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Engineering Investment and Business Alignment

You Don’t Need to Go At It Alone

As I’ve talked about in my previous two posts (Part 1 | Part 2), the engineering leadership gig is tough, and we learned some of the reasons that make it tough. Despite these challenges, all hope is not lost!  There is a light at the end of the tunnel! By leveraging the lessons learned by our peers, we can begin to solve the challenges and make our lives a little easier. Whether you’re new to the role or a seasoned veteran, there are resources that can help you navigate the challenges of the job.

Before we dive in, it’s important to frame how you might want to consider different resources. In our world where the problems aren’t always on the nose, and the difficulty is subtle but deep, often the most valuable support systems are the ones that allow for two-way dialogue with someone who understands what you’re going through. By talking through your situation and hearing others, you can often suss out patterns that we all can learn from. This can require commitment, but they force you to grow in ways you otherwise would not. Structured conversations about one specific topic offer a different value than open networking. At the same time, not every question requires a deep discussion. Some outlets can offer ideas on your own time. As you evaluate resources, consider what you need to get out of them vs. what you expect to get out of them. Get some skin in the game, as they would say.

To help us find these, I asked my colleagues to help chime on this. The list below is a result of our collaboration.  

Peer Advisory Groups


  • Highly curated membership
  • Ability to have deep and impactful conversations about current challenges
  • Significant investments required often include a membership fee, homework, and expected active participation

Peer Advisory Groups are some of the most impactful opportunities that you can take advantage of. Everyone invests in the sessions, and this fosters real conversations about incredibly sensitive topics. Often, homework for these meetings requires significant introspection regarding all the dynamics of your challenges. The memberships are often curated, but this curation fosters a sense of comfort in knowing that you’re safe to discuss the nuanced difficulties you’re facing. Sometimes they have membership fees, but for the right one, it could be that skin in the game to make it valuable.

Atlanta CTO Forum

Boston VPE Forum

Chicago CTO Forum

CTO Forum

LA CTO Forum



  • Like peer groups, excellent for working through the tough dilemmas
  • Some financial cost of mentoring service connections
  • Both one-on-one & small group sessions available depending on services

For first-time leaders especially, mentorship can be highly beneficial. It’s valuable to get a diverse set of perspectives and skillsets from someone that’s done it before. It’s also important to periodically evaluate if your mentors are equipped to help you through different stages of your career, varying company sizes, and maturities, etc. And with the world now so virtual, you’re not limited to who you can meet by your current locale. Clearly, you can find mentors on your own but below are a few services that offer mentorship opportunities.    

CTO Craft Mentoring Circles

ELC Peer Groups

Plato Mentors

Those two previously mentioned categories are a bit more formalized, structured, etc. You might not need these all the time. You might be looking for something lighter with less time commitment and something that fits your already busy schedule – so, here are other options to consider. 

Engineering Leadership Networks


  • Exclusive community of like-minded technical leaders
  • Helpful for networking with local engineering leaders as well as sharing self-service content 
  • Regular communication of general-purpose engineering leadership content
  • Some communities lack formalized agendas and do not require paid membership  

There are many communities (sometimes regional*) of like-minded engineering leaders that communicate regularly. Most of these have gone virtual now, but communications are still kept up between the members. Like the peer groups mentioned earlier, these are private networks, but they are more fluid in structure. They may have a slightly lower cost to enter but can be just as exclusive. Nonetheless, these are another way to build your network and find like-minded peers. 

Boston CTO Club

CTO School (New York)

New York CTO Club

Silicon Valley CTO Club

Silicon Valley Leadership Community

CTO Craft Community (non-regional)

Self-Service Content Options: Webinars, Podcasts, and Virtual Classes

It’s important to build out your knowledge of specific concepts that will help you connect to the business and help you manage your team. These content sources are good for tactical knowledge, answering common issues regarding managing your team, and keeping up with the latest engineering leadership trends. 

Authority Issues

CTO Connection

CTO Craft Learning

ELC Podcasts

Plato Webinars

Events & Conferences


  • Good for introductory networking and meeting a volume of new contacts
  • Some content sessions might be more applicable to you than others

When people think of events, most folks picture long days fulls of sessions. But the networking opportunities can be invaluable too! Events are a great way to meet and chat with peers that are going through similar challenges as you. While most events are virtual these days, many still offer networking in the form of virtual happy hours, dinners, and one-on-ones. 

Agile + DevOps

CTO Connection Summits

DevExec World

ELC Events

Plato Elevate

Tech Leader Summit

I’m sure that I’ve only covered a fraction of outlets out there available to engineering leaders. These few that I’ve mentioned have helped many leaders, and we hope they help you too. Please help us build it out if you see something missing or miscategorized. We’ll update this list as we learn more, so leave a comment below or DM us on Twitter. Remember, you don’t have to figure out all the answers yourself. Let’s continue to help each other bring our leadership game to the next level. We’ve got this!

*Some of these groups have asked not to be disclosed in this article due to their membership’s highly curated nature. If you’re interested in joining one and you don’t see one near you in this article, be sure to search for these types of networks in your nearby city.

Revisit the Blog Series

Part 1 | Part 2