Person-Market Fit: A Mantra For Career Navigation

I work at Thoughtworks and I love it. I love the work I do and the quality of the people that I get to work with. While it is obviously not without some difficult moments, on the whole it is by far the best workplace I have ever had the privilege to be a part of.

If that sounds a bit effusive, consider that I joined Thoughtworks almost 5 years ago after spending 18 years working in other places (including my own startup). Part of my affection for Thoughtworks comes from the contrast I can draw to those places. Part of it comes from the privilege of finally working at a place where I truly enjoy what I do and the wholesome culture within which I get to do those things. You could say that Thoughtworks feels like home; indeed that is a phrase that I have heard other Thoughtworkers use to explain why once they joined Thoughtworks, they found it so easy to stay on. However, for me personally, my preferred explanation is that in joining Thoughtworks, I found my person-market fit.

The term is obviously derivative of product-market fit but I find 'person-market fit' deeply meaningful in its own right. The thing is, to be quite honest, I have throughout my professional career before Thoughtworks, been somebody with high potential but inconsistent performance. During the decade that I worked as a strategy analyst in the telecoms industry, there were definitely parts that I would excel in, e.g. ideation or lateral thinking or complex problem analysis but many more parts e.g. internal networking, consensus building or project management that would numb me with tedium. Indeed there were phases in my career, where getting myself in to work was a daily struggle and getting to the end of the day was the primary highlight.

All of this led to a self-image of unprofessionalism. I would look around at other high fliers around me and think of myself not just as a laggard in comparison but as a deserving laggard. My professional persona seemed visibly deficient to my own eyes. Why was I not more disciplined, more switched on, more conscientious, more high energy as so many others around me clearly were? And the fact I wasn't, surely that was 100% on me, not on anything else?

In hindsight, this was really me fixating exclusively on the person side of person-market fit equation. It never struck me at the time that maybe I was in the wrong role. That the answer to my career angst could be as simple as a career change. That maybe the elements of my professional persona that I disliked were not an immutable reflection of who I was but rather a reflection of poor person-market fit.

At this point, you might wonder why did I not just change jobs or industries? Well the simple answer is that I found telecoms fascinating; I still do. It's a constantly changing industry at the intersection of business and technological shifts, replete with the kind of juicy, hairy problems that I like solving. And I did move from one telco to another only to realise that it was more of the same as far as the typical mix of work was concerned. It was therefore easy to internalise the belief that changing jobs would fix nothing; the real fault lay in my inability to rise above my own limitations.

Neither was this altogether wrong. Simply changing jobs would be unlikely to be effective. The levers that constitute person-market fit are much more fine-grained than the choice of organisation or industry alone. If you keep changing your organisation without true insight as to the difference that you are seeking, you are basically waiting to get lucky. That is not a smart strategy.

As it happened, around 2013 I chanced upon a book called "First Break All The Rules" which championed the idea of focusing on your strengths over your weaknesses and of intentionally changing your career context to one where your strengths carry high relevance while your weaknesses carry a low penalty. That book gave me the courage to launch my own startup which - this is not a fairy tale - despite initial traction, failed after 3 years. I joined Thoughtworks shortly after.

As I settled into Thoughtworks, I came to realise that I was now a different person, professionally speaking. Gone was the low energy; gone was the tedium. I woke up most days with a spring in my step, eager to get into work. How? Why?

It turned out that consulting in general and Thoughtworks in particular made for a perfect person-market fit for me. I love directional problem solving and am good at first principles thinking. Those strengths had limited value in the teams that I previously worked in for multiple reasons, including the fact that the supply of high complexity, high ambiguity problems was quite irregular.

Consulting in comparison is inherently focused on high complexity problems with a high enough ROI to justify the cost of engaging external consultants. Additionally, the ability to cut through ambiguity or complexity using first principles thinking in the face of tight deadlines is hugely valuable because you switch industries and problems very frequently. Ideation and lateral thinking become critical yet are typically in short supply; meanwhile team-based delivery means that you are always working with other people who can bring vital complementary skills like operational rigour and project management to the table. I could go on enumerating other differences but the key point here is that the significant contextual differences in consulting and at Thoughtworks translated into person-market fit for me. Achieving person-market fit in turn transformed my professional attitude and impact to a degree that even now I frequently find hard to believe.

If you have read so far, it may be that like me back then, you are in a place where you are spinning your wheels without achieving real career traction. Maybe you have changed jobs a few times already without seeing any real difference. Maybe you have already concluded that you are not destined to be a high performer, that you suffer from just too many weaknesses to be a rockstar.

If so, you may wish to reappraise your situation from a person-market fit lens. Consciously identify your strengths and seek out industries or roles where those confer disproportionate advantage. Stop thinking of your weaknesses as fundamental flaws and be more aggressive in optimising for the market component of the person-market fit equation. Specifically:

• Assess your core skills (the stuff where you truly shine) as well as your weaknesses. Remember that the idea of core skills also implies scarcity. A core skill is either a skill that few people have (relative to demand for that skill) or it is a more common skill that you have honed to a level of such refinement that few others (in your cohort / career stage) have. To assess your capabilities, consider a framework such as strength testing
• Assess whether your current role allows you enough opportunities to apply your core skills (For example, if you are a visual designer with a genius for hand drawn sketches unmatched by your peers, you need to be working in an environment where applying that skills helps differentiate the outcomes expected from your team e.g. perhaps in a digital agency. If you are stuck in a pre-sales support role in a large company that has a very templated approach to design without room for hand drawn sketches, you are in the wrong place)
• Assess if those core skill are important enough to the outcomes that your organisation cares about in the context of your role. To return to the previous example, even in a digital agency, if the designer is unable to find a way connect their skill to a critical business outcome (such as maybe differentiating client pitches) they are unlikely to get the career uplift they seek.
• After completing the above assessment steps, assuming you find a lack of person-market fit, try to form a preliminary view, maybe in discussion with a couple of people that are professionally close to you, of industries or roles that might offer you better congruence.
• Next, reach out to your network to find people in the shortlisted industries and roles. Set up 30 minute calls. Spend the first 5 minutes explaining context and the next 10 minutes walking them through your assessment. Then ask them: "Based on my strength profile, what could be some roles in your industry where you see a good fit?" Capture their thoughts and ask for references to people who are already playing those roles, if possible. If that list looks too slim, use LinkedIn to broaden your catchment.
• Once you have the references, reach out to them and set up another 30 minutes with each. Don't ask for a job. Spend the time to get into their shoes; to understand what constitutes success and the drivers that distinguish the rockstars from the also-rans. As you progressively capture this information, you should be able to determine the roles that you would love to play vs. the ones that leave you cold. For the 1 or 2 roles that seem the most interesting, schedule a follow up if need be.
• Armed with this information, you are now finally ready to do a proper pro-active job search. Search for the role(s) that resonated with you. Once you find open roles (whether through job boards or networking) go for them but also don't forget that organisational culture is a critical component of person-market fit. Person-market fit is really just shorthand for person-role-organisation fit so make sure you research the organisational culture in case there are practices or values that are incompatible with you.

This more or less is what I wish I had figured out much earlier in my career and I hope you will find it useful in some small way, in case you share a similar dilemma. Good luck and thank you for reading this all the way to the end.