Hire an assistant. Now!

When we started the company, there were three of us. The other two guys did the bulk of the design/development and I did some development, but mostly I ran the business. I spoke with all prospects, I managed all projects, dealt with accounting… all of it. Then earlier this year, one of those guys left to pursue other interests. Once he left, I took on the bulk of the design work on top of what was already on my plate. This was not a smart move.

For a couple months we rolled forward without making any significant changes to the way things were. We were working crazy hours to deal with everything on our plates and there was never a time when I felt like things were under control. I had lists of every shape and size. Notes on this project and that. But, there wasn’t anything that resembled a method to my madness. It was just… madness. Finally, when my stress level was reaching epic proportions, I made the decision. We need a project manager and we need one now!

As I started putting together the job description for this new position, I quickly realized that it wasn’t just a project manager I was looking for. I needed an assistant with project management skills. I interviewed half a dozen people for the position, but none felt perfect. As I was taking a couple of days to ponder my options, the exact person I had in mind for the position asked if the position was still available. Without a second thought, the position was hers. Welcome, Sarah.

Getting up to speed

Now that we had our person, the real fun begins. We set up an initial meeting to do a bit of a brain dump. I spoke for nearly 2 hours straight while she took notes. A lot of them. When the meeting ended and I saw the amount of information that had been floating around in my head, I was amazed. I knew I had been trying to manage a lot of information about a lot of projects, but seeing it all on paper was a real eye opener.

Over the next few weeks we worked together to find the processes that worked best for us. There is no such thing as a perfect solution when it comes to project management. We tried a few options and settled in on what felt comfortable. We’ve tweaked it over time and what we have now seems to be doing the trick. But, we’re still tweaking as we go.

Once we had the basic framework for project management in place, we started looking at all the areas of the business where she could take tasks off my plate. It should be no surprise that email was one of the first things that came up. On any given day I receive a handful emails from people looking for our services. I started by CC’ing Sarah on all client emails. Within a week she had taken over the ‘first line of defense’ answering the emails that have fairly standard responses. Over the next couple weeks she had taken over the bulk of all new prospect emails. If she did nothing else, she’d be worth her weight in gold! Lucky for me, this was only the beginning.

During those first couple weeks, Sarah turned my ramblings from that first meeting (along with all the emails and new prospects that had shown up since) in to an organized spreadsheet. We had tabs for existing projects, pipeline prospects and deals that we failed to capture. We’d meet a couple times a week to discuss each list. It's amazing how a 10 minute meeting looking over a list can be so much more productive than 2 hours of pouring through your inbox trying to find all the details…

These are only a few of the things she’s taken off my desk so far. As we continue to refine our processes, I know there will be more.

The Payoff

As I said before, I had a lot of information floating around in my head. Since I was always so busy with everything that was on my plate at the moment, it was virtually impossible to step back and look ahead or behind. I was just rushing from project to project putting out whichever was the biggest fire.

About 4 weeks in to having Sarah on board I had that ‘A HA!’ moment that let me know I had made the right choice. I received an email from a prospect who I had talked to a couple months before. We had exchanged a few emails about a project, but it didn’t go anywhere and he ended up falling through the cracks. Sarah saw his name on that original list of prospects, reached out to him with a simple email asking if he was still in need of our services, and the next day he emails us asking for a contract and invoice so we could start his project. Without Sarah sending that email, it's unlikely we would have landed that client.

While that is the most obvious example of the benefits of having an assistant, there are plenty of more subtle benefits as well. My time at my desk has been significantly more focused and productive now that I have less to manage on my own.

If I could give you just one piece of advice, stop trying to do it all yourself. Hire an assistant and in no time you’ll be wondering how you managed without them for so long.


  1. Andrea_R on July 25, 2011 at 9:42 am

    I think successful freelancers have a time where they are running a business but in your head youre still thinking you’re just this guy, you know? 😉

    Ron has me to be the assistant. 😀

    • John on July 25, 2011 at 9:50 am

      I agree 100%! Also, bringing on another person is tough because for a short time it actually causes MORE work while you get somebody trained up. But, in the end that extra work is SO worth it! I’m a much happier camper today than I was 2 months ago!

  2. Amanda on July 25, 2011 at 9:55 am

    the hardest thing in the world is the two fold recognition that

    a.) you are best served spending time on the items that have the highest ROI financially.
    b.) you CAN surrender the control over aspects of your business if you just spend the time to really find the right person to do so.

    The two most common mistakes I see are that people don’t spend enough time looking and vetting (a simple craigslist ad usually isn’t going to be enough), or they hire and then refuse to surrender control.

    Sounds like you made a great decision and the payoff is already in front of you.

    • John on July 25, 2011 at 10:05 am

      I was really lucky. Sarah and I had worked together before at a previous company and got along great. Plus, I already knew the awesome work she did because I had seen her do it for a long time.

      I am definitely a bit of a control freak. I know with 100% certainty that if I had not found the RIGHT person, I would have ended up not having over anything. It would have been a disaster.

  3. Paul Letourneau on July 25, 2011 at 9:59 am

    I’ve heard this so many times and it’s always great to hear. Do what you’re good at and hire others to do what they’re good at.

    So great! Very excited for you!

    • John on July 25, 2011 at 10:08 am

      Well said, Paul. And thanks, I’m pretty excited myself.

  4. Chris on July 25, 2011 at 10:14 am

    What a find! i’m so glad she’s part of your team. Welcome Sarah!

  5. Tyler Hurst on July 25, 2011 at 11:03 am

    What’s a typical pay scale for something like this? Seeing as how I’ve never hired an employee, my idea of what to pay people who don’t do exactly what I do is skewed.

    Also, she’s not full time, right?

    • John on July 25, 2011 at 11:22 am

      As I was doing my interviewing I had asked each person to give me their hourly rate. I had response ranging from $15 – $50 / hour. I don’t know if that’s typical, but those are the responses I got.

      And no, she’s not full time. Not even close. Currently she’s working 5-10 hours a week for us. I hope to get to a point where we need to bring her on full time. That would be excellent!

      • Tyler Hurst on July 25, 2011 at 11:28 am

        That’s about the price range and hours I expected. I’ve been toying with doing this for a while now, but my fear of letting control hasn’t quite subsided.

        I imagine it’s EXTREMELY important to have great chemistry with your assistant. If I have to spend hours explaining everything, I may as well do it myself (that’s what happens now).


  6. Ron on July 25, 2011 at 11:39 am

    Andrea & I went through a similar experience (although we didn’t hire an assistant as a result). Over the last year we’ve done a lot of work to restructure how we do things (and also what things we do). We still do some tweaking to the process as things come along that show us there is a better way to do things.

    • John on July 25, 2011 at 12:49 pm

      I’m sure there are plenty of things we could have done by setting aside some time and reworking our processes. There’s always going to be a better way to do things and it’s a constant battle to figure those out without spending so much time trying to sort them out that you lose sight of actually getting stuff done. It’s a very fine line. 🙂

  7. Jason Murphy on July 26, 2011 at 10:28 am

    Awesome news. Very glad to hear that Sarah is working with you again, I know that you play off each others strengths and weaknesses well and that is very key.

    Is it all spreadsheets or are you using a CRM? I’m trying to juggle the whole prospecting process, I can handle a few dozen leads okay, but when I’m playing in the hundreds like I am now, it’s a struggle. Any ideas or insight would be well appreciated.

    • John on July 26, 2011 at 10:49 am

      We use a CRM (BatchBook), but not really for pipeline prospects. That may be something we move to in the future, but I think until we find the project management tool we want to use long term, we’ll continue to pipeline via the spreadsheet. If/when we find a project management tool that we love, I’ll let you know!

      • Jason on July 29, 2011 at 8:59 pm

        Cool man. You know I’ll do the same if I come across something great.

  8. Brad Markle on September 10, 2011 at 3:44 pm

    It’s amazing that someone helping only an additional 5 – 10 hours a week could offer such a big payoff. Interesting article, I found myself reading the whole thing. Not because I need an assistant, but because I always have seemed to admire and look up to those that run there own small business.

    It’s somewhat surreal to be here at WordCamp LA. Here I am reading an article you wrote, and as I look up, here you come to check out a presentation I’m currently watching.

    • John on September 12, 2011 at 10:58 am

      It was great meeting you in person this weekend!

      One of the biggest reasons my assistant is paying such dividends is because she’s better at the things I’m sending her than I am. So, when it comes to writing documentation, she can knock out 99% of it in 1/3 the time it would take me. I can then go in and just make edits where needed. It keeps me doing the things that I’m better at.

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