Guide to taking initiatives at work

Interview with Matt Newkirk, Director, Engineering at Etsy
September 20, 2022
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Matt’s greatest joys in life come from helping people achieve their goals. He currently does that as a director of engineering leading international experience at Etsy, having grown the team over the last six years. He occasionally writes about what he’s learned on his blog when he isn’t exhausted from parenting his two awesome and energetic children. Matt’s earlier career in test engineering and quality assurance leads him to always be on the lookout for opportunities to improve things, and he’s seen enough test failures to get a sense of what not to do.

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What’s your advice for people who want to get better at taking initiative?

When I think about taking initiative, I have to first ask: Is the problem that I’m missing context or that there is a missing action? 99% of the time, I’m just missing context, and it’s a matter of finding the right person to ask the right question. When I’m not sure about who to ask or how to ask something, I find my manager to be quite helpful, especially if I can help them understand why I’m curious.

If there feels like an action that needs to happen, try to answer each of these four questions:

  • Does this solve a problem recognized by your audience (your team, your boss, or other leaders in the company)?
  • Is this problem important to solve right now, or can it wait (a month, a quarter, a year, indefinitely)?
  • Who are the right partners for this work, so you don’t attempt it alone?
  • Is there a specific way to communicate your intent at your company that will be best received (a document, a slide deck, a 1-1 conversation, etc.)?

Your manager is a great person to help you answer those questions for your company, and they can also help you hone your suggestion to be received well. 

This approach works on various topics, from team dynamics to hiring plans used across the company.

You should also be prepared for “no.” 

Considering competing priorities or finding someone more suitable for the work ​​could be a more viable option.

You may find an opportunity to start small and gain more confidence, like having your team try out a new process improvement before scaling it. Whatever the outcome, your manager will gain more insight into your ability to observe opportunities to improve, and how you follow through with your ideas. That additional trust can make it easier for you to take initiative in the future.

Why do you think the ability to take initiative is important?

Taking initiative means being able to participate beyond what someone has asked or told you to do. It’s crucial on two levels. 

First, being able to make a difference is one of the ways I fight burnout and feel engaged in my job. Second, taking initiative demonstrates leadership and communication skills and is a great opportunity to learn and grow. Healthy organizations make it safe for people to practice those skills, whether or not the initiatives succeed. 

Can you share an example of a report who had great initiative?

I asked a report to consider how we might approach building a complex system. I shared my goals with her, and she asked some additional questions about timelines. Then she followed her curiosity and intuition to ask other teams for their insights. She took the initiative to find all of the relevant domain experts, interviewed them, and put together a solid plan that laid out all known technical risks. Later, when we were brainstorming about the product experience, she used her new expertise to help us understand which options sounded hard but weren’t, and vice versa. If she’d waited for me to give her explicit direction on who to contact and what to ask, she likely wouldn’t have gotten as much information or gotten it as quickly, which would have slowed the project’s progress.

What do you think causes a lack of initiative?

The most common obstacle in seeking opportunities is not knowing where to begin. As I said, your manager can help you figure out who to ask and how to ask effectively.

Beyond that, I’ve seen a strong fear of negative consequences, whether for going beyond your role or failing to ask a question effectively. Few people want to be known as the complainer.

Early in my career, I think I was that complainer. I felt like I couldn’t talk to anyone unless my manager set up the conversation. I was afraid of stepping outside of my lane. When my curiosity reached the point that I would go beyond my scope, my communication was rough. I was often dismissive or rude and did not get a useful answer. I often started questions with, “Why can’t we just…?”

I got feedback that my communication could be improved, but I couldn’t see it. Asking questions seemed to only result in more criticism.

When folks bring their curiosity to me now, I try to reinforce that it is safe to have those conversations if they can be open-minded and kind in their approach. I also try to be a connector so they can find the decision-maker or domain expert they need, rather than trying to field every question myself. The more often I’ve reached out to someone in a position of leadership, the less scary it has felt, and I hope I can pay that forward.

What would you consider your biggest professional high and low?

My lowest point professionally was early in my career when I realized that I had eroded my partners’ trust in me beyond repair. I was responsible for solving organizational problems, but I thought that meant using my domain expertise to enforce best practices. I didn’t invest in effective training or bringing people along with a strong value proposition. I let my frustration show when my partners didn’t understand me or accept my plans. Unlearning those habits and ensuring that my partners were co-creating the plans that impact them has been a long road, but vital in my ability to be positively impactful.

On the other side of the spectrum, my professional high has been seeing my team grow at the organizational and individual levels. I’ve been fortunate to see so many individuals grow in their careers, taking on leadership in engineering and management capacities. Coming back after my last parental leave, I could see how the team grew and supported each other. There were responsibilities they wanted to give back to me, but my absence didn’t break anything. I like to feel wanted in my role rather than needed, which is more healthy and sustainable for all of us.

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