John Lees: My biggest challenges as a career coach

Firework faculty member John Lees outlines the most important road bumps in his coaching relationships and some of the strategies he uses to overcome them.

I’ve been challenged to think about some of the biggest challenges I face as a career coach.

Where I begin is with one word: transition.

Change is often what happens to us, or it’s imposed on us.

Transition feels like something we choose to begin and control.

When a client wants to switch career, it’s useful to remember this may be a bigger transition than they’ve ever made before.

There are a significant number of challenges here, for both client and coach.


Challenge 1 – Travelling without maps

Clients often say to me ‘I know I want to do something different, but I don’t know what it is’. This is sometimes quickly followed up by ‘and I don’t know where to look’.

In terms of history this is a relatively new problem.

Our great-grandparents’ generation probably had no more than 10-15 jobs to choose from locally. Today’s school leavers have tens of thousands of choices.

Knowing ‘what’s out there’ is more than it sounds.

Transitioning into a different kind of work often feels like setting off on a journey with a road atlas full of blank pages.

Coaches can sometimes supply industry information, but it’s important we reveal to clients the skill of map-making – ways of discovering the enormous variety of organisations and roles in today’s economy through lively conversations, information interviews, desk research and direct approaches to interesting people.

So my first challenge is to help clients move into unknown territory.

This usually means encouraging clients to follow their curiosity and ask honestly naïve questions.

Sometimes it works best if they start with a simple set of job ingredients (‘I’m looking for a role which allows me to use skills A, B and C in a context which is about X or Y’). At other times I suggest that the easiest places to look are often sub-sectors close to the world my clients already know.

Although people play with the idea of starting a career again from scratch, some of the most effective transitions find creative ways of building on existing skills and knowledge.

Once map making begins, what remains is all about following curiosity – discovering new and old career pathways, repeatedly asking ‘who else should I be talking to?’


Transitioning into a different kind of work often feels like setting off on a journey with a road atlas full of blank pages.


Challenge 2 – Working out what really motivates transition

Career coaches are used to receiving calls from people who say ‘I hate my job and I need to get out tomorrow’.

This impulse provides a fragile, short-term energy.

Looking for change because of negative feelings feels initially satisfying, but moving on from a position of disappointment often leads to confidence problems. When clients don’t get positive results immediately, the whole idea of change could suddenly feel unrealistic.

A familiar pattern emerges.

People who are unhappy at work apply for jobs they don’t really understand with a poorly prepared CV. They get knocked back, or hear nothing, so they stop looking – until the next time work makes them feel miserable.

Therefore my second big challenge as a coach is helping clients find a kind of positive energy which keeps them going through the ups and downs of exploration and discovery.

I often work with clients to help them reframe their reasons for change.

When asked ‘what are you looking for?’ they often begin with dissatisfaction and then describe uncertainty. I find I get better results if they talk about what they have already found stimulating in their working lives.

The distinguished Swiss career specialist Daniel Porot once advised me that when career changers talk about themselves the attraction of the new must exceed the repulsion of the old.

If clients talked repeatedly about why they want to escape their past, they get sympathy but not recommendations.

Focusing on areas of work that fascinate you means people remember you and opportunities start to turn up.


When career changers talk about themselves the attraction of the new must exceed the repulsion of the old.


Challenge 3  Getting past the first dip

Getting clients started on the process of career change is not difficult. Getting them to continue is often more of a challenge.

Coaching starts in a positive place; conversations and exercises tend to boost confidence.

The difficulty is what happens next when clients step outside their comfort zone for the first time. It’s easy to find discouragement, or discover that the interesting people you want to reach are too busy to return your call.

Information interviews (especially if they’re not set up clearly) can result in dead ends.

Clients often come back saying that exploration is hard work. Sometimes they say ‘I’m going to lower my sights’, they put the brakes on exploration, or they apply for unchallenging roles.

Sometimes this leads to negative feedback, but the most likely result of a low-energy job search is radio silence. Receiving no response is often the most damaging outcome – clients assume the worst about their employability.

Sometimes the biggest challenge is providing clients with the support they need just to keep going.

An effective strategy is to encourage clients to begin with people they find easy to approach. I advise clients ‘talk to the kind of people person you can pick up the phone to without having a script in your head’. Starting with easy people means clients get well as ideas and connections.

I often find clients often only need two or three supportive conversations like this to feel confident talking to strangers.

It’s good to remind clients of what brought them to their first career coaching session, and what they long to do.

This takes us back to the attractions of the new. What skills do they most enjoy using? What kind of tasks feel purposeful? What ideas, technologies, products, brands or approaches do they most like to hear and talk about?

These conversations re-kindle enthusiasm.

Enthusiasm drives curiosity.

Curiosity provides extra spark of energy people need to start the next conversation.


Sometimes the biggest challenge is providing clients with the support they need just to keep going.


Challenge 4  Fear of failure

I’m working with a client. Let’s call her Alex.

She says she wants more stimulating work. I’ve helped her remember what she’s good at, and how she’s added value in a number of past roles.

I’m delighted to see that Alex has some interesting connections in a range of industries. She’s got the idea of information interviews, and I step back to let her fly unassisted.

Sometimes this is what a coach needs to do.

However, like many clients, Alex comes back to me two weeks later. I’m surprised to discover she’s done very little.

She’s been too busy. Life has got in the way.

She’s approached a couple of people but the conversations didn’t seem to go anywhere.

She’s telling me she feels she might just need to keep her head down and think about a job change in a year or two.

I hear this a lot. It’s interesting that people start out saying they are desperate for change and will do anything to move forward, and sometimes only a few days later they seem to change their minds.

Clients know that map making (see challenge 1) needs conversations, but something stops them. It probably isn’t mistrust in the process, but fear of being seen to fail.

Clients wrap this up in phrases like ‘why would they want to talk to me? – I know nothing about the industry’.

They feel inadequate even asking for an informational interview, worried that they will not sound credible. They say ‘I don’t want to waste people's time until I know what I’m looking for’.

I like to invite clients to imagine they are in one of the jobs they currently find interesting. Then I ask them to run the movie backwards. How did they get the role? How did they hear about it in the first place? What was the first step they took?

Alex isn’t alone in her answer to this question: ‘I probably got there by talking to people’.

The threat to self-image is important - something I take seriously as a coach.

Job hunting makes everyone vulnerable. Talking about doing something completely different enhances that vulnerability. It’s easy to feel fake, uninformed, or a naïve time-waster.

So, I invite clients to project confident honesty. This means you never begin an informational interview apologising for taking up somebody’s time, you don’t talk about your lack of knowledge or experience, and you don’t pretend to know more about an industry then you do.

Confident honesty means using simple phrases like ‘I’m exploring a wide range of options and I’d love to talk to you about the work do’.

Exploring slides into networking, and I believe that the way my clients are remembered matters enormously.

If Alex cravenly asks for favours one day, it’s difficult for her to be recommended as a candidate with initiative the next.

When clients get closer to opportunities they will of course need to sound credible and to be really in control of skills evidence.

Early in the process, exploring is simply exploring. In order to encourage clients to keep looking, take threats to self-image seriously.

Encourage clients to operate first of all a safe territory, and to keep supporters in their corner throughout the process to maintain energy levels.


If Alex cravenly asks for favours one day, it’s difficult for her to be recommended as a candidate with initiative the next.


What have I learned from these challenges?

I’ve learned that the most important work that I do as a career coach isn’t just about asking great questions, but helping people find an energy within themselves that helps them reframe the past and see new possibilities in the future. 

I’ve also learned that career change isn’t a giant leap, but a series of small steps – moments of discovery, breakthrough conversations, fleeting insights. And small steps in terms of language as well – the short phrases that liberate clients so they can talk about themselves with clarity and confidence.


John Lees is a career strategist and author. He's one of the trainers for the Firework Coaching Programme, as well as leading on on our Firework Career Coach Masterclasses. John has published 15 books on careers and work including the bestselling ‘How to Get a Job You Love’. He was previously Chief Executive of the Institute of Employment Consultants and a founding board member of the Career Development Institute. He holds degrees from the Universities of Cambridge, London and Liverpool and is a NICEC Fellow. Find out more at