Idée fixe 1.3: Remote Work in 2020: Beyond the Concept

Part three: Intentional Hiring and Onboarding in a Remote Setting

🤗Thank you for being here, when really you could be a thousand other places.

If you are new to Idée Fixe, welcome. This is part two of a four-part segment on Remote Work, so if you haven’t read part one and part two yet, why not do that first. 🖐Heads up part two is 3,800 words and will take you approximately 22 minutes to read. ☕️So grab your beverage of choice and settle in.

For next month’s idée fixe, I’m thinking of digging into the lab-grown industry as a whole. As lab-grown diamonds are nearing mainstream acceptance, products like lab-grown meat and lab-grown cheese are just getting started. Regardless of the product, they are changing their industries with some unexpected consequences.

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🎧I cannot kick off part three of this remote guide without mentioning the story about how clubbers in China are basically raving remotely due to the Coronavirus outbreak, and subsequent quarantines. According to Business Insider, cloud raves hosted by nightclubs are happening all across the country, and clubbers are tuning in on popular streaming platforms.

For anyone in America I highly recommend, Jessica Yellin’s News Not Noise segment on the Coronavirus and why it’s news, no noise. And yet there is no need to panic just be prepared.

Part three:
Intentional Hiring and Onboarding

What you will learn from this segment:

  1. The benefits of a structured hiring process

  2. An efficient and intentional onboarding process

  3. Do’s and don’ts of diversity and inclusion

Building a Hiring Process Tailored to Remote Work.

My initial gut feeling when putting pen to paper on all the things I have noticed and learned about whilst being a remote worker, managing people remotely, and going through the transition from remote-curious to remote-first, is that there are more and better remote employees than there are remote managers. And there are many reasons for this.

There are also way too many leaders and managers who underestimate the amount of work and time it takes to build up all the necessary memory muscles, skills and good habits to be a successful remote employee, manager, and company.

My aim with this section is to focus on the small but mighty details you can change and add to make these big moments better for your new remote employees.

📥 A structured interview process

As mentioned in part one, one of the key benefits of remote-first is the broader and more diverse pool of potential candidates. That said, because of this great diversity we absolutely need to be aware of our unconscious biases.

We all have unconscious biases - whether you like it or not. “The trouble is, when left unchecked, they lead us to make snap judgments and fall prey to stereotypes in decision-making.”

If you define from the outset what you are looking for in a candidate and lay out what the process should look like, this is a sure way of reducing unconscious bias and leaving things to snap judgment.

There is one process in place and it applies to everyone. This structured process helps save time and creates a better experience for the candidates. This process also forces you to focus on the actual candidate and the skills that you can see for yourself, rather than be dazzled by a good CV which ends up being an inflated version of reality anyway. So don’t hire CVs, hire human beings.

What is a structured interview?

It generally meets two criteria: a set of planned questions (in the same order preferably) that do not vary from interviewee to another (1) and the same evaluation criteria (defined in advance) to assess the candidate's responses to those questions (2).

The trick in a structured interview process is to come up with some thoughtful and in-depth questions that allow for your candidate to open up about their strengths and skills.

Ask open-ended questions (i.e. the answer to the question cannot simply be yes or no) to get a sense about how your candidate may approach certain situations.

Here are some ideas of open-ended questions that will hopefully give you some good insights into the candidate’s thought process:

✅ “Tell me about a time when a customer was upset. And how did you solve the situation?”

✅ “How would your boss or teammates describe you?”

✅ “Can you tell me about the last piece of constructive feedback your manager gave you?”

✅ “What is the latest accomplishment you are particularly proud of?”

Check out Google’s guide to Structured interviews.

🎯 Intentional hiring

Just like remote work requires a handful of specific skills and intentionality (and isn’t for everyone), hiring for such remote workers requires a specific hiring process.

The hiring process will be similar in many ways but where it will differ, it will look and feel very different. Here are some of these steps:

Manager training: before any of the below can start, you need to ensure that all your managers are aware of your hiring process. If you don’t want to feel like you are herding cats, then it’s best to ensure that every manager that joins your company is aware of what your hiring process looks like and what is expected of them.

Write a clear and inclusive job spec: the main thing to remember is that you are writing for a much wider and broader audience. Clarity is going to be key here. You have an opportunity to ‘sell’ the benefits of remote work but please don’t undersell the complexity that comes with this way of working. Think about the skills required and make sure these are also front and center - great communication skills, good time management, self-sufficient, goal-oriented…

At Lever, a recruiting software company, they wanted to fix the disconnect between how the hiring managers were feeling about the job descriptions they were creating (seemingly, happy with them) and how these same job descriptions were being perceived by the candidates (seemingly, a lack of clarity).

To fix this disconnect, they created a new type of inclusive job description, that they have called the Impact Description. It has two key components to it: the outcomes a new hire is expected to achieve & their specific milestones (1) and it articulates what the new hire would be expected to know already and help others with (2). The overall idea is that a better job description will attract right from the outset a better-fit candidate.

Share the job description within a wide variety of online communities: be intentional in sharing in communities beyond your immediate circle. We are generally tempted to share within our inner circles (because it’s easier) but if you do this you will be missing out on. A great way to ensure you have a good sense of all these communities is to ask each new employee what circles they are a part of and why. Start cultivating a diverse list of communities right from the start.

👉Check-out this great list of Slack communities for remote workers.

Allow for communication skills to be detected: one of the biggest skills needed when working remotely is having great communication skills. As such you absolutely need to make sure you are checking for this during your interview process. The above-suggested interview process with open-ended questions will come in very handy here.

Video call interviews vs. on-site interviews: one of the key differences with hiring remote workers is that you most likely won’t be sitting down with them face-to-face. That said, it’s a great opportunity to get a sense of how this person shows up when all you have is a face on a screen. It’s also a great opportunity to get a sense of how the candidate does with technical complexities such as broken video conference links, bad wifi, time zones, surrounding chaos… all these things happen every day on the job as a remote employee so it’s a great way to see how your candidate will handle such things.

With that said be mindful that the person you are interviewing might not have as much practice as you do with remote conversations. So don’t be quick to judge and it’s your responsibility to make sure the person on the other end is set-up for success and feels comfortable and safe in what can be an unusual setting for them.

There is something to be said about setting these interviews up properly. Give a sense of what will be expected during the call, please do tell your candidate who will be joining the call on your end, remind people this is a video call and be clear on the duration of the call.

An easy thing to do is to task one person within your organisation to act as the facilitator for both the candidate and the employees they will be interviewing with. If there are multiple interviews happening (generally in round 2-3 of the process) try and schedule these calls within the space of a morning or afternoon.

🏜One of my all-time favourite and absolutely chaotic interviews was done whilst I was working for a client in Morocco. What I had not accounted for was that the conference we were putting on wasn’t happening in a conference center, but rather in the middle of the desert with no privacy and terrible cell/wifi connection. So my first face-to-face interview with my future employer - the founder & CEO, and the Chief of Staff of the company - was done with the absolute worst wifi connection, in the middle of the desert, with Joe Biden and his team testing the mics behind me. Talk about a backdrop though. It was awkward and terrible on every level but right there and then I got an incredibly good idea of the calmness and kindness of my potential future employers and they got a good sense that I could work from just about anywhere and no matter what happens, I would figure it out calmly.

Create spaces for your team to discuss internally: an efficient way to gather all the feedback from your interview calls is to create a closed Slack group where each manager can drop their notes. Nowadays there is a wide variety of tools for hiring - especially with a focus on remote hiring. The key thing to remember here is that this needs to feel like a collaborative effort. Which can easily be forgotten when you are all remote.

Run a mini-project (paid): the best way to assess if this person is right for your team is to actually work with them. Please be mindful that such a request is time-consuming and demanding, and offering a small fee for their hourly work should be the norm, not the exception. The task will vary widely depending on the job and the company.

👉The team at Moonlight put together a great little guide for setting up such projects, check it out here.

💪As a remote team - you should always be testing for self-accountability, independence, collaboration, great communication skills and whatever other technical skills needed for the job.

Extending the offer: once you feel confident that you have found the right candidate for the job and a perfect addition to the team. Give them the verbal offer, share your excitement and ask if there are any concerns. Use tools such as HelloSign or DocuSign for all the paperwork.

Create an Efficient and Intentional Onboarding Process

I have seen two big mistakes with onboarding new employees: either there simply isn’t an onboarding process (1) or there is an onboarding process but it’s not (well) documented (2). Both of these are counter-productive to creating a first great impression with a new hire.

"To be clear, instruction—telling people what steps to follow or what factual knowledge they’re lacking—can be truly useful: That’s why we have checklists in airplane cockpits and, more recently, in operating rooms." [and] Learning is less a function of adding something that isn’t there than it is of recognizing, reinforcing, and refining what already is.” -

The Feedback Fallacy by Marcus Buckingham and Ashley Goodall

It is worth noting that there will be two distinct types of onboarding. There will be the fully remote experience within companies that are remote-first and do not have a HQ (1). And then there will be the partially remote experience for new remote hires that are joining a company with one or more physical offices (2). With the latter, you will often find that companies tend to fly the new hires out to one of the key locations for 2-3 weeks for the duration of the onboarding.

The hidden cost of no onboarding

Onboarding is the single most important moment for any new employee, even more so when you are a remote team. You will very rarely have another opportunity (if ever) to welcome a new hire into your company. And very few companies are intentional with their onboarding.

“One third (33 percent) of employees know whether they will stay with their company long-term after their first week.”

Onboarding is how, as a company, you set the tone for what has yet to come, you set your employees up for success and give them all the knowledge they need to be able to hit the ground running. This is also the opportunity to make new employees feel welcome, help them understand what makes your company special and how it's going to run efficiently. 

🚀The more time you invest up-front, the easier it will be further down the line. An employee trying to onboard by him/herself will take up to 3-4x longer to onboard successfully. 

With that said, simply replicating the traditional onboarding steps with some changes to account for the lack of in-person and in-office scenarios won’t be valuable.

I believe there are three levels within the onboarding process:

  • Company onboarding

  • Team onboarding

  • Manager onboarding

Company onboarding

Onboarding, when done properly and with care, takes up a lot of time and effort from your HR and operations team, but it’s well worth the effort.

If you have onboarding happen in groups this will add some structure and avoid a certain level of chaos. The way to do this is to have people join the company at the same time. For example, have 2 classes of onboarding (and hence, start dates) every month. It’s worth noting that, when you are flying people out to your HQ for their 2-3 weeks of onboarding you are also eliminating the complexity of juggling multiple time zones.

Finally, this onboarding time allows for connections to happen right from the start, creates a sense of support between new employees, it allows for lessons to be learned regarding the onboarding process and it is way more efficient in terms of support and time needed.

First things first, onboarding actually starts before your new hire joins the company. Here are a few things to think about before your new hire’s day one:

  • Make sure that you are prepared for the onboarding weeks and ensure everyone at the company knows their involvement. This gets easier and more streamlined over time.

  • A few days before their first day, provide your new hire with all the information regarding the logistics of their first day - such as start time, directions and parking (if it’s an on-site onboarding), reimbursement, paycheck dates, where and who to meet, an agenda for day one…

  • Ensure all IT, access to relevant tools, access to social accounts and admin is sorted so that the technical onboarding can happen as smoothly as possible.

These first two weeks also need to be highly facilitated. Don’t underestimate the amount of time proper onboarding takes. When you are small and still starting out, get as many people involved as possible - everyone should be making time for this and feel a sense of responsibility to get new employees onboarded properly.

Getting input from people who might have had to onboard themself will also be extremely insightful. This generally happens when you are a small startup and the first 20 or so employees end up onboarding themselves and creating their own onboarding process.

  • What did you wish you had been told during your first week?

  • Where did you lack support?

  • What did you struggle with the most?

  • Where did you feel like you wasted a lot of time?

Clear documentation for all the tasks: have the onboarding process documented in Asana or Trello (or any other organising software) and make sure all the documents are easily accessible in shared folders. That way, when a new employee joins they can see what the whole process will look like, will know what to expect and what will be expected from them. Check out GitLab’s onboarding handbook and task list here.

Speaking of Asana, Stephanie Hess, Head of Global Communications and Corporate Marketing at Asana explains how documenting everything has been vital, especially during the onboarding process. In her own words, “We live the Asana approach that we share with customers and have onboarding templates for all new hires. When it comes to onboarding remote employees, our team has tailored these to ensure that all critical information, best practices on tech and tools use, calendar of ongoing training, all hands schedules and team cadence for meetings, and key projects are all included and accessible to our remote employees on day one.” 

Plan the first two weeks: good companies plan out the first day or two. Great companies plan out the first two weeks. All too often you see new employees sat at their desks wondering what they should do next. For some, it might be really easy to be outspoken and proactive, for others not so much. No one should be left wondering what the agenda for the rest of the day is. This feeling of being forgotten and left to your own devices is exponential when you are remote.

Over-communicate: this goes hand-in-hand with the above point about documenting everything. Throughout the next two weeks, there is no harm in repeating yourself over and over again. Whether it’s repeating the company’s values, the objectives, how you will measure success, what culture is and is not for you… Now is the time to share all this and more. Just make sure that all of this is documented so that your new employee has a way to reference all this and go back to it when needed.

Tell your culture story: at NationBuilder, a lot of time was spent on telling the company story, hearing from the Founders and the CEO, talking about the values and the mission of the company, doing story circles… all of this was part of laying the ground for what was expected of all new hires.

When joining an all-remote company fostering connectivity can be tricky. As such doing all of the above allows new hires to get an understanding of the roots of the company. As veterans open up and share part of their company story, the hope is that it will prompt new hires to share their story too.

Team Onboarding

Separating out the company onboarding from the team onboarding will only be necessary for larger organisations. The idea with team onboarding is that once your new hire has been acclimated to the company culture as a whole, they should now spend some quality time with their team.

The tech, tools, and software needs: I believe there is a basic IT set-up needed right at the start but if you want to allow your new hires to be fully immersed during their company onboarding they also shouldn’t be worrying about Slack messages, emails, needs from their team members… There is definitely a discussion regarding what tools will be needed during onboarding and what tools will be a distraction.

Make the expectations incredibly clear: as a team, it’s a great opportunity to clearly communicate the expectations of the team as a whole and how the new hire will contribute to the team’s goals and efforts. This is where the new hire will start to understand where they fit into the organisation and their team.

Team goals, priorities and success measures: take the time to communicate how the team’s progress is measured and how the priorities are set. One of the best frameworks for this is OKRs. Objectives and Key Results (OKRs) is a framework for defining and tracking objectives and their outcomes. If you are not familiar with it, I highly recommend you look it up as it’s especially useful for remote companies.

Help them understand and appreciate the impact of their job: when the team gets to meet the new hire, there is an incredible opportunity to lay out how what the team is focused on helps the company achieve its overall objectives. This is your opportunity to clearly define how the new hire’s role fits into the overall goals of the company.

Manager onboarding

Meeting with the new manager is going to be key, and the sooner the better. Your new hires should have enough time with their manager right at the start - it helps to take away some of the nerves. Allow for time again near the end of the two-week onboarding.

Google revealed that a simple “reminder alert” email to the hiring manager can reduce the new hire’s time to productivity by a full month, a whopping 25% decrease.

Below are some of the topics and tasks which the hiring manager should perform (and is also should be reminded about before onboarding, according to Google):

Have a role and responsibilities discussion: it’s always best to have this discussion a few times during onboarding and it will evolve slightly as the new hire acquires more information.

Create a buddy program: by matching your new hire with a peer buddy beyond the first two weeks of onboarding is a great way to ensure they will continue to feel supported even after the onboarding period.

Create a shadow program: this will allow the new employee to shadow a variety of people at the organisation and get a real sense of all the different jobs and skill sets required. Both of the above will allow for your new hire to build their own social circle within the company. It will also create some level of empathy towards fellow teammates and their daily tasks.

Stephanie Hess, Head of Global Communications and Corporate Marketing at Asana also shared with me her philosophy around wanting to replicate the closeness you can achieve when people are physically in the same space.

“We partner all remote hires with an onboarding mentor who is available to answer in the moment questions that typically come up for anyone who is new to a team. We try as best we can to replicate the feeling of being in the same room as other colleagues and leverage a chat buddy system during the day and in meetings so employees who are remote can ask clarifying questions - including meeting room volume control or content sharing.”

Set-up at 30, 60 and 90 days check-in: during the first 3 months you should have monthly check-ins simply to take stock of where things are, what’s worked and what hasn’t.

At a conference (see video below), GitLab co-founder and CEO Sid Sijbrandij shares what onboarding looks like within an all-remote environment.

Final thoughts on onboarding.

👋Once your new hire has gone through their onboarding, introduce them to the entire company during your next all-hands / staff meeting (I told you these were valuable in part 2).

Remember that onboarding shouldn’t feel like a one-off event, but rather like an ongoing process. With that said, once your employee has gone through their two-week onboarding process, make sure to get all the feedback from them straight away while it’s still fresh. Get them involved in the planning, get input fast and often, and especially in the beginning, adapt based on the input you are getting and what you are seeing. 

You can very efficiently create a short survey. It's also an easy way to collate all the information into one place:

  • What worked?

  • What didn't?

  • What did you like?

  • What's missing?

  • Do you feel ready and set up for success?

If you onboard people in groups (as suggested above) you could bring this same group back three months into their employment tenure. This is a great opportunity to see how they are getting on, what could be improved in the onboarding process, what might be missing…

Diversity and Inclusion

Two of the biggest mistakes we can make when thinking about diversity and inclusion, and possibly the most damaging, are the following:

  1. There is an ongoing misconception around diversity so it’s worth repeating that “diversity is not a fixed trait, but a factor that only becomes relevant when you are talking about ‘groups’ of people.” One person cannot be diverse.

    Please remember that if you have just one person from one demographic, you are putting an incredible burden on this one person. You are simultaneously asking this person to represent a whole demographic and you are asking this person to remain unique in what is often a fairly heterogeneous setting meaning this person always has to be the exception - this can become very exhausting very quickly.

  2. You hire diverse employees and then you don’t set them up for success. Jill Soloway said it best at an event I was at recently where they mentioned that the biggest mistake was thinking that merely identifying diverse people was enough. You actually need to be intentional all the way and create a program to ensure everyone feels set up for success. Hence, the incredible power of a well-thought-through onboarding program.

Just because remote work has the great potential for more diverse and inclusive teams, it doesn’t mean they will be. And similarly, just because you have diverse and inclusive teams, it doesn’t mean they will be successful. You need to keep on being intentional for it all to succeed.

🤩 Are you interested in a remote job? Check out the largest job market place for remote work curated by AngelList.

Share Idée Fixe by Toni Cowan-Brown

Note: Read part four of this Remote Work guide - Managing Remote Teams.


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In the most simplistic way an idée fixe is any idea that dominates one’s mind for a prolonged period. This includes both the delusional and the pedestrian ideas.