to succeed which can be hard to internalize in our online world.

So what happens when there’s a question I don’t know the answer to? I say “hey, I don’t know the answer to this. I think [person] probably does. Want me to introduce you two?” and once I have permission I make the introduction and provide context.

What happens when there’s a question that really would benefit from a whiteboard session or a discussion? I’ll give a quick answer in the doc like “this looks like an n+1 queries problem” and then add a note about when we can dig deeper with a specific time. Like “in our next 1:1” or “this afternoon at 2.”

When do I phase this out? I look for a couple signs that it isn’t helping anymore. The most obvious sign is if the mentee or mentor says it isn’t helping. I also look to see if we’ve all forgotten to ask or answer questions recently. Often the questions reach a level of sophistication that indicates someone is pretty ramped up and that’s a great time to retire the doc. But mostly I just look to see if the mentee is asking questions of the team in other forums and once I see that the questions doc has served its purpose.

I know a daily 1:1 could be used in a similar way, but I really like the async aspects of the doc. It allows the mentee as much time as they need to wordsmith an answer. It lets me take the time to write a well crafted response that links to resources that may be helpful. It also provides a record of everything that’s been asked and learned which has lead to good blog posts and good additions to our onboarding documentation. It also works across time zones with ease which can be a challenge when onboarding.

I know this technique/tool feels simple and kind of hokey. And it totally is. But that’s why it works. Anyone can set it up in 10 minutes. It takes 5-10 minutes a day on the part of the manager and mentor. Someone can ask a question during a meeting when someone uses a term they don’t understand. The mentor can answer questions in 5 minutes between meetings. It won’t solve all your onboarding problems but it is a tool that can help in many cases.