Learning from my hiring mistakes

I've made more than my fair share of hiring mistakes in some areas, and this post tries to dissect why.

Learning from my hiring mistakes

I've made more than my fair share of hiring mistakes in some areas, and this post tries to dissect why.

I'm a contrarian thinker, who tries to focus on the good in everyone — a contrarian optimist; or, better, an optimistic contrarian, which has a nicer ring to it. As a contrarian, I continually test the opposite point of view of advice and all received wisdom. As a child, I was told "don't ride a toy tractor down the stairs." That test ended with a black eye. "Don't put your finger in the fan" was another bloody one from childhood. As a young chap moving to the USA, I was told "110V doesn't shock you as much as 220V". They were damn well right: 110V is a gentle, massaging buzz, but 220V... Imagine deep tissue massage performed by the sharp tip of a red hot soldering iron attached to an oscillating Sonicare toothbrush, that's what 220V feels like! Normally these contrarian tests are dictated by logic and a risk assessment. The ones that end roughly are never repeated, the only exception being "don't have another drink" at 1:50am — alcohol dilutes logic, and the mornings after have been the most regretful of times.

As a people optimist, I see the best in everybody. I still try to interview all new hires, where time permits, as a sort of unexpected courtesy because being able to meet with the CEO is a great differentiator in the hiring process. Whenever candidates flunk it, though, I feel bummed out — I want everyone to be a winner.

Relating these to business, being a contrarian means that I often learn from mistakes rather than just accepting the received wisdom. To some degree, all start-up founders have to challenge the status quo, otherwise they wouldn't be doing what they are doing. However sometimes this means at Yellowbrick we've perhaps made a few more mistakes than necessary, like being a bit late to the cloud party. Being a people optimist, on the other hand, makes me too slow to fire people. When someone does substandard work, the voice says "they must know better and can learn..." and I want to give them another chance. My heart believes intelligent people can always better themselves and learn from their mistakes but in practice this is often not the case. So I like to give people another chance — because that's of course what Jason and I ourselves do, and what our Board has repeatedly been kind enough to let me prove I can do. But the honest truth is this has rarely worked, especially when their mistakes are the result of doing the same thing over and over again (see experience, below). This is why so many CEOs take a 'winning team' with them from job to job.

As well as these learnings about myself, I also wanted to share some collective mistakes or patterns in hiring in the hope that it helps others avoid falling into the same traps.

Don't confuse experience and initiative

For some hiring managers, if they have a position where they really, really need to trust the person to get the job done well with minimal oversight, they will look for people with a large number of years of experience.

Employees with a great deal of experience can be incredibly rare and valuable; however experience has to mean something other than "doing the same thing over and over again." Times change, customers change, buying habits shift, buyer personalities drift, and technology keeps moving at breakneck speed.

If I find an engineer that's only worked on file storage their whole career, a sales rep that sells to the same buyers with steak dinners over 5 jobs, a sales manager who isn't data driven or a product marketer who spent their career turning out uninteresting pages of PDF or crap PowerPoint diagrams — chances are they will do exactly the same thing again in the next job; even if they say they won't. If I hire this, what I've hired is a record that keeps repeating the start of the song again and again, and no matter how long you wait, never makes it to the good catchy riff with the thumping bass. Imagine Coldplay songs with only the beginning... The odds are that the extra money I've spent for those years of experience will be in vain. Managing that employee will be like having to watch that time-loop movie with Tom Cruise trying to save the world from aliens, where the day repeats itself over and over, waiting for a different outcome. I don't have time for so many repeats.

What we really want in a start-up is initiative. Initiative is largely orthogonal to experience. We want someone who loves learning new things because it's their passion. They work long hours because they love their trade and have a dynamo that won't stop spinning: The engineer that has hacked 5 different languages and worked in all parts of the stack with a ferocious appetite for learning. The sales and marketing folks who did well in the pandemic and have worked across different customers and can enter accounts using the latest in sales tech and MarTech, train with gong.io, and can transact without wine, golf or steak dinners. When I can combine initiative with experience — proof of initiative-taking over and over again through a storied career — that's the best of all worlds. However this is pretty rare.

For me at Yellowbrick, initiative is more important than experience. I don't want a company full of ants, people sitting around waiting to be told what to do. Staff have to adapt rapidly, take risks, go beyond organisational boundaries and work without processes; chances are, what they did last time won't work again this time.

Domain ignorance, and what to do about it

I started my career as a programmer, ended up being a programmer who loved to talk to customers. I've always loved the feeling of victory that comes along with bringing orders in, and for that reason have been "working in sales" — which really means helping sales — for almost as long as I've been programming. However, hiring leadership for the go-to-market side of the company—sales and marketing—is always something I've found hard. When I hadn't worked in those departments in the same way as engineering or  product marketing, I didn't have the on-the-job experience to make the best decisions, and made some mistakes: Especially in these positions, the best marketers and sales people do a phenomenal job of positioning and selling themselves since that's part of the skillset!

The way around this has been to recruit formal advisors and board members who are experts in this domain and have them advise me ahead of time, contribute to job descriptions, explain the sorts of candidates I'll find and help me think through what really matters at a given stage of growth. I ask them to be in the final interview round as well, along with a couple of other investor board members who I think can help. This has allowed Yellowbrick and I to continually raise the bar; as we grow, we find new advice from industry legends who have both the experience and initiative at the appropriate stage of the business.

Hiring people like us, who share our point of view

This is a really nasty trap, and it follows on from the previous point. It's really important for me to be consciously aware of the things I'm not truly 100% confident I'm an expert in. I know certain parts of software architecture from a few years ago, but there are gaps in my knowledge now. I don't know modern best practices in CI & CD. I've learned MarTech but never practiced it, and I've certainly never managed a sales force. When things haven't worked out in part of the organisation, I'll naturally learn enough to be dangerous to dive in and fix it.

However that doesn't mean that the person I hire has to do the same thing: I need to hire someone who knows better, and may as a result do things differently. In fact, if ones points of view are too aligned, this becomes dangerous because we run the risk of becoming a monoculture, focusing on the wrong things, or perpetuating things that haven't necessarily worked. New candidates must bring new insights and naturally challenge us and push us out of our comfort zone.

Not compromising because we have a hole

When small teams are growing, filling a position is of utmost urgency. We've had some times at Yellowbrick where an entire organisational function has been missing. Whether it's sales staff in a region or industry, engineering staff to build a new part of the product, or marketing staff to cover a certain discipline, it's just so tempting to say "well, this candidate may not be everything we are looking for, but right now we have nothing, so let's go for it." Normally these holes result from a period of unexpectedly fast growth resulting in budgets being released to grow faster.

The decisions to compromise in the name of expediency have, every single time, resulted in wasted time and regret. I understand why, because we're always under such incredible pressure. Many Yellowbrickers have been guilty of it and continue to be. My staff can be so persuasive as to the acute need to get something done, that I'll bend and agree to their wishes. It's that optimism of seeing and hoping for the best in people again. My old colleague Lance Smith used to drill in to me, repeatedly, that hope is not a strategy... and it inevitably comes back to haunt.

Generally avoiding big-company people

Big-company people often don't do well in small start-ups. My old colleague and incredible entrepreneur Joe Kinsella wrote a brilliant blog on "Start-up people" and has kindly allowed me reproduce some of it here. All of our hiring managers understand these points:

  • Big company people value their association to their company and its brand. Start-up people value the impact they’ve had on their business.
  • Big company people do what their teams are directed to do. Start-up people do what is required to build a business.
  • Big company people value process. Start-up people value results.
  • Big company people work to eliminate risks. Start-up people are surrounded on all sides by risks simply by coming to work in the morning.
  • Big company people organise cross-functional teams. Start-up people are the team.
  • Big company people get predictable compensation through bonuses and RSUs. Start-up people hope for a big payday, but know deep down inside: they'd be doing this without the money.
  • Big company people paint by numbers. Start-up people paint from a blank canvas.
  • Big company people are a small fish in a big pond. Start-up people are a big fish in a small but growing pond.
  • Big company people can hide their lack of performance for months or years. Start-up people who don't perform will quickly find themselves working at big companies.
  • Big company people have visibility only to their team. Start-up people have visibility to their company.
  • Big company people take time to analyse the data and make the right decisions based on the available constraints. Start-up people make decisions quickly and adapt.
  • Big company people are used to having support organisations to help them do things (e.g. IT, HR, legal). Start-up people know the support organisations aren’t showing up today and it’s all up to them.
  • Big company people take corporate politics into account in decision making. Start-up people know the right decision for customers and the business is the always the right decision. Period.
  • Big company people can stay within a comfort zone. Start-up people vaguely remember they once had a comfort zone.
  • Big company people get training programs. Start-up people self-train on the job.
  • Big company people go to meetings. Start-up people get sh** done.
  • Big company people view career success as having done a tour of duty with a big brand technology company. Start-up people view career success as having built a successful company.
  • Big company people value predictability in their role. Start-up people value playing multiple roles.
  • Big company people value work life balance. Start-up people realise great accomplishments come only from great effort.
  • Big company people come to work to do a job. Start-up people come to work to build a business.

Although we seldom hire staff from big companies, it's not true that people who come from big companies are necessarily big-company people. I myself came from a big company into my first start-up, but was able to successfully build agile groups detached from the mothership. An engineering leadership candidate I spoke to today spent his life at big companies yet has never been comfortable being part of one. Such a mindset can work just fine in a start-up but has to be probed carefully in interviews, preferably with start-up situational role plays. Start-up people are one of the main reasons why big companies acquire start-ups.

Engineering-specific concerns

This is probably the area I've been most successful hiring brilliant staff and have generally made relatively few hiring mistakes. Yellowbrick has an engineering team that could literally build anything: Challenge them to build a car or a submarine or an AI application instead of a data warehouse, and they would be able to do so.

With individual contributor engineers, we want to find staff with brilliant logical deductive skills with good work ethic who just get stuff done. Neither of these things requires extensive experience and it's typically not correlated: The working experience of some of our most brilliant engineers ranges from 2 years to over 40 years, they are males and females from different parts of the world, and they contribute to our products in equally wonderful ways.

Brilliant logical skills doesn't mean the people have learned and memorised tons of frameworks and APIs or OSS tools, nor that they are really good at stitching things together. It means they have a high IQ and can problem solve well. If a C++ engineer can't remember how to implement a templated functor's move operator, that's probably OK, if they are smart enough to learn it again. We don't need people's ability to recall knowledge, there's RTFM and google for that. We look for a strong grasp of fundamental computer science, the operation of the machine, and ability to solve complex problems with data structures. On top of that, the ability to break down complex problems into simple piece and model complex systems in an object-oriented way. Finally, debugging & review skills.

As the engineering group grows, communication become more and more important. The person who sits in the corner and doesn't respond, the people who argue excessively or take things personally with others, and the passive/aggressive can't be tolerated because the blast radius of their damage increases as the company grows. Negativity is particularly toxic and must be rooted out and eliminated because I've worked at companies where it spreads like a virus from within. When your staff become negative or the enemy becomes you colleagues instead of your competition, the organisation will fall apart. We can't hire people that spend all their time complaining, no matter how smart they are. Leaders and managers in particular must be brilliant communicators.

The last thing we look for is a strong work ethic and the ability to get things done. I can honestly state that the only mistakes I've made in engineering hiring are due to hiring too much experience rather than initiative in management, and hiring academics that can't get things shipped. If individuals are too excited about finding the perfect solution (good enough is truly good enough, and perfection can't get in the way of that—and remember that 'good enough' doesn't mean it always works!), have an academic curiosity that transcends the problem at hand, or simply can't handle the risk of shipping something they may know isn't quite right—that's where we've got into trouble. Therefore it's key to make sure engineers can actually get things out the door, do the last 10% of the grunt work that takes, and take pleasure from their work being in the hands of customers. We don't do research at Yellowbrick, everything has to ship.


I hope this quick take proves useful to some others to avoid some of my mistakes. The article rapidly turned into a screed, so worst case it can be used to help fall asleep at night.