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Leadership – August 31, 2020

Leadership in a Virtual Environment

Hawaii leaders discussed what they’ve learned and what best practices they follow while working with their teams from home.

Learning how to be an effective leader in a remote work environment is more important now than ever. For many people, it’s a brand new skill. During Hawaii Business Magazine’s 7th annual Leadership Conference, which was held virtually from July 28 to 30, the panel “Real Leadership in a Virtual Environment” addressed this topic head on.

“Digital collaboration is a skill and it is also very time consuming, so a lot of us are trying to get better at it,” says Sherri Okinaga, senior vice president & organizational effectiveness manager of First Hawaiian Bank.

“At the start of the year, I’m sure whether you’re a small or big organization, you had a strategy, you had goals and initiatives that you wanted to accomplish for the year,” Okinaga continues. “With Covid, we had to kind of stop, pause, pivot, take care of operations, make sure everyone was safe, and take care of all of that, so I think the challenge now is to shift back.”

Businesses must learn how to pivot what they do for the current times, while also continuing to stay on task with the company’s mission and goals. It’s a process that takes time, and asks companies to take another look at strategic plans.

Unyong Nakata, the senior director of sales & merchandising and operations integrator of Y. Hata Co., Ltd. moderated a lively discussion that asked some very timely questions about communication, connection and collaboration to panelists Katie Chang, executive director of Center for Tomorrow’s Leaders; Sherri Okinaga, senior vice president & organizational effectiveness manager of First Hawaiian Bank; and Mark Yamakawa, CEO of Hawaii Dental Service.


Here are four takeaways from the panel:

1. Increase communications and frequency, and call out people to engage in the conversation.

“I’m making it a point to be 120 percent present in a meeting because it is really easy to get distracted or to multitask, so I’m trying to be a better role model,” says Sherri Okinaga of First Hawaiian Bank. “It’s easy to hide behind a screen and to not give input so what I’m learning is that we can’t really take silence for concurrence, and so you have to ask better questions. So instead of saying, ‘Is everybody OK with this decision?’ it’s more like calling out, ‘Hey Unyong, what do you think about that decision?’”

Mark Yamakawa of Hawaii Dental Service adds, “I used to enjoy walking around the office and talking story with employees, but now I’m checking in with people on a one-on-one basis using video chat. We’ve insisted that when we get on one of these calls that everyone turns on their video because you want to be able to see the nonverbals, the ability to intuit if someone is disagreeing, or having a little bit difficulty understanding it. It’s really important that we see each other as much as possible.”

2. Be flexible about how the work gets done and avoid micromanaging.

“Benchmark performance results instead of really hunkering down on when people do it,” says Okinaga, and emphasizes that she’s not a fan of time logs as it sends signals that you don’t trust the work employees are doing. “Trust people to do it. I’m not a morning person and I do my best quality work at midnight. When I do it should not really matter if results are really strong. So I really like to remind people who are leading to not get stuck in the details and just really make clear your performance expectations and what support they need to get it done.”

3. Companies and organizations should invest in training now and offer mentorship opportunities.

“We’ve really doubled down on training and communications,” says Yamakawa. “Now is the most important time for us to improve our ability to communicate and understand how people communicate differently with each other, so we’ve pursued it and we’re actually doing a bunch of training right now virtually because we want everyone to be able to be better communicators and be able to work effectively, especially in this type of environment.”

Katie Chang of Center for Tomorrow’s Leaders answers “Absolutely mentorship,” in response to a question about new initiatives that they will carry on after Covid.  “Bringing together our different high schools, our different islands, to people who care about them in the business community and everything else. That was something that Covid necessitated but it ended up being much stronger. So it’s definitely something we’re looking to scale because it’s something our young people really need. That’s why I encourage it even within companies too.”

4. Non-managers can enact leadership from anywhere through intelligent disobedience.

“I would invite you to look up ‘relentless curiosity,’ but also ‘intelligent disobedience,’” says Okinaga. Intelligent disobedience is a term derived from the training of guide dogs for the blind, such as how and when the dog decides to disobey and go a different direction than what it’s told at the best interests of its human. Knowing when and how to bend or reinvent rules is intelligent disobedience.

“People have intelligence on the frontlines that people want to hear,” continues Okinaga. “What you can do is offer up some insights and wisdom from where you are with the intention of taking the business to the next level.”


Highlights from the discussion:

Session replays from the 7th annual Leadership Conference are available until September 30, 2020. Access the full discussions at

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