When people feel like they are growing, that’s when they feel the most motivated.

This is really important to understand as a leader, because you are playing a big part in defining the overall culture inside your team and also in your organization.

And it all starts with the clarity of defining goals for your people.

Do they want to become a Staff Engineer, an Architect, or a Manager? Or are they happy where they are at the moment and wish to grow by learning a new skill? What does growth actually mean for them?

Those are all very important questions that, as leaders, we should definitely help our engineers find answers to!

How to do that, you may ask? To help us with this, I am happy to bring in Simone D’Amico as a guest author.

Let’s introduce our guest author.

Simone D’Amico is a Technical Team Lead at Redokun, with 15+ years of experience building and scaling reliable, distributed software systems.

Over the last decade, he has transitioned from an individual contributor to a people-first leader who puts a big emphasis on building a great culture. He also writes Lead Through Mistakes, a newsletter on technical leadership and career growth.

I had the pleasure of meeting Simone at the Codemotion conference, in October last year, where I gave a talk called: Tech Lead Rotation in Your Engineering Team. It was a pleasure chatting, and I hope to meet again in the future.

Simone, over to you!

Part of our job as leaders is looking after our team’s professional growth and trying to make it work for both them and the company.

When people think about career growth, they usually picture something pretty straightforward:

a clear career ladder,

maybe some internal training courses,

the usual annual or semi-annual reviews.

That should cover it, right? Not even close.

Career growth is one of the least linear things out there. There are dozens, if not hundreds, of factors involved:

how big the company is,

what problems the company is dealing with right now,

what’s going on in someone’s personal life, their ambitions,

how clear they are about what they want,

what opportunities are actually available,

and a ton of other stuff.

You end up with this messy pile of scattered information, and you’ve got to somehow piece it together to help both the person and the company move forward. So what could you do in situations like this?

I’ve picked up some tools and patterns that have helped me navigate these moments, and they might help you too.

This article has been sitting in my head for a few years and is only now taking shape.

At the time, I was leading a platform team, and the most senior engineer on the team told me at the end of a call: “I don’t see how I can grow any further here.”

The call wasn’t even scheduled, not even a 1:1, so I was totally unprepared for this.

I told him he was wrong, at first. That there was plenty of room to grow, that we just needed to talk about that, and we’d have found a direction.

The truth was different, though. I didn’t realize it yet.

We were in the middle of a hiring freeze, the teams were basically stuck, and he was trapped in a management chain that wouldn’t allow him to get promoted unless his manager (me) and/or his skip-level manager were promoted first.

I had introduced the GROW framework some time before that conversation took place, and until then, I felt confident I could guide my engineers through meaningful growth conversations using it.

The GROW (Goal, Reality, Options, Will) framework helps individuals and teams define their goal, assess their current reality, explore options, and set up a plan to achieve that goal.

That conversation, however, made me realize that up to that point, I had simply been lucky, as the people I had used it with already had a clear idea of what they wanted.

That’s when I understood that the framework is a great tool, but only after you’ve figured out what growth actually means for each person.

As a leader, your work has an impact in two directions:

Toward the company → through results, process improvements, and so on. 1.

Toward people → by helping them grow.

And that’s the kind of impact that lasts the longest: helping someone grow leaves a mark that stays with them long after your time together.

For that to happen, though, you need to help people understand what growth actually means to them. And that’s often the hardest part.

When we talk about professional growth, the most meaningful conversations are the ones where you help someone discover what their goal should be, even before building a growth plan.

This discovery process looks different depending on at least three factors:

The size of your company

The resources available

The person’s starting point

In the next sections, I’ll go through these factors in a bit more detail.

Company size affects not just growth opportunities, but also how we think about growth in the first place. Let me paint three very different pictures.

I’ve intentionally simplified company sizes into three categories, but of course, every context is unique, and these don’t fit perfectly everywhere.

As already mentioned, when we think about growth, we often associate it with a well-defined career ladder.

The reality, though, is that more than 90% of tech companies have fewer than 20 employees. In this context, growth isn’t vertical, it’s horizontal instead. We should think of it more as an expansion rather than a climb.

The lack of a formal structure is a double-edged sword: on one hand, it gives you a lot of freedom; on the other, it can make you feel a bit “lost.”

I’ve worked with engineers for whom such an open environment had a hugely positive effect, and with others who left after a short time because they were looking for more structure. Both responses are valid.

Pros: It’s the kind of environment where someone who comes in with solid skills can easily find room to explore other areas as well. You can easily create opportunities that don’t formally exist in the org chart.

The challenge: Career ladder doesn’t exist. No clear progression, no examples of being a “senior” or “staff” engineer means.

Something that helped me a lot in this kind of environment is being transparent from the very beginning.

Instead of pretending to have clarity about the structure, I focused the conversations on skills rather than titles.

The kinds of questions that really make a difference in this context are:

“What can you do today that you couldn’t do six months ago?”

“What do you want to be able to do six months from now that you can’t do today?”

Another important thing is being transparent about what the company can and cannot offer.

There’s no point in making promises about things you know won’t happen, or about roles you know will never be introduced. But that doesn’t mean you can’t still help the person move in that direction.

A sentence like this, for example, is far more powerful than any promise:

“We don’t have a Principal Engineer role right now, and we might never have one. But we can help you develop principal-level skills that will serve you wherever you go.”

That last part is important: recognizing that growth might eventually mean leaving. It doesn’t always result in someone actually leaving, but being open about it helps build trust.

This is the stage where we start talking about teams rather than just a team.

And it’s also where things start to get a bit strange. Specializations begin to emerge, but not quite specialized enough. Roles can change quickly, and positions that existed six months ago can suddenly disappear because the organization is evolving.

I’ve seen Data Engineers become Platform Team Leads, not through promotion, but because the organization split and reshaped itself around new needs.

Informal mentorship that worked beautifully with 30 people collapses when you scale to 300. It’s also the stage where you no longer know everyone’s name.

Career conversations become critical, because the old “we’ll figure it out together” mentality no longer scales. This is the stage where these conversations also start to introduce direction: technical growth or people management?

Pros: You finally have concrete resources to help people grow. Unlike smaller environments, where role boundaries are always very thin, here there are specialized teams, roles opening up, and new projects constantly starting. You have much more room to experiment, to try different roles or create hybrid positions that wouldn’t be possible in more corporate settings.

The challenge: Finding your own path in an organization that’s constantly evolving. Career ladders start to take shape: they exist, but they may still be inconsistent. Opportunities are there, but they also start to intersect with office politics.

Growing in this context also means focusing even more on soft skills:

how to influence without authority,

how to manage stakeholders,

how to communicate effectively, etc.

You can help your engineers figure out their own path by asking questions like:

“Which projects from other teams make you think, I wish I were working on that?”

“What excites you more: solving complex technical problems or helping others grow?”

“If you could steal someone’s job in the company for a week, whose would it be and why?”

Large organizations offer something that’s hard to find elsewhere: a structured career ladder, clear and measurable progress, and specialized career tracks.

This is where L1, L2, and all the other titles start to really mean something.

Corporate companies undoubtedly offer more opportunities, but they also come with less flexibility. You can become a Staff Engineer, a Principal Engineer, or an Engineering Manager, but switching tracks often requires navigating internal company dynamics. This is something that can be very draining for technically-minded people.

Pros: You have resources that you couldn’t even imagine in smaller environments. It’s not just about roles and opportunities: there are also internal courses, bigger budgets, formal mentorship programs, and team rotation opportunities.

The challenge: With great power comes great complexity. You have access to an enormous amount of resources, but it becomes even harder to figure out the direction because you have less visibility into what’s happening outside your team.

Your role as a leader is to act as a kind of translator that turns the abstract skills of the career ladder into concrete improvements that make sense within a specific domain and team.

For instance, you might need to translate “strategic thinking” into something like “When you propose a design, you should also consider how it’d scale with 10x more traffic”.

Questions that may help clarify direction in this context are:

“If you didn’t have to think about promotions or titles anymore, what kind of work would you want to do?”

“What’s the last time you did something at work and thought, this is exactly what I want to do more of?”

“When you look at people at the next level, what do they do that feels natural to you, and what feels forced?”

Now that you understand how to help your engineers grow based on the company size, let’s define the 3 different types of engineers you’ll meet next!

No matter the size of your company, engineers usually fall into three rough categories when it comes to growth.

Each one needs a different kind of approach.

Do you know those engineers whose eyes sparkle? The ones who ask a thousand questions and have an insatiable thirst for knowledge and hunger for growth?

Those people you leave at the end of the day with a single input, and the next morning you find out they spent the whole night diving deep into the topic.

Often, though, that hunger for growth can become paralyzing because of the sheer number of options available and the feeling that choosing one path means giving up others that are equally interesting.

The question “Where do you want to go from here?” doesn’t really work at this stage.

Typically, it gets opposite types of answers: it ranges from “I don’t know” to “I’d like to go deeper into frontend because it’s needed for the project, but I really love the infrastructure side. Although, the idea of being able to manage a team doesn’t sound bad at all” (a real conversation 😅).

Even though none of these paths necessarily exclude the others, you still need to line things up and figure out where to start. With time and seniority, it will become easier to find the right path independently, but at the beginning, asking questions that focus on things that have already happened rather than on the future helps identify patterns.

Questions that can help are, for example:

“What work are you doing now that gives you energy?”

“When was the last time you felt proud of something you did?”

“Who in the team (or in the industry) do you admire? What specifically about them?”

If the answers to these questions are satisfying, there isn’t much more you need to do. It will be clear to the person themselves what the starting point should be.

On the opposite side, there are those engineers who know exactly where they want to go. They’re clear about what they enjoy doing, what they don’t like, and the steps they need to take to reach their goals.

In these cases, the work seems pretty straightforward: the hardest part has already been done independently.

The problem, however, arises when you simply can’t offer what the engineer is aiming for: bigger projects, technologies far from your current stack, or a role that just doesn’t exist in the company right now.

These are probably the conversations every leader dreads, but they’ve taught me something important:

Sometimes a growth conversation is about being honest that you can’t provide what they need.

But being honest doesn’t mean you can’t be helpful, even if it eventually means parting ways. Once it’s clear that there truly isn’t an opportunity within the team or the wider organization, pretending nothing’s wrong and hoping things stay the same is like hearing a strange noise in your car and hoping it fixes itself without taking it to the mechanic: sooner or later, you’ll pay the price.

Funny enough, I actually did that with my car for over six months, only to discover this April that what looked like a simple coolant leak was actually an early warning sign that the head gasket was burning out.

Better not try that with people! Trying to hold people back, or clip their wings, will only hurt both the relationship and the team’s morale.

So what can you do? You can still help them get ready for the challenges ahead. For example, by supporting their development for the role they want to grow into.

For a long time, I saw “no growth goals” as a failure. I used to label people as unmotivated or lacking ambition. But most of the time, there’s a perfectly valid reason behind it:

fear of failing or being told no

going through a difficult personal phase and simply not having the energy (a newborn, personal challenges, etc.)

Sometimes, stability at work allows us to focus on other areas of our lives without having to juggle too many things at once. What truly matters is making sure the person is happy with their current situation.

There are other situations, though, where growth is needed for business reasons: the need for deeper expertise in a domain, leadership on a project, or the inability to hire for skills that are missing in the team.

These are sensitive conversations, and coming in with “You have to do this” mainly means betraying the trust you’ve patiently built.

Once we acknowledge that “no” is a perfectly valid answer, often for reasons that might not be fully visible to us, what really helps in these circumstances is being honest about the fact that we’re asking the person for a favor, not offering them a gift.

Which also means that a “yes” may come with conditions, and negotiating those conditions is part of the process.

At the end of the article, I am sharing 5 key tips that can help us support people in this exploration phase, even before getting to concrete goals.

Some have already surfaced throughout the article, but I find it useful to gather them all in one place.

Focus on energy, not goals

“Tell me about a project where you felt truly energized and engaged.”

This question reveals natural interests and strengths much better than “What are your career goals?”

Look for patterns over time

Instead of relying only on 1:1s or isolated conversations, try to observe patterns over time: What lights them up or kills their energy? What do they repeatedly mention? What do they volunteer for without being asked?

Identity ≠ Direction

Many engineers tie their identity to a specific path (e.g., “I am a backend engineer”) and feel guilty about wanting to change direction. Help them see that it’s not their role that defines them, but their values and the kind of impact they want to make.

Say out loud what you notice

Sometimes people have the answer right in front of them, they just need a little nudge to see it. Making patterns explicit is often that nudge.

Create space for experiments before committing

Before someone fully commits to a growth path, help them test it. Small experiments beat big commitments when someone is unsure.

Special thanks to Simone for sharing his insights on this very important topic! Make sure to follow him on LinkedIn, and also check out his newsletter Lead Through Mistakes, where he regularly shares interesting articles!

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