I spent four wonderful years at a recruitment agency in Tokyo, mostly working with tech startups and foreign firms entering the Japanese market. My goal was to help companies find the best talent in the job market, to guide those candidates through (often lengthy) interviews, manage expectations, and negotiate offers. It was intense, to say the least, but extremely fulfilling.

Here are a few lessons I learned along the way.

#1. Don’t plan too much. Get sh*t done.

Monday morning I would set sales targets for the week with my manager. There was little discussion about how to achieve these results, just that they needed to be done. The targets were straightforward and consisted of making dozens of phone calls, messaging people on LinkedIn, and meeting potential job candidates in person. I often procrastinated to start, and spent too much time crafting the best approach. I realized that spending more than 10 minutes of planning didn’t actually get me closer to my goals — there were simply too many factors outside of my control (like whether or not people would even pick up my call, or be interested in what I had to say!). We often get caught up in planning the future, which is hardly predictable. Usually the best thing we can do is just get started.

“The reason I don’t have a plan is because if i have a plan I’m limited to today’s options” — Sherryl Sandberg

#2. It’s hard to listen when you’re talking all the time.

The biggest problem recruiters have is that they talk too much. I was no exception. In an initial meeting, I would spend the first 15 minutes in a lengthy monologue about the company and myself in hopes of establishing myself as “worthy” in their eyes. This backfired; I often set expectations too high, didn’t get to the point, and failed to gain a deeper understanding of how I could actually help them. I remember when I finally changed my approach in one meeting, I vowed to only speak for 5% of the entire conversation. The result was surprising; I learned a lot from the person, and at the end of the meeting he commented, “Wow, you understand the industry so well!” This struck me as funny, since I hadn’t actually said much.

#3. Life is a lot like poker.

On average I would speak to 50–60 job seekers per week. Out of those, I’d select 10–15 that I felt had the skills to do certain jobs and then present their resumes to hiring managers for review. They’d choose 5 or 6 out of the group to interview, and if all the stars aligned, one of them might get a job offer in a couple of month’s time. Those may seem like pretty low odds, but they’re the average in recruitment industry. There were times were I tried hard to “control” the situation, and would get upset or defensive when things weren’t going my way. But that’s not how the world works. I realized there’s no proven way to meet your sales target every single quarter of the year, no matter how great of a sales person you (think) you are. It’s tough to guarantee certain outcomes especially when you’re trying to influence other people. Eventually, I came to accept that we’re all dealt different cards in life — indeed, life was a lot like poker.

“Life, like poker, has an element of risk. It shouldn’t be avoided. It should be faced.” — Edward Norton

#4. Give the bad news first.

They say recruitment is the business of rejection. We’re either being rejected (getting lots of “no’s” when we are trying to get a new client) or rejecting someone (informing job candidates they didn’t pass the interview). Within a 3-month period, I’d speak to hundreds of people — all with dreams, aspirations and most looking for new jobs — but only a tiny fraction of them would succeed in landing jobs. This was emotionally exhausting, as I often became friends and built relationships with people; to give them the bad news that they had failed a final interview was never fun. Like many, I often hesitated to break the bad news; that is, until someone told me, rather bluntly, to “cut the BS and give me a straight answer.” People don’t like it when you beat around the bush — while it’s painful to hear negative feedback, they’ll respect you more for being upfront.

“Bad news isn’t wine. It doesn’t improve with age.” — Colin Powell.

#5. Ask Questions Early

There were several occasions where it was clear to people that I had no idea what the hell I was talking about. One such instance was when a client I was meeting kept talking about “OTE” (on-target earnings). I nodded and pretended to know what he was saying. This was a bad move, though, as he eventually picked up on my lack of understanding. He leaned over, looked at me piercingly and said, “Do you even know what OTE is?” I felt dumb, and had to ask him to clarify. The situation was infinitely worse because I didn’t ask up front, and I could have easily avoided the now awkward embarrassment. People say that you should be a “sponge,” but I think you need to be a bit more active than that. The point is that it’s ok to be the dumbest person in the room, but if you don’t understand something it’s important to ask questions sooner rather than later.



#6. Black Swans Are a Real Thing

I found the perfect candidate for a startup client and had worked tirelessly on their behalf to get to this stage — we were just a couple of days away from closing the deal. My sales target for the quarter depended on this happening. Despite my extreme certainty about the future, the events unfolded very differently than I had expected. Days before the end of the quarter, the client announced that they were shutting down their office, pulling out of the Japanese market and moving to China. No more deal. I was crushed, of course, but it was a great lesson. In retrospect, I should’ve hedged my bets and not put so much focus into one deal. I realized that ‘certainty’ is a dangerous word, as there will always be unpredictable events — Black Swans — that you can’t account for.


#7. Say Yes, Until You Learn How to Say No

There is a certain level of expertise and intuition that develops after doing a job for several years. Until you reach that point, though, it’s hard to know where exactly to focus your time and efforts. Some people said “no” to working late hours. I didn’t care about that. I was first man in, last man out. This paid off, as on one of my ordinarily late evenings at the office, the phone rang, I picked up, and a new account fell into my lap. I couldn’t work late every day indefinitely, though, nor could I say yes to every colleague who wanted help with a project. When I learned the ropes, eventually I became more conscious of my time, managed expectations and learned what was really worth my effort.

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