Should You Hire Your Friends to Work for Your Startup?

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Connor is often asked this question because of how long his partner and he have been working together. But as he explains in his book, Free Up Your Business, hiring friends and partnering with them are very different. The relationships still need to be kept separate, as Connor has said on many an occasion. There are also, however, several other factors that should be considered before moving forward. Both your company and your friends are important to you, and you wouldn’t want anything to jeopardize either of them. Below are the questions that you need to ask yourself before you decide to offer jobs to friends.

Are they the best fit for the job?

Working with friends might seem like fun. It might even seem like a good idea because you know each other and trust each other. Your business is not a game, though, and it takes more than good vibes to make one a success. If your friends have the right skills to carry out the tasks that your business needs to grow strong, then by all means, bring them on board. If your friends just need the money or think that startups are cool, it’s probably not a good fit. You are not running a charity or a club. It isn’t personal, it’s business.

Don’t give your friends positions that they are not prepared to handle. You may have a need that they are willing to fill because they care about you and want to help. If they are not the right person to do the job, however, they will not be happy about it for long. Their lack of skills or experience will also hurt your business. Both your business and your friendships are bound to suffer down the road when you have a square peg and a round hole.

Do they have the passion that you have for the business?

Your startup is like a baby. It needs nurturing, and this requires your undivided attention and devotion. Anyone else that you add to the business support team should have the same passion for your business as you do. You wouldn’t want a second-rate caregiver watching over your bundle of joy. You should never put your startup’s future in the hands of someone who doesn’t care that much for what you are trying to build.

You might be thinking at this point about positions that don’t really have a lot to do with management. A little data entry work, some customer follow-ups, maybe a piece of software. The risks are there nonetheless. Remember that all the cogs work together to make the machine run. No matter the position, something that is half-baked can never nurture your business. A single cog that is out of phase will prevent the machine from running at top efficiency.

Your friend may not be the sole factor in a hypothetical business failure, but desire is the key to motivation. Many startups have fizzled out because there just wasn’t enough of it to fuel the commitment that is needed for success.

Are they aligned with your company culture and values?

The way that you run your business has a lot to do with who should be a part of it. You and your friends may get along marvelously when you’re grabbing a slice or watching some ball. When you are in the captain’s chair, it is likely going to be a completely different story. Think hard about how you like things to go on a daily basis and if your friends fit in with that.

Having friends in the thick of things who don’t flow with the culture can be a very disruptive force within a business. You may be able to separate your personal and your business relationships, but other people on the team will always see you as friends. This is a position of influence no matter how you look at it. If there is tension regarding the way you run your company, it’s going to trickle down and create problems in the ranks. It is never wise to introduce unnecessary risks into your company, especially at the very delicate early stages. Better avoid the possibility than face losing both your friends and your business.

Are your friends truly comfortable working under you?

Working with friends is always going to be a delicate situation. As friends, you are side by side, on the level. Within the company, you are the boss. No matter how free your culture may be, you still call the shots at the end of the day. Some friends may be ok with that, while others may find that it makes them feel somewhat less than they are. The tension that this creates is an unnecessary burden that could end up pushing too deep. If there is any chance that your friends are not fully accepting and supportive of your role in the business, then it is best for your relationship that you keep the two separate.

Will your friendships survive if you have to cut business ties?

This is not something that anyone wants to think about. It is important to consider, however, even as early as before you make the hire. Because you are friends, the health and longevity of your relationship is at least as important to you as that of your business. You will not want to have to sacrifice one or the other if anything changes later on.

Anything can happen in the life of a business. Connor and his business partner hired good friends when they were building Portlight. They later had to let these friends go because their business needs and culture were evolving. They had been doing really great work for over a year and had done nothing wrong. The business had simply taken a turn, and it was no longer working for the best. It is one of the hardest HR decisions that they have had to make in their 7 years of building multi-million dollar businesses together. Think about this possibility before you hire your friends, and really consider whether your friendships can endure, or even whether you want to put them through it at all.

Final Tips

As you are going through your recruitment process, be careful not to give your friends any preferential treatment. You have known them for X number of years, but it is still best not to skip over anything. As awkward as it might feel, evaluate your friends as you would any other candidate. You may be surprised what you discover.

At the end of the process, make the hire only if you can concretely conclude that they are the best for the job. Don’t let your feelings get in the way of this decision. It will be hard if you have to let your friend down, but it will be much better for you both in the long run.

If you have decided to hire your friends after all, make your first step establishing clear guidelines and expectations for the roles and relationship. The company is at the heart of your business relationship, and this must be written out in no uncertain terms. You don’t want to be blindsided by clashes that will have no other impact than the steady weakening of your friendships and your business.


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About Connor Gillivan

In the past 10 years, I’ve started 7 businesses & built two to $10M+ in annual revenue, teams of 30+ & an exit in 2019. Today, I run SEO & growth for my 4 B2B companies while teaching millions how to make SEO simple.

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