Intro

One of the most important things a great engineering leader does is to create leaders.

And in order to do that, you need to become a great coach and mentor → to elevate everyone around you and help them grow.

You’ve probably had one or more managers in the past, who you don’t consider to be great managers → and the exact reason for that is that they weren’t leaders. They weren’t making everyone around them better through coaching and mentoring.

In order to have a great career as an engineering leader, it’s really important that you know and understand how to do coaching and mentoring the RIGHT way.

To help us with this, I am happy to bring in Andy Skipper as a guest author, who has been primarily focusing on coaching and mentoring for the past 9 years!

Let’s introduce our guest author for today’s article and get started.

Introducing Andy Skipper

Andy Skipper is the Founder and Chief Coach at CTO Craft, a community supporting thousands of CTOs and senior engineering leaders to thrive in their roles.

With over 20 years of experience leading technology at Made.com, Comic Relief, and startups, Andy now focuses on coaching and mentoring engineering leaders → helping them navigate the pressures, elevate their impact, and build stronger teams.

Today, he is kindly sharing his insights on what it takes to be a great coach and mentor as an engineering leader with us.

Let’s get straight into it!

1. The Evolution of Engineering Leadership

Remember the days when the path to becoming an engineering leader was simply a matter of being the best coder on the team?

We’d solve the most complex bugs, architect the most elegant systems, and our promotions felt like a natural extension of our technical prowess.

You were the hero who swooped in to save a failing sprint, the one everyone turned to when the documentation just didn’t make sense. And honestly, it felt great, didn’t it? Our value was tangible, measured in lines of code and solved tickets.

But somewhere along the way, the job changed.

The title shifted from “Senior Engineer” to “Engineering Leader,” and suddenly, the metrics that defined our success became less about what we did ourselves and more about what our teams accomplished.

It’s a tricky transition, one that often feels like trading a well-worn toolbox for a blank whiteboard. We were promoted for our technical skills, but the job now requires a completely different set of muscles:

• communication,

• empathy, and, most importantly,

• the ability to build up the people around us.

I Tried to Do Everything Myself as a First-Time Engineering Leader

I was gifted my first proper leadership role in a very early-stage startup where I’d earned the trust of the other developers to write solid code, but also of the founders for my ability to translate their needs into priorities for the developers.

In my ignorance, I took that as an expectation that I could only be trusted if I personally owned the hardest parts of building the product, alongside keeping the project on track.

I completely neglected the need to manage the people as well, didn’t delegate or show them the trust they deserved, and I burned out.

I’d swapped their trust in me for distrust in them. A lesson that has never left me.

This is the fundamental shift we have to make. We’re no longer the star player; we’re the coach. Our primary job is no longer to be the smartest person in the room but to create an environment where everyone else can be their smartest.

It’s about moving away from “I’ll do it myself” to “How can I help you do this?” This is where the true art of leadership begins. It’s the journey from being a technical expert to becoming a strategic leader who builds not just products, but people.

Coaching versus Mentoring

Before we dive deep into today’s topic, it’s vital to understand the crucial difference between coaching and mentoring, two terms that are often mistakenly used interchangeably.

Think of it this way:

• Coaching is generally short-term and task-oriented

It’s about helping someone solve a specific problem or acquire a particular skill by asking powerful questions and guiding them to their own answers.

• Mentoring is a more long-term, relationship-based approach

It’s about sharing your own experiences, offering career advice, and providing a model for professional growth.

As a leader, you’ll need to know when to wear your coaching hat (asking, guiding) and when to put on your mentoring hat (advising, sharing). The best leaders are adept at both.

2. Why Coaching and Mentoring Are Non-Negotiable

So, we’ve established the shift from hero-engineer to strategic leader. Now, let’s talk about the “why.”

Why should you, an already busy engineering leader, invest so much time and energy into coaching and mentoring? Isn’t it enough to just manage projects and hit deadlines? The short answer is no, and here’s why.

Right now, we’re in a period of unprecedented employee turnover. Studies from major consulting firms show that nearly 40% of employees are looking to change roles.

That’s a staggering number, and the reasons for their departure are directly tied to leadership. Among the top reasons cited are:

• Poor management or a bad experience with their direct manager. This is the number one reason people quit their jobs, and it is a direct reflection of a leader’s ability to engage and support their team.

• Misalignment with company values or changes in company values. When leaders don’t embody and communicate the company’s mission effectively, employees feel adrift.

• Lack of career growth or limited career progression opportunities. If an engineering leader isn’t actively mentoring their team and helping them see a path forward, they’ll look for one elsewhere.

• Burnout and feeling undervalued or underappreciated. This is a symptom of a leadership style that focuses on tasks and output rather than on the people doing the work.

These findings aren’t just statistics; they are a direct challenge to the way we lead. They indicate that engineering leaders need to develop stronger coaching skills and become more intuitive when it comes to employee motivation and energy levels.

It’s no longer enough to be technically brilliant; you must be emotionally intelligent and deeply invested in the growth of your people.

By actively coaching and mentoring your team, you’re directly addressing these issues. You’re not just a manager; you’re a career partner. You help them navigate challenges, build new skills, and find their place within the company’s vision.

When a team member feels seen, supported, and challenged in a positive way, they’re less likely to look for opportunities elsewhere. Your investment in them becomes their reason to stay.

Ultimately, your most profound impact isn’t the code you write or the features you ship. It’s the people you help develop. The engineers you mentor today are the tech leads, managers, and directors of tomorrow.

By investing in them, you’re not just doing your job; you’re building a legacy that will outlast any specific project or product launch.

Coaching and mentoring are not just “nice-to-haves”; they’re the cornerstone of effective leadership and the key to building a high-performing, sustainable, and truly successful team.

3. The Mindset Shift

We’ve established the “why” → the immense value of coaching and mentoring for your team, your company, and your legacy. Now for the “how” → it all starts with a fundamental mindset shift.

This is the hardest part, the true challenge of moving from a technical expert to a leader of people. It’s the shift from being a “teller“ to being a “coach.”

The “telling” mindset is familiar and comfortable for most of us. A team member comes to you with a problem, and you give them the solution. They ask how to approach a task, and you provide a step-by-step guide.

We do this because it’s efficient, and we often genuinely believe we’re being helpful. After all, you have the experience, the answers, and the shortcuts. You can solve it faster than anyone else.

But what does this really teach your team? It teaches them to be dependent on you. It tells them that their job is to execute your instructions, not to think critically or solve problems for themselves.

The “coaching” mindset, on the other hand, is built on a simple yet powerful premise: asking powerful questions.

Instead of giving the answer, you guide the person to find it themselves. When a team member comes to you with a problem, your first instinct should no longer be to offer a solution. Instead, ask questions like:

• “What have you already tried?”

• “What do you think the core issue is here?”

• “What are a few different ways you could approach this, and what are the pros and cons of each?”

• “What resources or people do you think could help you find the answer?”

This Approach Can Feel Slow at First

It takes more time and patience than just blurting out the solution. But the long-term payoff is monumental.

When you ask powerful questions, you’re not just helping them solve the immediate problem; you’re teaching them a repeatable problem-solving process.

You’re building their confidence, their critical thinking skills, and their ability to become an independent and resourceful member of the team. This is the difference between giving a person a fish and teaching them how to fish.

This mindset shift is about letting go of the need to be the hero. It’s about empowering your team and believing in their ability to grow.

Your job isn’t to be the smartest person in the room; your job is to build a room full of smart, capable people.

Embracing this coaching mindset is the single most important step you can take on the journey to becoming a truly great leader.

4. Practical Frameworks for 1:1s

The mindset shift from “telling” to “coaching” finds its most practical application in your one-on-one meetings. These aren’t status updates; they are the dedicated time you have to coach, mentor, and build a relationship with your team members.

Without a plan, they can easily become unstructured and unproductive. This is where frameworks come in. They provide a simple, actionable structure to ensure your 1:1s are impactful and effective.

While there are many excellent coaching models out there, two of the most powerful and practical that I come back to most often are:

• Solution-Focused Model

• CLEAR Model

Let’s explore how you can use each one to supercharge your 1:1s.

The Solution-Focused Model

This model is your go-to for situations where you want to move quickly and pragmatically from a problem to a solution.

It’s a forward-looking approach that empowers your team members by focusing on their strengths and what’s possible, rather than dwelling on what’s wrong.

• Identify the desired future

Instead of asking about the problem, ask about the solution. Shift the conversation immediately by asking, “What does success look like in this situation?” or “If this problem were solved tomorrow, what would be different?”

• Find exceptions

Help your team member recall a time when the problem was less severe or didn’t exist. This shows them that they already have some of the skills or resources they need. Ask, “Tell me about a time you handled a similar situation well,” or “What was working the last time you were tackling something like this?”

• Scale the progress

Use a simple rating scale to make progress tangible. Ask, “On a scale of 1 to 10, with 1 being ‘the problem is at its worst’ and 10 being ‘completely solved,’ where are you now?” Once they give a number, ask, “What would it take to move from a 4 to a 5?”

• Define the next action

Based on the conversation, help them identify one small, concrete step they can take immediately. Ask, “What’s one small thing you can do this week to move toward that 5?”

The CLEAR Model

For more in-depth developmental conversations, the CLEAR Model offers a comprehensive, agile-friendly approach. It’s especially useful for building trust and ensuring accountability over time.

• Contracting

Start by setting expectations for the conversation. “What’s the one thing you want to achieve today?” or “What would success look like for you by the end of this conversation?”

• Listen

Before diving into solutions, dedicate time to truly listen. Allow them to fully articulate the problem, their feelings, and their thoughts without interruption.

• Explore

This is where the magic happens. Use powerful, open-ended questions to help them explore the situation from different angles. “What assumptions are you making here?” “What other factors might be at play?” or “What’s an alternative way of looking at this?”

• Action

Once the team member has explored the issue, help them decide on a concrete plan. “What’s the first step you’ll take?” or “How will you know if your plan is working?”

• Review

This final step is often done at the beginning of the next 1:1. Check in on the actions they committed to and discuss what they learned.

These frameworks transform your 1:1s from simple check-ins into powerful coaching sessions. By having a clear plan for your conversations, you’re not just managing a project; you’re developing a person.

Handling Difficult Coaching Conversations

The most challenging, yet crucial, part of a leader’s job is navigating difficult conversations. These moments are often uncomfortable but offer the greatest opportunity for growth.

Mastering these situations requires courage and empathy to ensure the conversation remains constructive. When handled well, these moments can strengthen your team and your relationships.

Here are key scenarios where your coaching skills will be put to the test:

• Addressing poor performance

Coach the individual to understand the impact of their performance and collaboratively develop an improvement plan.

• Dealing with team conflict

Your role isn’t to pick a side. Coach both parties to understand each other’s perspectives and find a mutually agreeable solution.

• Giving and receiving negative feedback

Practice delivering feedback in a way that is specific, actionable, and focused on behavior rather than personality.

• Coaching an engineer who is not a good fit

This is perhaps the hardest conversation. Be compassionate and honest, helping the individual see that their skills may be better suited to a different role or company.

5. Developing Your Coaching & Mentoring Skills

So, you’re bought into the mindset shift and you have a few frameworks in your back pocket. Now comes the work of actually developing these muscles.

Becoming a great coach and mentor isn’t a one-and-done course; it’s a continuous practice. It requires a dedicated effort to cultivate a new set of skills that might feel unfamiliar at first.

Essential Skills to Master

• Active listening

This goes beyond just hearing the words. It means listening to understand, not to reply. Pay attention to body language, tone, and what’s left unsaid. Put your phone away, close your laptop, and give the person your full, undivided attention.

• Empathy

Try to see the world from your team member’s perspective. What are their motivations, fears, and frustrations? Empathy allows you to connect on a human level and tailor your coaching to their individual needs.

• Patience

This is a big one. It can be incredibly tempting to jump in with the solution, especially when you know the answer. Resist that urge. Allow your team members the space to struggle, think, and find their own way. Your patience is a gift that builds their resilience and confidence.

• Asking powerful questions

We’ve touched on this, but it’s worth repeating. The quality of your coaching is directly related to the quality of your questions. Practice moving from “Why did you do that?” to “What was your thinking behind that decision?” or from “You should do X” to “What are some different ways you could approach this?”

Recommended Resources & Where to Start

Building these skills requires ongoing learning. Here are a few places to start:

• Read the right books

  • The Coaching Habit by Michael Bungay Stanier is an excellent, practical guide.

  • Crucial Conversations by Kerry Patterson will help you navigate difficult discussions with grace.

  • Radical Candor by Kim Scott is a must-read for anyone who manages people.

  • A personal favourite of mine is The Coach’s Casebook by Geoff Watts and Kim Morgan, which includes many real-life examples and frameworks to use in your conversations.

• Seek out a mentor for yourself

The best way to learn how to coach is to be coached. Find a leader you admire and ask them to mentor you. Observe their style, and don’t be afraid to ask for direct feedback on your own leadership.

• Practice with intention

Don’t just wait for a major problem to arise. Use every 1:1 as a practice session. Pick one skill (like active listening) and focus on it for the entire conversation. Reflect afterward on what went well and what you could improve. It might feel a little clunky at first, but with consistent practice, these skills will become second nature.

Becoming a great coach isn’t about having all the answers. It’s about empowering your team to find their own.

Your journey to a coaching-first leader is a marathon, not a sprint. The most valuable investment you can make is in yourself, so you can then invest in your team.

Conclusion: The Legacy of a Coaching-First Engineering Leader

An engineering leader’s most enduring legacy isn’t the software they build or the deadlines they hit. These things are celebrated and then quickly become outdated.

The true, lasting impact you’ll have is on the people you lead.

Think about the mentors who shaped your career; their impact wasn’t a specific task they completed for you. It was a question they asked that helped you see a problem differently, or the confidence they gave you to take on a new challenge.

By prioritising coaching, you are creating a ripple effect that will shape the professional lives of others long after your projects are complete.

Your job isn’t to be the smartest person in the room; it’s to build a room full of brilliant people. The engineers you empower today will go on to lead their own teams, passing on the coaching mindset you taught them.

This is an act of humility and generosity → you’re giving away your knowledge, time, and trust so that others can rise.

In a world obsessed with code and metrics, a legacy built on empowering people is one that truly matters.

Last words

Special thanks to Andy for sharing his insights on this very important topic!

Make sure to check him out on LinkedIn and also check out CTO Craft → the community, events and mentoring circles → I’ve been a part of the community for 2+ years, and I definitely recommend checking it out.

We are not over yet!

Tech Lead is Becoming One of the Most Important Roles in Tech Because of AI

There was a lot of good feedback on Wednesday’s article and also from my talk at the Codemotion conference in Milan, Italy. In the latest video, I am sharing a bit more insights on the Tech Lead role becoming an increasingly important role in tech.

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