Deciding if a data leadership role is something you actually want to do

The current economic climate makes folks feel nervous about changing jobs, and yet I still see plenty of people playing the game of musical chairs. Perhaps it’s my network or the phase of career I’m in, but many of my peers are moving into positions with Head Of titles. When I was recently on the market, I also considered a few positions with Head Of titles and eventually ended up accepting one. As I’m sure you can imagine, the responsibilities and scope of those Head Of positions varied tremendously, ranging from an individual contributor doing developer relations to senior leadership roles in established organizations.

That lack of clarity probably sounds frustrating, but hey, it’s part of the job hunting game. Titles serve a lot of different functions simultaneously, and being a recruitment tool is one of them, even if it’s viewed with suspicion by the data community¹. As a group that loves neat, MECE categories, I’m not surprised to see so much skepticism from data folks about a vague or squishy title. But as someone whose job title has been “data scientist” for most of her career, I am a little surprised we’re still collectively getting mad about this instead of taking personal responsibility for figuring out what a company means by a given title.

Knowing how to do that due diligence is the hard part, of course. While I won’t pretend to be an expert, I will say that I was quite assertive during my most recent search². What worked for me may not feel authentic to you, but I figure it’s still helpful for me to write about the questions I asked and things I considered when trying to decide if a data leadership role was something I actually wanted to do.

A quick aside about titles

Titles aren’t everything, but anyone who tells you they don’t matter is probably already reaping the benefits of having a pretty good one.

For one thing, titles are very correlated with how much money you’ll make. In the case of companies with established people teams, they may even determine the range of money you’ll be allowed to be paid without some sort of exception. You can always get more money from a merit increase or by getting promoted, but keep in mind that most salary increases are based on percentages of your current salary. The higher you start, the bigger your raises will be.

In addition to functioning as a financial anchor, titles can be an anchor on how you’re perceived, both at your current company and on future job hunts. While it’s not true of everyone, it’s common for hiring managers to look at sequences of job titles as a proxy for your career trajectory. Quickly moving through the ranks can make you seem capable and ambitious, regardless of what the reality of those roles was.

There’s also baggage about what titles are appropriate backgrounds for particular roles. Some titles are perceived as having narrower or less technical skillsets than others, which means those people are sometimes rejected for roles they’re actually qualified for³. If you’ve ever wondered why people prefer the job title “data scientist” to “analyst” even when they’re doing the exact same work, this is why—the former creates more optionality.

This is all to say that you should care about your title, and that just because some titles are vague (like data scientist) or squishy (like any Head Of title) doesn’t mean they are guaranteed to be a bait and switch. You should be wary of getting in over your head with any role you take, but job titles won’t guarantee that that doesn’t happen. Rather than worrying about having a clear job title, you should worry about having (and negotiating for) job titles that will serve you.

So how do you really figure out what the job will be like?

The job you interview for is never the job you actually end up doing, and once you have an offer in hand, you will realistically only have a few hours of conversations to base your decision on. If you’re considering a management or leadership role, your first few conversations with the recruiter and hiring manager should give you a pretty clear idea of the size and seniority of your team, the problem space you’ll be working in, and what management responsibilities the company expects you to focus on (will you be doing a lot of hiring? does the company expect you to do any hands on work?). But these are sort of like the management equivalent of saying you’re a Python or R shop—they’re something you should definitely know about the role you’re stepping into, but they don’t help you understand what the job will actually be like.

A lot is expected of managers in the year of our lord 2022, and the specifics vary a great deal both across and within companies. If you’re interviewing for a position where you’ll be managing people (or setting some sort of vision for a data team), one of the most critical things for you to figure out is whether the company will support you. This is a hard thing to directly ask about because how it might happen is probably not something anyone can coherently explain, so you should focus on learning about the context in which this position will exist. You want to know about the team’s history at that company, who sits upstream and downstream of it, what skills the company thinks are important for a manager to have, and how you’ll work with your manager.

This is a lot to think about! And it’s worth acknowledging that while it’s impossible to really know what you’ll be walking into, you can still learn a lot during the interview if you’re deliberate about the questions you ask and by paying attention to how the process is conducted. The post below is a loosely organized description of how I recommend probing into these areas to make sure you have the information you need to feel comfortable about a position.

Ask why is this role being created now

This was my favorite verbatim question to ask because it was a very quick way to get folks talking about the history of the company’s data team, which in turn gives you a lot of fodder for follow up questions. For example, if the answer is that the old manager left, it’s very reasonable for you to ask why. The answer can also help you get a sense for whether the departure was amicable and whether the company thinks the existing team is doing a good job. It’s not automatically a trap if the team is not perceived as successful, but it’s a very different situation to walk into than one where the team is respected and well-loved by its stakeholders. Some people love running into the fire and turning around a struggling team, but it’s not for everyone and it’s definitely something you should know up front.

Relatedly, a response to this question I encountered frequently was that the company had hired a bunch of analysts who reported into functional leads (think sales, product, marketing, etc.), that this was starting to cause problems like inconsistent metrics or analysts feeling stunted in their career growth, and that the company realized they needed a central data leader. Essentially, it was a fixer-upper situation. This is again not automatically a trap, but it does provide you with some important information about how the company has (at least historically) thought about data. It suggests that data roles were thought of as more of a utility than as a function that is valuable in and of itself. Wanting to bring in a dedicated data leader may signal a shift in this thinking, but do your due diligence to confirm whether this is true or not. And even if it is a shift in thinking, be prepared for this situation to require a lot of effort from you.

Another common response was that the old leader of the team was looking to backfill themself, either because they were stepping into second line management or because the team was getting too large for them to directly manage everyone. This is an answer that does not immediately trigger red flags for me since it suggests your boss will understand your job well and hopefully value it. If this is the answer you get, though, you should probably focus on learning more about the manager themself.

Of all the responses to this question I got, my favorite was a variant of “we’ve hit an inflection point in our business and we think we’ll need a real data practice to make sure we’re executing successfully”. You’ll rarely hear it stated that straightforwardly, so look for signs that the company actually has a clear sense of what data teams can and should do, and that they can clearly articulate the ways in which they’ll constructively work with you. Probe on how the data team will be involved in decision making, how it will be supported by upstream teams and systems, who will be your allies, and so forth. But this is starting to get into the next area to pay attention to.

Ask who will you be working most closely with

This is also a question you can ask verbatim, with other versions being things like “who will be my team’s customers/partners?” or “what does the company currently use data for and what do they want to use it for in the next year?” This not only gives you an idea of your scope and the types of problems you’ll be solving, it also tells you who you’ll rely on in the role. If they’re not already people you’ll meet as a part of your interview loop, you should ask to meet them (especially once you have an offer in hand) or at the very least check to see if they have some sort of internet presence.

One of your goals in doing these things should be getting a sense of what they’re like as a person—you’ll probably have to spend many hours with them if you accept the job, after all. More importantly, though, you should try to assess how aware they are of the role they play in your team’s success. If they’re someone who’s responsible for data being collected, even if it’s only indirectly, do they know this? If they’re someone who will act on your team’s deliverables, can they speak in specifics about what formats they’d like to receive data in and what they’ll use it for? “Can you tell me about a time you successfully collaborated with a {insert data job title of your choice}?” was another question I got a lot of mileage out of in my job search.

This is another area where you’ll want to think long and hard about what you learn, and whether you’re ready for it. If the company isn’t able to speak to specifics about what they’ll want from you or your team (perhaps because they’ve never had a data team before), do they seem self-aware about this? If so, do they seem ready to put resources behind the things you ask for, and how conservative do you anticipate they’ll be about how many? If they’re not able to speak to specifics, do you feel prepared to educate these stakeholders and collaborators on what you will need to be successful? Be very honest with yourself if the latter is the case. Even if you feel ready to build something from the ground up, it always takes longer than you expect.

Pay attention to the skills that the interview loop seems to be assessing

Without going on a long tangent about how I personally feel about the typical subjects covered in manager interviews (and goodness, do they vary), the topics covered and the amount of focus put on each is a valuable signal about the company you’re interviewing for.

For example, if a role is meant to be a pure management role, how many technical sessions does the interview loop have in it? It should probably have at least one, but there shouldn’t be so many that it crowds out assessment of other competencies. You should also pay attention to whether the technical rounds seem like they’re assessing relevant skills or if they seem like a form of wishful thinking, screening for complex skills that the company/team aspirationally wishes the leader could teach everyone.

Even if the role is meant to be the first hire in a function who is supposed to lay a technical foundation, there should still be other sessions that reflect the skills for the role’s intended scope. If they want you to build a team, is anyone asking you about hiring and firing, giving and receiving feedback, or coaching people? If you’re expected to be a strategic thought partner to a leader of another function, do you get to meet them and do they talk to you about their concerns and priorities?

To be fair, designing interview loops can be hard, many loops are not well thought through, and at sufficiently large companies individual hiring managers may not have a lot of freedom to modify the subjects screened for. But even so, interview loops are an implicit statement of what a company thinks is important about the people it hires. If they clearly haven’t put a lot of thought into it, especially for an important leadership role, that’s worth noting in and of itself.

Make sure you understand the kind of relationship will you have with the person you report to

One of the greatest opportunities you have when interviewing for a new role is the chance to choose your boss. Advice from the section above about who you’ll work with applies here with respect to making sure you meet them and do some research on any public information about them. But this is an area where you’ll want to put special care, because if there’s anyone you want to have a good working relationship with, it’s your boss.

The most obvious place to start is taking a look at their job title. Their level of seniority already tells you about the role you’ll probably have in the organization—a Head Of reporting to a senior manager is a lot different than a Head Of reporting to someone in the C-suite. Their seniority is not the whole story since you’re not always exactly one level below your manager on a job ladder⁴, but it’s a helpful approximation of the level of responsibility the company thinks is appropriate for your role.

You’ll also want to consider the functional dimension of your manager’s title, as well as what work they have done at previous points in their career. The larger the company, the better the odds that you’ll report to another data leader⁵, but on the whole, data leaders are more likely to report to someone who has never done their job before, like a CTO, head of product, CFO, or even CEO. No arrangement is automatically better, but you will get different things from each. Think about what you want at this point in your career, whether that type of leader can help you with that, and where you might get it if they can't.

A leader unfamiliar with the subtleties of data careers and work will require you to play offense more when it comes to explaining your job and what resources are necessary to do it well—you need to be sure you have the energy to do this over the next couple of quarters or years. A non-data leader will also not be able to provide you with as much functional or technical guidance, so you should be prepared to seek that out elsewhere, whether from a coach, a mentor, or a group of trusted peers⁶.

Regardless of what your manager’s role is, you’ll want to get a feel for how they’ll evaluate you. How much say will you have in determining what goals you will be expected to meet, and how much autonomy will you be given in determining how you go after them? How do you think your manager will compare you to other people in their organization, especially if those people are in a more similar role to that of your manager? If you report to the CTO, for example, do they think of you as a special type of engineer or as something different? And if so, do they seem like they have a good framework for assessing your ability as a data leader?

On the whole, though, the absolute most important question for you to answer about your manager is how well your incentives will be aligned. Are they someone who benefits from, say, data being high quality and accurate, or is it orthogonal to what the rest of their organization is doing? Even if they do benefit from data being high quality and accurate, think through what might cause them to compromise on it, such as aggressive deadlines that mean things like implementing telemetry get deprioritized. How likely do you think that is, given everything you know about the company. Are you comfortable with the possibility that it will happen?

You do not want your success to be optional for your manager. This person will have a lot of influence on your career trajectory, so you want to make sure that when you win, you win together.

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There’s still more I could say about evaluating whether a given data management role is something you’d be interested in doing, but I’ve already written a lot more than I intended! Instead I’ll conclude by saying that part of being a leader is taking responsibility for shaping your role into something that benefits both you and the company you work for. Your obligation to a company will never be lower than it is while you’re still interviewing, so don’t feel bad about being nosy or saying no to a role you don’t think will work for you. It’s crucial to make sure you know what you’d need to know to feel comfortable taking this position, so stay focused on learning about it throughout the interview process. The company should be trying to court you as much or more than you’re trying to impress them.

1. Or at least Data Twitter, which is sometimes mistaken for the entire data community because it’s such a vocal subset.

2. So much so that one of the recruiters I worked with remarked, “Wow, you ask a lot of intense but fun questions!” 🙃

3. This may be a blessing in disguise since you probably don’t want to work for someone who thinks this way, but I digress.

4. If your title is unclear, you can also always ask what its equivalent would be on a manager/director/VP scale. The company may not have thought about it before then, or they may not be a large enough company to be systematic about it, but it’s still reasonable to ask about.

5. My favorite question for data leaders was “What is the most recent piece of critical feedback you gave to someone you managed?” I have had too many managers who had no useful advice on how I can improve, and it was something I wanted to avoid.

6. I’m pretty bullish on peer groups for this. Leadership can be lonely, and it makes a world of difference to be surrounded by people going through similar experiences.