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3 Typical mistakes startup founders make with their first employee (and how to handle them)

When you're starting a new job, you'll be filled with a mix of anticipation and excitement and if that new job is in a startup, those feelings may be heightened even more. If you happen to be the first-ever employee in that startup, you’re all set for a wholly unique experience. After all, until this point, the startup founder will have done everything in the business and now they've brought you on board, everything will have changed. Like all changes, it will probably take a little time to get used to. 

They will have to make a real effort to let go of their “baby” in a sense and they are going to have to learn how to delegate and perhaps most importantly, how to trust. And that certainly won’t happen overnight! However, it can be a lot easier if you and they are aware of some of the challenges that may arise - and have a plan in place to deal with them. 

Here are 3 of the most common mistakes that startup founders can make in those early days and how they and you, i.e. employee number one can handle them.


1 Assigning basic or junior tasks

As the employee…

If you've been recruited to do a certain role and you're not getting the chance to do it, you need to address it as soon as possible. Likewise, if you've got proven experience and are continually being given pretty basic tasks, you need to call it out - but in a tactful way of course. Reiterate to the founder that you’re keen to show what you can do, that you want to be trusted. Explain that you want to prove that you’re willing to support them to do whatever is required to develop the product or service and make their startup vision a reality.

Be enthusiastic, proactive and show that you want to be given the opportunity to be challenged and to learn more too. Remember, it's not about moaning and complaining about not being given enough work or the wrong type of work. Instead, it's about showing how you're competent, capable and willing to do so much more. Explain how being challenged more will actually motivate you, help you to grow and thrive and how that, in turn, will be beneficial for the business. 

As the founder…

When you hire your first employee, it'll take a little getting used to. You'll need to make a conscious effort to take a step back. It's not about relinquishing control, it's more about learning to delegate effectively and building trust in your new recruit.

Rather than simply assigning them basic tasks, perhaps start by delegating small tasks which are key to a project’s overall success. Set out your expectations and be clear in what you want your new employee to do. Then, give them the opportunity and the space to get on with it. You should be there to support as and when they need it, not be a constant overseeing presence. 

Remember too that they'll never actually earn your trust if you don't allow them to work independently. Play to their strengths, let them show you what they can do and as they prove their capabilities, increase their responsibilities. You'll need to accept the fact that although they may not do things exactly as you would, that doesn't mean they shouldn't be given the opportunity to try. Who knows, they may transpire to be even better than you in certain areas. 

2 Micromanaging

As the employee…

If the founder asks you to get their approval on every single task that you undertake - no matter how small or seemingly trivial, you're most probably being micromanaged. Likewise, if they ask you to provide them with incessant updates on every task and project, or if they appear to be fixated on you only doing things in a certain way. Rather than calling them out directly as a micromanager and potentially causing more friction, you should aim to adopt a more subtle approach.

You could, for example, make some suggestions that could inadvertently force them to assess their own behaviour. Explain that you are conscious of how busy they are and that rather than intruding on their time by continually interrupting them with requests or updates, you feel that you could maybe do this once a day or every couple of days unless there is something that is particularly urgent. Or, you could perhaps highlight how the continual need to update them on things is actually slowing you down and getting in the way of you completing certain tasks on time. Work together on a compromise of sorts - agreeing on the frequency of your updates and when and where you'll check-in. It's important to come up with a solution that works for you both.

As the founder…

You may have the best intentions, however, if you are attempting to oversee every single thing that your employee does, you're micromanaging them and if that continues, you're likely to lose them. It's understandable in some ways, as you're suddenly having to rely on someone else to do that task that you feel only you know how to do properly and you may feel you have to still be involved, otherwise you've lost control. You should however accept that there will have to be a transition period and during that time you will have to start building trust in your new employee. 

Remember that you hired them after all and were impressed with what they could add to your startup, so let them prove you right! As a founder your time is precious, so realise that by leaving them alone to get on with things, you'll be creating more time for you to get on with growing your startup. Also, if you don't take a step back, your micromanagement won't just alienate your new employee, it will also potentially prevent your business from succeeding. Start delegating tasks bit by bit and slowly let go. Give guidance and support but give them space too. Most importantly, you should aim to start building a culture of trust from day one.

3 Not sharing enough information…

As the employee…

Remember that by the time you start, the founder will already have amassed a huge amount of knowledge and learnt many lessons. You're playing catch-up. If they don't appear to be forthcoming in sharing what they know, then it'll be up to you to take the lead. Be curious, ask questions and show that you’re keen to find out everything. 

Explain why you are asking questions too, highlighting that if you are going to really prove your worth and be an asset to the growth of the business, you need to be equipped and ready. You need to show them that you don’t want to waste their time by asking questions for the sake of it, but that instead you simply really want to get to grips with the product or service and ultimately their vision for the startup.

As the founder…

Remember that your new employee needs to learn and that you are the best and only person who can teach them. You’ve been building your startup and learning lots of things along the way - now it’s time to share your knowledge and insights. Never make the mistake of assuming that they know what you do, because that will only lead to friction down the line. Don’t take it for granted that they’ll know how to do a particular task in a certain manner or handle a client in a particular way. They’re doing it that way because you haven’t told them otherwise.

As part of their onboarding, you should communicate as much as possible everything that you can about your startup - from your journey to date, creating product or service through to your market and customers. Take time to explain things thoroughly, focus on the details and encourage them to ask you questions. Do you want them to “get it”? Well, you’ll need to do your bit to make sure they do.

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