You want to take initiative at work? Great, make sure you do it right.

I found myself struggling with how to strike a balance between taking initiative and asking for permission. Here’s what I learnt:

Two months ago, when we started promoting the COMPASS 2018 event, I received one comment from a Leap social media follower that wrote, “these sort of career development events are just full of buzzwords and inspirational sentences. I’m afraid this is yet another one.”

To be honest, many management phrases are not well-defined: leadership, influencing, impact, and, the one I had the most questions about, taking initiative.

Not only are these terms not precisely defined, but from a cultural perspective, Asians are always told to be humble and to just blend in. Taking initiatives, on the other hand, means to stand out, raise my hand, and go ahead and do things that are not assigned to me…

I found myself struggling with how to strike a balance between taking initiative and asking for permission.

So I paid extra attention to the “Take Initiatives” panel where these prominent leaders in tech shared their stories on stage at COMPASS 2018:

The four panelists for Take Initiative panel @ COMPASS 2018

Here are my top 5 takeaways about taking initiative:

#1 Make sure you do your job really, really well.

You are probably thinking…lame, that’s so obvious. But is it really?

There are two things that will cause your boss raise his/her eyebrows: one, you’re doing something wrong or two, you’re taking initiatives. However, most people overthink the latter and miss the point of the former.

Worry about standing out later.

At first, you just need to get your work done flawlessly and as efficiently as possible. This requires you to be predictable, work smoothly within your team, and be a reliable resource for getting the job done.

However, often getting your own tasks done and taking initiative comes with tradeoffs. Many times, I’ve found that taking too many initiatives and trying to get those accomplished would in turn trump my ability to get my baseline responsibilities completed. Consequently, not only do your initiatives end up getting shut down, you also lose credit for getting your own tasks done.

So make sure you always keep this rule of thumb in mind.

#2 Do things no one told you to do.

Fully executing and implementing what has been assigned to you is critical and already requires a high bar of excellence. But to be qualified as someone who takes initiatives, you need to go beyond this.

Do more than what is required from you.

Li Gong, the former COO at Mozilla, offered his perspective, “I have never done a boring job. I approach everything with this mentality.” So he would take the initiative to do things that he felt were enjoyable to do and the right thing to do.

“Take initiative that’s interesting to you.”

The moderator, Wenxiang Ma, who is the CTO & EVP of Engineering at Arena Solutions, added on the importance of having the right mentality about taking initiatives, “It does not equal to making a name for myself in the company.” It’s not just about doing big projects, but also small and personal gestures.

Yiying Lu, the designer of Twitter’s Fail Whale, also designed the 4 Chinese culture related emojis. No one told her to do that for the community.

She shared the story that drove her to move and stay in Silicon Valley:

After she did a project with Twitter’s Capacity Team, the design work brought a big smile to the face of the team’s “most serious” engineering manager. She perceived her true calling of bringing more art and fun to the tech world, and decided to do the thing no one asked her to do: move to the Valley from 8,000 miles away.

“No one asked me to move to the Silicon Valley,” Yiying said, “I know it’s risky. I know it’s hard. I know that a lot of people think it’s crazy to move to Silicon Valley as an artist. But I still want to do the thing, do the thing I believe in.”

#3 Take full ownership of your initiatives and follow through

In order to care about and devote ourselves fully to something, we have to consider it ours. Thus, take full ownership of your initiatives at work.

Each success and each achievement of the organization is yours as well. As soon as you establish this mindset, you will start caring about the details and dedicating all of your effort to achieving great outcomes.

Initiative usually starts from asking the right questions, but remember to follow through with proposals of solutions and the behind-the-scenes planning and execution.

As my colleague, Vivian Chan, pointed out in her takeaways from COMPASS 2018, “people remember a job well done not a job well started.”

Panelist Maria Zhang, CTO of Tinder, shared how in 2010 she quit Microsoft to start her own mobile company without knowing anything about mobile development. She took the initiative to learn and followed through on her idea. Eventually, Yahoo acquired her company.

“Think about initiatives as a race!” — Paul Song, Director of Marketing Strategic Planning and Analysis @ Airbnb

Paul Song is the Director of Marketing Strategic Planning and Analysis at Airbnb. He once was surprised by one of his friends, who definitely knew how to take initiatives but didn’t apply that to the workplace.

“Many years ago, this friend was expecting a promotion at work but didn’t get it. The feedback was that he was not proactive enough. That was strange to me. He helped me get my house by telling me to take initiatives. He was the one who told me, you can’t just submit applications, sit on your butt and pray,” he said, “You need to show the owner how much you want to see your family in the house. He knows the importance of doing this. In a professional setting, it’s very similar.”

If you have difficulties taking initiative at work, think about how you’ve taken initiative successfully in other aspects of your life. If you think of yourself as the owner of your product, your company culture and your career, then it becomes easier to apply this same framework at work.

Paul also walks his talk. At work, he asks questions to all the related stakeholders: PM, marketing, business planning and gets to understand how the platform works as a whole.

But…there’s one advice on taking initiative that you’ve probably never heard of elsewhere:

#4 Take on risks knowingly — be respectful and do assessment mindfully

Taking initiative overall is a quality that’s encouraged and well-perceived. However, as one of our speakers suggested, “You need to do it with the intent of benefiting the company and with respect to your peers.”

“Follow your gut and passion. But be mindful. Otherwise, you would end up upsetting your managers, peers, and a good intent ends up costing damages,”

Li Gong started with a story of when he was at Sun Microsystem in 1996. He was doing remarkably well at the company, and then the management team asked him if he’s willing to help set up a team in China, where at the time, the labor cost was ⅕ of the US tech workers.

“So I took the initiative and brought the product line to China. At first, I hired 10 to 20 people. Then I hired more, up to 100,” Li shared, “Management team back at HQ told me, they never knew I could hire 100 good engineers in China. Then the team grew bigger and bigger all the way to 400 people.”

Things started to collapse at that point. People who were based back in HQ began to hear weird comments and formed discussions about how to get the promotion without anyone reported to them. Because all the jobs had been moved away from them!

Li Gong said, “I upset so many people without knowing. People told me you had controlled too many resources. So I want you to learn from these stories, don’t blindly take initiatives. Get to know your surroundings and who’s in your camp. Be sincere to them.”

Tinder’s CTO Maria Zhang shared the same point of view, “Acceleration comes from changes, but don’t do it bluntly.”

I want to end with some inspiration about “taking initiative” using Maria’s words:

“Why is change necessary? Because you want to solve a problem. Do you see potential improvement in efficiency? Do you see pain-points from the market, users, peers, colleagues, and your bosses? What can I help to introduce and lead and drive and define and champion these changes? Another way to put this is, that’s your initiative. And value the risk and rewards. Take these risk in a very deliberate, thoughtful and calculated way and have a plan to mitigate these risks. So we’re not gambling away. “

Actionable Tips:

1, Find a mentor, knowing where the company is heading to. Because you need to make sure your initiative is needed by the company or aligned with the direction the company is heading towards.

2, Starting by asking “Why not” instead of “Why,” and adopt this into your mentality.

3, Start asking your peers and managers, “How can I help you?”

4, Even if it requires working extra hours, master doing something that’s required for your job.

5, Voluntarily take care of things even if they are small.

A Real-Life Example of Taking Initiative

During the two months of intensive preparation for the COMPASS event, one of our volunteers stood out because of her ability to take initiative.

She signed up to be our content marketing volunteer. Instead of just waiting for us to give directions, she made suggestions to our content publishing plan and organized the discussions into a spreadsheet. Whenever we were 1 or 2 days ahead of the scheduled date for publishing, she would actively check in to see how the drafts were coming along. She followed through and did end-to-end delivery.

Besides content, she also actively spread the content to different communities and groups she’s part of. Not stopping there, she then stepped in to ask other volunteers to do the same for the event. The effort she put in and initiatives she took helped lift a lot of the workload off of our shoulders.

We eventually decided to take her in as our intern. :)

Working with her closely on the COMPASS 2018 project actually taught me how to take initiative.

Thanks for reading!

🙏 Also great thanks to these great speakers who shared their stories, thoughts and learnings :

Maria Zhang, CTO at Tinder

Li Gong, ex-President & COO at Mozilla

Paul Song, Director of Marketing at Airbnb

Yiying Lu, Designer of the Twitter Fail Whale

Moderator: Wenxiang Ma, CTO & EVP of Eng, Arena Solutions


The video for the full panel discussion here shortly so stay tuned! Subscribe to 🎬 this YouTube channel.

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