The Transferable Skills Trap - Jobseeker Basics III

Greg Wyatt • October 21, 2025

The following is Chapter 4 in A Career Breakdown Kit, my guide for improving your odds in a VUCA jobs market.


Fundamentally it's a chapter about selling yourself, and moving from features to benefits to how it matters.


Similar to the advice I give to employers in how and why they should move from generic copy+paste job adverts to specific, representative content that shows context and has meaning.


The same generic adverts you tailor your CV towards (a chapter for another time).


Put it this way -


Do you buy Pizza because it contains flour, yeast, dough, salt and water?

Do you buy it for the toppings?

Or do you buy it because of the way it makes you feel as a regular buyer or someone attracted to its packaging?


My favourite pizza has a bite, a sizzle, the richness juiciness of its sauce and how it combines with the stretchy delight of mozzarella. Oh, and that spicy kick from the Jalapenos!


Transferable skills are your dough - the basic ingredients - important in the right place, but must be defined in the right way to have meaning for your ideal readers.


Chapter 4 - The transferable skills trap


Maybe your top ten looks like this:


  • Strategic Thinking
  • Leadership
  • Communication
  • Problem-Solving
  • Decision-Making
  • Organisation
  • Analytical Skills
  • Project Management
  • Change Management
  • Relationship Building


If you’re a COO, that is.


If you’re in a different field, your list may look a little different - why not ask a large language model? Gemini came up with the one above.


I expect the results would be similar for an HR Director, with a little people strategy, employee relations and EVP development thrown in for good measure.


Here’s the rub - if these skills are in your top 10 list of transferable skills, they are likely in the top 10 list of your competition’s transferable skills.


And if everyone has the same skills, none of these skills stand out.


If transferable skills are your unique selling point… how are they unique?


The problem doubles down.


If, in our days of generic advertising, a company is looking for a COO or an HR Director, their essential required skills can often include these transferable skills.


Can you communicate at all levels with strategic thinking, fostering an innovative culture?


Me too!


We all ‘know’ that a customised CV is the way to go. (Is it though? Check out Part Three for my answers.)


What exactly are you customising against, if your custom skills are the same as every other applicant who applies to this advert?


This is the transferable skills trap.


Skills that in real life serve you well and are valuable in any context. Yet skills that are common enough they work against you, when you declare them your strength.


What can we do?


Move from transferable to applicable.


Applicable skills are precisely the same skills as transferable skills, with two differences:


  • Direction
  • Definition


The direction of any applicable skills is that of the employer.


How does your skill apply in their domain?


The definition of any applicable skill is the context in which you have applied them successfully. This can be synonymous skills, tools, processes, software, etc.


If the direction and definition don’t reflect each other, you may not be an ideal candidate.


Should you even apply?


And if they do reflect each other, the onus is on you to show explicitly how your skills work in the employer’s context.


In an ideal world employer hiring processes are skilled and knowledgeable.


In practice, you should assume the weakest link in their hiring process is the gatekeeper - an administrator, a recruiter, an HR assistant.

Maybe they’re lazy, maybe incompetent, maybe swamped, maybe inexperienced.


It doesn’t matter - a weak part of a hiring process doesn’t necessarily mean employment is unsuitable but can prevent you from being considered.


Help us do our jobs by showing how your skills apply, and we may see you as a suitable candidate.


With the benefit that this helps skilled recruiters too.


What is context?


This is the relevant background that adds sufficient substance to an assertion.


So, you’re a COO?


Are you a COO within a £2m bootstrapped start-up that’s achieving profitability?


Do you work in a multinational charity streamlining your operations to save money?


Or are you a safe pair of hands to keep the ship steady in your £30m family-owned manufacturing company with 120 employees?


These three COOs may well have the same transferable skills, and might each be brilliant, but their contexts are more important than their job title in assessing suitability.


Going further.


The ugly brother of transferable skills is responsibilities and experience.


In the same way adverts copy-paste job descriptions, how many CVs do the same under each job title in a CV?


There may be hundreds of applications each sharing the same explanations.


Fortunately, you can apply direction and definition here too, by showing impact, by showing your achievements (with numbers and context), and by showing how you can help.


These principles help you move from being a <job title> with a dry set of responsibilities and experiences.

To someone who shows how they can help, how you can solve problems, and how you can heal the pain of the people who might employ you.


It’s the same as moving from features to benefits in sales.


Features are what you do. Benefits are how the customer’s life is improved.


Transferable skills are highly valuable to your next employer. You should be proud of them.


Unless they are specific and relevant to the roles you apply for, they can get in your way.


If you can gain insight into what your potential employer needs, and show how you may solve their problems, your odds will improve.


The frustrating caveat to this is that sometimes you are only given a generic advert to try and glean this from.


If you can’t gain insight, is there any point in showing applicability by tailoring?


Apart from using their terminology (such as if they say Continuous Improvement, and you’re a Six Sigma Black Belt), my answer is no.

Instead, default to a good enough CV. One which plays to your strengths by showing how your skills apply through tools, process, context and achievements.


Apply with what you have, follow their instructions and diarise a follow-up. Then move on.


Treat transactional generic adverts transactionally and worry more about the ones that speak to you personally.


Don’t rely on transferable skills in the hope that others will see how they apply.


Help us do our jobs and see you as a great candidate by showing how your skills apply.


This won’t guarantee interviews. It will improve your odds.


Showing applicability is a strong gain for every aspect of your job search.

An inverted job search

By Greg Wyatt • October 7, 2026
I realise I've shared this chapter fairly recently, but there's good reason to revisit it. On Friday, I launched a new AI tool - Your Job Search Plan. You can find it here: https://your-jobsearch-plan.netlify.app/ It's based on the inversion principle below: the optimal job search is an inversion of how that job is optimally recruited. In other words, the first step in a job search should be to understand how recruiters and hiring processes seek to fill your ideal vacancy. Then to access all those channels while putting your best foot forward. It connects your applications, your networking, your CV, your LinkedIn profile, and so on, all of which should stem from your professional identity, the context of your career, the market conditions for that career, and therefore the work you'll need to do to boost your odds. One thing I'm pleased about with this tool is how it relates to the other tools and resources on www.bwrecruitment.co.uk/resources . So what seemed abstract, or painful activities without guaranteed outcome, become a practical arrow in the quiver of your search. I hope you find these tools helpful. They are a starting point, rather than a resolution. 20 - An inverted job search So, your broad approach to looking for a job is based on a product marketing strategy. How does this link to your job search and how companies hire? The next step is to recognise a job search is an inverted recruitment process. Whatever you can learn about the actual workings of recruitment, the better armed you are to navigate them. The first way in which this is true is around the routes to market employers take to fill a job. Employers want to fill vacancies in the most economical and efficient means possible. Sometimes they’ll rely on external advice, sometimes they’ll figure out their own way, and sometimes they’ll employ people to do it for them (such as a Talent Acquisition Manager or internal recruiter). When they rely on external advice, it may not surprise you it’s as varied and contradictory as job seeker advice. Take this nugget of wisdom: 80% of suitable candidates are not actively looking for work. By advertising, you’ll only have access to the 20% that applies to adverts. Hang on a minute! Doesn’t that sound an awful lot like the hidden jobs market? Of course, candidates aren’t hidden - much like hidden jobs, the priority is to understand the channels through which candidates are found. These channels directly mirror the channels through which you look for that job: Job boards; LinkedIn; Recruitment agencies; Confidential headhunting; Internal promotions; Secondments; Temp-to-perm hires; Consulting-to-perm hires; Referrals; Networking; Speculative approaches; Careers pages; Talent pools; Candidate databases Every job is different, dictated by principles like supply and demand, confidentiality, reputational risk, wherewithal, budget and capacity. The hiring process of a Software Developer is different from that of a Sales Director. If an employer only hires through an advert - this means if you don’t apply for adverts, there’s no way in which you can be considered for that vacancy. A second way it’s accurate is the notion that what’s true for one may not be true for others. This relates to candidate resentment . You may read online that some recruitment behaviours are signs of a bad employer. Yet, you should always follow the instructions given when applying for an advert or through an agency. They may instruct you to: 1/ Write a CV, cover letter and duplicate it on their ATS 2/ Tell them your salary when they don’t list theirs 3/ Do 17 interviews before reaching a decision 4/ Deliver a 6-month strategy plan by presentation 5/ Or any other request deemed unreasonable by Career Coaches, Job seekers, or people otherwise uninvolved in that process What some consider red flags, others will deem acceptable practice. It becomes your choice to play the game or not. Either follow their instructions or step away. You don’t have to apply if you don’t want to. In a similar vein, if you hear a hiring process has a preference, or if there are gaps in their employment armoury - these might be biases you can lean into. The hiring manager loves Arsenal Football Club and is biased towards people who love the same? Now might be the time to switch allegiance, if you can fake it or make it. They love a one page CV? Apply with a one page CV. You know the hiring manager of an advert with 400 applications? Give them a call - they might give you an unfair advantage. Poor practice from the employer, yet these are problems you can turn into opportunity. A third way in which this is true is by comparing inbound and outbound activity Outbound activity is where you go to your prospect (phone calls, messaging). Inbound activity is where the prospect comes to you (job adverts, content). Yet an outbound activity for a recruiter is an inbound activity for you (you receive phone calls and messages). While an inbound activity has you getting in touch because of their advert or content. When we talk about optimising your work, whether your CV, profile or interviews, it has to give the process what it needs. How can you be more discoverable, so you receive more relevant calls and messages? How can you improve your return on applications and your outbound messages? What about inverse non-recruitment? A brilliant, if strange question, with the same answer. When networking, going direct, seeking to become a referral, doorknocking, or other, what is the inverse of that activity? How does that person find or recommend people, if they become aware of a vacancy? How might they see you as a person to solve their problems, even if it isn’t a vacancy? You do these activities because of how they might help you and because of the benefit the other party experiences. What’s in it for them? If there isn’t anything in it for them, why should they help you? For each and every stage in recruitment, there is an opposed force, as candidates and the hiring process meet each other. It’s rarely an equal force, because every vacancy has supply and demand, resource, skill level, biases and intent at play. This is why each type of role has a different method of looking for work. Executive vacancies typically prioritise headhunted candidates, with fewer public adverts. Here the priority shifts towards building relationships with, and being discoverable by, Executive Search recruiters. If executives rely mainly on job boards, they may never think to focus on more suited channels. If you can learn what the other needs for that process to be successful, you can deliver the same. Speak to peers, speak to hiring managers you know, speak to recruiters, speak to former job seekers. How have they found work, and how would they recruit for your roles? Research your market to find viable employers, to identify recruiters and to build your network.  Then execute an appropriate strategy to access these channels.

Hierarchy of Pain

By Greg Wyatt • September 23, 2026
I had an aborted conversation at a networking event on Tuesday. It was about a problem vacancy a fractional people lead was looking at. Her client had instructed various executive search firms and none had produced a viable candidate. It seems the consistent approach was to match CVs to job description - pureplay transactional - and none were candidates that met the goal of the vacancy. You see that organisational pain that the vacancy heals wasn't defined by documentation, and therefore if you rely on that documentation to find candidates, it's happenstance that you come across someone viable. It's such a common problem, and when I 'fix' problem vacancies, it's invariably something that isn't described which was holding back a successful hire. The irony is this shouldn't be a hidden pain - presuming it's appropriate to share, it should be front and centre. What complicates modern recruitment is that, instead of better specifying vacancies, both sides of the hiring fence increasingly rely on LLMs to produce documentation that shaves the edges off. And as a result a candidate that has extensively healed the hidden pain a vacancy might even remove the evidence from their application in a bit to better match an advert or job description. The more transactional recruitment comes, particularly through reliance on technology, the worse this problem becomes. Probably not an issue for business as usual vacancy, but when a vacancy has impact, standard process of "5 CVs by Friday" will invariably hold you back. The chapter below is from A Career Breakdown Kit , my guide for navigating a skewiff employment market. It may be for job seekers, but the problem and solution are directly mirrored by the hiring side. It's taken word for word from the book, so some of the content is interconnected with other chapters. You can read most of them for free in the Jobseeker Basics newsletter. Hierarchy of pain This chapter reflects on how buyers make decisions, how this is reflected in hiring and why it matters in how you put forward your CV, application, interviews and other messages. If you’ve ever encountered sales in your career or life you are likely familiar with the concepts of Features and Benefits. The product is what is proposed. Features are what it does. Benefits are how it helps. However there are actually three other components in this hierarchy that make up commercial messaging. Value is what the benefits mean to you. “Sell the sizzle, not the sausage” - the sizzle isn’t a benefit, if you don’t like sausages. Outcomes are the tangible long-term results from using that product or service. “Sell the picture frame, not the screwdriver” - or rather what’s in the frame. Why does it matter? The idea being these peel back the layers of the onion to help a potential customer understand exactly What’s In It For Them. Yet, it may not matter whatsoever if your brilliantly put together message doesn’t achieve one element - show how you heal their hidden pain. In that frame example above, this might be a photo of a loved one, no longer with us. The photo is for our memories and feelings. The frame has to be right, to commemorate them properly. While it needs to be mounted well, using tools that make the job easier. Could you market that loss to sell a screwdriver? Hopefully not, though the message might be, “For memories that matter,” instead of "High Quality Screwdriver". It's a common pain many share, yet not one you might discuss down the DIY shop. Early in my career I had a lesson on hidden pain and its importance. I recruited an HR Manager for a high growth business whose requirement was for someone with broad experience in a similar environment. I presented an excellent candidate who was only available due to the shutdown of her employer - she had to stay to the final day to manage the process well, which limited her availability to start work. That was the only reason I explained her current situation to this new employer, because redundancy management wasn’t on the job description. She got the job! On day one of her new employment, her role was made redundant and she was offered a retention bonus to shut down the local site - everyone was to lose their jobs. The hidden pain here was redundancy, something not even mentioned to me during the vacancy briefing, and something I never broached with Julie. IIRC, there was no mention of it during the interview process either. Perhaps that’s an extreme example, but it does show what can happen behind the scenes. And if you happened to be out of work, a fixed term contract with a retention bonus might be quite appealing. Were you to apply to that vacancy, it would be important to highlight your redundancy experience - customising your CV might even have worked against you! So how does this hierarchy fit within your job search? You are the product, with your next employer on a buyer’s journey. Your features are what you offer. In a CV this is a combination of job titles, qualifications, skills and areas of experience. It’s also your salary requirement, where you are based and other elements like Visa status and working arrangements. Get these right and a little luck might mean they are all you need, considering that these same elements are what we source and filter on. I expect in this market you’re in competition with many people that offer the same Features, so the differentiator is what you bring to the table uniquely. The contexts of your career combined with how you helped, your impact, your achievements, and what the outcomes were. Related chapters: Principles of a Good CV Should I customise my CV? LinkedIn profiles that get found LinkedIn profiles that convert These are all resources that will help you communicate the benefits of your experience, the value you bring, the problems you solve, and the outcomes of these solutions. As for the hidden pain question, which in many vacancies isn’t articulated, how can you unpick hidden? Go back to why vacancies are recruited. How did they come about in the first place? They only fit into two piles - new and replacement. However these two piles have many subcategories relating to the problems they solve and the pain they heal. Researching the company can help. Inside knowledge definitely helps - it’s one reason good agency recruiters will be a valuable ally. But this knowledge isn’t always available, and sometimes the employer may not even know! I always come back to the principle, “You can’t be all things to all people.” And when you try to do this, you appeal to no one. It’s one reason why using LLM style AI to customise CVs is so problematic. The output is necessarily same-same because it’s a probabilistic determination of what you want based on an aggregate of data. It’s why, when recruiters receive a volume of AI augmented CVs, they all look the same. Your ‘good enough’ core CV ( Should I customise my CV ) leans into your strengths. While you might tweak it to meet the essential requirements, in the language of the employer, this should naturally support your greatest strength - the unique fingerprint that is your career. The downside of relying on customisation against vague, and often misrepresentative, adverts is that you can deemphasise and even remove your biggest achievements. The same achievements that would have helped you stand out. If your application doesn’t heal the hidden pain of a vacancy, it’s either because you have not defined your strengths correctly or you aren’t that close of a fit with the actual needs of the vacancy. An example to show this pitfall in practice. I caught up with a friend yesterday who has resigned from a post that was missold to him. His career is based on commercial acumen and enablement in a field that is heavily focused on risk management and compliance. So he’s already unusual in a good way (though his CV didn’t show this). On day one of his new job, he encountered a literal unexpected disaster. While these things happen, and he managed the situation effectively, this proved a consequence of the business culture and strategy. These problems kept coming up and his functional area in the business needed a complete overhaul at executive level. Rather than the commercial enablement picture they painted, they needed someone who relished chaos - a master of disaster. Completely the opposite of the career Simon wants. This isn’t something they could publicise in their recruitment process, for reputational reasons, yet it was a fundamental baked-in aspect of the role. I’ve no doubt Simon’s CV is a match for their job description. Yet he is not a match for their job. What if they’d seen CVs of people who’d leant into strengths of healing dysfunction? What if he’d leant into his strength of enablement? He may not have left his previous job for something he went on to regret. If you’re sceptical about how crucial hidden pain is in recruitment, think about your own hidden pain when applying for jobs. What’s going on in your life that impacts which roles are ideal for you. The same points you might not divulge when you’re just trying to get back into employment. Perhaps you've even experienced the pain I did when considering a hardware purchase. How did that pain inform your buying decisions? It’s no different for employers when they consider the pain and problems inherent in their vacancy.