Reaching out

Many of my best relationships have started with reaching out to a stranger on the internet, talking about a mutual interest, and staying in touch.

Folks that I share this with wonder how (and why) I’m able to do so, and whilst the obvious answers of “I contact people in the places that they are contactable” and “because speaking with other humans about mutual interests is fun and valuable” are correct, they’re not often met with satisfaction.

There’s not a great deal more to it, but I do believe it’s worth keeping a few things in mind, which I’ll try to articulate here.

1. Have an actual reason
2. Perform due diligence
3. Be brief and relevant
4. Drop the entitlement
5. Respect people’s time

Have an actual reason

Many folks who tell me they’d like to reach out to an internet stranger say something like “I’d like to pick [internet person]’s brain because they’re well-known/famous/insert-similar-motive”. This isn’t a great place to start from for a few reasons:

1. Asking of someone if you can “pick their brain” is both frightfully nebulous and incredibly lazy
2. Selecting someone exclusively because they’re well-known/famous is a tragically poor criterion
3. You’re unlikely to hear back, both because you were vague and because they receive many messages

Before thinking of who you’d like to speak with, it’s wise to have a good reason to reach out to anyone. This isn’t universally true, but I frequently see people choosing [popular person] and then post-rationalising a reason to speak with them.

The reason could be related to work, life, a hobby, an area of study, a global pandemic, a great book, or anything else that a person could reasonably know something about and which you would like to know more about—or exchange information about.

Let’s say you’re taking on more people-management responsibilities at work, for example, and you’re lacking confidence about how to transition from your previous role to your new one. Someone on the internet has undoubtedly charted that same course.

It’s worth articulating what you feel you do and don’t know about the subject, and to ask your chosen search engine for the obvious answers. Where there are no obvious answers, you’ve found a perfect reason to reach out to someone who may have one.

Using the above scenario, there could be a few areas you’re wondering about and would like support with (particularly if you work for an organisation that doesn’t readily offer that support). A non-exhaustive list of those things might look something like:

• How to manage the transition from contributor to manager and which skills might be transferrable
• How to build trust with people who until very recently were your peers rather than reports
• How to manage your tasks, time, and attention now that they don’t live in tickets on a Jira backlog
• How to deal with complicated or sensitive situations like disputes and poor performance
• How to balance confidently setting direction whilst remaining fallible and open to change

Those things, amongst others, are: complicated to navigate; difficult to find good answers to on the internet; very rarely intuitive or obvious, and; very likely to have been tackled by some very large number of people in the world. Choose one (or more) to tackle first.

Once you’ve selected something that you’d like to know more about or would like some help with, it’s time to find some folks who you believe would be well-suited to offer you anecdotes or advice, having very likely dealt with the same issues themselves.

Perform due diligence

You might have someone in mind that you’d like to speak with, having followed their work. If you haven’t, you’ll have some internet searching to do, but that’s outside the scope of this post—I’ll focus only on the case where you’ve chosen someone.

Even with someone in mind, it would be wise to doubly or triply make sure that they have indeed had the experience you believe them to have had. You could do this at a high level by checking places like LinkedIn, and at a lower level by browsing their Twitter account, blog, or portfolio (if applicable).

It’s worth checking also if they’ve previously published the advice you’re looking for—they might have written a post, given a written interview, or appeared as a guest on a podcast. There are myriad places on the internet to discover whether or not that’s the case. If it happens to be, but doesn’t quite answer your question, it’s still a good jumping off point for your reach-out and resulting discussion.

The things that you might want to research before reaching out to someone will vary depending on who they are and what it is that you’d like to know, but there are some good places to start:

• What the person does, who they currently do it for, and how long they have been doing that thing
• What the person has done in the past, related (and perhaps unrelated) to the thing they’re doing now
• Who in your network the person has worked with before, and where those people worked together
• Which project(s) the person appears to be most proud of and has communicated as much publicly
• What type of things the person appears to value both related and unrelated to their profession

I’ll stress that you’re not doing this to somehow “trick” the person into speaking with you. You’re doing this, hopefully, because you’re genuinely interested in those things and would like to talk about them should you have the chance.

It’s also helpful to provide context and to connect ideas/people before having a discussion. Perhaps they worked with someone you know, or worked on that product that you use, like, all the time. It should also help you to clarify that this person can speak to the challenges that you’re now facing.

I’ll admit that the above sounds like a lot, but it doesn’t need to take a long time; you’re sense-checking and doing some light reading, not writing an essay. It could take as little as 15-30 minutes, but if it takes longer, remember that you’ll likely be asking for more time than that yourself, and should be willing to invest your own time up-front.

Be brief and relevant

It’s tempting to think that, having carefully thought about the problem you’re looking to solve and then dutifully researched those you believe could help, you should write a very long and very detailed reach-out, but let me convince you otherwise.

The quantity of words you write is not correlated with the quality of your reach-out (to some degree, the exact opposite is true). You’ve thought through things so carefully precisely so that you can get your point across with as much clarity and brevity as possible. It can literally be as simple as:

Hey [name], I’ve been following your work for a while and I love the post you wrote about [subject]. I recently took on more management responsibilities at work and I’m trying to learn as much as possible about [same or similar subject] from folks that have done it before. Would you be open to jumping on a ~20m call to chat? ¹

Note that I’ve omitted many details here. The preparation was to make sure that: you’re confident that the person you’re reaching out to is the right person to help you; you can be specific about what you’d like to speak with them about, and; should they be open to chat, you have context to kick things off.

If you get a response, you can go into more detail later. You’re also more likely to get a response in the first place. For some folks, a long message will be enough to archive it immediately. For those that plan to respond, longer messages could cause them to (very sensibly) set a reminder to read through properly and respond later. But, you know, life gets in the way (and that is absolutely okay).

Once you’re happy with your message, send it via whichever medium you feel is most appropriate. If the person you’re reaching out to is on Twitter and has open DMs, that can be a nice, informal channel. If their email address is on their website, that could be a safe option. You could also reach out via LinkedIn, but be aware that your message will likely be neighboured by many poor quality messages.

Drop the entitlement

It’s easy to convince yourself when you start reaching out to internet folks that you’re entitled to a response—after all, we normally send messages to people who are expecting to hear from us, and who are very likely to reply. That’s not the case here, and you’re not owed a response whatsoever.

This hopefully goes without saying, but that means it would be unwise to follow up 2 days later with a message questioning whether they had indeed received your message, and asking whether they’re planning on responding to it any time soon. It would equally be unwise to call that person out publicly on Twitter, or to let them know a day later that you’re “bumping the message to the top of their inbox”.

That doesn’t mean you can’t follow up after some reasonable amount of time with a politely-worded message. Frustratingly there is not a generally-accepted reasonable amount of time I can speak to, but it’s probably longer than 5 days and shorter than 3 months, if that’s in any way helpful.

It’s reasonably safe to assume that the person received your message, should you have sent it via a common channel. It’s also safe to assume that should they wish to respond, they probably will (and that if they do not wish to respond, they probably won’t, and are unlikely to respond to your follow-up, either).

Assume positive intent whenever you don’t get a response. People are busy, and have many commitments that you’re unaware of. They could get many of these messages, and if they’re able to respond to any at all, might well have to be very selective with which they choose to respond to (which is also fine).

If you do get a response, great! In the best case they’re able to give you the time you asked for, and in the worst case (besides a lack of response), they’ve been kind enough to thank you for your message, and to let you know that they don’t have enough bandwidth at the present moment.

Assuming the best case, you can go into a bit more detail about what you’d like to chat about, and—assuming you’d like to chat with them over video—offer to send over a calendar invite for a day and time that would be least disruptive for them (expect to be flexible yourself, since you’re the one asking).

If you haven’t asked to speak via video or phone (or if they don’t have the bandwidth or desire to do so) you could ask your questions via email. This has the added benefit of allowing the person you’re speaking with to answer asynchronously and on their own schedule. Whilst I find speaking face-to-face to be valuable, written responses often convey more detail and sometimes include links to helpful references.

Respect people’s time

Once you’ve got the attention of the person you reached out to, it’s important to respect the time that they’re giving up for you. Most people have more things to do than they realistically have time for. If they’ve taken some of that time to help out a stranger on the internet, that’s a big deal.

This plays out in a few ways—some of them very obvious, and others that might not be immediately clear. A non-exhaustive list is something like:

• If speaking via video, look at the camera and pay attention to what the other person is saying
• Spend more time listening than speaking, and properly acknowledge what the other person says
• If you’re taking notes, let the other person know what you’re doing to avoid looking distracted
• If you’d like to record the conversation to make notes later, ask for permission and respect it
• Keep to the agreed timing and don’t cause the other person to have to excuse themselves
• If asking questions via email (or similar), be succinct and clear with the questions you ask
• Don’t ask questions that could be insensitive, particularly where cultural differences exist
• Thank the other person for their time (and leave enough time at the end to do so without rushing)

Depending on who you’re reaching out to and the channel you use, there might be more or different things to consider. Whilst it looks like a lot of things to remember, it’s largely things that you probably—and hopefully—do instinctively (and how you’d likely expect others to act if they were asking for your time and advice).

Lastly (and I acknowledge that all of the above might not have framed this perfectly) relax, and have fun. The vast majority of folks are kind, humble, and more than willing to share the things they know with others. Some large number of them will have learnt from internet folks over the years, too, and will be glad to pay it forward. With any luck, as I have, you’ll make many new friends and collaborators.

Apr 19, 2020