Making it easier to ask for help
Tactical tips to get us past asking-for-help resistance
I used to co-lead workshops for engineering leaders, and in one portion, we would ask attendees, “What are the stories you make up that prevent you from asking for help?”
The stories were abundant, with some extremely common, and some quite creative:
People will think I’m stupid
They’re too busy
They’ll be annoyed
I should know this already
I’ll learn more if I figure it out myself
They’re probably really busy right now, I don’t want to interrupt them
I should try to work on it longer on my own, and then ask for help if I’m still stuck
Now I’ve waited too long to ask for help — if I ask now, they’ll know I spent all that time not making progress
The person I’m asking for help may not know the answer, and by asking them, I will expose their lack of knowledge and embarrass them 🤔
Especially on a remote team, misalignment in expectations around asking for help is probably one of the biggest obstacles to predictable individual and team output.
The lack of serendipitous help you would get for free in an office makes remote onboarding (especially for early career folks) and ongoing growth a lot more challenging.
Teams can make it easier to ask for help by putting in place team processes such as regular sync or async check-ins where people share if they’re blocked. Another approach is to coach individuals to shift some of their mindsets and stories that prevent them from asking for help (I’ve had countless of these conversations in 1:1s these past few years!).
All of those are important. And I’ve also found that a few tweaks in language or what you ask for can make asking for help seem easier.
Here are some different tactical techniques I’ve found that work well to dispel some of the stories above, so that you can get the help you need and get unstuck. For many of these examples, I use engineering projects, but regardless of what function you’re in, the general tips are sound.
Ask for synchronous help
“I have a few ideas, but am not sure which to try first. Do you have a few minutes to chat?”
Async is great, but when you’re stuck, sometimes you don’t even know what to ask, so even formulating a clear question to share by email or Slack is challenging. Even a few minutes with someone can get you unstuck and headed in a promising direction.
Bonus: in this specific example, by the time you send a code review out for review, your approach has already gotten buy-in through this sync convo, so you mitigate the risk of spending days prepping a change, only to be told that there’s a different approach you should try instead.
Ask in public channels
“If anyone has 5 min to jump on a call and talk me through XYZ, let me know!”
Asking in public channels allows anyone who is available with relevant experience to jump in and help. If XYZ feels like something you feel like you ought to know already, you may feel some friction here, but opening it up to more folks feels more like you’re letting them opt-in to helping you.
If you’re in a senior role, please do this as often as you can, and especially with things that feel basic — this will model to others that they can do this too.
Be flexible with your timing
“Can you let me know if/when you have 30 min in the next few days? I could use some help with this pull request.”
This requires not waiting until the last minute to ask for help. This is great for things you know you’ll need to do, but are not urgent. People’s calendars are generally much more spacious next week, and giving them the flexibility to choose a time that works for them can make it easier to ask for help without it feeling urgent and disruptive.
Ask for a walkthrough
“I’m about to start on this new project and I saw that you’ve worked a lot in this space — it’d be super helpful to get a high-level tour of how everything fits together before I dive in.”
This one is my favorite, but it goes against most people’s natural instinct to try to figure it out themselves first for awhile. This is great when you’re about to work on some part of the codebase you’re not familiar with, or start an unfamiliar project.
Here’s the metaphor I like to use: you don’t know where anything is in a pitch black room and need to find your way around. You could wander around, guessing what things are — it might take you hours or days before you really familiarize yourself with your surroundings. Or you could ask someone who’s spent a ton of time in that room to show you around, give you a high-level overview, and shine a flashlight over the main areas.
Ask for someone’s thought process
“I haven’t done this before. Can you talk me through where you would start, and what you think all the different moving parts are?”
A quick brain dump can save you so much time. You can gather pointers to online resources to check out later, pointers to important parts of the codebase, and a general sense of what is involved in the project.
Or you might get none of those, and just get a “yeah I have no idea either.” Which is information as well! If no one on the team has more context than you, just do what you think is reasonable, and consider asking for help along the way — even if people don’t have direct context, having a sounding board can be immensely helpful.
Ask at the end of an existing meeting
“Can you stay on for 5 minutes? I could use some help.”
If you have an existing team meeting or regular standup, this is a great time to grab someone you would like help from, without the fear that you’re pulling them out of deep focus work. In office settings, this would happen naturally after stand-ups — as people meandered back to their desks, it was a natural time for people to get immediate help with any blockers that came up during the stand-up.
Be mindful of people’s next meetings though — normalize ending meetings early so you can create some space for this type of interaction.
Team alignment around asking for help
As a team, it’s important to align on norms for asking for help. What are your expectations? These are techniques that I’ve found useful, but some teams may decide that they want people to try to figure it out first for a few hours before asking for help. At companies where there is abundant documentation and internal resources, you may want people to tap into those first, and then asking specific people for help if they are still stuck.
Have a conversation with your team — feel free to drop this post in a slack channel to start a conversation, and ask people what holds them back from asking for help!
People like to be helpful
At the leadership workshops, after we heard everyone’s stories about what holds them back from asking for help, we’d also ask people to raise their hands if they would like being asked for help more often. Every time, almost all the hands in the room went up.
People like to be helpful. It makes them feel good.
And trust that people can take care of themselves if they don’t have time to help: “I can’t right now, but I have some time tomorrow. If that’s too late, maybe post on Slack and see if someone else can help you today?”
I am currently helping out a friend who asked me for help. I know he values self-sufficiency and helping others, but is extremely reluctant to have people help him, so when he asked, I knew he really needed the help. Rather than seeing it as a burden, I felt happy that he knew our friendship went beyond superficial niceties, and that if he needed something, he could ask me for help, and trusted me to take care of myself and only offer help willingly. It also makes me feel more comfortable asking him for help as well.
Lead Time Chats
Oops I forgot to share my latest Lead Time Chats last time, so I’ve got THREE to share.
Hiring on Remote Teams - I chatted with Hong Quan, long-time recruiter for early-stage startups about the changes he’s seen these past few years, and how companies can adapt.
Working Effectively Across Different Timezones - The Linear team is split in half across the US and Europe, so I chatted with co-founder Jori Lallo about how they coordinate projects across continents, meet up in person, and bond asynchronously. It was fun to catch up - we had met in Palo Alto over a decade ago (probably around the same time I met Hong, when I was working at Pulse)!
Navigating Conflict on Remote Teams - Suzan Bond proposed this topic, and I was so excited to dive in. We chatted about how remote teams see more conflict avoidance than what people typically consider conflict — and how to lean into disagreements and stay curious.
Things I've been enjoying
Buy Nothing group - I probably sound like a broken record, but probably because the things I enjoy keep coming back up. I got a big stash of yarn recently from someone — who coincidentally is married to someone I regularly play ultimate frisbee with! It’s a nice way to build local community. Also, I’ve been able to quickly give away a lot of unused pantry goods and accumulated household stuff as we prep for a local move!
Spacious time - I took Wednesday off to have some time to myself, and it was honestly glorious. I’m thinking of taking a Wednesday off a quarter (or more frequently) for a no-chores, no-life-admin, no-work day. I did some zoomed-out life thinking, reading, and brainstorming about book topics. I kicked it off with a very standard coaching tool called Wheel of Life, which you can access here. It’s just a structured way of looking at different areas of your life, and figuring out which you want to put some effort behind changing. I had done it before with just the wheel, but I appreciated the more detailed questions for each category.
I’d love to hear from you — what have you been enjoying? What stories hold you back from asking for help?
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