The Man in the Hole: Why Your Leadership Coach Should Be Someone Who Has Been There

Engineering leadership can often feel like navigating a maze, or sometimes, like falling into a deep, dark hole. You're faced with complex team dynamics, tricky technical decisions, pressure from stakeholders, and the constant challenge of balancing innovation with stability. It can feel isolating, and sometimes, you just need a way out.

There's an old story that often comes to mind when I think about the different ways we try to help people who are struggling:

A person falls into a deep hole and can't get out.

Several people walk by.

One offers sympathy from the edge: "Oh, that looks terrible! Hang in there!"

Another offers advice: "You should try climbing up the side, or maybe look for a rope!"

Another offers prayer: "I'll keep you in my thoughts!"

All well-intentioned, perhaps, but none truly understand what it's like in the hole.

Then, another person comes along, looks down, and without hesitation, jumps into the hole with the first person.

The person who initially fell in cries out, surprised, "What are you doing?! Now we're both stuck!"

The second person replies, "It's okay. I've been in this hole before, and I know the way out."

This story resonates deeply with me, and it's the core philosophy behind my engineering leadership coaching.

The "Hole" of Engineering Leadership

The "hole" in this story isn't a literal pit, of course. For engineering leaders – for you – it can be:

• The isolating pressure of being the final decision-maker on a complex technical strategy.

• The difficulty of navigating a performance issue with a key team member.

• The challenge of communicating upwards effectively to secure resources or buy-in.

• The feeling of being overwhelmed by technical debt and competing priorities.

• The struggle to scale your team and processes without everything breaking.

• Even the personal challenge of managing your own energy and mindset under pressure.

In those moments, hearing advice from someone who has only ever viewed the situation from the outside, or receiving sympathy without practical support, can feel incredibly distant and unhelpful. They may be offering theoretically correct steps, but they don't viscerally understand the slippery sides, the loose rocks, or the sheer frustration of being stuck down there.

I'm the One Who Jumps In

My approach to coaching engineering leaders is different. It's built on the principle of being the second person in that story.

I'm the one who jumps into the hole with you because I've been in those specific engineering leadership holes myself.

For over 20 years, I was deep in the engineering trenches, leading teams, building organizations, and yes, navigating the very challenges you face now. I've sat in the CTO seat, I've managed complex projects, I've hired (and had to let go of) engineers, I've wrestled with budgets, I've presented to executives, and I've felt the weight of responsibility that comes with leading technical teams.

When you tell me about a challenging team dynamic, a technical risk, or a difficult stakeholder conversation, I don't just offer textbook advice. I understand the nuances, the pressures, the political landscape, and the technical realities because I've lived them. I can empathize not just with the situation, but with the feeling of being in that particular leadership "hole."

The Value of Having Someone Who's Been There

Working with a coach who has relevant, lived experience means:

• Instant Rapport and Trust: You don't have to spend valuable time explaining the fundamental realities of engineering leadership. I already get it.

• Pragmatic, Actionable Advice: We can move quickly to brainstorming solutions that are grounded in real-world application, not just theory. I know what tactics tend to work (and which often fail) in these specific contexts.

• Faster Progress: Because I recognize the terrain of the "hole," I can help you identify the quickest and safest paths towards a solution, accelerating your learning and impact.

• Shared Understanding: You have a thought partner who genuinely understands the context of your challenges, providing more relevant support and insights.

While coaching skills are universal and essential, combining them with deep domain expertise in engineering leadership creates a powerful synergy. It means you're not just being coached; you're being guided by someone who has navigated similar paths successfully.

If you're an engineering leader feeling stuck in a challenging situation, or simply looking for a coach who truly understands the landscape you operate in, consider the power of working with someone who has been in that hole before and knows the way out.

Ready to work with a coach who understands your world?