Book Rec: The Tech That Comes Next

Hey there. I don’t usually share much of my own context on this blog. I’m a boundary holder. But we’ve been at this for two years now. I’ll tell you a little bit about me, shall I? (Don’t worry, this will turn into a management post eventually.)

I have a tattoo that incorporates a line from my favorite novel, Hopeful Monsters by Nicholas Mosley. The line is “I thought—But if human life were a matter of style, of means rather than of ends—”

I have it because I love the book, but more importantly because it reminds me of some friends who passed before they had a chance to see what ends their means could have. Steve and Claire both had incredible and lasting impacts on the people around them, but (as far as I know) they really only ever got to see that impact in short glimmers of possibility: the light in the eyes of someone resonating with their music or a thank-you note from a student they helped bring to a new place, light and gratitude not as ends but as quick pauses of recognition on someone’s way forward.

This isn’t to say that we don’t need to care about how things turn out – readers of this blog know that impact matters a great deal to me. I firmly believe that outcomes matter more than intent. But maybe it’s also worth talking about the fact that impact and outcomes, if we’re lucky, aren’t final. We build on them, and what we build is always a foundation for the thing that gets built next.

So maybe I’m predisposed to appreciate a book that asks the question:

“What could we create together without requiring that we know from the beginning what the end point will be?”

(Here, dear readers, is where this turns back into a management blog. Don’t worry, the feelings part is mostly over. I’m relieved too.)

The teams that I manage are in the business of creating tech solutions for social impact and philanthropy organizations, and, as you know, building an equitable world is kind of the whole point of this for me. So when I saw that Amy Sample Ward and Afua Bruce were publishing a book with the title The Tech That Comes Next: How Changemakers, Philanthropists, and Technologists Can Build an Equitable World, my interest was caught.

I want you to read the book, so I’m not going to give you a comprehensive summary, but I do want to tell you why I’m so glad this book is out in the world and why the managers who read this blog, specifically, should care:

This book is rooted firmly in the means, but it doesn’t ignore the ends. Amy and Afua set out a clear vision for the most important aspects of the equitable world we (I’m joining up with this) want to build– and then lay out strategies for moving in that direction with the support of thoughtfully deployed technology. The specifics of what that world looks like will be different from community to community, and the specific technology that supports the strategies will also be different and will change over time. Amy and Afua correctly (I think) leave those specifics for communities to build themselves. You won’t find any recommendations for specific products, but you will find guidance on how to think about choosing them.

The core of the book, for me, is the strategic principles that Amy and Afua outline for how we get there, structured around five key roles that are needed to collaborate toward this vision (technologists, social impact organizations, funders, policymakers, and community members). They frame the concerns that each role is uniquely and best suited to address, and outline how to work together to make sure the focus stays on the community whose needs and dreams are the targets of the work. And, importantly, they frame actionable questions that allow the people playing each role to hold themselves and each other accountable for keeping the community at the center of the process.

Why am I yelling all this at managers, specifically?

I’m lightly embarrassed that in two years of writing this blog, I’ve never talked about one of the key responsibilities managers have: finding tools that support the team’s work in equitable, effective ways. Often, we default to the thing that’s the fastest to implement or the most familiar; I’ve certainly been there. But you’re here because you care deeply about building teams that support and embody a sustainable, equitable future, and that means making even tech decisions with intention and an eye toward those goals. Most of us have never been taught how to make those decisions, and it’s not always easy or intuitive. Whether you consider yourself part of the social impact “industry” or not, when you’re making decisions about what tools your team uses, you would do well to follow the principles that Amy and Afua outline in The Tech that Comes Next.

This isn’t an ad, and I don’t get any compensation from this post or the links. I just want you to read the book. So, in case you missed that Bookshop link:

On being rested

Orchids on display at the Brooklyn Botanical Gardens in December 2021.

As you might know, I’ve spent the last three months between jobs following my second COVID-era layoff. I’m starting up a new role on Monday, and it feels like a good moment to think about what these last few months of very little work have meant for me and for how we can get our teams what they need in even “these times.”

I should start by saying that I’m extremely fortunate that my cost of living was covered by unemployment insurance, and I have a pretty reliable financial safety net with no one else depending on me financially. So this is all in the context of a confidence that I’d be able to pay for housing and food even if I didn’t get hired for several months. Also, the job market felt radically different this time than in March of 2020: companies were reaching out to me, lots of jobs that aligned with my skill set were getting posted, more companies understood how to make a remote interview work (though let’s be honest – lots of places have still got a long way to go there). I had the support of a broader network and more friends who weren’t also unemployed.

Under that radically different job market is – yes – the Great Resignation, a catchall term that stands in for those who have left the workforce because work can’t support their families or their dignity; those who can no longer work because COVID made it impossible; and a staggering death toll that we continue to gloss over. But under it is also the Great Unionization (are we calling it that yet?): victories of workers coming into their collective power, demanding better working conditions and management who can take a longer, more sustainable view of what makes a company AND the people who comprise it thrive.

So that radically different feeling, coupled with vaccinations, meant that while there was and is plenty to be broadly anxious about in the world, I could let go of much of the personal anxiety that characterized April and May of 2020 for me. I could be confident that I would be okay. I could let myself read books and give more volunteer time and look at art and take on a couple of interesting freelance projects.

Now, three months into that space, I finally don’t feel like I’m under the thumb of burnout that was pressing for so long and that frankly couldn’t be lifted during the early months of the pandemic, no matter how many novels I inhaled. I feel, at some level, ready to return to finding and solving new problems, ready to be a practicing manager again without worrying that I will constantly need to protect my team from my own feelings.

It took all this to get here. It took three months of relative security and confidence that I would be okay, with most of my time being able to be spent on things that energize me.

That’s all very swell for me as an individual, but it’s also so far from the norm right now as to be almost laughable. Like the lesson here is “have enough money.” Very useful information, Hands.

So the obvious next question for readers of this blog is: how can we, as leaders of companies and teams, systematize the benefits of the kind of experience I’ve had over the last few months? How can we normalize and support people taking sabbaticals from everyday work where the focus isn’t caretaking or producing? While we are actively working, how can we make sure there is room in our lives for the things that energize us, if work isn’t serving that purpose? (And let’s face it: it’s a rare job that doesn’t take more energy than it gives.) How can we set goals that match our capacity to sustain the effort they require?

The answer to most of these questions will require a lot of listening: listening to your teams, listening to what your own feelings are telling you (because feelings are not facts, but they are data!), listening to workers in and outside your particular industry, who face different kinds of identity-based challenges, and being brave enough to make changes that serve the long term even if it means not making that short-term goal.

My wish for all of us for 2022, fellow managers, is that we continue to listen and act and listen again.

Owning your power as a manager

View from Mt. Monadnock in southern New Hampshire. A boulder is visible in the foreground with some pine trees below it, and trees in autumn colors and ponds are visible in the distance. The sky is blue with wisps of clouds.

Recently I’ve noticed a pattern of managers having a hard time admitting or accepting that they hold power within their organization – specifically, that they hold power over others. I want to take a little space here to talk through why that’s hard, and why I need you to own the power you already hold. And I’m using the word “power” intentionally here – sometimes it manifests as influence, which is a more comfortable word for some people, but it’s crucial that we maintain awareness of power dynamics that exist whether we want them to or not.

I’ve heard arguments that managers, especially middle managers, don’t really have power because they are beholden to so many other factors: your organization’s culture can override your personal influence, other people can override your decisions, company policy is set by someone else, etc. Here’s the thing: power doesn’t have to be absolute in order to exist. Even boards and CEOs have limits on their power, even if the space between those limits is bigger than for someone managing a small team within a larger org.

What does that power look like?

Recognizing our power is easier when we have specific things to look out for. Here are a few that are common to most managers:

  • Literal hiring/firing responsibilities.

If this is part of your job description, it’s the most obvious/direct power you have over a person: at some level, you control their access to their current job and influence their ability to get other jobs in the future.

  • Performance evaluation responsibility.

This is bigger than it looks at first glance. No matter what the shape of your current organization is like, you are part of a broader culture where an awful lot of people put an awful lot of their personal self-worth into their ability to do their jobs well. I do think this is starting to shift for the better, but a great many of us are still stuck in it. That means that we managers have a responsibility to be aware of the power dynamic that creates: we have the ability to impact not just their work environment, but what reports think of themselves by virtue of our responsibility to evaluate their work.

  • The ability to decide what other people do (delegation)

Yes, delegation is a pretty limited power. But your ability to assign certain kinds of work to your team members, and to do it in a way that either enables them to feel successful or sets them up to flounder, impacts the quality of their day-to-day work life.

  • Influence over decision-making processes and resourcing

Whether you’re gathering data to show what your team is capable of and where you need more help, advocating for raises, or identifying processes that can be streamlined, you’re exercising power over the way the organization is run.

  • Holding a unique perspective within the organizational system

(Psst… everyone has this, not just managers.) We often forget that the folks above us in the org chart don’t automatically know everything we know and then some. If you have a boss or other authority that you report to, you have information about the way the organization is running that they don’t have… unless you give it to them. You know what challenges your team is up against and if you can share how those things are keeping the organization from meeting its bigger-picture goals, you’ve got a much better chance of solving or simplifying those challenges. (Yes, I’m talking about managing up – check out Lara Hogan’s excellent blog for more on that.)

  • The ability to facilitate career growth

Whether you’re coaching, mentoring, or sponsoring your direct reports, you’re in a position that enables you to facilitate their career growth in and out of your team.

All of these are directly tied to the amount of trust that you’ve built with everyone around you.

I think this is the part that makes people uncomfortable. We often associate the word “power” with brute force, assume that exercising power means pulling rank, making people do things they don’t want to do “or else.” There’s a general undertone that power is unfair. This association means that we feel like exercising power means exploiting the trust that we’ve carefully built with our teams. In reality, our jobs are a constant flow of building and relying on trust with our teams, and we’re doing that within the framework of a power dynamic that can either bolster that trust or diminish it. (There could be an entire blog post on the difference between exploiting trust and relying on it, but for now let’s just acknowledge that there’s an important distinction).

What if you don’t acknowledge your power?

  • Your ability to do your job diminishes: Your team loses faith in your effectiveness, which in turn reduces their ability to be as effective.
  • You miss opportunities for real positive impact at every level that you interact on: chances to advocate for individuals, to enable your team as a whole to work better together, to influence the culture of the organization in ways that align with your values.
  • You avoid necessary difficult conversations because you assume you don’t have what it takes to solve the problem.
  • You lose opportunities for your own growth. If you don’t believe you hold power, you’re less likely to take risks or try new things that can lead to real improvement.
  • You burn out because you don’t feel effective at what you’re doing.
  • Maybe most importantly: Your power manifests in ways you didn’t intend, which can hurt people unnecessarily.

What happens if you do?

  • You start to be able to use it intentionally and with integrity.
  • You become conscious of what actions build your power (hint: they’re mostly the same things that build trust) and what actions rely on the power you’ve built.
  • Your ability to use your power effectively reinforces your team’s trust in you, creating a positive feedback loop.
  • You find the edges of your power, which gives you space to create impactful alliances with others when your power isn’t the right kind for the task at hand. (This is why superheroes come in teams.)
  • You’re better able to create boundaries around what you do and don’t expect of yourself. You can say: here is where my power is, and within that I expect excellence of myself. Here is where my power isn’t, and if I don’t have the kind of impact I want over that area, I can still sleep at night.
  • You’re better able to identify when identity-based power dynamics at play: maybe you’re a white person with authority over BIPOC folks, maybe you’re not disabled but have reports who are, maybe you’re cisgender and have reports who are trans. When you’re cognizant of your power, you can be honest with yourself about when you’re doing right by those communities and when a misuse or neglect of your power is harmful to them.

When we’re managing well, we’re operating more from the trust we’ve built with our team than we are from a sense of authority conferred by our title. To keep managing well, we have to stay cognizant of the fact that that trust is a form of power, and accept both the responsibility and the possibility that comes with that.

Navigating the Great Resignation

Hi y’all. It’s been a minute since I’ve posted here! It’s good to see you.

A few weeks ago I posted something on LinkedIn that seemed to resonate with folks:

The Great Resignation is going to be, at best, a really unsatisfying game of musical chairs if employers and managers don’t take a hard look at ourselves and start treating the root causes of the burnout everybody’s hitting.

And of course, leaders and managers are burned out too. The hard work of addressing systemic issues in our organizations can only happen if we’re willing and ready to put our energy behind that work. So to you, my fellow leaders and managers: what are you doing to recharge that specific bank of energy and put it toward taking better care of your people?

Based on the comments on that post, the leaders I know are struggling. The best we can come up with on our own is often “take real time off” which is important! But let’s be honest: it doesn’t solve the underlying problem, it just separates us from it.

So. In an effort to help us connect and hold each other accountable for addressing the systemic issues that got us here – and keep our new hires from cycling right back out the door – I’m setting up (hopefully) affordable office hours through my employer, Now IT Matters, every Friday at 3:30pm ET/12:30 PT. Come once, come every week, whatever you need – it’ll be confidential, with no more than 7 people so we can really dig into what folks are facing, and I’ll be there to offer advice, guiding questions, and resources so that we can continue making our workplaces more equitable and effective. You can also book me for 1:1 coaching – I offer hour-long or half-hour-long sessions.

(I also owe a shoutout to Sara Wachter-Boettcher’s excellent workshop on leading through burnout, which I was lucky to attend a previous session of – if you’ve got the budget, I highly recommend registering for the upcoming session on 9/15. Not an ad, just an endorsement.)

Whether you’re new to managing or a seasoned leader, chances are pretty solid that you’re facing some brand-new challenges right now. I know I am. We don’t have to face them alone.

Update: Since writing this post I’ve separated from my former employer, but the above link will still work to book group coaching or office hours with me. Take care of each other.

What are you keeping?

Closeup on some white and purple crocuses in Rachel's front yard

About a year, ago, I did a little Q&A on Instagram to try to understand what folks who were being pushed into remote work were feeling most worried about. At that point, we were still imagining a shutdown that might last two or three weeks, and I can’t help but laugh at the “don’t worry about sustainability” advice I was giving then.

Now, a year in, with vaccine distribution starting to take hold, the world is starting to shade toward reopening. Maybe that will happen in a few months, maybe next year, maybe longer – you can see how hesitant I am to even imagine a world where more people are in the same physical place at once – but in order for it to happen successfully within our organizations, we need to start imagining what that possible world should look like.

Even for those of us who worked remotely long before 2020 and expect to stay that way long after, the last year has shifted the way that work fits into our lives: families are around while we’re working; illness, grief, and anxiety are increasingly major characters in our story; many of the things we used to do to get ourselves out of the house and recharge from work stress are inaccessible.

And it’s not just a question of whether we’re working remotely or in person. For so, so many, the substance of what we do every day has shifted radically. Jobs that sustained us, felt core to our identities, or fed our sense of independence and self-worth by allowing us to pay our bills and put food on the table, disappeared. Our relationship to work changed, not just outwardly or practically, but emotionally. I’ve talked with friends and colleagues who have felt that change in both positive and negative ways – often at the same time – and for me, at least, the jury is still out on whether on the whole, that change is for the better.

Amid so much change, many of us are spending our time dreaming about the things we get to go back to. At work, maybe that’s a return to seeing other humans in an office, getting to make art together, or creating space for serendipitous conversations. But I also think there’s value in thinking about the ways in which the difficulty of the last year have created space for new ways of approaching work and collaboration (and, of course, management) that deserve to be part of our next “normal.” Here are a few of the things I hope carry through (and if you aren’t doing these yet at your organization, it’s not too late to start):

Intentional connection.

Work doesn’t have to serve a community-building purpose in our lives. You don’t have to be there to make friends. But in a mission-driven organization, the sense of common purpose does tend to connect us to one another, and that can help us get through moments when collaboration is difficult or we’ve encountered a major challenge. The last year has forced us to create those connections intentionally if we want them to strengthen our teams. Some have done that by structuring in more regular 1:1 meetings or team connections; some by starting book clubs in a Slack channel; some by building a few minutes into the start of a meeting for everyone to get water or a snack, check on the kid doing virtual classswork, or just lie on the floor for a minute (goodness knows I’ve done my share of that). What if we kept those moments there when not everyone is operating in crisis mode all day every day?

Centering local communities.

Rallying around local businesses and organizations, the growth of mutual aid groups, and yes, endless walks around the neighborhood, have managed to help me feel rooted in my local community even as I feel disconnected from the ways that I’m accustomed to interacting with it. For me, it feels important to continue to center the people and organizations that keep me grounded in a sense of belonging once travel and more expansive interactions become possible again.

Asking for help.

A great many of us have had to let go of the fear of asking for help in the last year. We needed help applying for unemployment insurance (a nightmare even when the system isn’t wildly overloaded and laws aren’t frantically changing); looking for new jobs, prepping for interviews, and polishing up infinite resumes and cover letters; trying to keep programming afloat with reduced staff capacity; understanding new rules about payroll loans and sick time… the list is literally endless.

The point is, asking for help has been a critical part of getting us all through the last year, and that’s been really scary. There’s no room in the After Times to let that fear drive our actions.

We’re in this together.

If you’re at an organization that isn’t facilitating intentional connection, or that isn’t giving space for employees to ground themselves in a community where they can find belonging, or that discourages asking for help: know that it doesn’t have to be that way. You can do better, and you deserve better.

And if you hold power at one of those organizations, you owe it to the people who support your work to make progress on these things, because we won’t heal without them – in person or remotely.

Leading a remote team through a crisis

Update (February 24, 2022): I originally wrote this post in January 2021 after the insurrection at the US capital. As I write this update, the biggest crisis is the Russian invasion of Ukraine, but that certainly isn’t the only crisis that a US team might be facing, especially a team that cares deeply about DEI.

You may not be able to directly impact any of the ongoing crises. But you as a manager have the ability to help work be a place that makes things better for your team today, not worse. Keep your eye on what you have agency over, and exercise that agency with compassion.

I’ll be real with you: this post is very unlikely to help you navigate our current state of unrest and ongoing domestic terrorism in the US. My hope is that – assuming we all get through this moment – it will help you make enough sense of it to feel a little readier for the next crisis to hit your team, whether it’s brought on by external circumstances, internal conflicts, or anything in between.

I’m assuming you’re reading this blog as a manager (or aspiring manager) of a mission-driven team. You care about the work your team does on a level that isn’t just about being able to pay your rent. It matters to you that the work gets done – you care about the “effective” in “effective and equitable” – and so for you, it isn’t simply a matter of saying “work can pause while the world burns.” (If you are in a place where work can pause while the word burns, for goodness’ sake, pause it.) These are a few things I’ve learned from leading remote teams through difficult moments over the last few years; obviously none of those difficult situations were quite what we’re facing now, but I’m willing to bet that the lessons will continue to apply.

Crisis situations demand a focus point.

When something at work feels like an emergency, our instincts tell us to try to fix everything at once. We then fail to fix anything.

When there’s an emergency outside of work, maybe that captures all of our attention, and it becomes difficult to refocus on what we were there to do in the first place. Maybe we focus all our attention on work because that’s where we can exercise a little bit of control, but we end up focusing on things that don’t move our team forward.

In any event, the greatest gift you can give your team is a clear point of focus. What is the number one most important thing each person does? What changes about that when there’s a truly urgent situation? How can a team member know what’s most important for them to focus on, as quickly as a crew member of the Enterprise knows where to go when a red alert is called on Star Trek? How can you, the manager, help someone prioritize quickly in the event that some work needs to get dropped?

Review your work-emergency kit.

It’s likely that there are some foreseeable categories of crisis, and for those you can make specific incident response plans. These kinds of plans aren’t just for ops teams at big tech companies: system outages, family emergencies, power failures – these are things for which you can assemble a virtual emergency kit for your team to pull from when the time comes.

My work-emergency kits have included sample email language for rescheduling meetings or sharing a system outage; responsibility charts (ideally a full RACI or MOCHA chart) for who does what communication and who needs to approve lists or emails; report templates for lists of people I’m likely to need to email or call in case of an issue; and the EAP phone number if my workplace offers phone counseling as part of an Employee Assistance Plan.

You’re going to have to talk about it.

Dealing with all of this remotely adds another layer of effort: most of the time, you won’t be able to just look around the room and gauge how people are feeling. You won’t be able to intuit that folks are being affected by the situation at hand. You have to assume that at least some people are, and proactively make space for people to come to you if they need help prioritizing or can’t make their focus work that day.

You have to name that it makes sense for them to need you for this, and that that’s what you’re there for. Otherwise, people will hold back on asking for help for fear of looking unprofessional or wasting your time, and that’s a quick recipe for folks to spiral out into fear or anxiety before you realize what’s happening. By the time you see that they aren’t okay, they (and the work) may need a lot more effort to re-center.

It’s okay to not be ready. It’s not okay to be silent.

Many of us are navigating this particular set of circumstances for the first time. We’re inventing protocols and responses as the need arises. It’s expected and okay to not have all the answers, as long as you’re keeping lines of communication open and taking your staff seriously when they tell you they’re struggling. Be clear that you know that there are challenges, name the challenges you expect, and be open to understanding that others are likely facing difficulties you hadn’t even considered.

This is hard. It’s chaotic. But despite everything, I still put my faith in the power of a focused plan and empathy for the team. Let’s see what good we can do, friends.

If you need more concrete manager actions to take right now, read the unfortunately evergreen Managering in Terrible Times by Lara Hogan.

End of year book roundup

Readers, we’re so close to the end of 2020. Maybe there have been points this year where you’ve thought “gosh, I wish I could remember that book Rachel mentioned in that one blog post, but it’s just too [gestures broadly at everything] for me to go back and look for it.” Maybe not! Either way, I’m here for you.

In this post, I’ve gathered a list of all the books I referred to on the blog this year. Please consider buying them from your local independent bookstore or requesting them from your local library, and as you do, remember that their staff is also experiencing this 2020 holiday season, so be gentle about delays.

In order of appearance on the blog, here we go:

Lara Hogan, Resilient Management

Don’t be put off by the focus on tech teams – Resilient Management is great for understanding what your team members need from you, individually and as a group, and creating frameworks to meet those needs consistently.

Alison Greene and Jerry Hauser, Managing to Change the World

Required reading for all managers in nonprofit or for-impact organizations. If you’ve got a management question that starts with “How do I…”, chances are this book answers it well.

Shawna Potter, Making Spaces Safer

Learn about tactics for intervening when you see something happening that isn’t right. Not work-focused particularly, but the principles apply at work, especially if you’re on a small team without formal HR processes.

Karen Catlin, Better Allies

Hands-on, practical tips for being a better ally to all kinds of underrepresented groups in the workplace. Required reading for white folks, especially cis men.

Minda Harts, The Memo

Written by and for Black women in particular, and required reading for anyone who wants to understand how to do better at supporting and advancing the careers of the Black women in your org and your life (if you’re reading this blog, this is you).

Jennifer Brown, How to Be an Inclusive Leader

Helpful in breaking down the stages of understanding and action that we all go through, over and over again, in our efforts to become more inclusive leaders. If you’ve ever been frustrated because your team doesn’t look exactly the way you want it to right now, this book might be for you.

Christina Wodtke, Radical Focus

The definitive guide to OKRs (objectives and key results) as a way of framing goals for your org/team.

Brene Brown, Dare to Lead

Honestly? The hardest one on this list for me, reminding us of the importance and value of being vulnerable as a leader.

Carson Tate, Work Simply

This book had an outsized impact on my ability to collaborate with folks who don’t share my productivity style. Also, don’t miss the chapter on effective email writing.

Jeff Toister, Service Failure

Ostensibly focused on customer service operations, this book introduces the concept of maintenance and recovery anchors that have been key for me in framing what healthy teams look like.

I’m thinking about including some full book recap/review posts in 2021 – leave a note in the comments or email me to know what you’d like to see covered! (“Please cover my management book” is a very acceptable request, especially if you’re from a group that’s underrepresented in leadership!)

Have a safe New Year, all, and I’ll see you in January.

Growing your remote team

Stone steps leading up and away from the viewer, surrounded by greenery, in the Jardin des Plantes in Paris

In the last post, we started to dig into why hiring and onboarding team members remotely is such a challenge. In this post, I want to talk through a couple of ways to get ready to meet that challenge once your new team member is on board.

Get real about your remote training options.

Think of the onboarding process as starting before you even write the job posting. When forming a sense of what you need from a new hire, whether remote or in-person, I like to start from the end goal: six months into this person’s role, what can they do on their own? What do you expect them to be able to produce without a lot of intervention from you or other members of the team?

Now, think about what resources you already have to get them to that point. What written documentation, videos, or webinars do you have available about how to do the day-to-day tasks of the job? What relationships need to be built in order for the job to work successfully? What are you prepared to teach someone on the job? What do you need them to already know on their first day?

Remember, as you’re interviewing, that you’re hiring that day-one person. You’re responsible for getting them to that month-six person. What are you capable of doing in those months to get them there? What do you need from them in those six months? Once you’ve got an answer to that question – at least in broad strokes, if not in every detail – you’re ready to start interviewing candidates.

Make asking questions a key expectation.

So you’ve made your plan, you’ve done your interviews; now we fast forward to your new hire’s first week.

One of the shortcuts that gets lost when we onboard someone remotely is the ability to identify when they need help, without them having to ask. When you’re working in the same physical space and can see your direct report while they work, you can identify the cues they send up when they don’t know what to do. Maybe they’re looking around a lot, maybe they’re fidgeting more than usual – you see a change in their behavior that cues you to go up to them and ask how things are going. You also know when to leave them alone: you can see that they’re deep in concentration or on the phone with a customer.

Remotely, you have no way of seeing their uncertainty or fear. You have no way of knowing whether they’re in the groove or flailing hard. Except one: by talking about it with them.

As a new employee, asking questions is often a vulnerable thing to do. You want to prove that you can get the job done, that your new boss didn’t make a mistake when they hired you. You don’t want to ask a question that will prove that you don’t know as much as you think you should. On a distributed team, that feeling of vulnerability is increased by the fact that in order to ask your question, you have to actively reach out to someone: send an email or a chat message, pick up the phone, speak up in a meeting. You don’t want to feel like a bother to your new employer, or risk annoying a senior colleague during their first impression of you.

As a manager, though, you need them to ask questions. That means that not only do you have to create a space where it feels safe for them to ask questions – you have to create the expectation that they will ask questions. Make it clear that for their first X weeks (depending on the role), whether they’re meeting their job expectations or not will be at least partly contingent on what questions they’re asking. You have to establish the understanding that it’s riskier for them to not ask – and then back that up by taking their questions seriously, checking in about what questions they have during/after your scheduled meetings, and giving them a peer mentor who can field the questions they might be scared to ask their new boss.

If you don’t yet have the infrastructure in place to enable easy question-asking remotely, one word of caution as you start to build that out: the path for enabling people to ask questions shouldn’t be “let’s stay on a video chat together all day.” There’s a time and place for optional extended video chats that serve as spaces to “work remotely together” for those who like to have more company than our current environment affords us. For new employees, though, it won’t feel optional even if you say it is (because they’re trying to prove themselves!), and is likely to create counterproductive anxiety. And let’s be real: we’ve all got enough of that already.

No more shortcuts: Hiring remotely

Looking up through red autumn leaves against a bright sky

In the early months of the pandemic, when I was unemployed and looking around for my next move, I talked with a few recruiters who had similar stories: a fraction of their clients were theoretically hiring, but really what they were doing was trying hard to figure out how to make interviewing and hiring work remotely.

Having interviewed, hired, and onboarded dozens of (in my opinion) outstanding employees onto highly collaborative distributed teams, part of me wanted to say “hire me and I’ll help you figure it out.” Another part of me wondered why folks were finding it so hard, and in the next couple of posts I’m going to be digging into that question.

Maybe your team isn’t in a place right now to think about hiring and onboarding, but there are a few skills that go into doing it successfully that will serve you well in other parts of your work. These take time to build if you haven’t been focusing on them, and they take attention to maintain, so regardless of where you are in the hiring cycle – whether you’re a manager of a team that’s done comparatively well or whether you’re looking to get hired yourself – it’s worth thinking about them now.

Label your shortcuts.

One of the things people find difficult about hiring remotely is learning to translate the physical cues we’re accustomed to picking up when we meet someone in person. One reason that’s sometimes difficult is that we haven’t articulated what, specifically, we’re learning from those physical cues. It’s a shortcut – and shortcuts tend to be full of unconscious bias, so it’s worth unpacking these things even if you’ll go back to a co-located life as soon as it’s safe to do so.

If this is something you’re up against, consider what physical cues you feel you’re missing and what they signal to you. For example, eye contact is notoriously hard to replicate in a video meeting. What does eye contact convey to you? What does it stand in for that’s still important in a context where you might never share a physical space with your new colleague? Confidence? Attentiveness? Aggression?

Once you’ve labeled the shortcut for yourself, you’re in a position to figure out how to get there “the long way around” – by talking with them. Then, once we’re able to take the shortcuts again, ask yourself whether you and the person you’re talking to are really taking the same shortcut. Are you perceiving inattention from a lack of eye contact when they’re trying to convey respect? How can you use your words to figure out where that shortcut is leading?

After the interviews are over, there’s a whole new set of shortcuts that we take on in-person teams: cues that help us know how our new team member is doing, cues that help us as manager understand when to step in and when to lay back, and cues that help the new team member understand the cultural norms of the organization. In next week’s post, we’ll talk about some ways to get at those end goals with a distributed team.


Reader, we made it.

Now we get to make it.

In a lot of ways, for those of us in the US, the election might feel like an end point. It’s the milestone many of us have been working toward for the last four years. And it deserves to be recognized as the incredible accomplishment it represents.

My mission-driven managers, I encourage you to look at this as a beginning point as well. There are a lot of ways in which a Biden/Harris administration can make our path toward more equitable, effective workplaces easier, because we won’t be fighting against as many inequitable policies. There will be less ambient stress.

What that will allow us to do is to continue the work we’ve been doing under incredibly high-pressure situations, and to see how much farther we’re able to get without those extra weights.

The weight won’t be lifted from everyone on your team equitably. White folks in particular may be tempted to check out of the effort to create more equitable practices on your team, but checking out now cannot be acceptable. We’ve arrived at a place where there is much work to be done, we can see it clearly, and we’ve removed some major obstacles that made it harder to actually do it.

Don’t take your foot off the gas now. Take advantage of the opportunity to move forward toward the equitable, effective future our teams deserve.