The Three Career Paths

What to do when your employee asks for a promotion.

You make a great hire, and upon joining the company they go from strength to strength. Everyone’s pleased. But before long, they’re asking about next steps. If you manage employees in the early and middle stages of their career, you’ll be familiar with this scenario.

Often, young people see only line management, team leadership and the words “manager” or “head of” as markers of career growth. So when your brightest employees want a promotion, they’re aiming up the ladder and into a people manager position.

What’s the problem?

If you’re skilled at hiring, you’ll probably have a team of talented employees. You want to keep all of them motivated, and you want to provide all of them with progression and development opportunities.

But here’s the thing: not everyone can manage a team, not everyone is ready to manage a team, and not everyone should manage a team.

What’s the solution?

You need to show your employees that progression takes many forms. I used to coach my team on these three main career paths:

  1. Moving Upwards
  2. Moving Sideways
  3. Moving Deeper

Before we take a closer look at them, note that each of these paths share the following traits:

  • Every path can make you rich (if that’s what you’re into).
  • Every path will allow you to make an impact: on your field, function and the lives of those around you.
  • Every path can make you happy, or unhappy.

1. Moving Upwards

This path is the most familiar to young people. It’s about moving up an organisation’s structure, and managing people who manage a function.

Progression for people on this path is typically defined by job title, number of people they manage, size of budget they’re responsible for, geographical remit etc. All the classic career “status symbols”.


  • Leading and developing people is very rewarding.
  • If you’re good at managing people, they will look up to you.


  • It’s much harder than you’d think, and unless you’re exceptional you’ll plateau pretty quickly.
  • Once you’re managing you’re no longer doing, so you’re not necessarily developing expertise.

What it takes

Moving Upwards is not about being good at what you do; it’s about making other people good at what they do. Between two members of a commercial team, I’m not going to make my top seller Sales Director – I’m going to promote the person who has been leading initiatives, and training and supporting others to hit their targets.

That’s not all. People managers need to be skilled at hiring and interviewing, putting together budgets, reporting on metrics, forecasting resources etc. They also need the resilience and ability to deal with a wide range of challenges, conflicts and personalities.

There are two things you can do to prepare yourself for Moving Upwards:

  • Shadow good managers who will let you “have a go” at the tasks above, and share their thought-process, decisions, tactics.
  • Start yourself on the Moving Sideways path, so that you develop a wide-range of skills that will prepare you for management.

I’m wary of any company that puts someone without this kind of experience into a managerial role – it’s almost never in the best interests of the company or the employee. The same goes for someone who doesn’t have this experience but still feels they’re ready to move up – it doesn’t demonstrate good judgement.

2. Moving Sideways

I like to compare this path with a computer game – the kind where you’re finding weapons and gadgets to add to your inventory, ready to pull them out when you’re in a tricky situation.

Moving Sideways is about developing a wide range of cross-functional skills by getting exposure to as much as possible. It could be to prepare you for a pivot onto the Moving Upwards or Moving Deeper paths, or because you get bored easily and love the thrill of doing new things.


  • Knowing about a lot of things makes you better at what you do.
  • Bigger skills inventory = more options.


  • Although you’ll progress further and faster in the long term, in the short term you might find your salary doesn’t move much (it might even decrease if you choose to learn a specialist skill).

What it takes

This path takes patience, the desire to learn, a sharp mind and a supportive environment that encourages cross-functional learning.

It’s important to think about it somewhat strategically so that each skill you pick up contributes or leads to the next e.g. you start out in sales, move to customer success, move to project management, move to product, then move to marketing. There’s a logical flow to that.

Working for large organisations (yes, those corporate monsters) can be a good method for Moving Sideways. But if you prefer early-stage businesses, you’ll probably have a very safe future. CEO/Founders will reward your loyalty and love that you’re not just trying to jump into a management role.

This set-up has to work for all parties. You can’t jump from one role to the next every three months, and you won’t really learn many skills if you do. You need to spend a decent chunk of time (one to two years) in each, or agree on some other kind of arrangement e.g. a temporary secondment to a team, working two roles part-time.

3. Moving Deeper

On the third career path, you forgo the challenges and trials of Moving Upwards and Moving Sideways in favour of deepening – and I mean really deepening – your expertise in a particular field.

My friend is a great example. He loves doing visual effects for Hollywood films. In the many years he’s been doing it, he’s consistently turned down offers to jump into a supervisor role. What does this path mean for him? He has a reputation for being one of the best in his field. He gets to choose what films he works on (Star Wars), gets given the cool shots (usually something exploding), gets paid the most, and is responsible for nothing and nobody else.

Other common examples are developers, project managers, strategists, creatives and lawyers. They’re the people you’ll pay a lot of money because you trust they’ll get the job done. You need to be doing one specialism for several years to be considered on this path.


  • You’ll get paid a lot of money because you’re one of the best in your field.
  • If you tire of working for a company, you can quite easily become a consultant, freelancer or remote worker.


  • You may not get the same kind of “power” those Moving Upwards will get.
  • You’ll probably be 50 reporting into a 27-year-old.
  • You’ll need to love your chosen field, or all the politics and bullshit (and your 27-year-old boss) will annoy you.
  • If for any reason your “expertise” becomes obsolete (hello, switchboard operators), you’re fucked.

What it takes

Passion, commitment and a complete indifference to those Moving Upwards and Moving Sideways.

Perfection is gained by constant repetition and practise, but Moving Deeper also requires you to stay “in the know”. Depending on your industry, this may mean networking, reading, writing thought-leadership pieces or (if you’re my friend) going to the cinema and eating a lot of popcorn.

In other words, you can’t become complacent. Just doing the same job for a long time doesn’t mean you’re Moving Deeper. I’m not even sure it’s a path. You have to commit to continually fine-tuning your skills.

You’ve also got to know how to show your worth, because if you love what you do but aren’t ambitious, you could end up getting overlooked and underpaid. And if you employ somebody on this path, the onus is on you – it seems obvious to give a pay rise to someone who steps up into a management role, but it’s equally important to reward those who are happy to keep doing what they’re doing, and are very good at it. Otherwise they’ll leave and you’ll only ever have “OK” people, or those excited by Moving Upwards and Moving Sideways.

Putting your employees on the right path

If you’re managing people in the early stages of their career, it’s your job to talk them through these paths and to provide guidance on what might be right for them.

You should be helping them over time, not held to ransom by their ambition. I work with a lot of managers who stress because they’ve hired a new employee who is performing brilliantly, and after six months that person says they want to move up or else they’ll go.

That’s not how it works.

I expect an employee to work hard in a role for at least a year. I invest a lot of time and money hiring and training a new employee, so it’s fair that I get to see that return on investment.

In that time I learn a lot about them: how they perform under pressure, how they contribute to the culture, what they’re good at, what they struggle with, what seems to make them happy, what gets them grumpy. Every now and then I’ll push them, by giving them tasks they won’t know how to do or that make them uncomfortable. I’m also going to let them watch me work and learn from that.

After a year, we’ll be ready to talk about what kind of path makes sense for them. I’m going to be very honest about what I think, what they need to do to get on that path, how long it’s going to take, what I can help them with and what I can’t. We’re going to reach an agreement that allows me to keep getting what I need from their role, but enables them to start moving towards their path.

What that agreement looks like depends heavily on the company and how it’s performing. I can’t carve out a career path where there isn’t opportunity, and I need to be honest about that. I’d be devastated to see a superstar employee go, but I owe it to them to push them on their path – even if it’s away from me.

The relationship needs to be symbiotic.

The big picture

I’m always met with the same sort of questions at this point in a coaching session, whether I’m talking to managers or their teams.

Can you take all paths at some point? Can you be on multiple paths at the same time? Is there a hierarchy to the paths? Is there one path that will leave me stuck?

Here’s what I tell people:

The purpose of outlining these paths is to help you understand that progression takes many forms. Money can be made in many ways and personal success is not linked to a promotion.

It’s not about which path or the order of paths; it’s about understanding your options, constantly learning, and working out what makes you happy (which can change over time).

You might see Founders/CEOs as being “at the top”, but I can assure you most sensible Founders pay their developers more than they pay themselves. Personally, I’m grateful for having jumped around environments and teams a lot. Moving Sideways led me to Moving Upwards which led me to Moving Deeper.

There are many popular Abraham Maslow quotes about self-fulfilment, fear and ambition, but I like this lesser-known one:

A first-rate soup is more creative than a second-rate painting.

Convention may suggest one path, but there can be art, fame or fortune in all of them. I’d rather be the world’s best administrator than an average manager.

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