When your mindset isn’t the problem: getting adaptive training when you need technical training

When you hit a certain stage of your corporate career — like being a woman of a certain age, but better paid — you may end up in a lot of development training for various reasons, or pointed at coaching, or both. I learned, in one of these, a very useful distinction, what people development curriculum designers call adaptive challenges vs technical challenges.

Technical challenges are skills gaps, basically. You don’t know Australian tax law. You don’t know C++. You’re not a very polished public speaker. You aren’t well networked enough with senior leaders.

Adaptive challenges are when you’re getting in your own way. You learned C++ but you can’t bring yourself to apply for the job. You’ve practiced your public speaking but you turn down opportunities to do it. You know lots of people and they think highly of you, but you never ask them for help.

It’s possible to have both challenges at the same time, and for difficulties in one to inhibit the other; say, your dislike of attention (adaptive) is getting in the way of you investing in your public speaking skills (technical). But there’s also a huge tendency in corporate people development to spend a lot of time on adaptive challenges, particularly for underrepresented groups and in equity programs, relative to the investment in technical challenges.

My belief about why this is is that addressing adaptive challenges simply scales better. Whether someone is in finance or activism or programming or real estate or medicine, the techniques you teach them to get them OK with asking other people for help more, or asserting their opinions more, or for assessing their own work fairly, are similar. You don’t need to find someone with an overlapping professional background or from the same field to address adaptive challenges, and you can draw on an entire community of teaching and coaching practice. And on the provider side, you can position yourself as a coach who teaches assertiveness in a wide variety of fields, rather than someone who trains assertiveness for non-profit accountants!

It may also be a comforting story to tell yourself about your equity practices: probably the reason that underrepresented people aren’t succeeding in our organisation is that they’ve internalised messages from somewhere else, probably some large and uncontrollable force outside, that they aren’t worthy! Fortunately, they are now on a level playing field in your organisation and all you need to do is help them out of the mindset that other forces taught them.

Whatever the cause though, the result is a similar pattern to vague feedback holding women back. If what is stopping someone progressing in their career is that they don’t know enough about Australian tax law, at some point they just need to learn more about Australian tax law, and assertiveness training doesn’t have a lot to add. And they or their employer are going to have to do something not as scalable as assertiveness training to address it.

For employers: don’t leap to adaptive challenges as the answer for your equity problems. If there’s technical challenges, you are going to have to drill in to individual or small group teaching, or invest in external programs that require considerable time and money investment. (Their adaptive coach might encourage them to take an hour every week to reflect on their goals, but their taxation law professor is going to flat-out require that they pass exams.)

Managers: track investment in someone’s development over time: if an employee did Overcoming Impostor Syndome and Unlocking the Big You last year, you should question whether The Light Within is the course for this year, relative to the entrance requirements for a masters degree or a rotation into a team that writes more C++. Work with people to ensure that there’s investment in the actual skills they need to progress as well as into their mindset. In the worst case, you are really selling someone very short if you help them be big and bold and proud and self-actuating, and then you don’t listen to them now that they know enough about themselves to know that they really need to learn more C++.

Questions to ask of employers transitioning to supporting permanent telecommuting

Some employers are beginning to announce transitions to remote-friendly or all-remote workforces even after office work is judged safe again. This has a lot of potential upsides in reducing commutes, in increasing job opportunities outside of established tech centres, in giving people access to their preferred working styles.

But there’s also a lot of potential downsides where employees personally pay to recreate the parts of the office experience they need and nevertheless find that their career tops out early or that they’re summoned or semi-summoned back to a tech centre just as they’ve started to realise the benefits of remote work.

Thus, just as I’ve written before about questions you should ask when hired into an existing remote position, you should ask a similar set for a company or position transitioning to remote work, to make sure that it is invested for the long term and is clear about any career or financial sacrifices you will be required to make to be remote.

Are there limits on where employees can be located? It’s quite common for remote employees to be required to be based in certain timezones, countries, or states/provinces where the employer already has some kind of established presence.

Is this transition in fact permanent, or is there a review date? Moving away from a city is a very large investment, often in direct costs but definitely in opportunity costs. Best to make such a decision on a strong commitment from an employer to a long time frame.

Will compensation be adjusted downwards for employers who relocate to an area with lower cost of living (or lower market salaries)? There are some remote-first or remote-friendly employers who pay the same salary no matter where employees are located, but also many which pay against local cost of living or local market conditions.

Will all remote compensation be adjusted downwards on the assumption that everyone will leave high cost of living areas? Hopefully not! Because some people have substantial investments in their current area of residence, eg commitments to their partner’s career or to their local family or friends, or to the cultural scene or their hobbies, or to retaining the option to leave their current employer for another that will require them to be office-based.

Will employees who move to an area with less generous minimum benefits have their benefits cut? Eg, will they lose days of vacation or carer’s leave? Will their insurance be revised in line with their new residence’s minumums?

Will there be formal limits on which positions are available remotely?

Even in the software, creative, and research positions that can be done remotely, it’s common for companies to not allow all positions to be remote. Here’s some possibilities for what this might look like:

  • you can’t become an executive if you’re remote
  • you can’t become a people manager at all if you’re remote
  • you can’t do security-sensitive or personnel-sensitive work if you’re remote
  • you can’t achieve a certain job level if you’re remote

Best to know!

If the company is indeed open to all positions being remote, how are they going to ensure equality of opportunity?

If there are going to still be offices, it may in theory be possible to become an executive or a high level staff member while remote… but it eventually emerges that no one is actually doing those jobs remotely, that those folks are all office-based.

What does the employers plan for developing remote staff careers look like and how will they audit its success?

Will there be training and resources for workers transitioning to remote, for managers who are remote or managing remote workers, etc?

There are specific skills required to manage and be part of both all-remote teams and mixed-remote-office teams. Will these be taught to employees? Will there be trained support for specific situations that may arise (eg, it may be more difficult to reach remote employees in a suspected emergency)?

Will there be financial support for the costs of remote working?

Remote working passes the office maintenance costs onto employees, eg substantial extra energy costs (particularly in areas with very cold winters or very hot summers), additional space, need for office furnishings, higher Internet bills and larger mobile plans, IT equipment, etc. Will the employer reimburse these costs and to what extent?

Ideally this support isn’t too specific. Eg, “we’ll pay for a co-working space”: co-working spaces usually have open office plans and quite a few involve hotdesking (especially if you’re part-time). They’re thus generally not suitable for people who have a lot of sensitive meetings (ie most managers or HR staff), some people who need physical accommodations, or people who are unable to work well in open plan offices.

Conversely, “we’ll pay to fit out your home office”: establishing a home office requires that people have or can afford to move to a place with an extra room, and usually that there are only one or at most two people in the home who need a home office.

Flexibility is better.

Will business travel be mandatory or strongly encouraged?

Quite a lot of remote teams rely on an mandatory or near-mandatory all-hands in-person get together once or twice a year for team building purposes. This may be an easy trade for some to get the benefits of remote work, but it may not be for others, especially for primary carers.

This question may be especially relevant for people who are going to be one of the few remotes on their team and may be expected to travel to the office regularly; and also for managers, who are occasionally expected to travel out to each of their remote reports periodically.

Will there be allowed to be children/dependants in the house during working hours and are there restrictions on their care arrangements? At least when schools and daycares are open, it’s common for employers to insist that if there are children/dependants living with a remote worker, they must have a carer who isn’t the worker. It’s possible (jurisdiction dependent) for them to insist that the house must not have dependants present in work hours at all.

Creative Commons License
Questions to ask of employers transitioning to supporting permanent telecommuting by Mary Gardiner is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Navigating ambiguity is just one skill among many

Many jobs, especially professional jobs, have some rubric in which you are required to be comfortable with ambiguity, skilled in ambiguity, thrive in ambiguity, maybe enjoy it or love it. It makes sense. There’s a lot of unanswered questions out there, it’s not surprising that some jobs want you to answer some of them.

But there’s risk in holding this up as the standard of succeess, the single skill to grow in. I have been trapped, and seen others trapped, in very unhappy situations, either saying to ourselves “this situation is ambiguous, why aren’t I thriving?” or worse, having others say to them “this situation is ambiguous, why aren’t you thriving?”

Not all ambiguous situations are alike, and your expectation that you can navigate ambiguity, or even your experience of successfully doing it in the past, does not mean that you should either seek out or stay in ambiguous situations.

The key thing about navigating ambiguity: it is a useful skill, it is not the only useful skill. A situation being unusually ambiguous, or being more ambiguous than other places you could be, does not mean that it is the right place for you, a place where you need to force yourself to be in order to be the best you can be, or progress in your career, or make the most difference.

After all, what skills are you giving up or not using while you’re spending all this time navigating ambiguity?

Is there a reason for the ambiguity?

There’s an extreme version of wanting people to thrive in ambiguity that amounts to loving ambiguity itself, and creating it where it isn’t needed. Ambiguity can be necessary and good – the single worst mistake of my career was forcing a decision from a set of alternatives when the bad alternatives were a clue that I needed to spend more time exploring – but it’s stressful. Successfully navigating necessary ambiguity is different from “it’s all ambiguity all the time”.

Is resolving this type of ambiguity a skill you have?

Ambiguity can vary widely. Is this a defensible case or should I plead guilty? Is this skill one I should turn into an income or develop as a hobby or volunteer to teach to others? Is the wind going to move before the fire reaches here? Which of the two warring factions should I have tea with?

Your background, interests, training, support system equip you to navigate some types of ambiguity and not others. I can arrange a workable response team structure to an infrastructure software outage pretty quickly. I can design a passable fundraising strategy for your small not-for-profit and I have a bunch of general skills I can put to use in many situations.

But I am not remotely the right person to turn to in a humanitarian disaster to perform either medical or resourcing triage. I also have no experience navigating the changes in children’s fashion to figure out what your line should be 12 months from now. The mere fact that there’s ambiguity there and I have at times succeeded in navigating ambiguity does not make me an effective person in those situations. If you want to be able to navigate ambiguity better, play to your strengths in choosing what ambiguity that is.

Is resolving this type of ambiguity a skill you want to have?

Maybe you’re in a situation a little closer to your experience than children’s fashion futures are to mine, but still you’re not quite at home in this level of ambiguity. There’s more hurt, more money, more people involved that you’re used to.

Since ambiguity is a useful skill, perhaps this is a situation to stick around in, but you’ll want to have support. Do you have access to training, advice, mentoring? What’s the situation for you if you fail, or do a less than perfect job? Is there a way out if you decide it’s beyond you?

If not, again, you have a decision between whether navigating this type of ambiguity, with this level of difficulty, and this amount of risk, is the skill you want to be developing right now, compared to all the other things you could be doing.

Is this ambiguity one you have the power to resolve?

This is the big one. Regardless of how skilled you are in the domain, or how subtle your ability to draw out the opinions of others, if the structures around you don’t let you be part of resolving the ambiguity you’re going to have a very rough time.

For example, if you are in the midst of a humanitarian disaster, and you don’t have a network of local contacts, transport, communications, and, potentially, defence, there is likely a pretty low limit on what you can achieve even if you have coordinated other disaster responses.

A version software companies often run into is expecting new or junior or solo staff to be able to resolve major problems with the product or its infrastructure without access to hierarchical power (ie an inattentive, disempowered, or non-existent management chain) or a structure of intermediaries to work with. Being able to find and navigate the undocumented and hidden decision-making channels in these situations is a very useful skill but it’s not an easy one. Dragging something great out of this situation may not be a great use of your time and skills.

Navigate right on out of there?

There’s plenty of times that navigating ambiguity isn’t the right match for you, right now. Go ahead and navigate ambiguity by navigating yourself right out the door and into a situation with less ambiguity, different ambiguity, better help with ambiguity, or a focus on a skill that isn’t navigating ambiguity.

Learning more about a remote working position

I’m in the process of wrapping up a long period of working remotely at least part-time from home, beginning in 2006 when I enrolled in a PhD program and continuing through my time at the Ada Initiative and at Stripe to this year.

My take on working remotely in future is really “it depends on the details” (and likely different details for different organizations). To that end, I contributed some suggested questions you could ask to Hypothesis’s Working remotely guide, which they’ve incorporated in a slightly edited form. Here’s my original questions; I’ve also added a few more at my end after some feedback from Andrew (himself a veteran of around seven years of remote work).

Introduction

Before you start working remotely at a new organization, you should explore how they structure remote working and if there are any expectations mismatches between you and the organization. A particular remote job may or may not be a match for a particular remote worker.

Important: I don’t think there is any one right answer to any of these questions. It’s a question of fit between your working style, the position itself, and the relationship of the position to the rest of the organization. But the answers are worth knowing so that you can evaluate your fit and make plans for effective remote working.

Sources of information

This entry has a lot of questions, too many for a “do you have any questions?” section of an interview. But you can use other sources of information to get most answers, especially about organization-wide questions:

  • the job description, and descriptions of similar roles
  • the organization’s website, particularly the About and Careers pages
  • the section of the employee handbook dealing with remote work
  • the LinkedIn pages or websites of your future manager and colleagues
  • longer, separate, conversations with your recruiter or hiring manager
  • your offer conversation or letter, or your contract

Some questions you also may only need to ask if you hear of concrete plans to make a change to the organization (eg, you learn that a new office is about to open near you).

Questions

How are you remote and who are you remote from? This post is using ‘remote’ to mean something like “most days, you are not in face to face contact with any colleagues.” But you should be aware of the details: will you be working without in person contact with teammates or with the wider organization almost all of the time? Do you have any colleagues in your team or your wider organization in your city or region, or who regularly visit? Will you work on any joint projects with them? Will you be able or be expected to sometimes work with them in person even if there’s not a permanent office space?

Separately, is in-person contact with vendors or customers part of the job?

Is your immediate team remote? Is your manager remote? Being a remote member of a team that is all working remotely from each other is different from a team which is mostly located in an office with each other. Likewise, being managed by someone who is in an office has some potential advantages (for example, access to information circulating through verbal grapevines, being able to access answers from colleagues for you quickly), as does being managed by someone who is themselves remote (a direct appreciation for experiences specific to remote workers, a personal interest in advocating for them).

How many remote workers are there at the rest of the organization? What percentage of teams you will work closely with are working remotely, and what percentage of employees overall are working remotely? Working as one of very few remote workers for an organization where most employees are in an office together is different from a mostly or entirely remote-working organization.

What’s the future of remote work at the organization? If the organization is mostly or entirely remote, are there any plans to change that? If the organization is mostly office-based, are there any plans to change that? If an office is likely to be founded in your city or region soon, will you be able or be expected to work from it?

You may be considering a job on the understanding that the remote work will be of very short duration (eg, an office is opening in your city in two months time). Is there any chance the time will be longer, and are you OK with that?

What is your manager’s approach to remote workers? How frequently will they speak with you and through what media? Will they expect you to travel to them? Will they sometimes travel to you? Have they managed remote workers before?

How long have there been remote workers for? Is the organization new to having remote workers or has it had remote workers for a long time and bedded down a remote working style?

What is the remote working culture like? Is most collaboration over email, text chat, phone, video conf, or some other means? Are there watercooler-equivalents like social IRC channels or video chats? How active are they? Are remote workers mainly working from home or from co-working spaces? Are there occasional team gatherings for remote workers to meet colleagues in person and are they optional or compulsory?

How flexible are the hours? Not all remote work has flexible hours; you may have mandated work hours, or core hours, or shifts, as in any other role.

Are the remote workers spread across multiple timezones? If so, are your team and closest collagues in your timezone or another one? Are you expected to adapt your working hours to overlap better with your colleagues? How are meetings and other commitments scheduled across timezones? Do they rotate through timezones or are they always held in a certain timezone? Are you ever expected to attend meetings well outside your working hours, and if so, how often is this expected and do your colleagues in other timezones face the same expectations?

What are the benefits for remote workers? Will the organization reimburse any of your remote working expenses, such as membership of a co-working space, home office furniture, or your home Internet connection costs? If you’re working in a different country from most of your colleagues, will you get equivalent benefits to your colleagues (eg, health insurance coverage)?

What are the travel expectations for remote workers? Are you expected to travel to headquarters or other offices or customers, and if so, how often and for how long? What are the travel policies and allowances for remote workers? How do these travel expectations compare to those of non-remote colleagues?

Sometimes you will be remote from an organization with an office or even headquarters in the same city as you. Will you be able or expected to visit the office? How often? Will there be resources for you (eg, hot desks, meal provisioning)?

What are the career progression possibilities for remote workers? As a remote worker in a partly non-remote organization, could you move into more senior positions over time, such as team leader, middle manager, or executive? Could you move into other teams in the organization, and if so, which ones? Are there some roles that are closed to remote workers? Match these answers to your own career goals.

What’s the training process like? Must you or can you spend a period of time in an office or visiting a colleague for training? Must you or can you do your training remotely using documentation, videos and similar? Will a trainer or colleague have some time assigned to remotely train you?

Is there support for first-time remote workers? If you haven’t worked remotely before, will the organization support you in learning how to work remotely, and if so, how?

See also

A very partial list of resources, focussing on individual remote workers and their experiences and strategies:

Creative Commons License
Learning more about a remote working position by Mary Gardiner is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.