I wrote this originally in 2022, after getting my first Full Time Remote gig with Pythian. At the time I wanted to share my observations and advice with my previous colleagues. In 2023, after having successfully pivoted from a role as a Systems Engineer/SRE to a role in Software Development, and after seen some of my colleagues through a RIF (Reduction in (Work)Force – ie. layoffs), I thought it useful to repeat it, particularly with an eye towards a senior technical position.
I’ll soon be starting my third great adventure, having accepted a position as a Linux Site Reliability Consultant with Pythian. My first full-time remote position working as a self-employed contractor working for a foreign company. A somewhat ballsy move for someone who spent 20 years as a regular employee with their big local employer.
Now, in 2023, I’ll be starting my first role as a software developer in a SME (Small-to-Medium Enterprise), successfully pivoting in job role to follow my passion.
Obviously I can’t consider myself as representative of a large sample, but let me share my context so you can determine if my experience might be similar to yours… because I found a bunch of the typical job-hunting advice and previous experience were not at all useful, and could be disregarded in my context.
Be cognizant and explicit of what skills you can contribute, and what development goals you have for your target role.
I’m an experienced IT professional, with over 20 years of experience in two major roles; one of those being a decade of teaching in a University situation, and another being a decade of Systems Engineering / Administration in a data-centre environment. I don’t have a lot of cloud experience, but I am investing in my own development in that area.
I had a goal to secure a position in which I could rapidly build up my cloud / container skills while contributing the valuable experience I do have with a plethora of different software and working with complexity. So I have a lot of transferable skills including teaching/coaching skills.
It’s the passion for learning, not the certifications, that make you attractive. Which is not to say that certifications aren’t useful, but don’t wait until you have gained a certification before at least trying to make a move.
I was leaning on my transferable skills to make up for what I felt were my development goals. I suppose you could say in terms of a SWOT analysis that I was countering a weakness in cloud with a strength of experience working with complex systems, typically of an open-source nature.
I only wanted to apply for jobs that fit my skills and development goals…. BUT also had plenty of room for growth; as this was the main reason for leaving my previous position. In a time when people were looking for “T-shaped engineers”, I rated myself as having multiple areas of deep skills, but was lacking depth in the cloud.
To that end, I purchased a training course for an AWS Solutions Architect Associate level certification, and am proceeding through that at pace… it’s worth noting I was just starting that course when I landed the position.
The possibilities are remote.
I was looking for a remote position… Linked-In is a brilliant place to start looking if you want something higher-level / more specialist or international etc. I’ve become somewhat specialised in the New Zealand job, so there were a lot more opportunities I could bet myself on.
Two words of wisdom here, at the beginning of 2022… most job sites are not well set-up for filtering on Remote opportunities. Linked-In included. You might commonly find that the same role may be advertised multiple times. I often saw the same position advertised in New Zealand (or a particular city in Dunedin), and the same in Romania, etc. Sometimes the wording is not clear.
In 2023, sites like Linked-In and Seek.co.nz are getting better.
When applying for a remote job, it is useful to state assumptions early on… at the beginning of my cover letter, I tended to have something like the following:
Warmest greetings to you all at _____ from the city of Dunedin, New Zealand.
My name is ____, and I’m applying for a position of ____, advertised on ____, which I understand to be a full-time remote opportunity that can be worked from New Zealand.
Cool, so if I miss my mark, and the job actually requires someone in a different country or set of time-zones then minimal time has been wasted… maybe not so much on my side though, but at least I should be able to get faster feedback.
I also disregard the advice of trying to figure out who the hiring manager is and using their name in the salutation. It seems disingenuous to me because your CV should be read by a bunch of different people.
Configure your funnel.
No, I’ve never studied marketing or sales, but I do think this is much the same.
You’ll find you end up with multiple saved jobs. Evaluate each according to what you can contribute and what you can learn from each. Don’t allow yourself to have to match all the requirements. Pay attention to closing dates… but it’s useful to realise that such jobs are often open until filled, and will often be re-advertised. I suspect that’s more related to how long a job advertisement is listed for.
Rank (and re-rank) your prospective job advertisements. Pay attention to what you can offer and what growth opportunities you are looking for. Set yourself a target; I aimed to apply for two positions a week with a couple of positions in-flight further into the funnel. By re-ranking your prospects every time you find a new one, you’re making a more conscious comparison and making your best bets.
As a motivating device, I thought it would be useful to draw a funnel, which I put on the fridge. Each application would start out as a dot on the left; and each time it got further down the funnel it would get extended, and so a line either haltingly staggers across the page, or would be cut short with a rejection. It didn’t end up with many rows; here’s the short version:
- There were five applications in total.
- Three were rejected without an interview. Of those, one was due to incompatible timezone, one due to technical miss-fit (it was an explorational pivot). And one, which was one of the earliest I applied for, I rejected myself having secured a new position.
- Two made it through the interview processes. Of which one ended in an offer, and the other I terminated because I had secured an offer and they hadn’t come back to me with an offer of their own.
It is worth noting that this was in the December / January period, so hiring processes would have been more strangled in some businesses… It’s no wonder that recruitment has been likened to a cat-and-mouse game when feedback is often glacial.
You could consider my job applications as falling into different camps. Here is how I organised them:
- Safe jobs where there was a very large crossover from my current roles but might come at the expense of my growth areas. I selected these because they would broaden my experience with other enterprise environments, and should allow some growth or later movement within that company. To make this more real, these were support roles that I could use my enterprise experience in supporting cloud software that had significant on-premises integrations.
- Growth jobs where there was still a good crossover from my current role, but it would be re-cast into the growth areas I wanted. Eg. I could use my Kafka or Elasticsearch skills in the context of cloud computing… my existing skills will still be very competitive compared to someone who had cloud skills but not Kafka/Elasticsearch etc.
- Adventurous jobs, which represent more of a pivot. In my case, this would have been a foray into Data Engineering and Cyber-Security work, which were areas I had identified as being possible areas to pivot into, based on areas I was becoming more passionate about. But they are ‘adventurous’ because I wouldn’t be leveraging my current strengths to the same degree; I would likely need to accept a lower position, which I was okay with because I love to learn and any skills I do learn there would benefit me greatly in my more traditional type of roles.
I was expecting to spend a lot more time job-hunting, and perhaps I got lucky, but I did get consistent feedback in the interviews that my CV was very compelling.
Two pages for a CV is much too short.
Writing a CV and applying for a job takes a while. I’m established in my field, I wanted to target a particular type of fish by making my bait particularly attractive. I’ve no need to spread my seed like someone just hoping to get noticed. People with my skills are less common… I don’t expect the candidate funnel to have a very large intake. Therefore, I don’t need to optimise my CV for reading time… I need to optimise my CV to get further into the funnel, and to do that it should show experience, fit, drive and socio-technical capability.
Think of what experiences you have that would be applicable. Try to relate that to business value as well as what illustrates your technical capability. Particularly in more senior IT positions, recruiters need to see that you can view your role in the wider context. If you don’t know what that means, read a life-changing book like The Phoenix Project.
The next step… is probably not an interview.
My previous experience led me to believe that the next step would be a call for an interview, or a rejection email. Before I go on, let me just say that a rejection is not necessarily a bad thing: it’s feedback that you can use to improve your future attempts. The most frustrating rejection (also the most common) is a slow rejection. A slow rejection might indicate that you weren’t yet considered a top applicant, but they didn’t want to reject you just yet… and you don’t know where you were in that pool.
So I was hoping for an interview, and it threw me a bit when the next step was instead either:
- A technical screening test (may be a take-home test, or some other on-line testing environment… try not to form much of an opinion based on this.)
- Phone call from a recruiter, largely to check and set expectations, and quickly improve the quality of candidates going further into the funnel.
What I found was that there was not just one interview… there was a separate technical interview, and a separate ‘management’ interview. This was particularly useful when the different participants might be in different timezones. It also makes scheduling easier and gives both the candidate and recruiter faster feedback.
Technical roles will also commonly have some sort take-home assignment or quiz. For a Software Developer role you might have a task you can find in any programming contest, plus some sort of design challenge, and hopefully something more particular to the specialist area you’ll be working in.
From a candidate’s point-of-view, this I found to be really good. It certainly felt a lot less like a formal interview, and very much more like a two-way conversation.
The Two-Way Conversational Interview
Prepare for this… but maybe don’t expect the same old ‘soft-skills’ questions that would terrify people and make an interview candidate sweat: “Can you tell me about one of your weaknesses”.
There are plenty of example interview questions available online. Practice answering them to help overcome tension. Most applicants who make it to an interview turn out to be a disappointment because they don’t communicate well or have a view of the business that is too narrowly focussed on the technicalities of what they think they would be doing.
All my questions could be considered socio-technical. Here are some examples:
- Given a bunch of requests you might receive in the morning, discuss how you would prioritise these. [Can you show your reasoning about urgency and importance.]
- You’re having a disagreement with a colleague as to some technical issue. How do you go about resolving this? Or it might be phrased around some concept of ‘best practice’. [Can you balance different technical and business constraints? How do you de-escalate passionate asynchronous conversations? Do you routinely consider the fact other people might have valuable input and experience?]
- How do you share and record knowledge [What are the different types and purposes of documentation? Where should things be documented? How do you document you work?]
You might also get some technical questions too… while they can be more like a screening question, they can also be a good way (in a synchronous communications medium if a video-interview) of seeing the depth or experience of the ability to think on their feet. The answer is just part of the answer; the thought-process is the real answer. Don’t be silent; relate things to your experience, and ask clarifying questions. Use the interviewer as a proxy for determining what would happen next.
But the most important part of this interview is for the candidate to ask questions and have a conversation. So in your preparation for the interview, write down a list of good questions. Aim for a good handful and prioritise them. Some of your questions might get answered anyway; it’s a good interview that goes over-time.
Have a conversation that includes what you’re expecting to learn from this role, and what you expect to be able to contribute. This is particularly when pivoting and you need to reinforce how your transferable skills might map to the new role. The interview panel may need you to assist in making this obvious.
Here are some questions I found particularly useful for my context:
In my current/previous role, I got a lot of job satisfaction from using programming/scripting/coding to solve numerous problems. Can you provide some examples of how your team has employed these skills? [Context: when applying for a Site Reliability Engineer or SRE position, the concept of SRE is used quite loosely and a lot of places might not consider programming/scripting/coding to be something that an SRE would or should do much of. It’s useful to drill into because automation doesn’t necessarily include programming. For an SRE position, it’s a huge tell both of what a job might provide, and of how this activity is perceived by management.]
How do you ensure that your workplace and culture is inclusive and looked-after? [Show that you care about workplace culture. Do talk about mental-health and wellbeing issues such as loneliness in a remote workforce.]
How does work come into the team, made visible and get assigned? [This is not about whether a company uses Jira or something else; it’s a leading question into a discussion about making work visible, and to what extent management knows about concepts such as Lean, the extent of siloing, how unplanned work is managed and how the team communicates with other teams.]
How much technical debt are you having to deal with? How is that managed? [If you’re a managed-service-provider you probably don’t have much control over how old platforms are retired. This is a useful question to gauge how much fire you might be stepping into.]
I’m new to working day-to-day with team-mates in different timezones. How would my working day be different? [This is a useful conversational topic; it helps to see how other people scatter themselves throughout their day and helps set expectations around work-life balance, particularly around meetings.] I’m nervous about having to be a self-employed contractor, and I’m uncertain as to whether I would like looking after things like tax etc… Could you put me in touch with another of your team that works in my country? [While this wasn’t actually a question – more an offer – I was very happy I did this; it gave me the confidence to re-prioritise my options, and also gave me other opportunities to ask questions and get another perspective from someone from my own country. Also, if you’re in New Zealand, check out Hnry.co.nz if you would prefer to keep Tax/ACC/Invoicing simple… and of course, do your homework on company structures etc.]
Which part of my skill-set do you think you will be relying on the most, one year from now? [This is telling… more so for me because the answer I got was that at the beginning of the interview the answer would be my breadth of technologies; but at the end of the interview it would have been my ability to coach other staff, which is a more senior socio-technical concern, particularly when an organisation is in a growth phase.]
Don’t be surprised – or disappointed – if ‘communication’ is the answer. It just reflects the reality that successful people need to interface well with different parts of the business. This is so underrated by candidates, but is really the biggest point of difference moving between a Junior/Intermediate position to a Senior role.
Can you give me some examples of recent work you have been doing? [Ask it, but be prepared for cautious answers when confidentiality might be at stake.]
One other thing: pay attention to cultural clues. One thing that did consistently impress me about Pythian was that they all seemed to genuinely enjoy what they do; it was actually a rather moving experience because I felt a very strong attraction to them after that. Be on the lookout for signs of fire-fighting and fatigue from endless pivoting that might distract from you servicing your growth goals. And be realistic; you can never expect to be without competing and changing priorities. I’m sure there will be more, but these are the questions I consider to be awesome to ask in an interview, particularly regarding remote work when working for a foreign company.
Small City SME in 2023
I choose to live and work in a relatively small city. Employers find it difficult here to attract specialist talent. For me as someone wanting to pivot into a different area of IT, that’s something that works in my favour.
Focus on your transferrable skills. Be very explicit in drawing attention to this in your CV by using examples. Your ability to communicate, learn and understand the wider picture are some of the most important traits you need to show in the interview.
Communication is tough… I’m a native English speaker and I still find it tough, but interviews do get easier with practice, particularly when you treat it as two-way conversation. But most of the difficulties from my observation come down to these:
- Forgetting to answer all of a multi-part question. Resolution: write down the question key words.
- Derailing a question by going off on a tangent. Resolution: write down the question key words, ask clarifying questions before making assumptions.
- Poor structure and exploration. Resolution: the interview is partly about seeing how you think your way through a situation. Show you thinking, use a whiteboard, point your camera at a pad (turn the camera reflection off), take some time to jot down some notes and ask clarifying questions, if only to give yourself some breathing room.
- Not asking more questions about what the job entails. Take a list of pre-prepared questions. A good interview has questions going both ways; these are opportunities to learn more about the role, the company, the industry and the culture. It also gives more opportunities to show you passion, your knowledge, values and willingness to learn.
- Not relating to your experience. This takes preparation and reflection over time; think about the moments in your career that you’ve learnt from. It perhaps doesn’t hurt to slightly derail a question if you can move the conversation to something you know well.