Learning Cultures

Over the past few years, there’s a problem that I often grapple with: how do you foster a culture that likes to learn?

Naturally, this is easier to do if you’re part of a larger community that encourages this. But what if that culture doesn’t already exist?

This feels even more challenging for leaders in a business setting. You have a two-front problem: (1) you need to shift how your team thinks and (2) you need space and trust from your bosses/peers to succeed.

I don’t have a solution or template, but I do have some of my own experiences to share.



The first explicit thing I tried was to have people self-study whatever they were interested in. I regard this as well-intentioned, but mostly a failure.

This was structured as giving people some time each week to learn about whatever they wanted. There were no explicit restrictions, but it was implied that it should at least loosely be tied to work (pretty much anything relating to software engineering was fine). We also had occasional, informal teem meetings for people to share/present/discuss learnings.

Essentially, this was modelled around how I wanted to learn. If there was something that piqued my interest, I wanted to take time to investigate it. After (hopefully) drawing something useful, it would then be up to me to apply or share a concept to my work.

I think this failed for a few reasons. Ultimately, I think they can reduced to motivation—people didn’t know why they were doing this or what value it had for them.

Problem: Too Open-Ended

I got the sense that a lot of people simply did not know what they might be interested in. Some people picked things that I felt wouldn’t translate much to any applied learnings. Others tried to fish for topics from me.

This problem is particularly challenging if you’re a leader. Your opinion and how you act has an outsized effect on future topic choices.

I didn’t want to constrain topics. It’s not supposed to be: “you’re free to learn anything as long as I think it’s useful.” Additionally, there’s no way to predict what serendipitous breakthroughs and connections someone will make.

I also didn’t want to give topics (although I did feel that there were useful areas to focus on). Learning seems less fun if it’s an assignment rather than a more personal interest.

This problem is probably more common among junior roles. They often don’t know what’s out there nor how to apply things to an organization.

Problem: People Didn’t Do It

Participation was meh. Some people did it, some didn’t.

The biggest factor here, I think, is that people were too accustomed to the mindset of needing to deliver their current work. It might not have been clear how or why this could be helpful to them.


I think the biggest barrier here is organizational acceptance. That makes it feel like either (a) a chicken and egg problem or (b) a person at the top problem.

If others seem it as the norm, I think it’s much more likely to succeed. This is most evidenced through success at other companies.

Lead By Example

I would have done it regardless, but another approach is to just do what you’re saying is important. The hope is that people see it as an okay thing to do and start doing it more themselves.

For me, this translated to doing a deep dive into some topic, then coming back with some widely-applicable concepts and practices. I’d then document this and share this.

In terms of organizational influence, this was positive. The practices I shared improved how we did work (for the team and for the org). It also generated positive sentiment—people (above, sideways, and below) appreciated what I brought to the table.

In terms of creating a learning culture, this felt like a failure. I didn’t see others doing similar things, so it seemed like I wasn’t actually setting an example. (It’s possible that I simply didn’t get to see others doing this, which I hope was the case.)

Problem: Barrier To Entry

My guess is that is that it might simply be hard to replicate what I was doing. I was definitely taking advantage of a number of things:

I suspect some other issues were also at play:


I don’t think this approach should ever be thrown out, since I think leading by example should be done as much as possible.

Instead, I’d say that leading by example should be coupled with other things, not used alone.

Additionally, you have to find ways to get others to also lead by example. This should be done at multiple levels/scopes, so people are comfortable doing whatever is in their capacity.

This concept also comes up a lot in Turn the Ship Around!, where it’s often referred to as a leader/leader model (as opposed to leader/follower).

Themed Initiatives

Another approach is to set a theme and have people find ways to work towards that theme.

This isn’t a new concept, and you’re probably already familiar with it. Themed hackathons, themed sprints, themed quarters, etc.

It’s useful, but it also feels very transparent. People can easily be very accepting or very skeptical. I tend to assume skepticism, so I think presenting a themed initiative for the sake of learning/improvement will generally be poorly-received. That is, unless:

Without any of those things, I would bill this as business as usual. You can share themes, but it’s a thing that the team should spend effort on (rather than a thing for their personal benefit, even if it actually is).

In that scenario, I felt that people didn’t always see or feel the overall progress towards the theme. Here, people felt good when we celebrated our improvements at the end of the initiative—when people could actually see how things had gotten better.

Internal News & Media

A problem that we eventually noticed: people were learning things, but learnings were not widely circulated. For the most part, they stayed within the team that came up with it.

This means there’s no cross-pollination. There’s also no sense of which team might have an expertise in a particular topic.

I tried two things here: a newsletter and an internal blog. They both operate on the same underlying idea—people are already producing good content, there just needs to be a distribution mechanism.

Problem: High-Effort

With the newsletter, it was a very high-effort activity. I was the main force behind it. It also involved staying aware of lots of slack channels, identifying potentially interesting topics, and bundling it up into an easy-to-digest form.

That’s not easy.

It’s doable if you have people who are dedicating some of their time towards the effort. They also have to be reasonable curators—a newsletter has to grapple with being a high signal-to-noise medium. Polluting the newsletter with too much stuff will also make it ineffective.


I would actually recommend starting an internal blog. A few keys that I think are important:

If you’re looking for software, I’d recommend BlogIn.

The Next Idea

The next thing I’m curious to try: make it required. Yes, I know that’s eye-roll inducing.

The rough idea is this: people must share learnings with others or somehow help them to improve. This is a hard blocker to getting promotions.

This sounds draconian, but I’d argue that a lot of it goes about how you bring it about. It will be a decent amount of effort on the leader’s shoulders, as they are key to it working well.

Initial Adoption

The more reluctant your culture would be to this kind of change, the more I think it should be presented as a shock to the culture (because that emphasizes it’s important). If your culture already celebrates learning (in spirit, not just in name), it should not feel like a huge shift when it’s also a performance metric.

The main elements:

One of the underlying ideas here is that taking action will create a belief, rather than the other way around. It may feel inorganic at first, but the hope is that it becomes a key part of your culture over time.

Influential Ideas

There are a variety of ideas going into this approach (despite it sounding like a corporate program).

You might notice that some of these ideas stem from the ideas from earlier in this post.


There’s a lot of stuff that has to be done to make this successful. A lot of it falls on your leaders’ shoulders.

Spirits, Not Letters

The biggest obstacle, I think, is following the spirit of this approach. There will be the question of gamification, and it will largely up to your leaders to ensure that this isn’t a check-the-box exercise.

In particular, make sure that this is a regular effort and that people are appropriately helpful for their role.

Developing Others

You’ll need to ensure that people are spending time on impactful-enough efforts. This could involve coaching or helping someone to see how they can take their skillset and impact someone else with it. It’s fine to give someone more help if they don’t see how they can help others.

For example, if you have a pretty impactful engineer who’s on the quieter side, give them a foil. Pair them up with someone else (you if needed) who can identify something they’re good at and learn from them. The foil helps to identify what they’re good at and find ways to share that knowledge with others (which can include the foil themself).

An exceptional pairing would allow both people to help and learn from each other.

Passing the Torch

You may have someone who develops a niche. Maybe they’re the go-to person for solving compilation errors or something.

This gives a two-fold problem: the way they help others is not changing and others are not developing this skill.

Your leaders need to identify this and get them to pass the torch, helping if needed. Essentially, they need to teach others how to do what they do.

Again, this is nice because it does two things at once. The torch-passer has increased their impact. The torch-passee now has a new way to help others.

Discovering Success

An inherit flaw is that someone’s success is ultimately decided by their leader/manager. The leader should be aware of this (and that this will skew how people act).

If someone’s really helpful, you probably already hear about it.

For everyone else, you’ll have to encourage praise from others.

At higher levels of influence, helpfulness should be spreading outside of the person’s “tribe” (or reporting structure). Are other people observing that this person is having an impact?

In Closing

Hopefully you’ve found something interesting buried in all this text. If you’ve found some success with these ideas or know something I should try, I’d love to hear about it!