More Than Numbers
More Than Numbers
The Dark Art of Data Leadership

The Dark Art of Data Leadership

An interview with Alan Cruickshank from

“I like calling it a dark art, not because it’s occult in some way but that there’s something unspoken about this stuff.”

Alan Cruickshank is the Insights Director at, a pet food subscription service based in London. Like many of us, Alan fell into data, realizing its power to drive change when he started his career in operations improvement in manufacturing.

In this episode Alan and I discuss the dark art of data leadership, including:

  • The three buckets of data leadership

    • general leadership

    • functional leadership

    • data-specific leadership

  • the importance of coaching for data leaders

  • how to build trust

  • what data leaders should and shouldn’t focus on

  • the unspoken parts of the data leaders job

  • advice for new data leaders

Some takeaways:

  1. Data leadership can be split into 3 buckets:

    1. General leadership - things like building consensus, building trust, hiring and training your team

    2. Functional leadership - you are the top data person in the company, and that comes with certain responsibilities to make sure leadership is using data properly - things like data governance and identifying metrics that aren’t being used well

    3. The stuff no one tells you - being the catalyst for people to think more clearly and precisely - things like goal setting, and coaching

  2. Part of the key to being a good data leader is recognizing your soft power. You may not be able to impact things directly, but you do have a big say in the goals that are set and how people think about the business. Don’t be afraid to wield it.

  3. Leave the technical parts of your job to your team. Yes, you need to understand them, but your success hinges on how people use your data, now how well you can build an Airflow DAG.

  4. You cannot just do what is asked of you. This is true across all analytical roles, but it’s particularly true for data leaders. If your CEO asks for a dashboard, they likely have a different problem, 3 or 4 levels deep that they’re working on. Get to that point, and help them solve it.

    1. Doing this is scary for everyone. But if you sit down and work with someone to understand their problems and really try to help them, they’re going to appreciate it.

    2. Don’t fall into the trap of thinking ‘This is someone else’s job’. Sure, maybe it is, but it’s also our job to help people understand the business. Don’t be afraid to do this work first, even if you think it’s not your job. Once you’ve done it, then you can work out how to scale it and teach this to others. That’s another dimension of leadership.

  5. Pieces of advice for data leaders

    1. Build great relationships with the rest of the business

    2. Understand what the people around you want to achieve, and how you can help them get there

    3. Try to be as objective as you can about how your team is doing

    4. Communicate precisely - the same word may mean very different things to people, so it’s important for data leaders to model precise communication


00:00 Introduction to More Than Numbers Audio Edition

00:20 The Unique Challenges of Data Leadership

01:03 Alan's Journey into Data Leadership

04:59 Exploring the Dark Art of Data Leadership

05:55 The Three Buckets of Data Leadership

12:30 Navigating the Complexities of Data Leadership

31:50 Operational Clarity and the Role of Data Leaders

38:59 Final Thoughts and Advice for Data Leaders

Why Audio?

I’ve had dozens of calls over the last few months to collect the info and wisdom needed to put this newsletter together. In many of those, the person I’m interviewing will say to me at the end ‘Wow, that could have been a podcast episode.’ And while I don’t think the world needs yet another podcast, there is a kind of magic in the natural conversations that can get lost when I translate those talks into formalized articles. So we thought it was worth trying out. For this week’s article, we’re sharing the audio from the conversation I had with Alan, who is one of my favorite people to talk to about data, and in particular the unspoken parts of our world.

I hope you all enjoy the new format! And don’t worry, this doesn’t mean an end to the traditional articles; they’ll be back next week.

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More Than Numbers
More Than Numbers
Taylor Brownlow