Anna Shipman : JFDI

Finding the next level tech job

16 January 2019 / Career development

Last April, I joined the Financial Times as Technical Director for This has been a brilliant move. The job search was different from any of my previous job searches, as it involved an explicit step into technical leadership, and here I share how I did it and some things I learned.

This was very different from previous job changes

I joined my previous organisation, the Government Digital Service in 2012. At that point, I was a developer and I was looking for a role as a developer.

While at GDS I attained my long-held ambition to become a technical architect, ultimately leading a project to build a PaaS for government.

In 2016, I moved into a new, exciting role as the Open Source Lead. This role involved influencing rather than delivery, which meant I could have a huge impact, but I had no team and wasn’t delivering a product.

After a year, I had achieved what I set out to do in that role, and knew I was ready for a new job, but unlike any of these moves, it wasn’t obvious what my next step would be.

First, I had to work out what I actually wanted to do

I knew that I wanted a job that married my two previous roles – something that used my influencing skills and had a large impact, as in my Open Source Lead role, with the team and delivery of my Technical Architect role.

So I was looking for some kind of technical leadership. But within that, there is a lot of variation. For example, tech leadership can be just leading/managing technical people, or it can be just setting vision and direction for a technical product, or it can be a combination of both.

So it wasn’t immediately clear what kind of role I’d be looking for next.

Inventorying my skills

I was at an advantage because while I felt ready to move on, I was not obliged to rush. I still had a job and plenty of interesting things to do, so I could take a bit of time to make sure my next step was the right one.

The first important step was to work out what I was good at. This is something worth doing because although it seems like it might be obvious, I tend to focus on getting things done, and don’t always reflect on what skills it is that mean I’m succeeding (or what weaknesses mean I’m not).

There were four main ways I did this:

  1. I asked people directly what they valued about me. For example, a friend made an intro to her boss and I asked how she’d described me, and she reported that she’d said “more single minded than anyone else I know”. Another former boss called me “terrifyingly competent” (which I think was a compliment…).
  2. I did an exercise called a Johari window to learn what colleagues thought my strengths are, which I’ve written up here.
  3. As I started having interviews, I made sure to ask for feedback at every stage of the process. A good question to draw that out can be something along the lines of “Do you have any concerns about my ability to do this job? Are there any gaps I can perhaps set your mind at rest about?”
  4. And of course, as I live my life by lists, I made a list, and updated it when I noticed I’d done something well or badly.

Now that I’ve done this exercise it’s made me much more conscious and reflective about my strengths and weaknesses, which I think is helping me develop myself better.

Working out what I wanted in my next role

Because I wasn’t sure what my next steps were, I just started looking at job descriptions. As things happened at work, or I saw a job I was interested in (or very much wasn’t), I would make a note about what it was about it that appealed or repelled.

This was quite an interesting exercise, because it made me realise some things that are really important to me but it wouldn’t necessarily have occurred to me to mention to a recruiter.

For example, I cycle to work. This is a hugely important part of my life and I realised that when I see a job I’m interested in, the first thing I do is find out where the main location is, and then calculate the cycle time using Citymapper. If it’s too long a bike ride, that’s it, the job is out of contention. The interesting bit was that this was an almost unconscious process I was going through – the location was completely non-negotiable, but it didn’t appear in my list of characteristics of my ideal job.

Apart from cycling, I came up with a list of what I was looking for. It included:

Once I had this list, it was much easier to ask the right questions of recruiters and understand how well a job advert fit what I was looking for.

Parsing job titles is difficult

Unfortunately, identifying the kind of work I wanted to do didn’t mean I could then identify the job from the job title.

“Engineering Manager”, “Engineering Director” and “Technical Director” could all be either entirely people-focused, entirely tech focused, or a mix. Even “CTO” varies hugely from company to company. It’s not just that in a small company you’ll be hands-on whereas in a large one you’ll be many levels away from the code. In some companies, the CTO is actually in sales, or otherwise outward facing. (This is an interesting paper on the different kinds of CTO roles.)

I think this will be the case for the next few steps in my career; I’ll need to know more about what the actual work is. A recruiter with whom you have a good relationship and knows what you are looking for is useful here, as they will be able to parse the job titles for you.

I had 24 hours of chats

As soon as I started thinking about moving on, I reached out to people for advice, and by the time I’d found my next role I had had chats with 20 different people, including former colleagues, contacts and people I’d worked for.

Some of the excellent advice I got from the people I talked to included:

If you do nothing else, definitely have some chats

Many of the chats led to introductions to other people for more chats, and many of those resolved into an actual job that I could potentially apply for.

This meant some of the chats were with potential employers, almost a pre-interview stage, and these were also very useful. It was a lot of effort but it was good practice. The interview process is about learning about the company as well as them interviewing you, and I made some good contacts with people in companies that I never entered into a formal process with.

If you are looking for a new job and you only follow one suggestion from this, it would be do reach out to people for chats. Be explicit that you are looking for a new role. It took a lot of time, but it was the most fruitful part of this process.

I had 21 hours of interviews

In the end, I interviewed with four companies, which involved 21 hours of interviews with 31 different people. At this level, application processes can be very long.

It’s worth mentioning that I found out about all four of those jobs through chats. The jobs were all advertised, but that wasn’t how I found out about them.

I withdrew from one partway through the process (“Engineering manager”) because having been through two interview rounds, I felt that the role would not be challenging enough for me. I was unsuccessful in another one (“CTO”), having made it to the final round, but it was a very useful experience and I made some good contacts.

And I was ultimately offered two, “Engineering Director” and “Technical Director”. Both reported to the CTO, both had opportunities for development and both met all I wanted in my next role. Ultimately, I chose the Financial Times because I really believe in the mission, but it was a tough choice.

This all took a lot of time, but it doesn’t need to

I said earlier that I was at an advantage in that I didn’t have to rush, and if I’d moved when I started looking (September) then I would have missed the amazing opportunity that my current job is (came up in the first week of January) but that aside, it’s not clear it was totally an advantage; if I’d had more of an impetus, it may not have needed to take so long.

As my excellent friend pointed out, the risks of taking an imperfect next step might not have been so high.

I’m really happy with where I landed, and I learned a lot from the process, but if you plan to follow what I did, you don’t necessarily need to allow four months.

However, the right technical leadership role can take some time to come up – unlike developer roles, there isn’t always one out there somewhere. If you do find it takes time, you can always use that time to think about particular things you can achieve in your current role that will help you with what you are looking for.

Good questions I asked

Here are some of the questions that I asked in chats or interviews that got me really useful information about the job.

A good question to ask at the end of an interview is the one I mentioned above; “Do you have any reservations about my suitability for this role?” One person gave me ten minutes worth of very useful, actionable feedback after I asked this. So much so that I suspected I wasn’t going to get the job, but he put me through to the next round.

And a bonus, not necessarily for interviews but a really good question someone asked in a presentation once and I share here: “You’ve said how you see it working, how do you see this failing?”

Good questions I got asked

I got asked a lot of very good and/or difficult questions (though almost no competency-based questions). One advantage of doing a lot of interviews at once is that you get into the swing of answering questions like this. But it’s always worth practising, so here are some of the ones I was asked.

Bad questions I got asked

I also got asked some bad questions. A red flag was when people only wanted to talk about my previous job but one, i.e. my job as Technical Architect for GOV.UK PaaS.

My year as Open Source Lead was great, and I developed a lot of very useful skills, particularly around influencing, and identifying the highest impact areas to focus on. However, a few potential companies didn’t find my most recent experience relevant and only wanted to ask me very specific questions about team management, like ‘what dashboards do you make sure your team has up?’

Yes, I can manage a team, but that is not my main value to your organisation. When interviewers focused on this, it made it clear to me that this wasn’t the role I was looking for.

The hardest question I got asked

I had three interviews for my job at the Financial Times (with a total of 8 people). The last one was with the CTO John Kundert, now my boss, and the very first question was the hardest question I was asked in the all of the 21 hours of interviews in the previous few months:

As with some of the questions above, all of the thinking I’d done about my strengths and values, plus the practice I’d recently had in inteviewing elsewhere, made this something I could answer both honestly and usefully.

It was a very difficult question, especially as the opener, but it also demonstrated that this was an organisation, and a manager, who would challenge me to be my best.

How it worked out

I’ve been at the FT for eight months now as Technical Director and it’s everything I hoped for. It makes use of some of the skills I already have, for example influence, clarity of thought, bias for structure and execution; while giving me the opportunity to develop some others, for example stakeholder management, managing a budget.

I’m sure that at least one of the other jobs in contention would also have been great, and approaching this process in good faith had unintended benefits. For example, it was a very good way to network. I received a free invitation to a tech conference from one job that didn’t work out, and another one invited to be on a tech advisory board. Tech is a small world, and I’m sure I will be working with many of the people I met later in my career.

And I’ve even set up my own circuits club!

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