Michael Gutman is an interesting person. 

Besides being a recognized remote and hybrid work expert and educator, he’s also a former marketing director of FlexJobs – one of the leading platforms for finding flexible jobs. 

In his early 20s, Mike had a lucrative career in Silicon Valley that he ditched to travel the world and shape his core values. 

And he’s had many crazy experiences while visiting some of the world’s weirdest places. 

Having consulted hundreds of companies on implementing the hybrid work model, Mike knows a thing or two about succeeding in today’s evolving workplace landscape as a business leader.

Luckily he agreed to share his vast experience and knowledge with our audience.

What follows is a compelling interview with the man himself, where we talk about:

  • Hybrid work and what it takes to succeed if you’re just starting out
  • What are the best online resources to learn more about the hybrid work model if you’re a beginner
  • The most common challenges that leaders face when adopting a hybrid working model
  • The return to the office and how leaders should approach it
  • The fast-paced life of a keynote speaker and hybrid work consultant
  • Michael being robbed at gunpoint and walking a puma through the Bolivian jungle

And much more.

Read on.

Would you please introduce yourself to our audience and let us know what you do for a living?

I’ve led remote teams since 2008 and since 2013 I have been helping teams adopt flexible and remote work strategies. My roles have ranged from heading up customer success at a remote collaboration tool company to leading the marketing and partnerships efforts at FlexJobs, to building remote learning and development experiences for adults looking to upskill into tech.  

Currently, I am consulting and coaching leadership teams on implementing measurable remote work strategies, speaking at workforce development conferences, and authoring remote work courses on Linkedin and other platforms. My remote work courses have reached over 1 million learners to date.

How did your career start and why did you choose this path?

I’ve been working remotely since 2007 and I’ve always supported having access to work flexibility. But back in 2013, I had an “Aha!” moment.

At that time I was running a social enterprise focused on helping companies engage in corporate social responsibility. Part of the work involved teaching K-12 students about energy conservation and sustainability.  

It was my belief that if we can change one person’s behavior to consume less and recycle more, we can make incremental changes in the world.

However, the model I was working with did not scale. We could only hold so many workshops and change so many people’s minds.

My mindset shifted to ask the question… how do we layer a sustainability model on top of behavior that people already want?  

My answer was remote work. People want it. 

The behavior reduces consumption from office space, fuel emissions, and general infrastructure. It is a behavior that does more with less and people are pushing for it. So I dove in and have been on a mission to help connect people and companies to the value of flexible and remote work ever since.

What was it like to be a Marketing Manager in Silicon Valley?

To be honest, it never aligned with the answer to the question “What do you want to be when you grow up?”  

That being said, there were many aspects that I enjoyed. I was learning a lot, making good money, working with clients I never would have encountered, and managing large budgets. But at the end of the day, I realized I needed to make a career shift and align my work with my values. 

Back then I was in my 20’s so I was still trying to determine what my values were. 

(Maybe we never fully know) So I took a career break to figure out where I wanted to pivot. I did some traveling and lots of fierce introspection and realized I wanted to be intentional about helping humanity and the planet in some way.  

And here we are today!

What was your biggest challenge as a director of marketing at “FlexJobs”?

I was at FlexJobs from 2016-2019. Our mission was to help increase the number of flexible jobs available so people could live better lives. 

My biggest challenge (and opportunity) was to show people that flexible or hybrid jobs were real, and show companies that offering work flexibility could be a viable strategy for productivity and profit.

Remember, before the pandemic, the number of remote and flexible jobs out there was slim compared to on-site, 9-5 jobs. 

Our approach was a methodical and strategic process that took time.  

One of the silver linings of the pandemic is it gave people and companies a glimpse into what flexible and remote work could feel like and how to manage it properly. Which achieved the mission of connecting people and companies to flexible work in a matter of months.  

How did you decide to become a remote and hybrid work consultant and speaker?

People just started asking me for help.  

I have been living, breathing, and working to support remote work since 2013, and working remotely even longer. I’ve spoken to countless leaders at Fortune 100 companies, government agencies, start-ups, nonprofits… all people trying to get remote work dialed in for the communities they work with. 

So I have a diverse perspective on how different stakeholders approach remote and flexible work.  

So over time, people looked to me for my expertise. There is a big need for expertise from people who have been at this for a long time.  To meet that need I am now giving keynotes on remote and flexible work and helping leadership teams dial in the employee experience for their employees.

What are the three most important things that leaders should know about hybrid work before adopting the model within their organization?

First, leaders should be asking what each employee needs to be successful. Each employee will have different needs. From home office set-ups to communication preferences, to work-life balance, to optimizing productivity, to health and wellness.

michael gutman quote

The list goes on. Also, people managers also need training to be successful in this environment. And if you don’t know what people need, you can’t support them.

Second, leaders need to measure the success of their program. You can’t optimize what you can’t measure. 

Third, ensure whatever model you adopt is a flexible model.

The landscape of our work and lives is changing and if you create a rigid model that does not have room to evolve, it will break.

How should leaders better educate themselves on the topic of hybrid work, especially those who are new to the concept?

For leaders who are just learning about hybrid work, there are plenty of resources available.  A simple google search will yield many results.  Below are some specific resources I recommend. 

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Additionally, I recommend all leaders chat with their colleagues or people in their professional networks about their experience. Ask people what is working for them, what they have learned, and what their best practices are. If you are a leader working in a hybrid environment, I also recommend asking the people you supervise this one powerful question.

“What does an ideal hybrid work experience look like for you and how can I help you with that?”

Based on your experience, what are the biggest challenges that leaders face when trying to implement the hybrid work model?

The biggest challenge for leaders is that they often feel like they have to have all the answers to support remote or hybrid work experiences, just because they are in leadership positions.

I tell new clients that they are never going to get their hybrid or remote model right straight away.

It is just impossible to please everyone. With that in mind, I suggest that a new model should be rolled out in phases.

The first phase should be informing the initial plan. So what I suggest is asking teams what an ideal hybrid model looks like, and then trying to roll out the first phase of the implementation strategy that tries to align with the feedback.

Then build in feedback loops to evolve the plan over time in the following phases.

Companies can also fall into the trap of having a communications strategy that promises hard and fast deadlines for their plan. They should keep their communications strategy flexible as well so as to never overpromise.

What approach should employers take to bring employees back to the office and is the return to the office dead?

I always encourage a people-first approach. Ask your people if they want an office, and if so, what for. Then craft an office experience that aligns with the culture of the team. Maybe they want to use it for collaboration days, professional development time, or creative time.   

Most people don’t want to be forced back in to be heads down at their desks. They could do that at home and be more productive.

So it comes down to being intentional and being able to justify why your return to office policy exists.

If you can’t justify why you are forcing people into the office, people will start to resent the policy over time.

What’s the most valuable insight about hybrid and remote work you’ve learned after consulting clients?

Simply put, people want choice. The choice to choose when, where and how we get work done. 

The biggest question leaders have is how they can manage choice and autonomy at scale. 

This can be done by moving to a results-centered performance management strategy. Where you know if productivity goals are being met, regardless of when, where, and how.

Now, the million-dollar question: What’s the future of hybrid work?

This is too big of a question for me to predict. I only have a small sliver of insight.  From a remote and hybrid perspective, I believe that remote work is here to stay.

As future generations grow more and more into leadership positions, we will see more and more distributed work.  

For example, I didn’t have a cell phone or email until I was 18. Generations who are connected to the globe as children will know how to communicate and collaborate from anywhere better than we can currently. I believe these generations will pave the way for reducing the friction of remote and hybrid working. 

You’re an avid traveler. What’s the weirdest place you’ve ever been to?

Hmmmm…. I’ve been through a lot. Here are some of the strangest experiences off the top of my head. 

  • I’ve been lost at sea in a small boat, in a rainstorm, at midnight in Panama. 
  • I’ve walked a puma through the Bolivian jungle for 12 miles a day for a month at an animal refuge in Bolivia. 
  • I’ve been robbed at gunpoint
  • Survived giardia 
  • Lived in a garage in a yoga community
  • Been inked by an octopus 
  • and was forced to pay the police the equivalent of $100 for crashing a motorcycle… 

…and I survived to tell the tale.  

Where can people find you online?

I encourage people to connect with me on Linkedin or to send me a note through my website SucceedRemotely.com 

Asen Stoyanchev
Senior Content Marketing & SEO Specialist | OfficeRnD
Asen is passionate about flexible working and the future of work. He firmly believes that work flexibility directly impacts one's health and well-being. When he's not writing, Asen spends his time devouring business literature, hiking, and parenting.