Why startup founders need to start trusting themselves and recognise the blindspot that can encourage them to put too much faith in expensive and counter-productive "adult supervision"
It is one thing to seek advice as a founder and have the humility to continually collaborate, listen and learn. It is quite another to invite costly expertise into your startup (as a director, executive or investor) and lose your precious resources, culture, shareholding or company as a result.
Rapid learning is the single most important survival skill for a founder - economic imperative tends to mean those without the capability fall by the way-side pretty quickly, or burn through large amounts of personal cash as they stubbornly drive their business into a wall. This means entrepreneurs who survive long enough to get their startup out of their head and properly on the path to commercial reality tend to have their learning gears fully engaged at all times.
Beware of a common first-time founder blindspot
Most startup founders are hyper aware of what they don't know. They fully buy into the standard advice of hiring people "smarter" than them. And that works well in specialist/functional roles - for example I really want to hire marketers and accountants and developers who are way better at doing their job than I would be.
But I have also observed that the more senior the role and the more credible the company names on the candidates CV, the more trusting and unquestioning many of us can be around challenging or validating that individual's competency. It seems especially true of executive roles we perceived to be more important or difficult than our own. And as a result of this blindspot, we can let characters into our exec teams and onto our boards who we'd never have hired into a junior role where we'd be more confident in assessing competency.
Expensive senior hires who are bad players - for example all talk and no delivery - will seriously hurt startups, through damaging productivity and cultural impact, as well as in cost. Whereas problematic opportunists, particularly those who insist on equity, voting rights, board seats or special terms, can be fatal. These characters can be so expensive, emotionally taxing or damaging to the share structure to remove, that the founder may lose the will to fight on and walks away, presses reset or is pushed out.
I have observed in myself and many other founders this blindspot that leads to a predisposition towards a certain type of impressive seeming character who for reasons of existing convention and lazy shorthand I am labelling "adult supervision". I am not implying any negative comment about age in that - I have encountered "adult supervision" younger than me - it is about an imbalance in their perceived value, competence and experience relative to the founders.
Who wouldn't want a Fairy Godmother? (Shame they don't exist...)
Occasionally "adult supervision" is forced on us, but mostly as founders we're fully complicit in the selection of the individual, even when the initial requirement for it wasn't our idea. (Recent recipients of angel and early stage investment, young/female/minority ethnic or first-time founders, or participants in certain types of growth programmes, are particularly prone to finding themselves suddenly requiring expensive "adult supervision" - especially in sales, financial and technology leadership roles).
And sometimes as founders we're so well conditioned by external expectations that the need to go hire "adult supervision" is entirely our own idea.
I'm not judging anyone, I really have been there too! Being a founder, especially a solo-founder and a first-time founder, is a lonely, stressful and frequently terrifying experience. We're often generalists making major decisions about things we know very little about, while simultaneously trying to execute sales and tech strategies without any formal qualifications and without any of the experience people spend entire careers accumulating.
Who wouldn't want to helicopter in an experienced grown up to reassure us that it is all going to be OK, and magically make all the problems and screw-ups go away in a puff of smoke?
This is not an irrational thing to want - who wouldn't want a non-evil Fairy Godmother if presented with one? It is, however, an irrational thing to believe will happen, however much you wish it. When we go out, our hearts open and hopes high, searching for a saviour to tell us its all going to be OK - we tend to find exactly that. We find the person willing to tell us what we want to hear - that we should stop worrying our little heads about things we know nothing about, because they are the solve to all our problems.... "trust me, I fixed this for X."
These may be people who had good job titles at big companies we have actually heard of. We imagine what their career's worth of contacts and lived experience must be like and immediately feel a little bit more useless and a little bit more desperate to get our hands on it. Or perhaps they are portfolio investors or NXDs associated with startups that we admire and suspect to have had very good exits. Having them onside will make other people think we know what we're doing and some of that fairy dust is bound to rub off!
And we may be so keen to get a particular set of responsibilities off our shoulders and into the hands of a competent grown-up who isn't pretending to know what they're doing day in day out, that giving up a bit of power, a chunk of future success and way more cash than you'll ever earn yourself doesn't seem so unreasonable - after all you'll be in this together, right? (Er, wrong, actually... they have no skin in the game, however much they convince you they're taking a risk by just being in the same room with you.)
If founders are not self-aware of this potential blind-spot, we are really open to getting exploited, both deliberately and accidentally, by those with all the talk, the names, the brass and the BS required to instil serious self-doubt in the founder, while temporarily impressing boards and investors. So if fear of missing out (or desperation for a grown-up to step in and help) is causing you to justify skipping proper referencing and due diligence, you're finding excuses for why it's OK to compromise on your core values in this instance, or you're moving faster and offering far more than you planned to, then pull the emergency brake and walk away. A real Fairy Godmother would be putting your needs first!
The relative value of the adult supervision's experience is over-estimated relative to the founder's
Until founders have been burned by "adult supervision" a few times - and sadly this is one of those mistakes you can repeat several times until you realise there is both a personal blindspot and an exploitation pattern at play here - we tend to believe as I did that expensive and experienced is better. It is common to assume that someone who did an impressive sounding job at a company you've heard of must be more skilled and competent in their field than you, the upstart, scrappy generalist.
The whole business ecosystem tends to disproportionately over-value experience gained in a corporate firm, and under-value experience gained in self employment or a small company - and makes no concession to the agencies and admin support staff that enable corporate teams to function. So it is no surprise to me that as founders we internalise those same biased assumptions, even to our own cost.
But experience counts for nothing in startups if it was gained in a company more than a stage or two ahead of yours and if no actual "doing" was involved. You can't expect someone who ran a marketing team at a big brand to come in an execute your marketing strategy the way you understand the term (you know, as in write the email, design the email, send the email, track the email) - they may never have actually done that, and worse still different teams or agencies will have owned different pieces of that execution process, so they won't have a detailed end-to-end view to replicate.
Recency matters too - contact books age out very quickly and can never replace your carefully nurtured relationships. Be very wary of "adult supervision" leading on this one, especially if they can't name and book right there and then a meeting they will take you along to next week.
Now I have I shone a spotlight into my own blind-spot around this one, I will no longer hire anyone to a board, management or leadership role who believes themselves inherently superior to me - or more importantly - to the rest of my team.
As a founder, I believe in creating a respectful culture where we are always curious to collaborate and learn, because we are all there to solve problems for our customers, stakeholders and colleagues every single day. The person who thinks that they are above all that because they know everything already, and sees self-learning as weakness or waste of time, is not going to help achieve that and will likely break your company's culture and your personal emotional health and future wealth in the process.
Having someone in your team with deep corporate experience, who has learned the process of staff and client management and has the right attitude can be absolute rocket fuel for a startup - especially as a co-founder (I know this, I have one!) But that is not what we're talking about here. Implicit in the term "adult supervision" as I use it is this assumed entitlement that they always know best - they are competent, the rest of you incompetent. They are informed, the rest of you uninformed.
Now to the lessons I have learned so that you don't have to
Two of the biggest mistakes I made in my last business relate to the "adult supervision" blindspot - and if you've read my blog before, you already know how that one ended.
1) I gave my own power away when I didn't need to. When times were good and I wasn't thinking about the future downsides of giving away control and responsibility, I created a board structure and my own executive contract and line management in a naively egalitarian way. I failed to consider how that might work out for me or the company if it all got a bit Lord of the Flies.
2) I believed other people's hollow claims that they knew more about running my business than I did. It wasn't even from a lack of confidence (though I did lose my confidence as a result) - it was down to the blindspot I've highlighted here, combined with being very open about my own limitations and prone to seeing the best in others. And so instead of evidencing the substance of those "adult supervision" claims from a safe distance, while they actively earned both my trust and the team's respect, I invited them in with open arms and optimistic expectations. Then I discovered just how hard and costly it can be to undo that kind of mistake.
These were mistakes of my own making and I have since learned that they are very, very common. It doesn't matter that they were made with the best of intentions and from a place of openness, optimism and willingness to learn. Without those errors, I probably could have managed the other problems when they came. It is still a painful thing. And while objectively I do know I should feel some pride in what that last company achieved - because we really did achieve a huge amount and there were some incredible highs - I don't feel it. I just feel sad. But I will not make those same mistakes again and I hope other founders will learn for them too.
So how to fill important knowledge gaps in your startup without making the same mistakes I did?
Don't build walls and stop listening to others out of fear of being burned - you'll never grow that way, and nor will your business. Instead build a learning culture based on mutual respect at every level of the company - and constantly reinforce that. Continually develop your people and yourself, and learn to trust your own judgement and instincts.
Do not hire management roles until you are revenue positive and have product market fit - everyone has to be a hands-on doer until that point. And always hire people into those posts who've directly (and ideally recently) experienced the same stage of business that you're at. That business stage will often change quite rapidly, so don't hire anyone in a way that you can't easily unhire them again if the business needs change (this is particularly important to consider before you award equity, board seats etc).
Hungrily seek out external advice - talk to peers, mentors, informal advisors, invite experts to lunch or to do internal team talks, even buy in specific consultants and trainers if you really need it. Think about building an advisory panel. But always apply your quality control filters, hone your BS detector and don't waste your time and money on indulging advice that is too pleased with itself and disinterested in you.
Challenge yourself to recognise what (or who) it is that is causing you to just assume someone else knows more than you do, and prepare a personal plan for how you will validate those assumptions, so that next time you can recognise when you are at risk from a blindspot. Accept that you will never have perfect information, and that sometimes you just have to jump in and see what happens. And keep working with anyone who actively catches you when you fall.
Never, ever bring anyone inside your startup as an employee, manager or (most importantly) a board director if their personal values do not align with those of the company - and have a process ready for validating that and for quickly removing people that don't. I feel like I'm overusing this quote, but your company's culture really is defined by the worst behaviour you as a leader are prepared to tolerate, so do not compromise as you hire.
Problem opportunists are among the hardest of people for a young business to remove (and usually well practised in their particular technique, whereas the founder is experiencing it for the first time). But however hard they are to deal with (and you absolutely do have to get them out if you want your job/company to survive) the costs of not dealing with them are worse. It is, of course, way better to never invite them in at all.
You do not need adult supervision, even if you sometimes feel you want it.
At some point you simply have to trust yourself to be the adult and lead - even if you don't know exactly what you're doing. You know enough and you will never know everything - and don't trust anyone who claims they do.