So You Fired Your First Assistant

A client wrote me this recently.

“Do you have a heart-centered guide for finding an assistant? I need it! My intention is to find someone who can support me and the business as we grow; start with a bit of work and take on more as needed.”

“I’ve already had one assistant and had to let her go, so I’m feeling overwhelmed at starting the process again and needing guidance.”

Let me tell you, I have been through a LOT of learning in this area the past five years. Hockey-stick learning curve with many painful and some good experiences and few really good experiences.

I had written The Two Hiring Help Freak-Outs That Stop Momentum. Looks like my client took that advice, but it ended up not working out. So let’s take it a step further.

First: It’s Unavoidable

It would be amazingly wildly fortunate if the very first time you hired someone to help you, the very first time you tried this out, you found the exact right person and it worked forever.

It didn’t work like that for me. I went through two or three before arriving at Susan. And then I’ve been through two more people at a higher “operations manager” level, and still haven’t landed with the right match, though I know that person is out there.

Second: Three Questions to Ask

The biggest mistake I’ve made, and that I’ve consequently seen others make, is to focus way too much on the hired person.

That person is coming into an environment and relationship that can be, at times, intense. If you don’t prepare for them, your business and your personality will kick them out unconsciously, over and over again.

• First question: Where is your business going?

Although I’ve never seen myself as visionary (I’ll wait until you stop laughing. Ahem.), I do have a sense of where the business is going. In fact, a strong sense. (That’s why they call it “visionary” right? Sigh…)

Your assistant needs to know the big picture so they can understand and even begin to anticipate what’s going on.

If your person is not interested in the big picture at all, then they may have more an employee mindset than a team mindset, which is Not Good. More on that below.

• Second question: What is your role in helping your business get there?

This can be really hard to answer, because up until now you’ve done everything. This is a BIG question, far bigger than these two or three paragraphs, but it needs asking.

You can ask this in several ways: what needs to be done that only you can do? What needs your input? I’ve seen it divided up into the following convenient categories.

• You must do yourself. (Example: Set direction for the business, create core content.)
• You don’t have to do it, but you must have input into how it’s done. (Example: Work with clients.)
• You don’t have to do it or have input, but you must know about after its done. (Example: After client orders, product is shipped.)

Make sure the answers are truly true. For your business, maybe no one else works with clients except you, so it would go in the first category.

I highly recommend learning about yourself, through perhaps the Enneagram, a book like The Synergist, or another resource.

It will probably take you a few days to a few weeks to get super clear on this list.

• Third question: What support do you need so you can focus on your role and not get distracted?

Notice the wording of this question? It’s not just about other people getting things done for you. You may also need someone to help you co-create processes that the business uses. You may need someone to talk and meditate through strategic questions with you.

Forget about budget. Just get clear on the ideal support you need here.

Warning: this will probably entail more than one person. For instance, you may need a graphic designer, an administrative assistant, a project manager, a web developer, a bookkeeper, a marketing consultant, etc, etc.

• Fourth question: What can you afford to start with?

Strategically, what support removes the most distraction for the least money?

Asked another way, what takes up the most amount of your time and mental space during your average week that isn’t on your “I must do myself” list?

Ask those questions, and you are going to be much more ready to get help than before.

A Couple Other Random Learnings

I’ve learned over the years that some people have an employee mindset and some people have a business-owner mindset. You don’t want employees, even if they end up on your payroll.

You want people who are interested in what you are doing and are wanting to help your business achieve its goals. In these cases it helps if your business has a goal that is larger than “make me comfortable.”

That’s why that first question is so important. Here’s a hint: enrolling a new team member is, in many ways, like enrolling a new client. The process can be very similar.

Also, you want to start small. Rather than try to hand off everything to someone immediately, pick one small project to start, preferably one that will take a few weeks to complete.

You’ll learn over the course of those weeks what your working relationship is like, and how they handle themselves outside of the “good behavior” period of the initial few meetings.

Our team member Susan Lucibello has been unfailingly polite, caring, open-hearted, honest, and sincere for years now. Someone can fake that for a few days or a week, but not for a month, and certainly not for years.

Although this topic is wide and deep, I think this will get you more than started into the process.

How about you? What wisdom can you share from your experiences? Or what questions do you have? Tell us on the blog.