When startups hire execs
Observations and advice for execs joining startups and startups hiring execs
Let me tell you a story about a match made in heaven.
On one side, an exuberant team developing an exciting new product. A team full of untrammelled talent and fast execution. All that's needed is an experienced expert who understands their vision. Someone who'll supply expertise without suffocating the team through structure and old thinking. A person who'll push team to the next level, harmoniously.
Over on the other side, we have an outstanding exec. A person famed for their expertise and track record. Seeking a new challenge and reinvention. All that's needed is a fresh team to avail their proven talents, to energise them, and help them redeploy their feted skills in a brand new setting.
The pair meet. It's love at first startup. Contracts are signed hurriedly to solidify their union. Tech news sites take note as the pair speak glowingly about each other's qualities in public. Privately, commitments are traded and cap tables updated. Both pledge unyielding fealty to their shared vision. They're ecstatic. Investors are happy. Everyone is happy, and the future is bursting with opportunities that'll flourish as a result of their kinship. With this union in place, the founding team are set accelerate the rocket ship and live happily ever after Series A. They’ve found their missing piece.
Soon cracks emerge. Starting with small misalignments which escalate. Unspoken expectations lead to surprise conflicts. And it's soon apparent that things won't work out. Minor mistranslations compound and reinforce the inevitable. Within a short while their whirlwind romance is over. Both parties move on quickly, sheepishly erasing the episode from their memories. It's over sooner than it started. And the search continues.
How did this happen when they were made for each other? Everything lined up for success at the start. Each had what the other needed, but failed to provide it. Each had what the other provided, but failed to receive it. Despite being made for each other it just didn't work out. Well, it can work out. In this post I'm going to share how.
The story I've recounted above is a fictional one based on a patchwork of real observations, stories, lamentations and experiences I've come across. Below, I'll provide observations and tips for anyone interested in this scenario.
To simplify things, I'll refer to startups, founding teams, and scale-ups as "founders." And I'll refer to execs, senior people, experienced people, and subject matter experts as "execs."
Note: I’m mainly talking about non-technical execs, but I think technical execs may find this useful too.
How incoming execs can feel and what they should do about it
I'll speak to execs directly here.
Often you'll be joining a founding team, containing several engineers and people who've built things from scratch. You might be the first Chief Risk Officer, General Counsel, Customer Success Lead or Chief Marketing Officer. You’ll encounter some of the scenarios below.
You will have to work harder to spread your ideas. Your suggestions are likely to be contested very often. This will be tiring especially if you aren't used to it. And it won’t just be you, it’ll encompass your entire discipline: known conventions in your field will be contested like they're outrageous ideas from novices. Unchallenged centralities in your field might be received as fanciful, fringed ideas in your new setting. It can be unnerving. And it will be tiring until you get used to it.
This can be really irksome for highly trained execs in vocational roles such as Chief Financial Officers and General Counsels, who, by way of accreditation, may (understandably!) feel aggrieved when untrained generalists question the fundamentals of their fields.
Intellectual intrusion. In your old environment, interdisciplinary conversations were bounded by unspoken social parameters which everyone understood. Nobody credibly attempted to negate the data person - precisely because she was the data person. Nobody used to challenge the marketing person, because they were the marketing person. Everyone had a monopoly on their domain of knowledge, and their intellectual territories weren’t crossed by intruders. You all stayed in your lanes.
This will be different in a startup. You'll find that knowledge domains are spaces that are there to be contested and won, regardless of ownership.
Lack of structure will be disorientating. You're accustomed to ingrained frameworks that steer decision making within organisations. OKRs, RACIs, RAPIDs and more. A suite of sensible frameworks that make it clear who'll be doing what. Everyone is trained to understand how and when to use these frameworks.
In the earliest stages of a startup, these structures often are bypassed, because everything is bootstrapped and there's a relentless bias towards fast execution.
You’ll need to find your own internal, adaptable methods for managing this lack of structure. You might feel like you don’t definitively own anything. In the early days it’s better to think in terms of what needs to be delivered, and how you can contribute towards its delivery, rather than what you own.
You might feel disrespected. Receiving challenge might seem disrespectful or heretical. Disrespectful in that it undermines your expertise as an individual. Heretical in that it undermines conventions in your discipline. More often than not, it is neither of those things.
Founders tend to be indifferent to roles. The main mode of identification is with the aims of the vision, and things like role, experience, expertise all operate in service to the vision and its requirements. You might be an experienced Chief Risk Officer who’s mastered operational risk frameworks, but you'll clash unless you reorient your identity such that the shared vision is the star your professional identity orbits around.
You give more than you get back. This happens when the incoming experienced exec has the belief that they are there to dispense, rather than receive. Of course, nobody in real life is this one-dimensional, so it's more about a misshapen internal balance between what the exec thinks they should give, versus what they think they'll gain.
As a exec joining a startup, you are not gracing your new team with your divine favour. You should consider this as transactional as your old gig was, and those risks you're taking should be reflected in your compensation package. Once that's settled, you relinquish any claim to superiority based on your experience alone.
Paradoxically, you'll have to redevelop your reputation in your new setting as though have no reputation, even though your reputation got you there in the first place.
I've spoken to people who've credited their success (in spite of lower wages), and enjoyment in startups, to the following perspective shift: the amount you can learn from these whipper-snappers is equivalent, or greater than, the amount you can teach them. That perspective shift is key to developing a salubrious adaptation to your brand new environment. It will add a positive hue to every contestation, incursion or doubt-inducing comment that you'll hear from your younger peers.
Embrace it, enjoy it and remember that, if all else fails, you can return to a business like your old one with a fresh set of ideas, a sharpened modus operandi, and skills that differentiate you from your former colleagues. Old dogs that learn new tricks continue learning new tricks.
You feel like you can't keep up. Whatever was conceived in the morning was deployed in the evening. Out of nowhere your CEO will announce a crucial community event next week everyone's pivoting towards. All of sudden your only data person has to immediately shift from setting up your team’s business intelligence environment, to producing new metrics for an investor’s surprise enquiries. This is all happening while you’re adapting to a new language and while you’re using Slack or Microsoft Teams for the first time. It’s overwhelming.
You're afraid to ask questions. Some execs create their own limitations because they don't realise that in a startup, the reputational penalty for failing to know everything is very small. So ask many questions. Your value will be based on your speed of knowledge acquisition and dynamism as opposed to just your corpus of knowledge.
Of course, your experience is important - it’s why you were hired! But when a startup is growing in a new space - or indeed growing a new space - everyone is somewhat ignorant, because you're all exploring and expanding and building in uncharted terrain, together. It is not shameful to ask questions that might seem basic. You should be asking those questions a lot. Nobody will think you're stupid if you ask "How do I ctrl+alt+delete on a mac?"
The only thing worse than asking the question too many times is never asking the question at all.
You'll love it if it works out. Execs who succeed after joining startups, struggle to return to larger organisations. The intensity, energy and reciprocal learning dynamic can be really addictive. For those who get over that initial bump, they're likely to move on to other startups, or become founders themselves.
Have fun. Seriously. Well non-seriously. You know what I mean.
Being in a fast-growing business is stressful, unpredictable, enlightening, rewarding, terrifying and exciting. Whatever happens, you'll learn. Learning is assured. So discover your place in your new place and embrace it. Have fun.
Those were descriptions mixed with observations that you might find helpful. As an exec these are scenarios you’ll probably encounter at your first startup.
Now let’s turn to the founding team.
What founding teams should look out for and consider
The previous section focussed a lot on the intersection between the individual exec and the organisation. This part will be longer because it involves group practices and social conventions to consider. Founding teams, this is for you.
For those in the founding team, there's a broader perspective needed, precisely because you're already a team, with your own customs, conventions and practices.
Even if you've only been together for a few months, you've still developed your own second language which might be inscrutable to a newcomer. Be as understanding as possible and don’t underestimate how far your language, internal customs and traditions have developed already.
Pair your exec with a tenured mentor during onboarding. Ideally someone on the founding team. Your selected mentor should commit to spending time with your new exec throughout onboarding. They'll answer their questions or direct to them to someone who can. They'll catch up at least once a week for open conversations. They'll help the person feel included by translating the hidden signals that make your company special. Select a mentor from a completely different discipline or business area - someone who wouldn't ordinarily come into contact with the exec. This brings benefits which I might discuss another time. Believe me, it’s really worthwhile.
Judge them slowly. In joining your company, your new exec is risking their reputation and credibility. You all have a lot to lose from failure, but failure will probably sting your exec more harshly. Recognise that at least initially, your new exec might be more conservative or erratic. Be compassionate and take time to internalise their decisions from the perspective of how risky this is for them. After all, if this doesn't work out, you can parlay your experience of failure into another venture quite easily, especially if youth is on your side. Whereas for the exec, their profile might take a bruising. It might be harder for them to reinsert themselves into a familiar professional environment. So don't judge their early decisions too harshly. Be compassionate.
Make it easy for them to learn from you. Praise them for asking questions and be mindful of how differently your criticisms might land on an experienced individual. Make sure you reinforce an appreciation for both. Saying "you should know this" to your junior product manager isn't going to be received the same way when it's said to your first Chief Financial Officer. Don't use acronyms. Explain in-jokes. Inclusion is often the precursor to learning.
Recognise your appeal to novelty. Two points (1) founding teams tend to be drawn to the novel anyway, almost by definition and (2) founding teams, especially younger teams, sometimes condescend execs as people with outmoded methods. Some people mistakenly think that younger generations fare badly with innovation and complexity. "You used Netscape on the World Wide Web? Pah ha ha! We use a GPT-3 model wrapped in a distributed big data web 3.0 BroCoin Docker metaverse container, how could you possibly get this?" Well, anyone born after the 18th century has grown up in an era of unprecedented change. Don't write people off because simply they're mature or reference older ideas.
Reinforce appreciation of your exec’s expertise. It doesn't matter if it feels forced. You all need to say "hey exec, we appreciate what you bring" and you need to say that regularly.
Give them wins. Remember the intellectual intrusion thing from earlier on? That can be really hard to deal with when you’re an experienced exec. By all means, promote first principles and challenge ideas. Challenge your exec’s ideas. But let some little domain-specific things go, unless they present fundamental conflicts with core aspects of your shared vision. Do everything you can to lessen the cold shock they'll experience after they dive into your ocean. Support them. Don't just throw a rope. Swim with them. Wherever you can, embrace your exec’s ideas, give them wins and celebrate them.
Take time to identify what you do and document it. Before you hire your exec, take a little time to write down the community practices that are present in your founding team. Even if they aren’t standardised or intentional.
For example, you might notice that you have unplanned intense debates over lunch that energise the entire team. If you've identified that, and want to encourage it, write it down. Put it in a document. Then share that document with your exec in their first week to help them interpret your environment.
You really should note this sort of stuff anyway, it’s helpful to know and it builds self-awareness as a team. Later on this will form the basis of your company values.
Challenge your assumptions about their assumptions. Consider job titles. You allow anyone to select their own job title. Then you hire your first senior legal person and they insist on exclusivity around their title. It can be easy to assume that they’re arrogant - don’t. Don’t immediately assume this is an ego thing - it might just be a hedge. It might be that they fear profile deflation. They've taken a gamble in joining your company. Explore what's driving their attitude rather than reflexively negotiating against it.
Be very upfront about what you can't provide. I'll elaborate here as this is a significant point.
Some execs struggle in startups - not because they're incapable, but because they aren't used to performing with limited resources. Even world class professionals unaccustomed to their usual set of resources would struggle. The person might be used to having a chief of staff, an executive assistant and a personal assistant. Be very clear about what you expect them to do. There are outstanding professionals who haven't done the "nitty gritty" for years. They’re still outstanding. You need to make sure you're as ready for them as you expect them to be for you.
In other words, you might be able to entice a superstar striker to play for your local football team. But if that superstar can only perform alongside a team of top sports psychologists, massage therapists and more - and you don't have that yet - then you should probably opt for the solid senior professional who'll score fewer goals, but work independently, in harsher conditions, ultimately providing a better fit for your team, given where it is now.
And for those who don’t know - you might be surprised at what some execs require in order to deliver world class value. They might need a network of specialists tasked with optimising the exec's undoubted ability. To reiterate, it doesn't mean that the exec "can't do the work", it means that at scale, many companies effectively operate as conglomerates in which each exec is the CEO of their own business area. Just as a CEO needs a team to accomplish their vision, your exec might need one too.
I've often seen a misalignment of expectations here: the exec is assured support, but that isn't spelled out, so the exec feels hampered and hamstrung as they're forced to do research and crunch data alone, possibly for the first time in decades. Sometimes, if you want a superstar, you need a team of superstar supporters around them.
This is all to say that sometimes, when you're hiring for your exec, you should consider an allocation for another hire that your exec will need to perform at their best. This might be a trusted executive assistant or data person. It’s not an unusual practice and it's important that you communicate that to your team, and that you cover this in conversation prior to making an offer. It shouldn’t surprise you if you make your offer and your exec says “I’ll need to bring in my data person.” When senior execs leave and say "I didn't have support", this is often what they're referring to.
In your initial conversations, plainly discuss expectations concerning the dedicated support the senior person will get, when they'll get it, and express an understanding that their ability to deliver might be muted until they have a group of subordinates who can help them bring out their best.
Hiring for person is better than hiring profile; but don't underestimate profile. It can have good and bad unintended consequences. Obviously it's better not to hire ex-Google just because they were at Google. It can feel tempting and as though you've made it when you hire your first senior FAANG person. "We're attracing people from the big shots now. We're really moving along." It feels good. Give your hiring people recognition, but realise that this isn’t necessarily what'll propel you to the next level. Hire for person, not profile.
At the same time, don't over-correct and deliberately avoid hiring those people, because even if it doesn't work out at all, it can lead to surprising second-order effects. Even if your ex-Googler isn't a good fit, the fact that you've been able to attract them can make it easier to attract other people with that standard of expertise, experience or profile. And it'll help you surface expectations that might not be apparent until your shiny ex-FAANGer has already joined.
There are no bad questions. They aren't a bad legal officer because they think your engineers are talking about literature when they argue about Kafka. Be compassionate.
We’ve covered things from the standpoint of the founding team, and the exec. Let’s bring this to a close.
Closing thoughts
I hope this is helpful for experienced senior execs who are considering taking a leap into the world of startups, and for founding teams who wish to hire them.
For execs, joining a startup can be tough, but it can be life-changing and worthwhile. Talk to people, persist when it gets hard, and enjoy it. You’ll learn a lot.
Founding teams - hiring execs is exciting and a milestone on your path to success. You have a duty to make it work for you. More importantly, you have a duty to make it work for them. Get it right and you’ll take your team to another level. You’ll learn a lot too.
Good luck!