Why Solving Familiar Problems Keeps Engineering Leaders Stuck | Lena Reinhard, Leadership & Executive Coach

This week's Dialog guest is Lena Reinhard , an engineering leadership & executive coach. She spent most of her 20-year career in executive roles, including VP of Engineering at CircleCI and Travis CI , and as a SaaS startup co-founder and CEO.

Lena has worked with leaders across startups, scale-ups, and corporations, helping them navigate rapid change and challenging markets.

She hosts Leadership Confidential, a podcast about the real challenges of engineering leadership, and writes practical leadership guides for engineering leaders. Lena is also an international keynote speaker at conferences including O'Reilly Velocity, LeadDev, QCon, and GOTO.

📝 Takeaways

• Engineering leaders fall into "operational comfort zone traps" because solving familiar tangible problems feels easier than dealing with ambiguous strategic work.
• Execs who spend more time with people outside their team avoid getting trapped in operational work and stay focused on the strategic, cross-functional leadership their role requires.
• Strategy time won't happen unless actively blocked. Starting with 10 minutes each morning and one hour every Friday builds the habit without overwhelming your calendar.
• Skip-level meetings with everyone in your org, using structured questions and sharing back what you heard, build the visibility into team reality that leaders lose as they move up.

Yassine: You highlighted two neglected leadership practices: skip-level meetings and working closely with peers. Both seem like obvious wins, yet you say they're "dangerously underutilized." What's driving this neglect?

Lena: On the topic of working closely with your peers and skip-level meetings - These topics require two very different strategies to tackle, so I've separated them into their own sections.

Peer relationships:

The biggest obstacles are:

1. Looking "down" instead of "up and across": You're bogged down in operational work.
2. The "operational comfort zone trap": You find it much easier to solve tangible problems that are somewhat familiar within your own area than dealing with the ambiguity of strategic, org-level work, how to do it, and how to do it well.
3. Empathy: You're super busy. You know how busy your peers are. You don't want to waste their time.
4. Incentives: You're mostly measured by how your teams are delivering.

Yassine: What's the first step you recommend for leaders who want to start leveraging these relationships more effectively?

Lena: Meet with your peers regularly, start with 30 minutes every week.

If you're unsure what to talk about, start with one of the following; all of these will not just help you build a relationship, but also gain more visibility into each other's work and get more organized:

1. Problem-solving: Everyone brings a problem they could use help/advice for, you split the meeting time evenly to discuss.
2. Managing up: Discuss how working with your shared boss is going, what's worked for you, and what topic(s) you want to raise with them.

Managing across & out: If you share similar stakeholder groups (e.g. Product, Design, Sales, Customer Success, Recruitment), discuss: What's been working well in your partnership with them? What topics do you want to prioritize with them?

Skip-level meetings:

I found this more straightforward with skip-level meetings: Many leaders want to make sure those meetings are valuable for everyone involved, and struggle to commit to the time they take on a recurring basis.

1. First step: Do one round of skip-levels.
2. Book them with everyone in your org, attach my template with questions to the invite.
3. Bonus: Share back with everyone in your org in an email or department meeting what you heard in those conversations.

Nota Bene: Most of us know all the intricacies of how to be a good leader, but the complex reality of the role and organizations still make it hard to apply it all, consistently.

Yassine: You coined the phrase "operational comfort zone trap," where leaders slip back into hands-on problem-solving during uncertainty. For engineering leaders on the verge of this trap, what specific practices or guardrails can they put in place to pull back out and stay focused on the bigger picture?

Lena: The way you spend your time is the kind of leader you are. Make sure you're spending it on what matters:

1. Review how you spend your time: What percentage of your meeting time is with people in your org, vs. with people outside? Use a simple spreadsheet to review your calendar. Directionally, 50/50 is a decent and ambitious goal for most leaders; at more senior levels (Director+), aim for 60/40 for time spent externally vs. with your org.
2. Spend more time with people outside of your org: This includes people from Product, Sales, Customer Success. Identify key people and speak with them regularly.
3. Block time for strategy: I'm a big proponent of dedicated strategy time; if you don't actively make time for it, it will not happen. Start with 10 minutes in the morning and an hour every Friday. You can read more about how to do this here.

Don't get sucked into operational work; put people in place to tackle it. Do you regularly need to jump in during incidents? Do you own several lower-level operational projects? Do you own knowledge that no one else has? Get rid of that work. Mentor and train other people to take it over. Know that you will likely miss that work - we all like to feel useful, after all - and put more energy into getting better at strategic leadership.

Yassine: You've been openly skeptical about the AI hype, pointing out that boring but useful engineering work is still crucial. When you coach engineering leaders under pressure to "AI-everything," what guidance helps them resist hype and prioritize substance?

Lena: Like with any adoption of new tools and processes, take a balanced approach.

1. Don't take all headlines you see at face value.
2. Get to the core of what's really needed by asking questions like: "What business/user problem are we trying to solve?" "How short-term vs. long-term viable is this?" "What are privacy, security, societal issues associated with it?" "How will we mitigate the risks?" "How much $€ is this worth to explore?"
3. Do good, boring engineering work; monitor, contain costs.
4. Invest in your operations and culture, and build good teams.
5. Choose who you work for, hold companies accountable.
6. Build things & businesses not for fast returns and global scale.
7. Hold yourself accountable.

A few resources that go more in depth on this information and taking action on it:

• Identifying if AI is useful for your team and getting started: A practical guide for Engineering Leaders (Article)
• Managing Up: Debugging the most critical relationship in your work life & Working Better with an imperfect boss (Article | Video).

📚 Lena Reinhard’s Go-To Resources:

3 people you follow and recommend:

• Rebecca Murphey
• Yvette Pasqua
• Neha Batra

A podcast I make time for:

• Art19: What Went Wrong

Newsletters I rarely skip:

• 404media, formidable tech reporting by an employee-owned independent media company

Books that shaped my thinking:

• Into the Planet: My Life as a Cave Diver by Jill Heinerth

Thank you Lena for your time and insights!

This interview is part of the “Exec Engineering Dialog” series where I interview seasoned tech and engineering leaders on tech talent, culture, and leadership.

If you liked the insights shared in this interview, consider giving feedback and/or sharing it with your network, it’s the best way to help this segment improve and grow.

P.S. If you prefer your content on Substack, I'm also there.

Yassine.