A Letter To My Younger Self On Becoming An Engineering Leader

As a life-long hacker, I have spent my life taking things apart, figuring out how they work, and attempting to improve them. Far more of my hacking projects have failed than will ever grace the pages of this blog, sometimes in spectacular and unexpected ways. It’s through that repeated failure and reflection that I learn to succeed. I share those successes (and quite a few of the failures) with others, and they are often the backdrop of my leadership coaching.

What I have done far less of (especially on this blog) is publically reflect on the lessons I’ve learned in engineering leadership. As I wind down my world travels and gear up for my next executive role, I think back on the past few years of my career and reflect. I ask myself: “How would I coach my younger self on being an engineering leader, knowing what I know now?” The below letter is my attempt to answer that question, and hopefully provide some guidance to other fresh engineering leaders.


You’re now the Director of Engineering. I wish I could be there to start you off on the right foot, to ready you for the heartbreaks and the struggles, to prepare you for the responsibility. As it stands, this letter will need to suffice.

Make it your calling to support the people within the business. No organization can grow long-term without the growth of its employees. This is as true across other departments as it is within your engineering organization. You won’t see this on your performance reviews, but you won’t hit your stride as a leader until you start supporting folks in other departments. Put in the extra hours at socials and meet-ups that are not directly related to engineering. Cross-train anyone that shows interest. Create opportunities for others every day and inter-departmental leadership will become one of your greatest strengths.

What does that mean for your day-to-day? What is your job, really? You’ve been in the field for a long time, so you know there are as many types of engineering leaders as there are businesses.

Ours is a sales-driven business within a large conglomerate. That means much of your work will focus on the technology related to supporting ads and their sales, and on reporting.

Your day-to-day will be rather hectic. You need to be focusing on the three major facets of your role:

  1. Mentorship and coaching, building leadership across all teams
  2. Organization, Facilitation, Frustration
  3. Reporting

Facet 1: Mentorship and Leadership

There is no greater investment than employee growth, focus on this. Encourage the management layer to do the same. Foster a culture of mentorship and mutual respect, and it will lead to better employee retention, better knowledge retention, and a better working culture. Some of the most outrageous ideas will become the most successful projects, and some of your best memories.

Facet 2: Organization, facilitation, frustration

In your role, you’ll be called upon to create the processes, rules, and structures that define your organization. You’ll need to provide support when we have staffing issues. There are days you’ll need to act as a TPM, PM, QA, individual contributor, manager, and so much more. Wear every hat with gusto and in the service of the team. Trust the team and their judgment. Prevent crunch time and always be the example for the team. Teach work-life balance, and in your role especially, be an example for your management team.

Your role will frustrate you regularly. You are the last line of defence for your users, your organization, and your managers. You will always be on PagerDuty as the final level of support. This will mean sleepless nights. If something serious happens (and it will), you will be up with the team for the duration. This will mean anything from an hour spent rebooting servers at 3am to a months-long war-room emergency. In both situations, you’ll need to be tough but please keep an open heart. Assemble a team, organize the work, attack the problem. Buy dinners, Lyft folks home, and give folks reciprocal time off.

Facet 3: Reporting

Your role in a conglomerate business is to understand, summarize, and channel information between the teams you support, your executive peers, and your executive stakeholders.

In practice, you should understand what every team in the company is working on, at a very fine level. You’ll be called upon by your local c-levels and those across the parent business to provide this information, as well as an analysis of team progress, company goals, potential technical hurdles and the like. Brush up on your powerpoint and deck-building. This is absolutely one of your primary responsibilities. A deep understanding of non-engineering departments is critical to your success. Practice writing company and department-wide summary reports and recommendations, and be ready to execute on them quickly if approved. Most importantly, you must get over your fear of the parent-company executives and investors. Your meetings with them will often be intense, but do not shy away from the bad news or tough discussions. How you handle these challenges will define you as a company leader, and you’ll eventually come to lead across the conglomerate.

I wish you the best of luck in your role here, and I know if you come in with an open heart, you’ll succeed. There will be seemingly insurmountable challenges, trust that with perseverance you and your teams will make it through. Your teams are primed for your arrival, and they are talented, consummate professionals whom you will come to care about greatly.

Serve them well Hunter. /Hunter