My friend Mike Darlington, the CEO of Monstercat, asked me the best protocols for hiring an assistant – What to look for, how to keep them motivated, should he or she be entrepreneurial or somebody who takes direction well?

As somebody who has had more assistants than the number of years I’ve been a manager, I didn’t think I was qualified to answer this question. But it’s that experience which is why Mike asked me the question in the first place.

So what have I learned?

Hiring an assistant, especially when your day-to-day responsibilities and vision are grand, can be difficult.

Regardless of who you hire, there will be a considerable adjustment period for the assistant to understand their role.

During this initial period (usually 3-12 months), it is critical to set the standard of what is expected.

We will all make mistakes. Which ones are acceptable? Which ones aren’t? For the ones that aren’t, why did they happen and what can be done to ensure they won’t happen again? Sometimes an assistant doesn’t have access of the entire chain of execution and needs their boss to inform them how it works so they can understand their part in it.

When an assistant enters a new role, they are not sure what to expect or what the job entails – nor should they. Being an assistant can mean a plethora of different things depending on who you are assisting. Some executives require personal tasks and duties can revolve around the clock, whereas others function within the confines of 9-5 PM.

Consequently, it’s the person who hires the assistant’s job to effectively spell out the various roles and responsibilities for the assistant. It’s important to be as transparent as possible of the demands ahead of time. Any documentation that can be put together before the assistant begins will greatly help them get acclimated.

Their role may adjust or expand at any time, and as it does, it’s important to maintain consistent check-in’s (at least once a month, if not weekly) to ensure the assistant is learning, growing, and consistently aware of their responsibilities.

It’s most effective to give feedback in real time as it’s much easier to learn in the moment. Most assistants are aware the relationship is largely based on the executive’s preference for how things are handled – Therefore, it’s critical to be both honest (even when things are wrong) and supportive (in order to get them right in the future).

When giving an assistant feedback, it can be valuable to write down what the feedback was in a consistent place for two reasons – 1. To create a system that holds the assistant accountable and measures their progress 2. So when the assistant moves on you have a log of pre-existing rules for how you like things to be done.

This is an area I wish I would have taken more ownership of over the years and definitely will in the future. Luckily, my last assistant Jenni Call, who now works for APG, created a great document for future assistants with all necessary reference information for basic processes.

Being an assistant is more than referencing information. It requires a certain flow. There are successful entrepreneurial assistants who deliver value in ways which may be different than what was expected, and there are career assistants who achieve precisely what is expected of the role. What’s most important is that an assistant entering the job is accountable to the tasks clearly delegated to them that needed to be completed in excellence. Over time, an assistant should get a better sense of what needs to happen before it’s even been assigned to them. If they don’t, it may be important the executive sets a certain process in place for dealing with the same types of situations.

Before an assistant gets a job, I like to test how they handle being wrong – Do they make up an excuse? Or do they ask for feedback, take it on the chin, and implement it moving forward? We all make errors and how we choose to deal with these situations defines who we are. Those with a growth mindset who can brush their ego aside and replace it with their desire to improve make far better assistants.

I prefer to hire assistants who have demonstrated their ability to lead in some capacity before, whether it’s a project at another company or a school group. While many think of assistants as the ones needing to be managed, it often works at least as much in reverse. Assistants are tasked with managing others (even their boss) – coordinating schedules and ensuring tasks delegated to others are executed.

Assistants have far more power than most people, including themselves realize. The people they support are responsible for creating immense value for the entity they work for. Therefore, assistants can tap into the power of their superior. This may be easier said than done as assistants are often looking for that next leg up rather than focusing on how they can create value in their current position. Then again, who can blame them? Most people don’t aspire to be assistants and instead see it as the necessary step towards a greater goal. However, I do believe some assistants have more potential in their role than even a junior marketing or A&R person, solely because of their access to information. What they choose to do with it is up to them.

Assistants are usually highly integrated with both internal and external operations so finding someone who can balance (or at least tap into) both extroverted and introverted energy is essential – They need to collaborate with people from all walks of life and also be capable of focusing intensely on solo deep work in order to prioritize effectively.

It’s a lot easier to give a great interview than it is to be great on the job. While intelligence, chemistry, and passion are all important, I’m interested in working with someone who has already demonstrated commitment to their career and the music industry – How many books have they read about music? Who are their idols and why? How have they began to build their network in music? What are the obstacles they’ve overcome to get where they are? 

If they don’t already have a small circle of friends they talk shop with all the time, they may just be dipping their feet in to see if the industry is the right fit. I am interested in working with individuals who already know music is the only career path for them.

With that being said, similar to Mike, I am currently hiring an assistant so if you know somebody you think you can be great, feel free to send them my way. As you can tell from the way I write this newsletter every day, I am very disciplined in pursuit of my goals and am looking for someone who is ready to create together at the highest level alongside me.

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