Consultant to Creatives

The Clarity Journal

Tactics, Tools, and Truth for Creative Entrepreneurs

How to Build A Strong Partnership with Your Assistant

As an entrepreneur, an assistant is often our first hire (or, in other cases, the hire that we dream about on bad days.) Hiring an assistant is only the first step; utilizing your assistant effectively is a steeper learning curve than it seems.

To get some needed advice on how to work well your assistant, I talked to my husband, Travis Wussow. He’s had a variety of assistants throughout his career, and has learned how to rely heavily on the support of others in order to increase his own productivity and effectiveness. Read our conversation below to learn about mistakes people make working with their assistants, things to consider before you hire, what to expect from the on-boarding process, and more!

What is the key to having an effective, productive relationship with your assistant?

The relationship has to be built on mutual respect. He or she has to respect you for what you do, and you have respect him for what he brings to the table. Even more than that, you have to cultivate a sense that what he is doing is itself a true profession, just as yours is. And the basis of this profession is solving problems and keeping the details in order.

I have lots of software, tools, and programs that make tasks easier for me. These are helpful, but at the end of the day these tools can’t replicate the kind of problem solving that my assistant does for me on a daily basis. Take scheduling as an example. A piece of software can’t answer the question, “Hey, can we meet at this place instead?” That requires all kinds of different inputs and information that software doesn’t have, such as, what is traffic like at that time of day, what meetings do I have afterward, where is the other person coming from, and on and on. Only a human can solve that kind of complex problem on my behalf, and this is one of the simplest examples of problems that my assistant is empowered to solve for me.

This is a long way of saying that being an assistant is a true profession, and that profession must be respected and understood in order to have a successful relationship.

What are some of the common mistakes people make when they are working with their assistants, especially when they are just starting out?

The worst thing you can do is hire somebody to help you and then not let him help you. I often hear stories of leaders who don’t give their assistants access to their email or even to their calendar because of the feeling that they need to continue to control that aspect of their lives. This is, to put it bluntly, crazy.

Your assistant has to become an extension of you in a comprehensive way. If you can’t trust a prospective assistant to look at your email or add things to your calendar, then don’t hire that person. If you’ve already decided to cabin off certain parts of your life or work from your assistant because because you aren’t ready to give up control, then don’t hire an assistant. You aren’t ready for one.

The second thing I’ll say is that you need to be honest with yourself about how you like to work. If you like something done in a certain way, you have to say so. I am a type A person, I’m not laid back, and I’m not chill. If I delude myself into thinking that I am somehow easygoing with my workflow, my relationship with my assistant will be filled with conflict because I will not like her work but have not communicated what I like. I like my emails to be written in a certain way. I like the location of my meetings added to my calendar in a certain way. It’s better to recognize this and communicate it clearly so that I can be supported in the way I need and my assistant can be successful at her job.

How do you flex your assistant’s responsibilities according to their strengths and weaknesses, or even their likes and dislikes?

I think you have to be careful with that. To some extent, the job is what it is, and there are undesirable parts of every job. That being said, you want to make sure that your assistant has a good mix of responsibilities that are energizing and enjoyable and not too many things that are draining.

For my current assistant, I know the stuff that drives her crazy. So I try to be aware of that and not ask her to do 10 things that will drain her in a single day. That’s because I care about her as a person, but also because I want her to be fulfilled in her work and effective. But, those 10 things still need to be done. Sometimes what that means is that I myself need to handle some of those if she is jammed up and has had a bad day. If our relationship is built on mutual respect, then we can share each other’s burdens in that way.

What should people expect from the on-boarding process?

You’re going to have a lot of mistakes in the first three months and fewer mistakes in the next three months. In months six through 12, there will be even fewer mistakes, but those mistakes will be bigger and more problematic for you. At that point, you will have handed so much trust over to that person, the mistakes will matter more.

When big mistakes happen, you have to learn how to have corrective conversations in a way that isn’t going to crush the other person. As a leader, you have to enter into these conversations with grace so that you don’t harm the relationship.

For entrepreneurs who are considering hiring an assistant for the first time, what are some important factors to consider?

What’s very tempting to do, especially on a small team, is to hire someone for a split role. In other words, hiring someone to be a social media manager AND an assistant or a business development person AND an assistant. That almost never works over the long-term. The first reason is that split roles require, oftentimes, two very different skillsets that don’t reside in the same person for the long-term.

Second, if you hire someone for a split role, that person is almost always most interested in the non-assistant aspects of the role. People who take jobs as assistants plus “something else” almost always took the job because of the “something else” and not because they want to be your assistant.

If you need an assistant, but you don’t have the resources to hire a full-time, dedicated person, there are other ways to handle that. You can hire a part-time person or a virtual assistant who works with other clients.

But if you decide to hire for a split role, put a timeframe on it so that the person knows how and when they are going to earn the right grow up in your organization and grow out of the assistant responsibilities. I would also urge you to make the assistant responsibilities explicit in your job description. Don’t hide them or minimize them, or you will guarantee yourself a frustrated employee and a frustrating leadership problem to solve.


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