Your Best People Should Be Better Than You

There comes a point in the development of most businesses when the founder is no longer the person who knows the most about everything. In fact, if you're building anything with serious ambitions, you should probably reach a point where there are lots of important things happening inside your business that other people understand considerably better than you do. That sounds obvious when you write it down. Living through the transition is rather different.

When you start a business, knowledge and control tend to sit in the same place. You understand the customers because you speak to them every day. You know the processes because you created most of them. You understand why that slightly ridiculous workaround exists because you were there when something broke five years ago and invented it. When somebody has a question, they ask you, and being the person with the answer gradually becomes part of your value to the business and, whether you realise it or not, part of your identity.

Growth eventually challenges that relationship. You employ people with deeper expertise, different experiences and skills you simply don't possess. Suddenly the person who built the business has to become comfortable with not knowing everything about the business. I was reminded of this during a recent Viking Chats conversation with Verona Frankish, CEO of Yopa, when she talked about the team around her and was remarkably matter-of-fact about the fact that the people heading individual functions know more about their disciplines than she does.

Verona isn't an estate agent trying to prove she knows more about estate agency than everyone working for her. She sees considerable value in having experts around her and drawing upon their knowledge. That prompted a question I've been thinking about since: at what point does a leader's value stop being primarily about what they personally know and start being about the organisation they create around them?

Never be the smartest person in the room

“Never be the smartest person in the room” is one of those pieces of business advice that gets repeated so often that it risks becoming another meaningless LinkedIn cliché. Strip away the motivational-poster quality, though, and there is something important behind it. If everybody you employ knows less than you do, agrees with you and waits for you to provide the answer, you've placed a pretty low ceiling on how good your business can eventually become.

I've spent more than two decades in property, first building base property specialists and more recently building The Depositary. There are areas of residential property where that experience means I can walk into a conversation with a fairly good understanding of what is happening. Equally, there are significant areas of The Depositary where I absolutely should not be the person with the greatest expertise.

My business partner Ann is the most obvious example. Likewise, when Carla joined us as Head of Operations, she brought years of CRM experience and technical knowledge that I simply didn't have. We've deliberately brought people into the business because they can do things we can't, understand things we don't and challenge assumptions we might otherwise have carried forward. I don't see any embarrassment in admitting that. I'd be considerably more worried if, several years into building a technology company, we hadn't managed to employ anyone who knew more than the founders.

The scale of the ambition matters here too. If we wanted The Depositary to remain a useful little piece of software serving a handful of agents, perhaps a couple of founders could keep most of the important knowledge in their heads and muddle along quite successfully. That isn't what we're trying to build. Our ambition is to establish a digital standard for tenancy conclusions that can operate across the UK and potentially beyond it, and that requires expertise across product, development, operations, customer success, data, integrations, platform security, regulation and an increasing number of emerging technologies.

No founder can credibly be the expert in all of those things. More importantly, no sensible founder should want to be.

The founder's job has to change

I found this transition harder at Base than I have at The Depositary, largely because Base was such a personal business. We built a small independent London agency with something approaching a family mentality, and our reputation felt inseparable from the people running it. Handing responsibility to somebody else didn't always feel like delegating a piece of work. Sometimes it felt like handing over a small piece of something we'd spent years building and then having to watch somebody approach it differently.

I suspect most founders recognise that feeling. You know how you would handle something, you can see somebody else taking a different route and every instinct tells you to intervene. The temptation becomes even stronger when you can see that they might make a mistake, because allowing somebody to learn through experience feels rather different when the lesson is taking place inside your company, with your customers and your money.

There are obviously times when intervention is necessary, but if the only way your team can consistently deliver the standard you expect is for you to personally supervise every meaningful decision, you haven't really delegated anything important. You've delegated activity while retaining responsibility, judgement and authority at the centre. That might work in a small business, but it becomes increasingly difficult as the organisation grows.

The Depositary has forced a different mindset because the ambition was larger from the beginning. My role today is much more about overall direction and balancing commercial reality with operational aspiration. There are things we would love the platform to do, things customers understandably want from us and opportunities presented by integrations, automation and AI that could make tenancy conclusions dramatically easier and faster. Sitting alongside all of that are less glamorous but fundamental questions about security, data standards, architecture, resources, development capacity and what customers are actually prepared to pay for.

Those competing considerations are where leadership increasingly sits for me. I don't need to know how to write the code. I do need enough context to ask whether building something is commercially sensible, operationally useful and consistent with where we're trying to take the business.

Sometimes the bottleneck is there for a reason

There is a fashionable school of founder advice that treats becoming a bottleneck as an unambiguous failure. Delegate everything, get yourself out of the process and let the team run. I understand where that advice comes from, and there have unquestionably been moments when Ann or I have slowed something down because too much still depended upon one of us. However, I'm increasingly wary of pretending that speed is automatically evidence of a healthy business.

Some of those delays have saved us from making mistakes. Occasionally the reason an idea hasn't immediately become a feature is because we need to understand the implications properly. Sometimes the technology can do something before the commercial model justifies doing it. At other times an exciting shortcut creates a security, data or operational question that deserves considerably more thought than the initial idea did.

The challenge isn't therefore to eliminate the founder from every decision. It's to become much better at understanding why you're involving yourself. If I'm challenging something because I can see a commercial implication that hasn't been considered, perhaps I'm adding value. If I'm asking uncomfortable questions about customer outcomes or data security, that may also be useful. If I'm interfering because somebody has chosen a different route from the one I would personally have taken, I probably need to examine my motivation a little more closely.

That's an important distinction because experience does have value. The answer to overbearing founders isn't to pretend that the knowledge accumulated over 20 years suddenly becomes irrelevant. Good leadership involves knowing when that experience adds something to the conversation and when it is simply making it harder for somebody else to exercise their own judgement.

If people have responsibility, they need room to get things wrong

There is an inconvenient consequence to genuinely empowering good people: occasionally they will make the wrong decision. It's easy to celebrate autonomy when the team independently arrives at exactly the answer you would have chosen yourself. The test comes when they don't.

You can't give somebody genuine responsibility while reserving the right to prevent every possible mistake. If every important decision requires approval and every deviation from the founder's preferred route is corrected before it happens, you've created the appearance of delegation without much of the substance.

What matters far more is what happens after a mistake, and that brings me back to another part of my conversation with Verona. She talked openly about psychological safety and her own experience of working in an environment where that safety wasn't present. The phrase can sound like management jargon, but the practical consequences are incredibly simple. Can somebody tell you they got something wrong without immediately worrying about protecting themselves? Can a new employee admit they don't understand a process? Can the person closest to a problem tell the most senior person in the room that their proposed solution won't work?

A business where people are frightened of looking stupid doesn't miraculously contain fewer mistakes. It contains more hidden ones. Problems survive longer because nobody wants to be the person who points at them, while questionable decisions gather momentum because challenging the person who made them feels harder than quietly going along.

For any business trying to innovate, that is dangerous. For a technology company, where today's sensible decision can be overtaken remarkably quickly by a new capability or a different way of working, it is particularly dangerous.

There is nothing wrong with saying “I don't know”

One of the things I liked most about Verona's attitude was her willingness to admit when she didn't know something. Earlier in her career, when she was asked to take responsibility for lettings, she didn't suddenly reinvent herself as a lettings expert. She was open about the fact that it wasn't an area she knew particularly well, but she was willing to learn it.

I think that takes a degree of bravery, although I'm not entirely sure why we have created working environments in which it should. What leader, or indeed what human being, genuinely knows everything? If somebody believes they do, I would regard that as a considerably bigger leadership red flag than somebody saying, “I don't understand this well enough yet. Explain it to me.”

Property can be particularly susceptible to certainty because experience is rightly valued and many businesses still operate with fairly traditional hierarchies. The person who has been doing the job longest becomes the person assumed to have the answer. The danger comes when years served become confused with universal expertise, particularly at a time when the tools available to us are changing so quickly.

Someone relatively junior in your organisation may understand an emerging technology better than the person who has been there for 15 years. A property manager may understand the practical reality of a workflow better than a director. Someone in customer success may identify a product weakness long before the product team because they're listening to customers struggle with it every day. None of that diminishes experience. It simply means experience has to sit alongside curiosity and a willingness to listen.

Expertise shouldn't live in one person's head

This is particularly relevant to what we're trying to achieve with The Depositary. Tenancy conclusions have historically relied on enormous amounts of individual effort, knowledge, memory and administration. Experienced property managers know the shortcuts, remember which landlord needs chasing, recognise the awkward situations and often carry a frightening amount of operational information around in their heads.

Those people are incredibly valuable, but a process that only works because an experienced individual knows how to compensate for its weaknesses isn't a particularly good process. It also creates risk. People go on holiday, change jobs, get ill or simply forget things because they're human.

Good technology should help capture process and institutional knowledge so that excellent outcomes don't depend on having one particular person sitting at one particular desk. That doesn't remove the need for expertise. It gives experts more time to use it where it actually matters: judgement, negotiation, unusual situations and human relationships.

Leadership isn't fundamentally different. If the entire organisation depends upon the founder personally knowing every answer, the business can never become more knowledgeable than the person who started it. That would be a strange ambition for any company claiming it wants to grow.

The goal isn't to make leaders irrelevant, nor is it to celebrate ignorance. Leaders still carry context that others don't. They set direction, make difficult trade-offs, protect standards and decide which opportunities fit the business they're trying to create. What changes is the expectation that authority and expertise must always occupy the same chair.

As The Depositary has grown, I've increasingly found myself in conversations where somebody understands an important subject far better than I do. Far from finding that threatening, I've come to regard it as evidence that we're building the kind of company we intended to build.

Perhaps “never be the smartest person in the room” still isn't quite the right advice. You need to be smart enough to recognise expertise, confident enough to employ it and secure enough to admit when somebody else knows better. Then, crucially, you need to give them enough room to prove why you hired them in the first place.